Self Driving Road Trip Itinerary Consultant

Shoutout to our amazing travel agent Sherry and the unforgettable vacation she planned for us! From the very first conversation, she took the time to create multiple options for vacations that worked within our timeframe and budget. We actually chose a cruise she recommended that wasn’t even on our radar. Every detail was thoughtfully arranged—from the flights, accommodations before the cruise, and transportation to and from. What could have been a stressful planning process became completely effortless thanks to her expertise, organization, and genuine care. We were able to relax, enjoy every moment, and make memories without worrying about a thing. Her professionalism, attention to detail, and dedication to creating the perfect vacation truly sets her apart. This trip exceeded all of our expectations, and we are so grateful for the care and passion that went into planning it. If you’re looking for someone who can turn your travel dreams into a seamless, stress-free, and extraordinary reality, we highly recommend Sherry. Thank you for giving us the vacation we needed—we’re already looking forward to our next adventure with you!

From start to finish, Sherry helped me with everything. Everything was easy to navigate, I felt completely informed every step of the way and the best part of our travel experience was the VIP service as soon as we stepped off the plane. My friends plan to use her in the future as well as us with our next adventure!

This cruise was fun. The weather was way colder than expected. I like the magnet on our door was cool for the home is where the murder is. That was a great show to watch in person. We had several issues with our flights so that was frustrating.

We had a group of 10/9 for a 13 day vacation in Europe. A week in Italy and then a cruise. We took planes, trains, autos, busses and boats on this trip. There were all sorts of last minute curveballs that would have been an absolute disaster without her. Knowing our family could reach out DURING the trip to help with last minute changes relieved a lot of stress. My next vacation will definitely booked through her.

Sherry Chesley has organized and designed multiple large trips for our family over the last decade. She has identified wonderful places to stay, eat (both casual and more upscale), and explore. This trip was no different. We asked her to help us find a cruise around Italy and to plan for several days before and after the cruise to explore the local culture. She found us a fantastic 11-day cruise from Rome to Venice. The cruise included amazing stops and excursions in Florence, Pisa, Portofino, the Amalfi Coast, Sicily, several stops in beautiful historical coastal villages in Croatia and Montenegro, and finally in Venice. We could never have seen so many places and enjoyed ourselves without the expert assistance, guidance and overall regional knowledge that we received from Sherry. Sherry is a travel pro's pro.

My family just got back from a trip to Canada to see Niagara Falls. I wasn’t sure where to start with planning, so I reached out to Sherry. She has helped me plan numerous vacations in the past, from cruises to weekend trips. Sherry always recommends the best places to stay and to visit, and has insight that helps us make the best out of the trip. We had a great time and everything went smoothly thanks to Sherry. Any time I plan on traveling- near or far- I always reach out!

Sherry Chelsea did an incredible job of helping us to plan our trip to Tuscany. Nothing was left to chance and we traveled worry free. We knew Sherry had taken care of every detail. We couldn’t have asked for better service.

Diamond Club booked has its perks. The resort staff were kind and friendly for the most part. Let’s be real. Customer service is hard work. Grateful we were located on the 5th floor, building 6 overlooking the ocean where were able to witness lovely sunrises and sunsets. The highlight of our trip was seeing the baby sand sharks in the shallow waters. In the mornings we could see other small fish along with stingrays(mostly in the early morning from our balcony). Our room was clean and maintained by housekeeping. I will say this. As Diamond Club members, we did not receive resort robes for our stay nor did we receive our complimentary beach bag. We did receive slippers. We received the complimentary wine and champagne. Mini refrigerator was full. Some snacks were replenished once we asked. Our butlers, Andre and Monique were attentive and made reservations at the restaurants(5) five to be exact on our behalf. They checked on us often throughout the day and left messages o

Great experience from planning to excursions! This was a trip canceled in 2020 so when it came to planning over again, we wanted to make sure we were taking advantage of everything possible to make it a trip of a lifetime. Sherry understood what we wanted and was great about directing us to additional excursions outside of what was offered on board. When we had a couple weather issues necessitating changes to excursions mid trip, we reached out and she was able to get the changes made seamlessly. We never felt we had to wing it, and appreciated the hand holding when we needed it! Great small ship cruising experience we hope to repeat next year!

