Out & About Holidays

1728 W Roscoe St, 60657, Chicago
1728 W Roscoe St
60657, Chicago
+1646-354-3370

Opening hours

  • sunday: (closed)
  • monday: 9h-18h
  • tuesday: (closed)
  • wednesday: (closed)
  • thursday: 9h-18h
  • friday: 9h-18h
  • saturday: (closed)

Luxury Travel Agency.
Out & About Holidays, LLC is an Independent Affiliate of Q Cruise+ Travel, a VIRTUOSO Member Agency.

Our comment from TraTraTravel about Out & About Holidays:

Out & About Holidays has established itself as a premier travel advisory service led by James Lilla, known for his exceptional attention to detail and ability to create personalized travel experiences. Clients frequently express their gratitude for his meticulous planning, ensuring every aspect of their trip is flawlessly executed.

Highlights from client feedback emphasize:

  • Tailored Itineraries: James takes the time to understand personal preferences, creating customized travel plans that suit individual needs perfectly.
  • Seamless Experience: Customers appreciate how James manages logistics, from transfers to accommodations, making travel stress-free and enjoyable.
  • Personal Touch: Many clients noted the thoughtful extras, such as welcome notes and special surprises, that enhance their experience.
  • Expert Recommendations: James's extensive knowledge of destinations leads to insightful suggestions for hotels, dining, and activities.

While clients overwhelmingly praise James for his innovative planning and communication skills, some note that the process may involve adjustments to meet their specific desires. However, the outcome is invariably a well-organized and unique travel adventure.

In summary, Out & About Holidays offers exceptional travel planning services that transform ordinary trips into unforgettable experiences. For anyone looking to explore new destinations without the hassle of planning, James stands out as a trusted partner in ensuring an extraordinary getaway.

Tratra.travel cannot guarantee that the companies that appear in the directory are certified travel agencies or that they have the corresponding licenses. The majority of companies that appear in the directory are travel agencies, but other types of companies also appear such as tour operators, guided tour providers, etc. We recommend that you request the Travel Agency registration number of the business you are going to attend.

Out & About Holidays: Reviews

5/5 (90 Reviews)
Allison Paulish 1 month ago

Fantastic experience: I cannot thank James enough for planning the most incredible trip to Greece! From start to finish, everything was perfectly organized, and we truly had an unforgettable experience! James took the time to understand our preferences and tailored our itinerary to match exactly what we were hoping for— amazing hotels, beautiful beaches, and incredible dinner options! What really set this experience apart, was the personal touch! James was always available to answer any of our questions and provided the best recommendations to make our trip to Greece the trip of a lifetime! If you’re planning a trip, I highly recommend working with James! He truly went above and beyond to make our vacation flawless. Can't wait to plan our next trip with him very soon!!

L. Roeger 2 months ago

Fantastic experience: We worked with James to plan a recent trip from Shannon to Dublin/Ireland and he was absolutely fantastic. Super detailed and always a step ahead. He arranged all of our transfers and put together a fun and organized itinerary that made the most out of our time in Ireland. I highly recommend working with him.

Danielle Smith 5 months ago

Fantastic experience: James planned an amazing Scotland trip for my family! We were visiting my daughter studying abroad, and he perfectly worked around all our needs, organizing everything we requested. We couldn’t have done it without him and his great team of people working for him. We really loved our tour guide who also worked hard to make sure we saw and did everything we wanted. This is my second trip planned with James and I highly recommend him, and visiting beautiful Scotland!

Out & About Holidays
Out & About Holidays

Hi Danielle, Thank you for the glowing review! I’m so glad you were able to enjoy such a special trip with your kids and your Mother!

Justine Wright 7 months ago

Fantastic experience: James Lilla planed the most amazing Euro-Trip for my fiancé and I! We decided to do a pre-honeymoon multi-countries trip to Paris Nice Sorrento,Capri,Positano Rome Siena Zurich Crete Santorini London Not only was this trip planned in short notice but all covid protocols were made aware , hotels were perfect including hotel credits/great amenities, and James was available to speak throughout the entire trip and responded quickly. I had no idea how much easier traveling could be with a travel planner! All the recommendations for food, experiences and things to do were amazing! James listened to our travel style and interest and Delivered such a perfect trip! We highly recommend booking James for travel advisement and we would definitely use his full service again!

Out & About Holidays
Out & About Holidays

Thank You, Justine! I loved collaborating with you and Steve on your magical vacation of a lifetime!

Maddie Phillips 8 months ago

Fantastic experience: James planned the best vacation to Europe! We told him all the places we wanted to go and he took it from there. We stayed in reasonably priced but beautiful hotels. It was the trip of a lifetime for sure! We didn’t have to worry about getting to and from train stations or airports (which was my biggest concern) and we had the most amazing time!

Wesley Bonner 10 months ago

Fantastic experience: James booked us the most magical week in Costa Rica. The resort was absolutely stunning and we were even upgraded to an ocean front villa! Highly recommend to anyone seeking a friendly, easy to work with travel advisor.

Kerry 10 months ago

Fantastic experience: James’ passion for travel shines through in every trip he plans, ensuring that his clients have unique, memorable experiences. With his deep knowledge of destinations and strong connections with luxury travel partners, James tailors each itinerary to match the client's preferences, ours was an epic cruise to AK! His attention to detail, seamless planning, and commitment to making every journey special. James makes travel stress-free and unforgettable. Thank you James!

Chuck Mc Donald 1 year ago

Fantastic experience: James Lilla did a great job for my family. He made sure that every detail of our five person Silversea Alaska cruise was handled to perfection. His efforts to please his customers and his attention to detail are appreciated by all of us.

Out & About Holidays
Out & About Holidays

Thank you for your wonderful 5-star review! It was a pleasure to help create such a memorable experience for your family. I look forward to your next adventure!

