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Gretchen Winterstein

Chesapeake, Virginia Travel Agent
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Gretchen Winterstein

Gretchen Winterstein

Chesapeake, Virginia Travel Agent
Recharge Travel, an independent agent with Lamacchia Jet Stream, WI, a Travel Leaders Network Affiliate Agency
28 Reviews | 100% Recommended
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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

Admiring the houses in Copenhagen
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 ... Read more from my Europe - Customized Vacation Experience bio.

Hawaii Vacations Expert

View of Waikiki Beach on Oahu
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 ... Read more from my Hawaii Vacations Expert bio.

Family & Multi-Generational Travel

Geared up for a River Float in Alaska
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 ... Read more from my Family & Multi-Generational Travel bio.

Family Travel, Caribbean and European Specialist

Royal Caribbean in St Thomas
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 ... Read more from my Family Travel, Caribbean and European Specialist bio.

My Travel Stories

Scarlet Lady
Virgin Voyages - Scarlet Lady
View of the German Alps
Germany & Danube River Cruise
Hanauma Bay
Hawaii - Oahu

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 ... Read more from my Tauck Family River Cruise - Douro River, Portugal story.

My Reviews

Rating: 5 28 Reviews | 100% Recommended

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 Perfect Trip from Start to Finish!

Reviewed By Reade - Chesapeake, VA | Traveled to Ireland ~ Europe
Gretchen was the ideal travel agent, starting with the planning process and ending with emails and a phone call, even once the trip had ended! During the planning process, she helped us to find the best route around Ireland and booked the rail tickets between each of the 4 cities we decided to visit.
She also suggested and booked some amazing activities and day trips for each city, and even helped us to find 2 guided bike rides which were perfect for sight-seeing and learning about the history from the guides. Gretchen found great hotels in each city, and all 4 of the hotels were very accommodating, comfortable, and perfect locations for getting around. Each hotel also included a huge Irish breakfast!
Gretchen has traveled extensively herself, and is very knowledgeable about so many destinations. We loved the trip so much that we have already booked our next trip!
I would recommend this agent to my family and friends
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Best Trip Ever!

Reviewed By Kevin W - Virginia Beach, VA | Traveled to Playa Mujeres ~ Quintana Roo ~ Mexico
Worked with Gretchen on my last 4 vacations and she has been marvelous. Gretchen is an excellent communicator, follows up quickly with all the right info, sends out really thorough info and follow our trip to make sure we are taken care of. And then sends us a “Welcome Home” note. Highly recommend Gretchen!
I would recommend this agent to my family and friends
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Great Trip

Reviewed By Elaine - Fallbrook Ca | Traveled to Panama Canal ~ Panama ~ Central America
Gretchen was great to work with. She handled everything beautifully!
I would recommend this agent to my family and friends
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Best travel experience ever!

Reviewed By Kim - Windsor, VA | Traveled to Caribbean
Gretchen listened to us and what we were looking to do and came up with multiple options for us to pick from. Once we chose what we wanted to do, she assisted us the rest of the booking process all the way until we returned home. She checked in on us the day after we returned to find out about our trip. She is passionate about her job and wants to ensure her clients are satisfied.
I would recommend this agent to my family and friends
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Best overall experience and a great trip

Reviewed By Jack A - Carrsville Va | Traveled to Caribbean
When we contacted her we really did not know what we were going to do she gave us some options and we decided to cruise she suggested a cruise line and helped us book our ai fair and a room the night before and our excursion off the boat We received great help booking our trip and quick responses to our questions I would definitely use her on our next trip
I would recommend this agent to my family and friends
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Incredible family experience

Reviewed By Alexis - Wyckoff NJ | Traveled to Sedona ~ Arizona ~ USA
Exceptional experience. We are a family of five with a nine-year-old, six-year-old, and four-year-old. It is difficult to find accommodations and activities. Gretchen surpassed our expectation, and we will only be using her services for all our travel needs moving forward
I would recommend this agent to my family and friends
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Zermatt Ski Trip

Reviewed By KW - Virginia Beach | Traveled to Zermatt ~ Switzerland ~ Europe
Gretchen is a fantastic communicator for all things needed for trips and she does an excellent job of keeping up with the details and providing info for your travel destinations like available activities, restaurants, etc.
I would recommend this agent to my family and friends
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Winter Beach Trip!

