Jess Dorsey, Travel Agent in Longwood, FL

Jess Dorsey

Longwood, FL Travel Agent

Jess Dorsey

Longwood, FL · 8 Years of Experience

Jess.Travel, a Travel Leaders Network Affiliate Agency
5.0
(12)
100% Recommended
Jess is our go to travel agent. We work so hard to travel along with the family, that we hardly have any time to plan.... Read More >
About
My Travel Specialties
Reviews
Certificates & Awards
My Places
Travel Stories & Media
Client Testimonials

Areas of expertise

Destinations:

Belgium, Spain, At Sea, Canada, Hawaii

Interests:

Adult Only, Bespoke Travel, Family Vacations, Cruises, Hiking & Backpacking

Suppliers:

Classic Vacations, Pleasant Holidays, Project Expedition, Virgin Voyages, G Adventures

About Me

Multicity Custom Travel for Independent Thinkers

Most travelers can book one city. Very few can design five cities across two countries without wasting time, money, or sanity. That’s my jam. I specialize in fully custom multicity itineraries with layered logistics that actually flow. Coordinated transfers. Smart routing. Strategic hotel choices. Private guides when they matter. Local experiences that don’t feel staged. Spain to Italy. Greece to Japan. Canada to Florida. Luxury, active, cultural, family-focused, adult-only. We build it around how you travel, not how a supplier wants to sell it. No cookie-cutter tours. No “hope this connection works” train jumps. No copy-and-paste itineraries. Just clean, thoughtful, well-built travel plans that feel easy once you’re on the ground. If you’re the kind of traveler who likes flexibility, personality, and smart spending instead of being herded around with a flag… we’ll get along. Start by emailing me. I’ll help you turn it into something that actually makes sense.

My Travel Specialties

Custom, Personal Travel Planner

Custom, Personal Travel Planner
I’m Jess, a travel-obsessed CRNA, mom of two, and the kind of person who actually enjoys travel planning. Years ago, I started crafting custom trips for friends and family, turning their “I just want a fun vacation” into “Wow, that was perfect.” Before I knew it, I was running a trave...Read More ▶

Banff-Jasper British Columbia Alberta Canada

Banff-Jasper British Columbia Alberta Canada
I'm an expert travel planner for epic Canadian Rockies National Park road trips. See below for info on my own personal trip, last Summer.  Calgary: The Starting Point I kicked off in Calgary with a visit to the Calgary Tower for panoramic views of the city and the Rockies....Read More ▶

Spain's Basque Country

Spain's Basque Country
The Basque Country in northern Spain was an unforgettable 10-day journey, blending rich culture, stunning landscapes, and the most delicious food I’ve ever had! From cities to quaint coastal towns, I discovered a world within Spain that was completely its own. Days 1-2: Bilbao and ...Read More ▶

Virgin Voyages: Cruises that don't suck

Virgin Voyages: Cruises that don't suck
Why This Cruise Expert is Obsessed with Virgin Voyages (And Why You Should Be Too) Look, if you're expecting towel animals and endless buffet lines, honey, this isn't your ship. But if you're ready for the sexiest week at sea that'll make you forget everything you thought you knew about cr...Read More ▶

Belgium Winter Holiday

Belgium Winter Holiday
Spending Christmas in Belgium was a dream come true for our family. From the moment we touched down in Brussels, the festive atmosphere was infectious. Each day brought new surprises and gorgeous sights. If you’ve ever thought about visiting Belgium during the holidays, here’s our week-long itine...Read More ▶

Personal, Custom Travel Planner

Personal, Custom Travel Planner
I’m Jess—a travel-obsessed CRNA, mom of two, and the kind of person who actually enjoys planning. Years ago, I started crafting custom trips for friends and family, turning their “I just want a fun vacation” into “Wow, that was perfect.”Before I knew it, I was running a travel business, making it...Read More ▶