Erik Olsen 1 year ago

Fantastic experience: James planned our 10 year anniversary trip to Ischia and Capri last Fall. It was nothing short of the best trip of our lives. Every small detail was considered with the selection of boutique hotels, restaurants, flights, tours and transportation. We felt our trip was carefully curated with a thoughtful balance of local knowledge, taste and budget. We appreciated the fact that James was flexible in his planning approach that he could be at arms length for decisions or heavy in involvement or taking care of everything for us. Once we were in Italy, James was always available if something wasn’t exactly as planned. James organized this trip as he was going to be enjoying it himself and that showed. Having every activity and dinner planned for in advance let us focus on enjoying our time together rather than worrying about logistics during the vacation. We would highly recommend Out and About for any meaningful trip, small or large. THANK YOU, JAMES!

Out & About Holidays
Out & About Holidays

Hi Erik,
Thank you for the most amazing review! I’m so glad you had such an unforgettable time across Italy. I LOVE the pictures, too. Where are we going next!?

Nicholas Nadhir 1 year ago

Fantastic experience: I highly recommend working with James. He helped us (5 people) plan a vacation to three separate countries in Europe and everything was seamless. The transfers, hotels, tour guides and all accommodations were exceptional. James was very knowledgeable in the recommendations that we should be doing our holiday, extremely responsive and available if there are any changes that needed to be made. We will definitely be using James again.

Out & About Holidays
Out & About Holidays

Hi Nicholas,
It was a wonderful experience collaborating with you and your family on your amazing trip to Portofino, Saint Tropez and London. Looking forward to the next one!

Stacy Falls 1 year ago

Fantastic experience: Thank you for your help planning our lovely Irish getaway! We are at the airport now, on way home. We had an amazing trip and everything went perfectly. Smooth and effortless! An incredible place with amazing beauty! Please extend our thanks to Paula. Everything was planned perfectly, we had a great time!!!

Jason Epstein 1 year ago

Fantastic experience: James is great to work with. He did a great job of helping us plan our trip to Scandinavia. He made it so easy to coordinate everything for our family of 5. Can’t wait to plan our next vacation with him.

Out & About Holidays
Out & About Holidays

Hi Jason,
Thanks for the kind review. I’m so glad you enjoyed your time with your family of 5 in Copenhagen & Stockholm. Looking forward to planning something next summer!

Archie Gianunzio 1 year ago

Fantastic experience: I never knew how easy planning a major trip could be until I found James and Out & About Travel.

Out & About Holidays
Out & About Holidays

Archie, Thanks for the review. It was lovely collaborating with you on your Anniversary trip across Costa Rica!

Trish Halper 1 year ago

Fantastic experience: We highly recommend working with James! He helped us plan an amazing trip to Italy for our family of 5 (3 teen/college age kids). Logistics for a group of 5 can be tricky, but James made it all easy. Every transfer was seamless, every tour guide was amazing, the hotels/restaurants were top notch. We went to Ischia per James’ suggestion and it was our favorite place! Cooking class and boat day in Sorrento were both amazing! This won’t be the last time we utilize James for our travel needs!!

Out & About Holidays
Out & About Holidays

Hi Trish, Thank you for the thoughtful feedback! It was fun getting to know you and your family and I’m so glad everything went so smoothly across Italy! Shhhh, don’t tell too many people about Ischia :) Looking forward to Spain in the Spring!

Melissa Beanblossom 1 year ago

Fantastic experience: James was wonderful to work with. He listened to what we wanted and then took care of everything. We were taken care of throughout our trip, with great guides and beautiful accommodations.

Out & About Holidays
Out & About Holidays

Hi Melissa, Thank You for entrusting me with your luxe Anniversary trip to Spain! I Can’t wait to hear more about Bilboa and San Sebastián!

Julie Justicz 1 year ago

Fantastic experience: We worked with James on a special anniversary and 60th bday trip to Mexico. His planning, insights, communication, and suggestions were all fabulous. He's warm, funny, smart, and in addition to planning a great itinerary he adds amazing caring gestures -- like chocolates on a birthday, champagne on an anniversary. We had a blast-- every hotel he suggested was terrific and the activities were just what we wanted. He steered us correctly at every turn. Thanks James! J & M, Chicago

Out & About Holidays
Out & About Holidays

Hi Julie, Thank you for such a kind review! I’m so happy to hear you loved your time in Mexico City and then on the beach in Cozumel. I’m glad you got my , too!

Stephanie Paul 1 year ago

Fantastic experience: James was so attentive & accommodating to our needs!

Out & About Holidays
Out & About Holidays

Hi Stephanie,
I’m so happy to hear you had such a fun spring break at the Langham in London & SO/ Paris. Your pictures looked amazing!

Kelly Gibbons 1 year ago

Fantastic experience: James was amazing! I used James as a travel agent for my wedding in Mexico and he was helpful throughout every step of the process. He had great insight into what to look for when selecting a resort and once it was selected he worked with them to get a large room block and set up a website where our guests could go to book their room and transportation from the airport. Without James it would have been impossible to keep track of 115 guests that were invited & I heard nothing but positive feedback from our guests when they were in contact with James! He is so organized and always on top of deadlines! Highly recommend!

Out & About Holidays
Out & About Holidays

Thank You so much, Kelly! I’m so relieved everything went as planned for your 100+ guest. It was quite the feat!

Patrick Gaerlan 1 year ago

Fantastic experience: James has booked travel for me in many cities: Paris, London, Madrid, Barcelona, Sevilla, Menorca, Gran Canaria, Athens, Mykonos, San Miguel Allende and Mexico City. All incredibly planned experiences that will always be treasured.

Out & About Holidays
Out & About Holidays

Hi Patrick, It’s has been a pleasure planning your travels across the globe. I’m looking forward to hearing about your travels in Greece again this Sept!

Aude Banicki 1 year ago

Fantastic experience: James is amazing! He goes above and beyond and had every detail for our travels mapped out. Highly recommended.

