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
(140)
100% Recommended
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... 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

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

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

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

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
140 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 140 reviews

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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A Trip to Europe full of lifetime memories
Reviewed By RoRo and T - Hampton, VA | Traveled to Rome | Italy | Europe
Gretchen listened to our goals and wishes, formulated a plan for us and took care of the details. Something you want from an experienced travel professional. Will use her services again and recommend her to friends and family. Thank you Gretchen.
I would recommend this agent to my family and friends.
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Peacefully immersed in Japan
Reviewed By AliciaM - Kyoto | Traveled to Japan | East and Southeast Asia
We couldn't have done this without Gretchen! She was incredibly knowledgable about how things operated on the other side of the world (Japan). She gave us so many tips and tricks to make our travel successful. She was also incredibly patient with us as we kept running different ideas by her at the last minute. Always friendly and professional. Always helpful, and she was super responsive any time we had a question. We will look forward to working with Gretchen again in the future!
I would recommend this agent to my family and friends.
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Stress free family vacation
Reviewed By JMAndrews - Chesapeake, VA | Traveled to Costa Rica | Central America
Will never book another trip without Recharge travel again! Gretchen took care of every detail for us and it was the most incredible stress free trip. She found 2 perfect hotels for our family of 5 in different areas of Costa Rica that I wouldn’t have found on my own, reserved reliable transportation to and from airport, hotels, etc. and booked all of our excursions. She is so easy to work with and very helpful with tips and suggestions! We already booked our next trip with Gretchen for our group of 16, a European cruise. If you’re going to a new destination, are overwhelmed with choices or don’t know where to start, you 100% need to call Recharge.
I would recommend this agent to my family and friends.
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Gretchen is great to work with
Reviewed By Dave - VA | Traveled to Caribbean
Gretchen made planning and executing this trip painless. She listened patiently to all my (and my never-ending changes) and figure out how to make everything work just the way I wanted. She found me several discounts that I was unaware of, and took care of all of the negotiations and discussions with the cruise line.
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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