Self Driving Road Trip Itinerary Consultant

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Sherry Chesley, Travel Agent in Kingston, NH

Sherry Chesley

Kingston, NH Travel Agent
Super Agent

Sherry Chesley

Kingston, NH · 5 Years of Experience

Adventure Travel And Cruising, an independent agent with Cruises & Tours, Unlimited, a Travel Leaders Network Affiliate Agency
5.0
(46)
100% Recommended
Sherry is amazing. She is personable, down to earth, laid back, but can definitely take care of business! She planned our honeymoon from just a n... Read More >
About
Reviews
Certificates & Awards
My Places
Itineraries
Client Testimonials

Areas of expertise

Destinations:

USA, Alaska, Hawaii

Interests:

Family Vacations

About Me

London, Scotland & Ireland Self Drive Itinerary
London, Scotland & Ireland Self Drive Itinerary

Looking to travel a destination at your own pace by car? Whether you're looking to take your trip within the US or internationally, I am here to help. Each road trip itinerary is prepared specifically for you and your interests. We will work together to get you the perfect itinerary for you. All of your accommodations will be booked ahead of time so no looking for vacant hotels, all activities that can be booked ahead of time will be booked and entered into your itinerary, restaurant recommendations will be included as well. You will also get a link to an app with your itinerary all layed out for you as well as a printed copy in case there are times when cell service isn't available. Want more information or samples of my self drive itinerary? Contact me today! 

REVIEWS

Rating: 5.0
46 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 46 reviews

Bermuda Honeymoon
Reviewed By Sd129905 - Zanesville Ohio | Traveled to Bermuda ~ Caribbean
Sherry is amazing. She is personable, down to earth, laid back, but can definitely take care of business! She planned our honeymoon from just a n are bones statement of
" we need to plan our honeymoon." She helped us pick a cruise vs resort, where we could go without passports, etc. She helped with documents, papers, and making sure we knew what we needed to do. We couldn't have done it without Sherry!1
Sherry Chesley responded
"Thank you so much! I am so happy you enjoyed your honeymoon and it was an absolute pleasure to work with you! I look forward to helping with those anniversary destinations! "
I would recommend this agent to my family and friends.
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Sherry saved my Honeymoon!
Reviewed By Alyssa M - Kingston, NH | Traveled to Puerto Rico ~ USA
Sherry is on top of everything! Sherry planned our honeymoon (and rescheduled due to flight cancellations), she was patient with me while I was freaking out, responded quickly and was able to answer every question we had. Since then, I go to Sherry for even the littlest things like booking a hotel room and future vacation ideas.
Sherry Chesley responded
"Thank you Alyssa! I'm so glad you enjoyed your honeymoon in Puerto Rico and I look forward to helping with all of your future travel plans! "
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
A Stunning City with Amazing Friends
Reviewed By On The Move - Amesbury, MA | Traveled to Paris | France | Europe
My friends and I enjoyed a fabulous week in Paris. Sherry's meticulous planning and thoughtful suggestions made our stay seamless. There was enough structure to ensure we saw what we came to see and enough down time to enjoy the things we discovered along the way. Sherry was patient and professional through the planning process, coordinating the wants and needs of five independent ladies. I highly recommend her!
Sherry Chesley responded
"Thank you Cindy, i'm so glad you had an amazing vacation and you were all an absolute pleasure to work with. "
I would recommend this agent to my family and friends.
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Amazing, stress-free vacation!
Reviewed By Chris & Lynn - Kingston, NH | Traveled to Caribbean Sea | At Sea | At Sea
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!
Sherry Chesley responded
"Welcome home and thank you so much for these amazing words. It was an absolute pleasure working with you and I look forward to helping you make many memories together in the future. "
I would recommend this agent to my family and friends.
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Best vacation we've had so far!
Reviewed By RachnKen - Negril | Traveled to Jamaica | Caribbean
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!
Sherry Chesley responded
"Love this Rach! So glad you had an amazing time! I look forward to helping with your next adventures :)"
I would recommend this agent to my family and friends.
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Certifications & Awards

The Book with Confidence logo tells you that this Travel Advisor has direct access to comprehensive resources for safe and healthy travel, available at their discretion for sharing with clients.  This includes vetting the details on the health and safety protocols implemented by each travel provider in order to recommend the ideal itinerary for each client’s unique needs.
Trusted Travel Advisor: A Trusted Travel Advisor credentials, resources and global connections translates to today’s consumer in respectful interactions, confidentiality, knowledge, and client advocacy of travel services provided in parallel with building long lasting client relationships that builds with each interaction.  A Trusted Travel Advisor knows their client better than the client may know themselves and puts those polishing touches on each travel collaboration.

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.

Client Testimonials

Italy Trip of a Lifetime
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.
Jameson P., Stratham New Hampshire
Multi-Generation Family Vacation Success!
Sherry booked an amazing multi-generation family vacation for us! Our ideas probably changed 100 times as we began planning: Would we go on a cruise? Stay at an all-inclusive resort? Rent a house? Sherry was always willing to answer questions, give experienced advice on each option and send us pricing packages... and never seemed frustrated as we kept changing paths We ended up pleasing everyone in our extended family of 9 with a day at Disney, a day at Universal and a beach house rental (plus flight, car rental, hotel...) Sherry got everything set up and booked for us, including travel insurance, and followed up on any further questions we had. Before we left, she presented us with personalized folders of our travel documents and reminded us of her availability if we needed anything during our trip. We had the best time, and it was exactly what we all needed/wanted! I whole-heartedly recommend working with Sherry for all your vacation needs: I know I will!
Sara Graham
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