Out & About Holidays
Out & About Holidays

Hi Aude,
Thank you for the review. I’m happy you enjoyed your Riad in Marrakech and your Glamping experience in Morocco. I’m Looking forward to our next trip together!

JJ Banicki 1 year ago

Fantastic experience: James does his research and covers all the details. Highly recommend his expertise if you want a friend on the inside of international travel

Out & About Holidays
Out & About Holidays

JJ, thank you for the review. I’m so happy you and your wife loved Morocco!

Amy Anesi 1 year ago

Fantastic experience: I highly recommend working with James! He is knowledgable and incredibly responsive. He planned an amazing 4 days in Paris for us (2 couples) and everything he did for us was top-notch. One of our favorites was a walking tour of Montmartre which concluded with a wine tasting. Another favorite was the day we had a private driver for the sites of Paris that also included Versailles. Finally we truly enjoyed the hotel he suggested (great service and great American showers!) and will absolutely work with him again on another trip.

Out & About Holidays
Out & About Holidays

Amy, It was so lovely collaborating with you and your wife for this special celebration! Thank You for entrusting me with my hotel and dining recommendations in Mexico City and Cozumel!

Daniela Ellis 1 year ago

Fantastic experience: My friend booked a villa in Cabo for her 40th birthday and everything was amazing!!! James had everything organized and top notch! My friend uses James for all her trips, but he has gained a new client in me!

Out & About Holidays
Out & About Holidays

Hi Daniella, Thanks for the review. I’m so happy you all enjoyed your stay at your beautiful Villa in Cabo! How was parasailing!?

Nick Ray 1 year ago

Fantastic experience: I highly recommend using James to plan your next International trip. We started working with him in Dec 2022 to plan a trip to Paris and Italy (Florence, Tuscany, Cinque Terre, Rome) in Sep 2023. This was our first Europe trip (for fun) and he made the planning process simple. He answered all questions about flights, travel between countries, and provided amazing hotel and restaurant recommendations. The properties we booked through him were INCREDIBLE and we received many perks at these Virtuoso properties (welcome packages, resort credits, upgrade rooms, preferred checkin/checkout, etc). He was so proactive and responsive, exactly what you'd want when planning a special trip. I'd highly recommend his services if your looking for a Partner to help plan your next trip! Reach out to him now!

Out & About Holidays
Out & About Holidays

Hi Nick, I’m so happy everything went off without a hitch across your 5 destinations. Also, thank you for referring your brother. That’s the best type of “thank you!”

Stephanie Cochin 1 year ago

Fantastic experience: Our stay at the Halekulani was perfection! James had us set up for an upgrade to Oceanview. We also had a bottle of champagne waiting for us along with beautiful snacks and dessert. Thanks to James, our vacation was a dream come true!!

Out & About Holidays
Out & About Holidays

Hi Stephanie, I’m so glad you enjoyed your birthday celebration and Thanksgiving in Hawaii! Get used to the 5 Star treatment when you’re working with me :)

Laura S 1 year ago

Fantastic experience: We trusted Out & About Holidays to plan our honeymoon to Costa Rica and it has been the best travel decision we've ever made! Every single detail was considered, transportation was smooth, upgrades were incredible, there were thoughtful surprises throughout the trip, and the people he chose to connect us with were 5 stars across the board. As an organized person who is well traveled, I could not have pulled together myself what James was able to do. Do not underestimate the power of hiring an expert!!

Out & About Holidays
Out & About Holidays

Hi Laura, Thank You for the kind review! I’m so happy that you & Adam loved my favorite two properties in Costa Rica and trusted me with your well deserved and adventurous Honeymoon.

Vaidehi Hoyer 1 year ago

Fantastic experience: James planned a 10 year anniversary itinerary around Italy for me and my husband and it was fabulous. He is extremely knowledgeable about the country and luxury properties across all regions. He designed an itinerary that was a mixture of must do's and hidden gems. The transfers between cities, train stations and airports were all prearranged, so there was really nothing for us to do but enjoy our trip! We will be using James again for future trips and have already forwarded his info to our friends!

Out & About Holidays
Out & About Holidays

Vaidehi, Thank you for entrusting me with such an important event in your life. It was a pleasure getting to know you through the collaborative planning process :)

Julia Young 1 year ago

Fantastic experience: We were lucky enough to have James plan our honeymoon in Greece and his expertise is priceless! My husband and I had the best time! And, most importantly, we didn't have to worry about any potential logistical issues because we knew James had it all taken care of. His recommendations led us to experience the best services in hospitality. I can't imagine ever tackling another trip again without the help of Out and About Holidays! Thank you, James!

Out & About Holidays
Out & About Holidays

Julia, the feeling is mutual. I loved working with you these past 9 months to put together this Big Fat Greek Honeymoon!

Rachel Norris 1 year ago

Fantastic experience: Don't walk, RUN to have James help with planning your trip!! I was hesitant to use a travel agent for our honeymoon because I like to be in full control of planning, but James went above and beyond what I would have been able to do. Not only does he have excellent taste in hotels and restaurants, but every travel/train/car/connecting detail was thought of and planned out for us. We were welcomed with champagne and room upgrades for every hotel we stayed at throughout our 2-week trip, and James was so helpful when we had flight cancellations. You will not regret it!! Can't wait to use him again.

Out & About Holidays
Out & About Holidays

Hi Rachel,
You and Jacob were an absolute pleasure to work with AND get to know! Your positive attitudes deserved every upgrade and bottle of champagne I surprised you with :)

Jacob Rivers 1 year ago

Fantastic experience: James was an absolutely amazing resource for planning our honeymoon. He listened to our goals and made them happen, additionally when we weren't sure what we wanted he helped steer us in the direction to make some really great choices on our hotels/restaurants. We had free upgrades at every hotel we stayed at, most hotels had welcome bottles of champagne/wine, and we got to stay at hotels we would have never known about without James' experience. We truly had a once in a lifetime trip and it is all thanks to James. Having him as a resource while we were planning our wedding was a life-saver. We will definitely be using Out and About Holidays again and I would highly suggest reaching out to James if you are planning an extended trip of any kind.

