Gypsy Soul Tours 

5.0/5 (1 review)
 208 Harbor Drive, Stamford, CT 06902, United States

Gypsy Soul Tours 

Stamford, CT, United States
37 feet
6
5.0/5 (1 review)

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.

Loading...
Loading
Loading
Loading

Customer reviews

Loading...

Rating

5.0
(1 review)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

All reviews (1)

Showing 11 of 1 review
Kevin Matyger
Kevin Matyger
us
Delaware, US
Member since 2026
5.0
Verified
New
Captain Jon was Fantastic!
3 Hr – Unforgettable Sailing Trip - 6:30 PM on July 18, 20263 adults
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!
Response from Captain
July 20, 2026
Thank you, Kevin. it was terrific having you all aboard.

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
July 2026
SuMoTuWeThFrSa
Loading...
Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
3 Hr – Unforgettable Sailing Trip
FREE Cancellation 3 days notice
3 hour trip multiple starting times (11:00 AM, 3:00 PM, 6:30 PM)
Seasonal trip
May 1 - Nov 1
+2
US $750
Private tour: up to 6 people
There is 1 person looking at this charter.

Customer reviews

Loading...

Rating

5.0
(1 review)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

All reviews (1)

Showing 11 of 1 review
Kevin Matyger
Kevin Matyger
us
Delaware, US
Member since 2026
5.0
Verified
New
Captain Jon was Fantastic!
3 Hr – Unforgettable Sailing Trip - 6:30 PM on July 18, 20263 adults
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!
Response from Captain
July 20, 2026
Thank you, Kevin. it was terrific having you all aboard.

FAQs about Gypsy Soul Tours

Loading
Loading
Loading
Loading
Loading
Loading
Loading

What the boat is like

Boat category
Other
Boat type
Sailing
Boat manufacturer
Beneteau
Boat Model
Oceanis 373
Year built
2005
Boat length
37 ft
Capacity
6 persons
Engine model
Yanmar
Max crusing speed
6 knots
Powered by
1 x 30HP
Engine Type
Inboard
Fuel Type
Diesel
Number of cabins
2 cabins
Number of berths
2 berths
Number of heads
1 head
Number of full baths
1 full bath
Number of toilets
1 toilet
Boat category
Other
Boat type
Sailing
Boat manufacturer
Beneteau
Boat Model
Oceanis 373
Year built
2005
Boat length
37 ft
Capacity
6 persons
Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading

Compare similar boating charters

Loading...
Loading...
Loading...