Jennifer De Witt
Based in Sarasota, Florida
Trip budgets start at $400/night
Jennifer De Witt
Ask me about
My Story
After traveling solo to 40+ countries and counting, I now design thoughtful, unhurried journeys to Europe and Japan for solo women and couples over 50.
Travel Style
People tend to find me when they want travel that feels intentional rather than overstuffed. I focus on Europe and Japan, working mostly with solo women and couples over 50 who want meaningful experiences without the stress of planning them. I handle the trip from beginning to end—thoughtful accommodations, culturally grounded experiences, and the kind of pacing that leaves room to breathe…and occasionally wander into something wonderful.
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Reviews (7)
Judith S.
a year ago
Jenny really excelled when she booked me into this hotel. Nothing pleases me more than entering an impeccably clean, interesting space. The Hendricks was a classy choice. The staff was friendly and the food at breakfast was excellent. I could not have been happier.
Elizabeth G.
a year ago
I can’t imagine how we would have organized a trip to Japan without Jenny’s guidance and hard work. She asked lots of questions that helped us schedule must-see spots, but also time to explore on our own. She provides lots and lots if insider information about transportation, connectivity while out of the country and so much more. I would highly recommend Jenny’s help if your wanting to take an adventure and don’t enjoy or have time to do lots of research and plan the myriad details. So many of our plans and transportation tickets were booked in advance, giving us confidence in our schedule and access to some places that we wouldn’t have seein if we hadn’t booked well in advance. The Fora app was our daily go-to with everything handy including confirmation numbers, tickets and more. This was a special trip and we’ll be talking about it for years to come!
Jessica B.
2 years ago
Jennifer was such a delight to work with, she made traveling so much easier with a toddler. I had no idea what I was going to do in Cambridge with a toddler and she found so many activities for the two of us to do. She took care of everything, from hotels and transportation to and from the airport as well as meals and activities! She was also available if we had questions mid trip!
Jess S.
2 years ago
Jennifer did a great job planning our trip. It made it so much easier for everything that honestly made our vacation so much more enjoyable. We had one tiny hiccup about a museum but was not her fault as the museum doesn’t note this on their site. She will 100% be booking our next vacation. Thanks Jennifer!
Ashley R.
2 years ago
Couldn't have been easier. I needed somewhere affordable but as close as possible to the event I was attending. Jennifer couldn't have gotten us any closer if she tied and she did it at a great price! She listened to exactly what I needed and delivered! Even went beyond by recommending some places to eat that we enjoyed. Would book with her again.
Judith S.
a year ago
Jenny really excelled when she booked me into this hotel. Nothing pleases me more than entering an impeccably clean, interesting space. The Hendricks was a classy choice. The staff was friendly and the food at breakfast was excellent. I could not have been happier.
Elizabeth G.
a year ago
I can’t imagine how we would have organized a trip to Japan without Jenny’s guidance and hard work. She asked lots of questions that helped us schedule must-see spots, but also time to explore on our own. She provides lots and lots if insider information about transportation, connectivity while out of the country and so much more. I would highly recommend Jenny’s help if your wanting to take an adventure and don’t enjoy or have time to do lots of research and plan the myriad details. So many of our plans and transportation tickets were booked in advance, giving us confidence in our schedule and access to some places that we wouldn’t have seein if we hadn’t booked well in advance. The Fora app was our daily go-to with everything handy including confirmation numbers, tickets and more. This was a special trip and we’ll be talking about it for years to come!
Jessica B.
2 years ago
Jennifer was such a delight to work with, she made traveling so much easier with a toddler. I had no idea what I was going to do in Cambridge with a toddler and she found so many activities for the two of us to do. She took care of everything, from hotels and transportation to and from the airport as well as meals and activities! She was also available if we had questions mid trip!
Jess S.
2 years ago
Jennifer did a great job planning our trip. It made it so much easier for everything that honestly made our vacation so much more enjoyable. We had one tiny hiccup about a museum but was not her fault as the museum doesn’t note this on their site. She will 100% be booking our next vacation. Thanks Jennifer!