Out & About Holidays
Out & About Holidays

Hi Jacob,
I loved collaborating with you and Rachel! Your easy going and light-hearted attitude made it a lot of fun planning your 2 week honeymoon across Italy. Looking forward to the next trip!

Heather Wright 1 year ago

Fantastic experience: James was really really great! He planned the perfect honeymoon to Italy for us. Everything went smoothly- the hotels, transfers and activities he suggested for us were spot on, and he made it easy for us to zip around Italy like pros (even though it was our first time in Europe)! It was a truly magical trip.

Out & About Holidays
Out & About Holidays

Hi Heather,
I’m so happy you had such an unforgettable Honeymoon! Thanks for entrusting me with such an important task. Looking forward to the next one!

Jansen Dahl 2 years ago

Fantastic experience: James helped me plan an Epic Birthday trip to Africa. The trip was incredible- every detail was considered - James even created several "magic moments" on the trip that made it so special, including a Birthday surprise in the savannah of Botswana! Highly recommend James and Out and About Holidays!

Out & About Holidays
Out & About Holidays

Hi Jansen,
Thank You for entrusting me with such an important milestone for you and Kim. I’m glad everything worked out so smoothly across South Africa, Botswana & Zimbabwe!

Jeff Fleitz 2 years ago

Fantastic experience: James set up an amazing Alaskan cruise on Seabourn for us. It was the trip of a lifetime.

Out & About Holidays
Out & About Holidays

Hi Jeff,
Thank You for entrusting me with this important trip with your Wife & Father-in-law! Looking forward to the next one, Neighbor!

Mary Kahn 2 years ago

Fantastic experience: James Lilla opened my eyes to a whole new world!! James helped me plan an EPIC trip for my husband’s 60th Birthday! A novice traveler, I relied on James’s expertise and experience from beginning to end. James charted a 5 city /12 day extravaganza around Italy culminating in Rome to meet up with our daughter who had been studying there during her Spring semester. He crafted the perfect itinerary, and he selected some of the most beautiful venues/hotels I’ve ever seen. From layering in inter-city train travel with amazing tours, to making dinner reservations and adding just the sweetest little surprises at each hotel, James did it all with patience and panache! James is not only an expert in Italy but all over the world! Before we know it we’ll be starting to plan our next trip, this time as a family to Greece and we can hardly wait to see what James has in store for us! Do yourself a favor, life is short, TRAVEL! and do it with James Lilla, founder of Out and About Travel!! Ciao Ciao!! Mary & Jason Kahn ‘23

Out & About Holidays
Out & About Holidays

Hi Mary,
I’m so happy to hear and see how amazing your 2 week trip across Italy was! Looking forward to Greece Summer 2024!

Jacki Block 2 years ago

Fantastic experience: James was incredible in helping my parents plan their trip to Italy. There is no way we could have come up with such a wonderful itinerary on our own. From the transportation to the tours, restaurants, hotels and more, my parents had a trip of a lifetime. Thank you James for making this experience so seamless, easy and enjoyable!

Out & About Holidays
Out & About Holidays

Jacki, it was so fun re-connecting with you and helping your parents plan their dream Italian getaway! Thank you for the referral.

Kate Foster 2 years ago

Fantastic experience: James planned a fabulous 10 day trip to Spain for our family. We’ve never used a travel advisor and now we are spoiled! From the private transfers, to the wonderful accommodations, it was amazing. And when we encountered an issue with our apartment, he immediately responded and helped rectify the situation. Highly recommend!

Out & About Holidays
Out & About Holidays

Hi Kate,
I’m so glad you had such an amazing time in Spain with your family! Thank you for your patience with the Madrid apartment and the amazing feedback in Seville and Toledo! I’m Looking forward to collaborating with you again in the future.

Jennifer Peros 2 years ago

Fantastic experience: James at Out & About Holidays planned an amazing weekend for me and a group of girlfriends in Ischia, Italy. From the moment we stepped into our hotel, everything was first class. We were welcomed by the manger with cocktails, and shown to our (upgraded suite. Thanks, James!) The staff went above and beyond to show us an unforgettable time, by providing us local recommendations, setting up car transfers and making sure we had everything we need at all times. You can tell everyone at the property loves James, which is what you look for in anyone you have planning your trip. I’ll definitely be using Out & About for my next trip!

Out & About Holidays
Out & About Holidays

Hi Jennifer,
Thank you for the wonderful review! I am so glad we were able to get you upgraded into the infinity pool suite. Those sunsets from the private pool are magical!

kristen prior 2 years ago

Fantastic experience: I had the most amazing trip ever because of James. A++ service. Upon arrival to my trip to Italy, I was double upgraded to the most beautiful room all because of James.

Out & About Holidays
Out & About Holidays

Hi KrisTEN,
Thank you for trusting me with your previous vacation time. I knew Marco at San Montano would take care of you

Colleen Fitzgerald 2 years ago

Fantastic experience: James was amazing! Can’t wait to plan our next trip with him again!

Out & About Holidays
Out & About Holidays

Hi Colleen, I’m so glad you and your group of 7 had a memorable journey though Ireland!

Alexander Armonta 2 years ago

Fantastic experience: I’ve always been opposed to using travel planners, however after my experience with James, I’ll never go back to planning my own extended trips again! James worked his magic to ensure we had the most fantastic 2 week trip to the Greek islands- included organizing private cars to hotels from airports/ferry stations, planning out excursions such as private yacht charters, walking tours, cooking classes, and so much more! Additionally, he made sure personal touches were added to our hotel rooms upon our arrival making us feel welcomed and appreciated. Would definitely use him again in the future! 10/10 would recommend!!!