REVIEWS

Rating: 5.0
12 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 12 reviews

Jess does all the work!!
Reviewed By Cassandra - Puerto Rico | Traveled to Spain | Europe
Jess is our go to travel agent. We work so hard to travel along with the family, that we hardly have any time to plan. So we just tell Jess where we are going, she takes care of the rest and we don’t have to worry about a thing! She even suggests additional venues within our original plan trip and her suggestions are always spot on. This year, Jess will plan our 3rd vacation in Europe! Can't wait! Thank you Jess!
I would recommend this agent to my family and friends.
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Making the most of travel
Reviewed By Dave400000 - Orange City FL | Traveled to Australia & New Zealand
Jess and her team has found unique experiences that I enjoyed immensely and would not have found on my own research.
I would recommend this agent to my family and friends.
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Perfectly planned, stress-free getawat
Reviewed By Ashley - Atlanta, Georgia | Traveled to Toronto | Ontario | Canada
Jess is an absolute pro. It's almost like she read our mind and planned the perfect vacation for our family. She knew all the hot spots for food, shopping, museums, and attractions and gave us a smooth itinerary that matched our speed. And she had suggestions for each family member's interests. This was a vacation to remember and it's all thanks to Jess' magic!
I would recommend this agent to my family and friends.
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Great trip and WAY less stress
Reviewed By Travelz - Saint Cloud, Florida | Traveled to United Kingdom | Europe
Jess planned our 3-week trip to England and Scotland for our family of four and it really had something for everyone. Our roadtrip was a mix of castles, hikes, tiny towns, cities, and great food all planned out in bite-sized days. She found hotels that actually worked for a family of four with teenagers, not just a tiny room with small beds to share. The kids have a hundred pictures of the Highland cow farm she found and my husband keeps bringing up that scotch tasting in Oban like it changed his life. It was the first big trip we’ve taken that didn’t feel so stressful or like I had to worry and manage everything. Jess just got us.
I would recommend this agent to my family and friends.
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Perfect Girls’ Trip
Reviewed By Zwaigs - Toronto | Traveled to Niagara Falls | Ontario | Canada
Huge shoutout to Jess Dorsey for planning the perfect reunion trip! My friend and I (from opposite sides of the border) just got back from 5 amazing days in Niagara-on-the-Lake, and we’re still glowing. Jess totally nailed the vibe. We asked for something relaxing, fun, and full of local charm. She balanced an itinerary that included everything from classic historic sights with stylish and modern gems like the gorgeous 124 on Queen Hotel and Spa. Everything was planned so thoughtfully: wineries, hikes, yoga, incredible food, and even free bikes to tour the area! She made it all so easy. She is super responsive, detail-oriented, and genuinely caring. We just showed up and had the best time. Can’t recommend her enough!
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.
Seacademy - Gold Certification
Seacademy - Gold Certification
Seacademy - Scarlet Certification
Seacademy - Scarlet Certification
Seacademy - Silver Certification
Seacademy - Silver Certification
Seacademy - Violet Certification
Seacademy - Violet Certification
Virgin SeaAcademy Graduate
CLIA
IATA
TRUE
Host Agency Reviews Nebula Award
Host Agency Reviews Luminary Award

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.

My Photo Albums and Videos

Virgin Voyages
View Album
Jess, Book the Trip!

My Travel Stories

Touched for the very first time

Why This Non Cruiser is Obsessed with Virgin

Look, if you're expecting towel animals and endless buffet lines, honey, this isn't your ship. But if you're ready for the sexiest week at sea that'll make you forget everything you thought you knew about cruising? Keep reading. Joe and I just got back from our millionth Virgin Voyages cruise (okay, maybe our seventh, but who's counting?), and I...
Read more

Part French, Part German, Part Dutch, All Yours

Winter Holidays in Belgium

Spending Christmas in Belgium was a dream come true for our family. From the moment we touched down in Brussels, the festive atmosphere was infectious. Each day brought new surprises and gorgeous sights. If you’ve ever thought about visiting Belgium during the holidays, here’s our week-long itinerary—a mix of bustling cities, serene countryside,...
Read more

Bilbao, Spain

Spain's Basque Country

The Basque Country in northern Spain was an unforgettable 10-day journey, blending rich culture, stunning landscapes, and the most delicious food I’ve ever had! From cities to quaint coastal towns, I discovered a world within Spain that was completely its own. Days 1-2: Bilbao and a Day in Guernica Landing in Bilba...
Read more

Columbia Ice Fields Jasper National Park Alberta

Western Canadian Rockies Banff/Jasper/Yoho

Embarking on a road trip from Calgary to Vancouver through the Canadian Rockies was an adventure like no other. From city highlights to breathtaking landscapes, this journey was packed with unforgettable experiences! Calgary: The Starting Point I kicked off in Calgary with a visit to the Calgary Tower for panoramic views ...
Read more

Client Testimonials

Spain Trip
I recently used Jess Travel for my Spain (San Sebastian and Barcelona) trip, and I must say it was an outstanding experience. From the initial planning stages to the execution of the itinerary, I found their services to be exceptional. I highly recommend Jess Travel for anyone looking for a well-thought-out and personalized travel experience. The attention to detail, local expertise, and professionalism made our trip memorable and enjoyable. I will definitely consider their services for future travels.
Cassandra Voltaggio
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