Sherry was unbelievable to work with. No request or question went unanswered and they were always immediately done with a positive, informative and friendly response. She is extremely knowledgeable and I would highly recommend her as I can only refer her with supreme accolades.

I found Sherry online and from our first email interaction I knew I wanted to work with her! She asked about our wants and needs, and also things we weren’t interested in so that she knew what to stay away from. Based on our conversation, she quickly provided us with three possible options that might suit us, but in a very no-pressure way. We then had a virtual meeting to really discuss details and for us to ask the hundred questions we had come up with over the previous couple of weeks! She was super friendly and attentive, as well as patient. We have a camper and we take 4-6 camping trips per year, but we hardly ever fly and it had been over a decade since we had traveled internationally. Needless to say we had many questions! After our virtual meeting, over the course of the next 10 months between then and our April 2025 trip, there were many emails exchanged. Any time I thought of a random question, I would email Sherry and she always responded quickly! She never made me feel like

I've always wanted to go to Patagonia but was intimidated by planning such a big trip in an area I'd never been so I kept putting it off. I contacted Sherry and she immediately got me into a tour group and helped with all the planning. She was available through the whole process to answer all my questions and it gave me so much peace of mind to know she was there behind the scenes if I needed anything.

Sherry helped us build the perfect trip and assisted me plan a lot of our trip details. Reminded us prior to trip to not forget the small pretrip details, and helped us stay organized and prepared throughout. Was available around the clock to answer my crazy questions, and always quick to reply. I appreciated her help and had a trip filled with so many wonderful memories. Thank you Sherry!

Sherry helped me with several trips over the past few years for my son and I. Our latest trip was a cruise out of New Orleans. Sherry was actually on a trip of her own the week prior to ours and when I found out we had a major storm scheduled to hit the night before our flight I was concerned we would not be able to get out of Boston. Sherry calmed my fears and helped me get into New Orleans a day early with a hotel, etc. Even though she was away, she was still available to help me. Sherry has helped me make memories with my son for a couple of years now and I will continue to have her help me in the future. I recommend her to everyone!!

Absolutely amazing experience—truly life-changing! I can’t thank Sherry enough for making my wife’s 40th birthday so special. She went above and beyond to create an unforgettable event, and we are beyond grateful. Highly recommend!”

Great 3 generation trip to Puerto Rico. Accommodations were amazing and the resort had everything from golf to its own water park and beach. We got off to a late start planning for this Christmas week trip so it took weeks to find family friendly accommodations but Sherry never gave up!

Sherry was excellent to deal with. Great listening a few texts , calls and boom done. Everything she planned worked out wonderful. The app she provided worked great and was a nice addition to our multi stop trip. It was convenient to have everything one click away including train tickets and plane tickets. She took the stress out of international travel. We highly recommend her.

Sherry is amazing. I let her know I am thinking of a trip, not sure what I want to do, but something fun with my son (he is 10) and she always sends me multiple options. Our most recent trip was to Aruba. She took care of transfers to and from the airport, hotel, excursions, the works. I even received a call from her one morning because the ride to one of our excursions was running late and she did not want me to worry. I have our next trip already scheduled and she is working on helping me with solo trips as well. I recommend her to everyone!

She's awesome always answering my question

Sherry was supremely easy to work with! From the moment we reached out to her with some thoughts on where & when we'd like to travel, through booking all the pieces, juggling last minute changes (SO THANKFUL Sherry took care of that for us!) and until after we returned home, she was reachable, knowledgeable and honest. We never questioned that her goal was to plan the best vacation for our family, one that would make all ages happy! Our three teens (and Mom & Dad) loved cruising the Mexican Riviera and we were able to relax and enjoy ourselves thanks to Sherry's detailed planning!

Sherry was amazing. Answered all my questions exceptionally fast. She put together a wonderful schedule and had all our tickets prebooked. The app she uses was user friendly and all our trip details were right at our fingertips. It also had a great message feature that keep us in contact with her the entire time, which allowed her to handle a small issue we ran into very fast and professionally. We will definitely be using her to plan more trips in the future. Highly Recommended!

Sherry was incredible from start to finish. She's extremely responsive, professional, and lucky for us...flexible as our plans changed a lot during the planning process. Sherry remained nimble, helpful, and patient every step of the way and was an absolute pleasure to work with. I highly recommend her!!