Out & About Holidays
Out & About Holidays

Thank You so much, Alex! Let’s meet up in Greece again next Summer ️

Katherine Penick 2 years ago

Fantastic experience: James created a beautiful vacation for my husband’s 40th. He not only found us a little hidden gem of a vacation spot and the perfect resort- he also had the patience as we continued to change our plans. He takes so much of the worry and stress out of travel planning - and he does it with a great sense of humor and charm. Thank you, James! Can’t wait to work with you again.

Out & About Holidays
Out & About Holidays

Kat, Thank You for trusting me with Royal Sanremo. I hope it was so magical that you and you’re family return for years to come :)

Laurie Siok 2 years ago

Fantastic experience: James is amazing! Planned a trip to Italy for myself and two friends and every detail was taken care of! Was the trip of a lifetime for us all thanks to James!

Out & About Holidays
Out & About Holidays

Hi Laurie,
Thank You for trusting me when I steamed you towards Sorrento & Ischia vs Positano & Capri. I knew you would love it! Looking forward to working with you on the big family trip to Italy next year!

Heidi Esposito 2 years ago

Fantastic experience: James planned our 50th bday adventures through Italy! Every suggestion he made was tailored to my group! He offered the best ideas, planned everything for us & even had sweet surprises in our rooms upon arrival! There was not one single glitch with our travels, right down to the driving arrangements! I will definitely be calling James for my next big adventure! Thanks James!

Out & About Holidays
Out & About Holidays

Hi Heidi, It was such a pleasure collaborating with you over the past few months. I’m so glad you had such an unforgettable trip with your Girls!

Becca Hunt 2 years ago

Fantastic experience: James is exceptional! He helped me plan the most perfect trip. I have nothing but amazing words to say about my experience with James and my trip.

Out & About Holidays
Out & About Holidays

Thank You, Becca! Looking forward to the next one!

Ankoor Bagchi 2 years ago

Fantastic experience: The entire experience with James and Out & About Holidays was excellent. The level of service was impeccable -- it truly felt like we had a personal concierge handling our entire trip from the moment we left home until the day we returned. All of our questions were answered quickly and comprehensively. Beyond the excellent service, the actual trip was amazing. The hotel recommendations were perfect for our needs. James knew the property and made sure we experienced the best of it. Travelling with a toddler is always a challenge, but the location was perfect and the hotel made us feel absolutely pampered. The check-in upgrades were a wonderful treat as well. And the personalized message left was such a nice touch. We're absolutely looking forward to working with you again!

Out & About Holidays
Out & About Holidays

Hi Neighbor,
Thank You for entrusting me with your valuable family time. Looking forward to the next!

Maura McKee 2 years ago

Fantastic experience: James did a fantastic job planning our trip to Barcelona and Seville. We were given great recommendations for dinner, and were at ease with these already being booked for our group.

Out & About Holidays
Out & About Holidays

Hi Maura,
I’m so happy to hear you had such a memorable time in Spain with your equally amazing parents!

Tara McKee 2 years ago

Fantastic experience: Thank you James Lilla for helping us plan an amazing visit to Barcelona and Seville. From hotels, to “must do” suggestions and restaurant recommendations, everything was spectacular and exceeded our expectations. Highly recommend James and Out and About Holidays! Can’t wait to plan our next adventure!

Out & About Holidays
Out & About Holidays

Hi Tara,
Thank you for trusting my advice! I’m so happy you had a fantastic time with your family :) Where to next!?

Rachel Sheridan 2 years ago

Fantastic experience: James helped us plan accommodations for a bachelorette trip to Austin. He found us the perfect hotel with a suite upgrade and made sure that all the girls were taken care of for the weekend. Highly recommend his services!

Out & About Holidays
Out & About Holidays

Hi Rachel,
I’m so happy you had a great time in Austin with Kristen! She’s the best!

Samantha Jones 2 years ago

Fantastic experience: James was wonderful in helping us plan a trip to Austin for a bachelorette party. From booking us the perfect hotel to offering recommendations for food & entertainment - we had the best weekend!

Out & About Holidays
Out & About Holidays

Hi Samantha, I’m so happy you all had the best post-COVID Bachelorette party!

Kristen Egan 2 years ago

Fantastic experience: James helped plan my Bachelorette party in Austin and it was amazing! He hooked us up with great deals on hotels - getting us a credit so we could us it at the spa, breakfast included, and had Champaign waiting on arrival. James helped make sure we had a packed agenda of things to do and places to eat. You are in good hands if you work with James :) We're also planning to have James work with us to plan our honeymoon - so excited!

Out & About Holidays
Out & About Holidays

Hey Neighbor, Thank you for the kind review! I loved being a part of Bachelorette. Don’t mess with Texas

Emily Collins 2 years ago

Fantastic experience: James planned a truly epic 10-year anniversary trip to Italy for my husband and me. My top priority for this trip was for planning to be stress free and James delivered that and more. He took care of every single logistical detail -- from hotels (with upgrades), to dinner reservations, to excursions, to transfers -- making it easy for us to fully enjoy the experience (a true gift!). And when we ran into a weather snag that prevented us from traveling to one of our destinations, James spent 5 hours on a Sunday morning (very early on his end) rebooking us and ensuring the hotel we had to cancel refunded our money. He saved us $650+ AND we were able to get to Tuscany early -- a change that in hindsight, made our trip even better. We can't wait to book our next trip with James.

Out & About Holidays
Out & About Holidays

Hi Emily,
I’m so glad you had an amazing 10th Anniversary in Italy! There is no better thank you than your referrals…. So Thank You

Harley Beck 2 years ago

Fantastic experience: James Lilla is an absolute wonder, he planned a trip to Paris for myself and our daughter. Every detail, communication, excursion and suggestion made for a perfect week. Not only were we greeted with five-star service at S/O Paris, we had a personal note from James awaiting us with champagne. We were given an upgrade in our room, top notch service during our stay and more attention than we deserved. Looking forward to having many more Out & About Holidays. Simply said, look no further, it will be flawless and superb.

