Revitalize Your Spirit through Sailing
Whatever your reason for wanting to charter a sailboat cruise, your USCG certified Captain and everyone at Gypsy Soul Tours promise to leave you with the most exciting, soul-revitalizing and rewarding experience on the water ever.
Our Services
Our services are tailored to provide you with the most exquisite yacht charter experience. Choose from a variety of options to suit your needs.
To explore a custom charter, complete the form or text Captain Jon at 917-972-6507
You'll get a response immediately or within a few hours
Tailored Experiences
Indulge in luxury with our bespoke charters, personalized to meet your every desire. Experience a level of service that exceeds expectations.
Memorable, meaningful bonding and learning (optional)
Treat your family to a special experience with a fun, bonding and learning adventure with breathtaking views, exciting motion and delightful swimming/floating/splashing! Consider add-on options like sailing lessons, great food, personal photography and live music. Let's create your unforgettable memories for your family photo album and social media reels!
Bond with the BFF's or just enjoy an extra cool hang on the water
Enjoy worry-free voyages with our experienced crew, ensuring every detail is taken care of for a smooth sailing experience.
We primarily cruise Long Island Sound from Stamford Connecticut with a focus on service, comfort, and safety. Captain Jon Flaks is a U.S.C.G. Certified Captain and a creative spirit, committed to every voyage being an extraordinary adventure.
Discover the beauty of a sailboat charter and let us help you curate your perfect maritime experience. We will take you on a voyage you'll never forget.
I sailed out of Stamford with Jonathan Flaks on Tuesday, September 23, 2025. At all times he gave me a sense that he was in complete control of the ship. Using the engine at first and then raising the sails he took advantage of the wind that was available. The return docking was extremely smooth. He has a wealth of knowledge about the Sound, and the experience was very enjoyable. I would like to make another trip with him in the Spring of 2026 and bring my wife, daughter, and son.
I have sailed with Captain Jon multiple times over the years as both a passenger and a First Mate on day trips and multi-day trips. I’m happy to offer high praise to the Captain for his professionalism, courtesy, charisma and boating skills. Jon does meticulous prep work and is not a risk taker so I always feel safe and assured that he’ll do the right thing. He's got a great personality and is fun to be around. Gypsy Soul is sturdy, stable and provides comfort in the cockpit and the cabin. Captain Jon welcomes suggestions on where to sail so you always feel like you’re on your unique adventure. Highly recommended.
Jon took us for a beautiful day trip on the Long Island Sound. He is a charming captain/host who offered us a variety of experiences from total relaxation to captain-in-training…we chose somewhere in the middle and learned a lot! The sailboat is well maintained and well appointed. It was a joyful day! I have recommended Captain Jon to friends and look forward to our next sail with him.