Reviewed By Anna - Kansas City, KS | Traveled to Puerto Morelos ~ Quintana Roo ~ Mexico
Gretchen was fantastic in helping to plan this trip. At the very beginning, she presented multiple options for resorts and used our feedback to help narrow things down. She was very thorough and made sure that we had everything that we needed for another awesome Mexico trip.
I would recommend this agent to my family and friends
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Disney 2024

Reviewed By LDZ - Chesapeake, VA | Traveled to Walt Disney World ~ Florida ~ USA
Gretchen is very enjoyable to work with! She is knowledgeable, very responsive, and easy to work with. She is on top of what needs to be done/booked/paid and sends updates before you head out with info you need to know (ride closures, events, etc). This is our third Disney vacation booked with Gretchen and all aspects of her planning have been perfect!
I would recommend this agent to my family and friends
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Quick response to a tough request

Reviewed By Edward - Chester, VA | Traveled to Europe
Very knowledgeable. Great response time. We gave Gretchen only a week's notice to book a 2 week vacation including Germany and Spain, and she surpassed our expectations.
I would recommend this agent to my family and friends
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Finally made it to Napa!

Reviewed By April - Chesapeake, VA | Traveled to Napa Valley ~ California ~ USA
Gretchen helped plan a bucket list trip to Napa Valley in CA. There were multiple hotels to coordinate and she did a great job. Gretchen also made recommendations on sites to visit or places to explore. Overall, it was a great trip, made better by Gretchen's expert travel planning and advice.
I would recommend this agent to my family and friends
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Easy to work with!

Reviewed By April - Chesapeake, VA | Traveled to London ~ England ~ Europe
Gretchen is easy to work with. She is responsive and is willing to provide multiple trip options that work within your budget and schedule. I will definitely use Gretchen again for future travel needs.
I would recommend this agent to my family and friends
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Best All-Inclusive Trip So Far!

Reviewed By Courtney - Virginia Beach, VA | Traveled to Dominican Republic ~ Caribbean
Gretchen is AMAZING! She has planned several couples and family trips for me over the past few years. She listens to what you are looking for, gives thoughtful recommendations, lists pros and cons so you can think through options, and keeps things within your budget. I change my mind a lot too and Gretchen has always been patient and run other scenarios for me so I can feel confident about my choices! I have given her information to many friends to help them bring the ease back into vacation planning! There is way too much information out there, let someone with experience handle it so you can get the best bang for your buck! She recommended a new all-inclusive in the DR and I could not have had a better trip!!! Thanks Gretchen:)
I would recommend this agent to my family and friends
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Best All-inclusive experience to date!

Reviewed By Courtney - Virginia Beach, VA | Traveled to Dominican Republic ~ Caribbean
I have worked with Gretchen for years and it is ALWAYS a great experience. Gretchen listens to what you are hoping for, makes great recommendations, and keeps it budget friendly. One thing I love about Gretchen, she will tell you the pros and cons of any plan so that you can make the best choice for you! Gretchen is also accessible (quick and thorough response) and patient! I have gone back and forth on some trip ideas and I never feel rushed. I have passed her information to anyone talking about a trip and recommend they use Gretchen to bring the ease back into vacation planning!
I would recommend this agent to my family and friends
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Fantastic 50th Wedding Anniversary family trip!

Reviewed By Lori - Chesapeake, VA | Traveled to St. Lucia ~ Caribbean
Gretchen was AMAZING! She helped planned everything for our family’s St. Lucia trip to celebrate my parents 50th wedding anniversary. She arranged everything from our flights, our transfers, to our rooms. This trip consisted of a total of 21 people from 6 different families, traveling from 3 different states, and 4 different cities. Our age group ranged from 8 years old to 70 years old. She found us an all inclusive resort (Coconut Bay) that had something for everyone. Activities ranging from a kids club, paintball, and a petting zoo, to water slides and lazy rivers. She even helped coordinate our dinners and also walked us through having a surprise anniversary cake.
I would recommend this agent to my family and friends
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Fabulous trip with Grandchildren

Reviewed By Nancy - Annandale, Virginia | Traveled to Germany ~ Europe
A few years ago I wanted to take my young teen grandchildren on a European Adventure. Gretchen suggested a river cruise with Tauck Bridges, geared towards multi generations. This was the perfect solution!
With her expert guidance we arrived a day early to get acclimated to the time zone change. It also allowed us the opportunity to explore a new city on our own before the tour began. We cruised the Danube River and loved every minute! Each day was filled with new adventures, along with regional food, that we could all enjoy together. River cruising is great. We loved the ambiance of a small ship, delicious food, nightly entertainment, and the scenic journey through different countries. The trip was so popular that we had Gretchen plan two more river cruises, the Rhine and the Douro River in Portugal! Her expert advice has made these three adventures lasting memories for all of us. She did exceptional planning for air flights as well as early accommodations.
I would recommend this agent to my family and friends
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Exceptional Travel Agent

Reviewed By SFrank - Ocean City, MD | Traveled to Paris ~ France ~ Europe
We have used Gretchen as our travel agent several times and plan to continue using her. I can't imagine anyone else being better than she is! She is incredibly knowledgeable, responsive and has always gone above and beyond our expectations for gathering information. I would highly recommend her to anyone planning a trip.
I would recommend this agent to my family and friends
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Gretchen is amazing!