Out & About Holidays
Out & About Holidays

Hi Harley, I’m so glad we were able to hook you up at SO/ Paris! I’m looking forward to many more European adventures ‍

Ryan Schermerhorn 2 years ago

Fantastic experience: James was referred to me by a co-worker, and he did a fantastic job of planning our honeymoon (France and Italy). We had an initial meeting to discuss our goals and then James took it from there. He booked our hotels, airport/train transfers, and flights/trains between cities, and then he suggested and booked tours in each of the cities we visited. He was very responsive and easy to work with, and I've already recommended him to friends of ours.

Out & About Holidays
Out & About Holidays

Hi Ryan,
You & Jenna were an absolute delight. Thank you for being so flexible along the way across your 4 destinations.
Also, Thank You for the referrals!

Kara Schrenk 2 years ago

Fantastic experience: My partner and I decided to plan our elopement abroad and by luck I came across Out & About Holidays. James Lilla helped us curate the most amazing two week vacation around Spain. He was attentive to our wants and needs and knew exactly where to guide us. Every single recommendation was perfect. Hotels, restaurants and entertainment was spot on - not a single miss! Not only did he plan the best trip, it also felt like I had a cheerleader in my corner. His energetic and warm personality is amazing to work with. His hotel recommendation for Barcelona ended up making our elopement the success that is was! I can't say enough great things about James professionally and personally.

Out & About Holidays
Out & About Holidays

Kara! I loved being part of this special trip with you and Max. Thank you for entrusting me with your wedding & honeymoon! Can’t wait to plan all the Anniversary trips :)

Gregory Franks 2 years ago

Fantastic experience: James is a professional !! This is why WE ALL use him with our travel planning and travel requirements. He is there to take care "of things, to organize things" we don't realize or have no idea of... That is why James does what he does - for all of us, and for ME. And dealing with James gives me peace of mind, so I can do my thing...

Out & About Holidays
Out & About Holidays

Gregory, It has been such a pleasure getting to know you. One of my favorite things about this business is the new people I meet! Thank you for the kind review

Joe Wojewodzic 2 years ago

Fantastic experience: Planned a trip to Paris and Amsterdam this fall. James was great to work with, put together an epic adventure, highly recommend his services.

Out & About Holidays
Out & About Holidays

Thank You, Joe! It has been amazing collaborating with you guys on two trips in 3 months. Where to next!?

Caitlin Brazda 2 years ago

Fantastic experience: James was so helpful for planning our family Christmas vacation in Bahamas. He made it so easy, was very knowledgeable about our resort, and was quick to respond to questions. I will DEFINITELY be using him in the future.

Out & About Holidays
Out & About Holidays

Thank You, Caitlin! It’s been a lot of fun re-connecting with you and your entire family :)

Heather Kettler 2 years ago

Fantastic experience: James was amazing to work with - very attentive to all our details even when we wanted to change things. He always responded in a timely manner and made good suggestions.

Out & About Holidays
Out & About Holidays

Thank You for the kind review, Heather! I enjoyed working with you and the entire clan of 12 to make a memorable Christmas & birthday celebration in the Bahamas!

Linda Konop 2 years ago

Fantastic experience: James is amazing! I highly recommend using him to plan your next vacation. Because of him we got a double upgrade on our room. He thinks of everything including the nicest welcome note which was the perfect way to start our stay!

Out & About Holidays
Out & About Holidays

Linda! I’m so happy you and your Mother had such a memorable experience at the Ritz Sarasota!

Jessica O'Beirne 2 years ago

Fantastic experience: Spectacular! We had the most relaxing, fun, worry-free vacation of our lives. Not only was our three-country vacation incredible, but James delivered by anticipating our needs like a mind reader.

Out & About Holidays
Out & About Holidays

Jessica, it was so fun collaborating on my first Scotland and England Castle road trip! Where to next?

Kelley Nicholson 3 years ago

Fantastic experience: Could not say enough wonderful things about James - you need him to help you plan the best trip ever!! He’s so communicative and really strives to get you exactly what you want. I’ll be planning all future vacations with him!

Out & About Holidays
Out & About Holidays

Kelley- I loved getting to know you and Ryan. Your trip to Monaco & Amalfi Coast was epic! I’m looking forward to collaborating on your next trip.

Anita Johnson 3 years ago

Fantastic experience: James was absolutely incredible in planning my long delayed Eurotrip! My guy and I did 5 cities across 4 countries, James helped us navigate entry requirements, accessible areas for my guy, transportation and finding the perfect location for accommodations. This trip will remain unforgettable for the both of us. Can’t wait for the next adventure with James’ guidance!

Out & About Holidays
Out & About Holidays

Anita- how fun we got to meet up in London! Where you going next!?

Brian Thompson 3 years ago

Fantastic experience: James is my go to for travel advice!

Out & About Holidays
Out & About Holidays

Thanks, Brian! Tell your friends!

John Rogers 3 years ago

Fantastic experience: GREAT planning, attention to detail, and booking of resort and amenities and Mexico. Flawless execution!

Out & About Holidays
Out & About Holidays

Thank You, John! I’m so happy this amazing group trip worked out so well. Cheers to PSG’s 2023 Trip!

Nic Prenger 3 years ago

Fantastic experience: James is incredible, and he was a total godsend helping us organize this trip to Mexico. He is one of the most upbeat, positive, knowledgeable and fun people I have ever met. Every single thing was taken care of. We didn't have to worry about anything - even a last minute flight changes didn't phase him - he worked with the resort and arranged private transfers and got everything squared away. I will never plan another trip without James. He's the best. THE BEST!

Out & About Holidays
Out & About Holidays

Thank You, Nic and Prenger Solutions Group. Cheers to us for pulling off this much deserved trip in the middle of Omicron!

R I 3 years ago

Fantastic experience: James is essential for all travel. He is so detail-oriented and has opened my eyes to the amazing travel advantages and hotel perks of working with a travel professional. He saves me time and a lot of headaches. It's a 1st class experience that starts before you even start packing!

