Gretchen Winterstein, CTA, Travel Agent in Chesapeake, VA

Gretchen Winterstein, CTA

Chesapeake, VA Travel Agent
Super Agent

Gretchen Winterstein, CTA

Chesapeake, VA · 10 Years of Experience

Recharge Travel, an independent agent with Lamacchia Jet Stream, a Travel Leaders Network Affiliate Agency
5.0
(162)
100% Recommended
Gretchen is, without question, the best travel agent we have ever worked with. She met personally with the three of us and took the time to... Read More >
About
My Travel Specialties
Reviews
Certificates & Awards
My Places
Travel Stories & Media

Areas of expertise

Destinations:

Hawaii, Europe, Caribbean, Alaska, Orlando

Interests:

Beach Vacations, Family Vacations, European Culture, Solo Travel, All Inclusive

Suppliers:

Disney, Funjet Vacations, Tauck, CIE Tours, Royal Caribbean

About Me

Family, Hawaii, Europe and Caribbean Expert

My goal is to connect with you and create a vacation that meets your needs, interests and budgets. I work with families, couples, singles and groups to help you relax, recharge and reconnect.

My Travel Specialties

Europe - Customized Vacation Experience

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Europe - Customized Vacation Experience
As a child, I spent six years living in Europe between England and the Netherlands. We traveled extensively whether in search of the Loch Ness Monster or a crepe on the streets of Paris. I saw how the culture, language and food of each country was so unique and I fell in love with the history and...Read More ▶

Hawaii Vacations Expert

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Hawaii Vacations Expert
I first traveled to Oahu back in high school and I fell in love with the beauty of the islands, the warmth of the local people and the views of palm trees and mountains from the beach. I have traveled to Oahu, the Big Island, Maui and Kauai in total 8 times and have sent couples, friends and fami...Read More ▶

Family & Multi-Generational Travel

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Family & Multi-Generational Travel
As an only child in a military household, we moved and traveled extensively. I grew up with the idea that the world is there to explore. With my own two children, we have focused on giving them experiences rather than material things resulting in many stamps in their passports and some amazing me...Read More ▶

Family Travel, Caribbean & European Specialist

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Family Travel, Caribbean & European Specialist
I have over 15 year's travel experience working in the airline industry, corporate Disney and the travel agency setting. I grew up in a military family and was fortunate enough to spend six years living in Europe and in various places across the US. I have two teenagers who have traveled e...Read More ▶

REVIEWS

Rating: 5.0
162 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 162 reviews

Experienced and extremely knowledgeable about all traveling.
Reviewed By Dennis and Robin G - Virginia Beach, VA | Traveled to Alaska | USA
Gretchen is, without question, the best travel agent we have ever worked with. She met personally with the three of us and took the time to understand exactly what we wanted from our Alaska vacation. She helped us select the right flights and then arranged executive-level transportation for us and all of our luggage—from the airport to our hotel, from the hotel to the cruise ship, and back to the hotel and the next day to the airport at the end of our trip. Everything was handled professionally, smoothly, and without us having to worry about a thing. But what really sets Gretchen apart is her knowledge of the destination and the excursions. She knew the options inside and out and helped us make outstanding choices. Her advice made a tremendous difference in our experience and contributed directly to what turned out to be the best vacation we have ever taken. Gretchen didn't simply book a trip for us—she helped us create an incredible travel experience from beginning to end. Her attention to detail, personal service, knowledge, and genuine commitment to making sure her clients have a great trip are exceptional. We recommend Gretchen without hesitation and as highly as possible. In fact, we were so impressed with her that we are already working with her on our Mediterranean cruise next year, visiting Italy and Greece and sailing from Barcelona, Spain. If you want a travel agent who will go above and beyond, knows her business, listens to her clients, and makes sure every important detail is taken care of, Gretchen is the person you want. She is simply the best!
✓ I would recommend this agent to my family and friends.
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Stress-Free Planning
Reviewed By Patty - Richmond, VA | Traveled to Hawaii ~ USA
Gretchen is wonderful! She has helped us book a Disney trip w/ family, a couples trip to Hawaii, and a family getaway to Mexico. She is detail-oriented, stayed within our budget, was able to provide insight into local hot-spots and fun activities to enjoy. We have referred her to so many of our friends who have all raved about her as well. Gretchen is outstanding to work with and we can't wait to tap into her for our next trip to ensure it is a stress-free, relaxing experience.
✓ I would recommend this agent to my family and friends.
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My 2nd time to use Gretchen for our Alaska cruise and look forward many more trips
Reviewed By Stacy Justice - Dallas, TX | Traveled to Alaska | USA
Gretchen is very informative about the best suited cruise line for us, detailed with excellent followup. Would definitely call on her for future trips
✓ I would recommend this agent to my family and friends.
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Last Minute Disney Trip
Reviewed By LDZ - Chesapeake, VA | Traveled to Walt Disney World | Florida | USA
Gretchen did a great job pulling together a last minute Disney trip for our family! We loved her recommendation for Beach Club and appreciated her help when we had a very late change to our plans! She handled it all with a smile :)
✓ I would recommend this agent to my family and friends.
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WEST TRIP
Reviewed By Debbie - Moseley VA | Traveled to Grand Canyon | Arizona | USA
The trip was amazing. We came away with beautiful, life long memories never to be replaced or forgotten. The attention to detail, consistent professional and careful planning by Gretchen was beyond expectations. She is extremely knowledgeable and organized! The only hotel that we felt was below expectations was the Arabella in Sedona. The room was very small, well worn and not comfortable. We loved the Canopy in Scottsdale!
✓ I would recommend this agent to my family and friends.
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Certifications & Awards

Regent Seven Seas Luxury Cruise Expert
Regent Seven Seas Luxury Cruise Expert
Seacademy - Gold Certification
Seacademy - Gold Certification
Viking Expert
Viking Expert
Windstar Star Specialist
Windstar Star Specialist
Certified Travel Associate
Tauck Specialist
Hawaii Destination Expert
Certified Sandals Specialist
Disney College of Knowled

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

Windstar - Greek Isles Cruise
View Album

    My Travel Stories

    Silver Spirit by Silversea

    Scandinavia aboard Silversea

    In June 2025, my family (3 generations) embarked on a Scandinavian/Baltic Sea adventure. We had been to Copenhagen, Denmark twice before but enjoyed it so much we decided to spend some additional time here prior to our cruise. Copenhagen is a city full of culture, history, wonderful Danish people and the beautiful Tivoli Gardens (inspirat...
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    Wind Spirit in the Aegean Sea

    Windstar Greek Isles Cruise

    In June of 2024, I embarked on the Wind Spirit, a four masted sailing yacht with only 73 oceanview cabins for a one of a kind experience sailing round trip from Athens, Greece. The crew of the Windstar yacht was outstanding, exceedingly friendly and got to know all of the passengers by name. As a smaller ship, the vessel felt more intimat...
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    View of the Douro River from Pinhao

    Tauck Family River Cruise - Douro River, Portugal

    In July, 2022 my family including two teenagers, traveled to Madrid, Spain to start our adventure. We visited many sites in Madrid including the Real Madrid soccer stadium for a behind the scenes tour, Las Ventas bull fighting ring, Plaza Mayor, The Prado art museum and more. We ate dinner at Botins, founded in 1725 and the oldest restaurant in ...
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