Reviewed By Tasha - Amherst, NH | Traveled to New Orleans ~ Louisiana ~ USA
Gretchen made everything so easy and thought of things we did not. We will use her every trip!
I would recommend this agent to my family and friends
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Actually, many trips

Reviewed By Tim - Elizabeth City. NC | Traveled to Jordan ~ Middle East
Best travel agent ever!
I would recommend this agent to my family and friends
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Deightful and thorough - The perfect combination

Reviewed By Eileen - Chesapeake, VA | Traveled to Europe
We have booked several trips through Gretchen. Her customer service is unmatched, and she is very fun to work with. She has created week-long itineraries for our family based on our interests, as well as taken care of all of our needs in booking cruises and tours. Poor Gretchen even spent one unfortunate evening on the phone with us until midnight after an international flight was cancelled.
I would recommend this agent to my family and friends
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A wonderful family celebration!

Reviewed By Kate - Menlo Park, CA | Traveled to Europe
We had a great experience working with Gretchen for a very special family trip to Switzerland, Italy, Austria and France in June and July 2023. 
Gretchen was very responsive, flexible, knowledgeable and easy to work with. She helped shape our ideas into a wonderful trip. She was very organized, kept on top of deadlines, and gently nudged us when we needed to make a decision about something.
It was a delight and so easy to have Gretchen to set up our trip, research and book trains, hotels, cars and airplane flights. It was so much less effort than doing the planning ourselves.
Gretchen provided us with an exceptionally organized day by day packet for our trip,  covering the entire itinerary and any actions we needed to take (i.e. a museum reservation) while traveling. She was readily available for any questions or changes we had while on the trip.
We are looking forward to using Gretchen again for future travel and highly recommend her services.
I would recommend this agent to my family and friends
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Best Travel Agent Ever!

Reviewed By Kristen - Norfolk, VA | Traveled to Disneyland ~ California ~ USA
Gretchen is so easy to work with and has helped me book many amazing trips.
I would recommend this agent to my family and friends
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Amazing Alaskan Cruise

Reviewed By S. Moore - Falls Church VA | Traveled to Anchorage ~ Alaska ~ USA
Gretchen is so great to work with. She really gets to know your needs and your group so that she can curate your trip to you! She gives you a range of options for your trip to ensure that you can take advantage of all that your vacation has to offer.
I would recommend this agent to my family and friends
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Amazing, personalized experience

Reviewed By Danielle - Richmond, VA | Traveled to Costa Rica ~ Central America
Gretchen was amazing to work with. She planned a trip to Costa Rica for me and my 16 year old son, and managed to hit the perfect balance of enough luxury so that I could enjoy it, and enough fun activities, so he had a blast too. We both agreed - best trip ever!
I would recommend this agent to my family and friends
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Hawaii - Bucket list completed!

Reviewed By Mickey - Chesapeake, VA | Traveled to Hawaii ~ USA
Gretchen is thorough and very good at booking (or in our case) rebooking travel. When one of our travelers got COVID two days before the trip, Gretchen took the time to call and cancel and rebook the trip for us for about a month later. She helped us understand the restrictions, the rebooking fees and also helped us create amazing experiences with ideas of things for us to do. We love Recharge travel and would use Gretchen again!
I would recommend this agent to my family and friends
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Memorable (in a great way) Family Cruise

Reviewed By Aaron J - Chesapeake, VA | Traveled to Aruba ~ Netherlands Antilles ~ Caribbean
Outstanding Experience!!
In the initial stages of our trip planning, we really didn't have a good grasp on 'what' we wanted to do. Gretchen was able to use her travel and planning experience to guide us to the best solution. She knew our family, budget and our interests and was able to tailor incredible, budget-conscious options to choose from.

I was a difficult customer with many distracting things going on but she was very understanding and genuinely wanted my family to get the best deal and experience.

Her custom approach to our needs and specific family requirements covered health considerations, travel and safety concerns, "inside information" and local knowledge of the areas we went--in addition to the trip's organization and packaging. Gretchen went above and beyond what we were expecting of a travel agency. We received a 'boutique', custom experience and definitely will use Recharge Travel again. We were not disappointed and will d
I would recommend this agent to my family and friends
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Europe & Disney

Reviewed By LDZ - Chesapeake, VA | Traveled to Europe
Gretchen has booked our last three Disney trips and every detail has been perfect. We have been to Disney many times before but she added new insights and planning tips that were great. She is super responsive and super nice to work with! She recently helped with some aspects of our trip to Europe and was very knowledgeable and again was super responsive!
I would recommend this agent to my family and friends
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My Travel Experience

Places I’ve personally traveled to or destinations I’ve booked for my clients.