Out & About Holidays
Out & About Holidays

Thank You, Rebecca! From Chicago to Dublin to Glasgow to Edinburgh, it’s always a pleasure connecting with you!

Lisette Martinez 3 years ago

Fantastic experience: We cannot thank James enough for planning a perfect getaway for our first wedding anniversary in Tulum, Mexico! We had some unforeseen circumstances with the first reservation we had, but James quickly came to the rescue and found us something even better! He was always so responsive and provided awesome suggestions for dinner reservations, beach clubs, and activities which made our trip even more special. We will be booking future trips through James moving forward! We highly recommend working with him!

Out & About Holidays
Out & About Holidays

Lisette, I am so happy this trip worked out so well for you! It’s not everyday a hotel shuts down the day before your week-long stay. I’m glad we were able to pivot the night before, even while I was in Spain, to make this a special Anniversary!

Shaun Hawley 3 years ago

Fantastic experience: Working with James was a breath of fresh air - so professional, knowledgeable, he went above and beyond to ensure our entire vacation was stress free - during Covid. The hotel he booked was amazing. Also if we needed anything he was always so responsive and had answers to all our questions. I can’t recommend Out and About enough - save yourself the stress and have James book your next vacation.

Out & About Holidays
Out & About Holidays

Hi Shaun, It was so fun re-connecting with you on your Mexico trip. Can’t wait to see what Jamaica has in store!

rhinowills 3 years ago

Fantastic experience: James organised a fantastic holiday in Mexico from my wife, he made the whole experience so easy. From recommending a fantastic hotel (the best all inclusive I have been to) through to transfers and booking an amazing restaurant. He was so professional and answered all the questions we had.

Out & About Holidays
Out & About Holidays

Hi Will,
Thank You for the glowing review! Thank You two for trusting me with your beach vacations to Riviera Maya and Montego Bay!

Nick & Alicia Scafiezzo 3 years ago

Fantastic experience: Everything you need in planning your vacation... James was THERE! We planned a family trip to Hawaii for Thanksgiving. I called James with pretty specific needs and he went above and BEYOND for us! We were so happy with the resort we were at and the villa's we rented. We had four children under the age of 8 and it was perfect! Every step of the way James was there to help us out!! Next trip and every single trip in the future - we will be calling James!

Out & About Holidays
Out & About Holidays

I’m so happy the Villas worked out for your extended family over Thanksgiving. Good thing we booked early because we got quite the deal for Maui!

Janelle Fox Herbert 3 years ago

Fantastic experience: We loved working with James to book our anniversary trip to the Amalfi Coast! He provided us with the most amazing recommendations! We loved how educated he was about the area and we really appreciated his knowledge around COVID protocols and restrictions. He was very in tune with our travel style and was always supportive of our preferences to make sure we had our perfect trip of a lifetime. He is a true professional and so fun to work with!

Out & About Holidays
Out & About Holidays

It was such a pleasure to re-connect with you Janelle! I can’t wait to send more clients to Ischia. Thanks for putting that on my radar!

Rebecca Davidson 3 years ago

Fantastic experience: I worked with James to plan a trip to Mexico City with friends and he was absolutely amazing to work with! He was so attentive, honest and easy to communicate with. It was like planning a trip with a good friend who also knows the best spots in town! I would 100% recommend using James for all travel going forward. He is so professional yet easy to work with, always available any time of day or night for any needs!!! I couldn’t recommend enough and can’t wait to plan my next trip!

Out & About Holidays
Out & About Holidays

Thank You, Rebecca, The feeling’s mutual! It was so fun planning this group’s trip for 8 to Mexico City. Can’t wait to meet in person!

Steven Young 3 years ago

Fantastic experience: James took all the stress away from planning! His attention to detail and hotel options were great. We had a large trip planned for Paris, Nice, Sorrento ,Rome, Siena, Zurich, Crete, Santorini and London! I highly recommend James as a travel advisor.

Out & About Holidays
Out & About Holidays

Steven, It’s been so fun getting to know you and Justine over the past two months! I can’t wait to collaborate on the next trip this winter!!!

Brandon Mapes 3 years ago

Fantastic experience: James was fantastic when booking our first trip abroad in 2 years. My wife discussed what we were looking for over the phone, and James suggested Nobu in Cabo San Lucas for its excellent food/drinks with a relaxing atmosphere. He was also able to get us daily breakfast and spa stipends. We look forward to working with James again!

Out & About Holidays
Out & About Holidays

Brandon, Thank you for the kind review! I’m Glad everything worked out perfectly at Nobu Cabo. Can’t wait to get working on Croatia 2022!

Rochelle Albert 4 years ago

Fantastic experience: I can’t recommend James enough! He planned an amazing trip for my family to France with a very short lead time. We loved the hotels he picked for us, the excursions and meal recommendations. We definitely benefited from upgrades and VIP treatment by working with James. He is already planning another vacation for us to Croatia. We now understand why it makes sense to use a travel advisor and will use James for all of our future travel!

Out & About Holidays
Out & About Holidays

Rochelle, It was so fun re-connecting with you here and seeing you have such an amazing time in Paris with your entire family! Loved being able to pull some strings and hook you up with daily breakfast and resort credits, too!

Christine Chun 4 years ago

Fantastic experience: I’ve worked with James more than once and find him to be extremely resourceful and knowledgeable. I used to book my own travel, but time is also money, so he’s my guy now. Thank you James!

Out & About Holidays
Out & About Holidays

Thank You! The Villa we secured in Palm Springs was AMAZING!

Elizabeth Fiorile 4 years ago

Fantastic experience: James was SO helpful with planning our trip to Tulum...recommendations, bookings, organization - all of it! It was especially nice to have our cars pre-arranged between the airport and hotels. He also was able to get us an upgrade to a beautiful ocean front room for our last night in Cancun!

Out & About Holidays
Out & About Holidays

Elizabeth, I’m so happy I was able to hook you up at the Ritz Cancun with the free upgrade!