Travel ideas (2)
A Luxe Visit to Valencia: The Three-Day Itinerary
Valencia is one of my favorite cities in Europe. It is where Spain’s rich history meets modern elegance, all wrapped in a breezy Mediterranean setting. Its compact size and accessibility make it effortless to visit, with an efficient transit system and plenty of hidden gems tucked into its historic center. Known for its innovative architecture, vibrant markets and deeply rooted culinary traditions — including being the birthplace of paella — Valencia offers a sophisticated yet laid-back escape. Its golden coastline provides a refreshing contrast to the city’s lively plazas and artsy enclaves, making it the perfect destination for travelers who want both cultural depth and indulgent relaxation.
A Luxe Visit to Valencia: The Three-Day Itinerary
Valencia is one of my favorite cities in Europe. It is where Spain’s rich history meets modern elegance, all wrapped in a breezy Mediterranean setting. Its compact size and accessibility make it effortless to visit, with an efficient transit system and plenty of hidden gems tucked into its historic center. Known for its innovative architecture, vibrant markets and deeply rooted culinary traditions — including being the birthplace of paella — Valencia offers a sophisticated yet laid-back escape. Its golden coastline provides a refreshing contrast to the city’s lively plazas and artsy enclaves, making it the perfect destination for travelers who want both cultural depth and indulgent relaxation.
Your Perfect Weekend Guide to Antwerp, Belgium
Welcome to Antwerp, a city that tastefully intertwines centuries-old heritage with contemporary flair. This city has it all - from world-class museums and exquisite architecture to sublime dining and shopping experiences. While Belgium is a great destination any time of year, late spring and summer in Antwerp are my favorite times to visit. Life in the city seems buzzy with excitement and ready to celebrate the return of sunny warm weather.
Your Perfect Weekend Guide to Antwerp, Belgium
Welcome to Antwerp, a city that tastefully intertwines centuries-old heritage with contemporary flair. This city has it all - from world-class museums and exquisite architecture to sublime dining and shopping experiences. While Belgium is a great destination any time of year, late spring and summer in Antwerp are my favorite times to visit. Life in the city seems buzzy with excitement and ready to celebrate the return of sunny warm weather.
A Luxe Visit to Valencia: The Three-Day Itinerary
Valencia is one of my favorite cities in Europe. It is where Spain’s rich history meets modern elegance, all wrapped in a breezy Mediterranean setting. Its compact size and accessibility make it effortless to visit, with an efficient transit system and plenty of hidden gems tucked into its historic center. Known for its innovative architecture, vibrant markets and deeply rooted culinary traditions — including being the birthplace of paella — Valencia offers a sophisticated yet laid-back escape. Its golden coastline provides a refreshing contrast to the city’s lively plazas and artsy enclaves, making it the perfect destination for travelers who want both cultural depth and indulgent relaxation.
A Luxe Visit to Valencia: The Three-Day Itinerary
Valencia is one of my favorite cities in Europe. It is where Spain’s rich history meets modern elegance, all wrapped in a breezy Mediterranean setting. Its compact size and accessibility make it effortless to visit, with an efficient transit system and plenty of hidden gems tucked into its historic center. Known for its innovative architecture, vibrant markets and deeply rooted culinary traditions — including being the birthplace of paella — Valencia offers a sophisticated yet laid-back escape. Its golden coastline provides a refreshing contrast to the city’s lively plazas and artsy enclaves, making it the perfect destination for travelers who want both cultural depth and indulgent relaxation.
Your Perfect Weekend Guide to Antwerp, Belgium
Welcome to Antwerp, a city that tastefully intertwines centuries-old heritage with contemporary flair. This city has it all - from world-class museums and exquisite architecture to sublime dining and shopping experiences. While Belgium is a great destination any time of year, late spring and summer in Antwerp are my favorite times to visit. Life in the city seems buzzy with excitement and ready to celebrate the return of sunny warm weather.
Your Perfect Weekend Guide to Antwerp, Belgium
Welcome to Antwerp, a city that tastefully intertwines centuries-old heritage with contemporary flair. This city has it all - from world-class museums and exquisite architecture to sublime dining and shopping experiences. While Belgium is a great destination any time of year, late spring and summer in Antwerp are my favorite times to visit. Life in the city seems buzzy with excitement and ready to celebrate the return of sunny warm weather.
Travel photos
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