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
(131)
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
131 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 131 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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Cousins Cruise
Reviewed By Laurie - Glastonbury, CT | Traveled to Key West | Florida | USA
Great way to travel with a group of women. Gretchen was so helpful accommodating everyone’s specific needs!
I would recommend this agent to my family and friends.
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Outstanding trip start to finish!
Reviewed By Mar - Glastonbury, CT | Traveled to Bahamas | Caribbean
Gretchen did an outstanding job coordinating our female family cruise!!! Attentive, thorough and always pleasant are just a few of the positive adjectives I can use to describe how it was to work with Gretchen! Would highly recommend her travel agent skills and will certainly work on future trip plans with her!!
I would recommend this agent to my family and friends.
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Great girl cousin trip
Reviewed By Sjustice - Dallas Texas | Traveled to Bimini Islands | Bahamas | Caribbean
Gretchen was very timely and detailed; she was even able to find my Celebrity cruise info from my first cruise 20 years ago! Look forward to having Gretchen arrange our next adventure
I would recommend this agent to my family and friends.
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Scandanavian Aurora Lights
Reviewed By Bob Rose - Helsinki | Traveled to Finland | Europe
Gretchen worked tirelessly for us in every way imaginable. She was always pleasant and a joy to work with. She is an amazing person and never stops helping and advising us in every aspect of our trips. All of our connections were great as we had 8 different flights during our 8 day vacation. I will always be using her for our travel agent and make sure you listen to her recommendations as she knows best. Thanks so very much Gretchen. You the bestest!!!!
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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