Jessica Lin Leon 4 years ago

Fantastic experience: If you are looking for someone you can trust and guide you on a trip whether it is domestic or international Out and About Holidays with James is your go to! In fact, I am never planning a major trip without the delightful James! James was very patient and detailed, especially during traveling with COVID he made going to Mexico so easy. Our group was worried about all the regulations and changing rules and James took the lead to make sure we would be safe and stress free. The most important thing is that when James is planning your trip it is almost as it is him traveling so you feel you are getting all needs met. I highly recommend getting James as your travel advisor it will make your life easy and planning more fun! Plus, he has a vast knowledge of travel so you get a great deal and recommendations.

Out & About Holidays
Out & About Holidays

Thank You so much, Jessica! I’m so happy to hear how amazing your trip was! Can’t wait til we plan your European getaway!

Mike Canzolino 4 years ago

Fantastic experience: The extra perks I receive from going through James for my vacation planning and the incredible deals have made me a lifetime client!

Out & About Holidays
Out & About Holidays

Thank You, Mike! I’m
Glad I was able to get your entire family such a deal in Napa this September!

Adrienne Pankey 4 years ago

Fantastic experience: I'm never planning a vacation without James again! Who knew you could get WAY better deals and stress less while planning a vacation? I didn't... and I'll never go back. For starters, James is an overall delight AND he works his butt off to ensure you're getting what you want. He'll help you with as much or as little as needed and get you the deals you deserve along the way. With my recent girls trip to Maui - he saved us a significant amount on the villa we'd been looking at and provided amazing recommendations for activities and restaurants we took advantage of! Do yourself a favor and work with James the next time you're looking to travel! I know I'll be back (hopefully sooner than later!)

Out & About Holidays
Out & About Holidays

Thank You, Adrienne! It always a delight partnering up with you... and I loved saving you $1000 off the Resorts best direct rate!

Lauren Sehy 4 years ago

Fantastic experience: I had a great experience working with James - he was able to get us an incredible deal and we enjoyed the amazing service. Will be back for next time!

Out & About Holidays
Out & About Holidays

Thank You, Lauren! I loved hearing about your VIP treatment and perks @ Andaz Maui!

John Kinnemann 4 years ago

Fantastic experience: James takes all the stress away from planning our trips and helps create a wonderful travel experience. I greatly appreciate his communication throughout the entire planning process and his attention to detail. Highly recommend James for all travel needs.

Out & About Holidays
Out & About Holidays

You’re the best! Juan loves tacos!!!

Meghann Kettler 4 years ago

Fantastic experience: Travel Advisors hook it up so nice! James got us several great deals on our European vacation! Things like free breakfast daily, a $100 hotel credit, and we stayed in the most stunning hotels! We were treated like VIPs every step of the way. You’ll save so much time using a travel guru to do all the hard work for you. Highly recommend!

Out & About Holidays
Out & About Holidays

Meghann, we can’t wait to partner with you and your group for your Portugal- Spain Summer 2021 trip!

Mark Whitt 4 years ago

Fantastic experience: James has planned all of our trips the past few years and it’s always a great time because I just have to show up! I’m really looking forward to his help in planning my epic (delayed due to Covid) bday trip in mid-2021! I highly recommend James for all your travel needs!

Out & About Holidays
Out & About Holidays

Thank You, Mark! We are looking forward to curating your 40th Birthday fiesta in Mexico

Steve L 4 years ago

Fantastic experience: Very responsive. Easy to work with. Professional and very knowledgeable.

Out & About Holidays
Out & About Holidays

Thank You, Steve! I’m looking forward to sending you to Jamaica in a few weeks . YEAH MAHN!

Timothy L 4 years ago

Fantastic experience: I don’t know how he got me a better price in Mexico than the big travel websites. Plus free airport transfers.

Out & About Holidays
Out & About Holidays

Tim, we appreciate your business and kind review! If only everyone knew the $ and perks Travel Advisors provide

Madeline Fox 4 years ago

Fantastic experience: Working with James to plan our first vacation away from our baby was an absolute delight. He not only was knowledgeable about every facet of the industry, he brought a sense of excitement and passion in planning our itinerary that was felt through every suggestion and reservation he booked. I am so incredibly grateful for his expertise and cannot wait for him to help us plan our next adventure. Thank you Out & About Holidays for being so amazingly good at what you, and with all of your help planning this busy mama's perfect getaway!!!

Out & About Holidays
Out & About Holidays

Thank You, Maddie & Matt! It was so much fun researching Sedona for your Birthday weekend and I’m so happy you enjoyed the surprises. I’m already on to researching some ideas for Greece 2021!

Shannon Y 5 years ago

Fantastic experience: James planned the most memorable trip of my life to Greece. I cannot wait to go back for a repeat

Heather Sullivan 5 years ago

Fantastic experience: I love to plan my own trips but, given James expertise with Greece, I put it all in his hands and I'm so glad I did! It was the trip of a lifetime for my friends and I. The highlight was definitely the chartered yacht!! Heaven! Can't wait to have James plan my next trip!

Out & About Holidays
Out & About Holidays

Heather, I’m so glad we got you to Greece in 2019! We have to get you to Crete for your 2021 return!

Jessica Jordan 5 years ago

Fantastic experience: James is simply the best! I receive five star service every guest experience, I am very impatient and James provides a zen-like attitude with rapid speed quotes. He’s great at following up, and ensuring I am happy with all of my high maintenance requests. One example, I have several dietary restrictions and he contacted the venue to communicate my concerns, and made sure there were plenty of options on the menu, as well as ensured they were able to customize if needed. I also enjoy how James keeps in touch with me and has become more than a trusted advisor, but also like an extension to my family. I highly recommend Out & About Holidays for your next excursion!

Out & About Holidays
Out & About Holidays

Jessica, thank you for the amazing review and your continued referrals. You’re such a loyal friend and client! France 2021!!!!

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