Gypsy Soul Tours
Gypsy Soul Tours
Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound. Step aboard a beautifully maintained 2005 Beneteau Oceanis 373, a comfortable and spacious sailing yacht designed for relaxed cruising, special moments, and personalized adventures at sea.
With space for up to 6 guests, this yacht is ideal for intimate gatherings, romantic escapes, and special celebrations. Powered by a reliable 30 HP Yanmar diesel inboard engine and cruising smoothly at up to 6 knots, she combines classic sailing charm with dependable performance.
Onboard comfort is a priority, with air conditioning, WiFi, an audio system with inside and outside speakers, a refrigerator, ice box, and a well-equipped interior featuring a full galley and one bathroom. The open deck offers a bow sundeck, bimini shade, and a bathing platform, perfect for sunbathing, swimming, or simply relaxing while taking in the views.
This experience is perfect for romantic sunset cruises, birthdays, family outings, friends’ trips, and other special occasions. Optional add-ons such as drinks, snacks, lunch, paddleboard, and snorkeling gear are available to enhance your time on the water.
Led by U.S.C.G. Certified Captain Jonathan Flaks, every charter is designed to be safe, smooth, and fully tailored to your preferences. The vessel is fully equipped with modern navigation and safety systems, including GPS, radar, autopilot, VHF radio, depth finder, sonar, and life jackets.
Limited availability! Reserve your private sailing experience in Stamford today and make your time on the water truly unforgettable.
Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound. Step aboard a beautifully maintained 2005 Beneteau Oceanis 373, a comfortable and spacious sailing yacht designed for relaxed cruising, special moments, and personalized adventures at sea.
With space for up to 6 guests, this yacht is ideal for intimate gatherings, romantic escapes, and special celebrations. Powered by a reliable 30 HP Yanmar diesel inboard engine and cruising smoothly at up to 6 knots, she combines classic sailing charm with dependable performance.
Onboard comfort is a priority, with air conditioning, WiFi, an audio system with inside and outside speakers, a refrigerator, ice box, and a well-equipped interior featuring a full galley and one bathroom. The open deck offers a bow sundeck, bimini shade, and a bathing platform, perfect for sunbathing, swimming, or simply relaxing while taking in the views.
This experience is perfect for romantic sunset cruises, birthdays, family outings, friends’ trips, and other special occasions. Optional add-ons such as drinks, snacks, lunch, paddleboard, and snorkeling gear are available to enhance your time on the water.
Led by U.S.C.G. Certified Captain Jonathan Flaks, every charter is designed to be safe, smooth, and fully tailored to your preferences. The vessel is fully equipped with modern navigation and safety systems, including GPS, radar, autopilot, VHF radio, depth finder, sonar, and life jackets.
Limited availability! Reserve your private sailing experience in Stamford today and make your time on the water truly unforgettable.
Trip availability and prices
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Customer reviews
Rating
All reviews (3)
We had such a wonderful afternoon on the water with Captain Jon! The boat was beautiful, the day couldn’t have been better, and our only complaint was that we wished we could have stayed out longer. Jon was incredibly welcoming and accommodating and made the whole experience feel easy and relaxed. He is clearly a very confident and accomplished sailor, and also a fantastic host. We felt completely comfortable in his hands and were able to just relax, enjoy the gorgeous views, and spend time together. It was the perfect way to celebrate a special occasion, and we’d absolutely sail with Jon again!
Thank you for your lovely review and the great time we had together. See you again anytime you'd like to set sail again.
We sailed with him out of Stamford on an unexpectedly windy day. And he handled the boat perfectly - calm, skilled, and easy to relax with. He was also great with my three year old aboard even with everything else going on. Highly recommend if you want an enjoyable sail with a captain who really knows what he’s doing. Would definitely book with him again!
Thank you, Kevin. it was terrific having you all aboard.
Captain Jon and Andrea were amazing ! They provided different options for sailing/swimming and our kids loved it! We would definitely bring our family back !
Thank you, Alison. Happy Birthday to "M"and thank you for bringing your family aboard to celebrate with us!
FAQs about Gypsy Soul Tours
What are the trip rates for Gypsy Soul Tours?
- US $750 per group - 3 Hr – Unforgettable Sailing Trip (3 hours)
- US $750 per group - 3 Hr – Unforgettable Sailing Trip - 3:00 PM (3 hours)
- US $750 per group - 3 Hr – Unforgettable Sailing Trip - 6:30 PM (3 hours)
Which amenities are available onboard with Gypsy Soul Tours?
- GPS
- VHF Radio
- Radar
- Chart Plotter
- Depth Finder
- Autopilot
- Anchor
- Dinghy
- Wheel Steering
- Life Jackets
- Bimini
- Kitchen
- Shower
- Bow Sundeck
- Bathing Platform
- Air Conditioning
- WiFi
- Audio System
- TV
- Inside Speakers
- Outside Speakers
- Refrigerator
- Ice Box
- Galley Stove and Oven
What add-ons can be available with Gypsy Soul Tours?
- Paddleboard
- Snorkeling Equipment
- Snacks
- Drinks
- Lunch
Which kinds of activities does Gypsy Soul Tours offer?
- Sailing, Catamaran & Gulet Tours
- Sunset Dinner Cruises
- Birthday Celebrations
- Bachelorette & Bachelor Parties
- Proposal & Engagement Trips
- Corporate & Group Events
Your operator
Captain Jonathan Flaks is a U.S.C.G. Certified Captain based in Stamford, Connecticut, operating a Beneteau Oceanis 373. He specializes in private sailing trips, sunset cruises, and special occasions on Long Island Sound, delivering safe, smooth, and memorable experiences on the water.
Captain Jonathan Flaks is a U.S.C.G. Certified Captain based in Stamford, Connecticut, operating a Beneteau Oceanis 373. He specializes in private sailing trips, sunset cruises, and special occasions on Long Island Sound, delivering safe, smooth, and memorable experiences on the water.
What the boat is like
Which kind of activities are offered
Which amenities are available onboard
What's included in the trip price
What’s allowed on the boat
What additional terms you should be aware of
Security deposit is not required
A refundable deposit is not required by the charter operator.
Fuel is included
Fuel is included in the price of the rental.
How cancellations work
Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
How you can pay
Reserve with a 15% booking deposit, pay the captain the rest
When the captain confirms your trip, BoatBooker charges your credit card a 15% booking deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express
PayPal
Bank transfer
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