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
(144)
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
144 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.
Search reviews:

Showing 144 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.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Incredible trip of a lifetime
Reviewed By Fantastic Agent - Chesapeake, VA | Traveled to Asia
I would like to personally thank Gretchen for the incredible job she did planning our trip to Asia. From the very beginning, Gretchen took the time to understand what we wanted and handled every detail with exceptional care and professionalism. The flights, hotels, transportation, and recommendations were all perfectly coordinated, allowing us to relax and fully enjoy our travels. What impressed me most was Gretchen’s responsiveness, attention to detail, and genuine commitment to making our trip special. Because of her hard work and expertise, our journey was seamless, stress-free, and filled with wonderful experiences and memories. I truly appreciate everything she did for us and would enthusiastically recommend Gretchen to anyone looking for an outstanding travel advisor.
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
One of the best trips ever!
Reviewed By Gretchen - Chesapeake, Virginia | Traveled to Cancun | Quintana Roo | Mexico
Easy direct flight to and from destination. The transfer from airport to resort first class. The resort was fabulous! Everything about our vacation was spectacular. So many choices for restaurants and bars. Day eight we had to go home. Our transfer company was on time with a forty foot white limo and champagne for our ride to the airport….. Awesome and beyond expectations. The whole experience was Excellent!!
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
Perfect Vacation!
Reviewed By Gunzo56 - Newport News, VA | Traveled to Italy | Europe
Gretchen set us up with an amazing itinerary for our visit to Italy. She took all the stress out of the planning process and provided us with the perfect vacation.
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
Lots of logistics on this three week trip.
Reviewed By lawrence cove - Richmond, va | Traveled to Frankfurt | Germany | Europe
We spent three weeks in Europe this Spring with lots of coming and going from country to country. Gretchen worked out all our logistics perfectly. We took plans and train and rental cars. Gretchen pre booked all our tickets and we didn’t have one single glitch. Fantastic job! Thanks!
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO

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...
    Read more

    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...
    Read more

    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 ...
    Read more

    BESbswy