Family Travel, Caribbean & European Specialist

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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
Reviews
Certificates & Awards
My Places
Travel Stories & Media

Areas of expertise

Destinations:

Europe, Caribbean, Hawaii, Alaska, USA

Interests:

Family Vacations, European Culture, All Inclusive, Escorted Tours, Disney Vacations

Suppliers:

Tauck, Viking, Celebrity Cruises, Holland America Line, Disney Cruise Line

About Me

Mykonos, Greece
Mykonos, Greece

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 extensively, and I am ready to share my passion and knowledge for trips with and without children.

I specialize in family and multi-generational vacations, couple's getaways, friend's trips, ocean and river cruises, Disney vacations and customized European and US adventures for all budgets.

My goal is to get to know you and your traveling companions to create custom vacations that meet your needs and budget allowing you to get the most value and enjoyment out of your vacation, worry free.

Are you ready to GET RECHARGED? Welcome to Recharge Travel - reconnect, recharge and discover something new.

Family Destination Favorites

Some of my favorite destinations:

Kauai, Hawaii - The Garden Isle

Copenhagen, Denmark - An Enchanted City

Newport Beach, California - Southern California Favorite

Porto, Portugal - Adorable, Windy Streets & Wine Valleys

DisneyWorld, Florida - A Magical Place

Aruba, Caribbean - One Happy Island

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 Travel Stories

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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