My daughter decided to study abroad in South Africa and so we decided to go visit her while she was there. I knew when we planned the trip that I would need help and a friend had recommended a different travel agent. I quickly learnt that not all travel agents are the same. I found Sherry online after only a few interactions with the other agent. Within a few days of talking to Sherry, I had a full presentation of places to stay, choices of flights and a list of excursions. We did every excursion that was on Sherry's presentation and they were all fantastic. If I had a question, both before and during our trip, Sherry always got back to us so quickly. We stayed at three different hotels and they were all great. The people in South Africa were so friendly. I would highly recommend a trip to South Africa and I would highly recommend working with Sherry to book it. I can't say enough great things about Sherry and how great it was to work with her on our trip!

Sherry was easy to work with. I didnt know where or what I wanted. She asked some pointed questions and sent me some suggestions. We made a quick choice. She got right to work on excusions on the island for us. There was never and pressure to do or spend. She helps us create the perfect balance of adventure and relaxation. It was out first time to the islands, to an all-inclusive and oit od the country. She answered all our questions. The app she used was perfect for keeping us on track!

Sherry's expertise and knowledge helped us tremendously to plan all aspects of a two week UK and Ireland driving tour. She helped identify excellent places to stay (including a castle), eat (many great local restaurants and pubs), and visit (palaces, castles, distinct landmarks and fun local places of interest). This is our second trip that she's helped to plan. Her experience, work effort, and resources are second to none!

Sherry made things very easy for me and had a great itinerary to follow and suggestions on where to go and eat if wanted.

Very professional and easy coordination

Sherry did a phenomenal job at planning our family vacation! She quickly and thoroughly reviewed options for us across various locations. Sherry is a true professional. We have already used her for our next trip, and will continue to use her for our future travel plans!

Sherry is the best. Helped me plan an amazing vacation that I wish I was still on.

Sherry is great. Always available to answer questions. Thank you for a great trip

Sherry was so easy to work with. No matter when I reached out with my crazy questions or change in plans she responded immediately!

Sherry works hard to build us vacations of a lifetime. We like to immerse ourselves in the culture and let it take us where the wind blows, rather than have a planned itinerary. Sherry understands our travel style so well, always finding niche offerings & out of the ordinary experiences that we really enjoy. Traveling at the height of Covid presented all of us with unique challenges and restrictions, but Sherry made it her mission to send us off completely prepared and with good understanding of the rapidly changing rules.. I have recommended her to everyone I know and would never use anyone else. Her enthusiasm and willingness to go the extra mile make it truly a pleasure. Thank you, Sherry.

She’s amazing!!

Sherry is by far the best at what she does, our group in all honesty caused so many headaches for her with plans changing/extreme circumstances… and she STILL came through 100% all the way. Do yourself a favor and use Sherry!

Fast, Professional, and Amazing. Couldn't not have gotten better service any where else. Will book with her every time for now on.

Working with Mrs. Chesley was an absolute pleasure. She is knowledgeable and knew exactly what we wanted and accomplished it 100000000%.

Sherry was extremely helpful throughout the whole process from initial planning to dealing with crisis at 11pm when our 6am flight was canceled.

I wanted to surprise my wife but didn't know where to start. So I went to google and found Sherry. She was easy to talk to and very helpful with ideas for a weekend getaway. I didn't have to do a thing. And we had a great time. I will contact her for our family reunion plans in the future.

Sherry went over and beyond

Sherry has been a pleasure to work with. We have already started working with her on our next adventure. She is very thorough and explained all our options. She was able to get us an awesome vacation at a great price. Highly recommend her to anyone looking for help planning their next vacation

She is absolutely amazing

This past year we decided to use a referral for an experienced travel agent/person to help us in planning a trip to Disney with the family that has never been. (five of us)
Sherry went above and beyond what we expected. She took care of everything and anything. Left us with only planning what clothing items we would bring on the trip. I never realized how easy she could actually make things happen. I would rely on her expertise no matter where or when we are planning a trip. I have also happily referred her to others.

Gold Standard Service, Sherry helped us out with every aspect of our travel planning. Zero hiccups, we are definitely going through Sherry for our next trip.