Captain
Jonathan Flaks

Member since June 2026 Stamford, United States
Background
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.
Techniques
Sailing, swimming, relaxing, entertaining, stand up paddle, rowing, floating, laughing, adventuring, diming, sunset watching, photographing!

Hey, I'm Captain Jonathan Flaks

Stamford, United States
Background
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.
Techniques
Sailing, swimming, relaxing, entertaining, stand up paddle, rowing, floating, laughing, adventuring, diming, sunset watching, photographing!
3
Reviews

My Listing

Gypsy Soul Tours

Excellent
5.0 / 5
(3 reviews)
Stamford
trips from US $750

Customer reviews

Rating summary
Excellent
5.0 / 5
out of 5 stars from 3 reviews
See details
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
5.0 / 5
Photos & videos by reviewers (2)
Awesome Bachelorette!
Captain Jon was Fantastic!
Customer rating
3
0
0
0
0
Customers claimed
Good experience
100%
Friendly captain
100%
Recommend this charter
100%
Appropriate for children
100%
Satisfied with the boat
100%
Sort by:
Featured  
Showing:
3 of 3 reviews
Samantha F.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Awesome Bachelorette!

VERIFIED   NEW  3 Hr – Unforgettable Sailing Trip - 6:30 PM on August 15, 2026
We had such a wonderful afternoon on the water with Captain Jon! The boat was beautiful, the day couldn’t have been better,...
Samantha F. recommends Gypsy Soul Tours
Mark review as helpful
You found this review helpful
  Jonathan Flaks Captain replied
Read more
Kevin M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Captain Jon was Fantastic!

VERIFIED   3 Hr – Unforgettable Sailing Trip - 6:30 PM on July 18, 2026
We sailed with him out of Stamford on an unexpectedly windy day. And he handled the boat perfectly - calm, skilled, and easy...
Kevin M. recommends Gypsy Soul Tours
Mark review as helpful
You found this review helpful
  Jonathan Flaks Captain replied
Read more
Alison C.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great sailing trip !

VERIFIED   NEW  3 Hr – Unforgettable Sailing Trip - 3:00 PM on August 29, 2026
Captain Jon and Andrea were amazing ! They provided different options for sailing/swimming and our kids loved it! We would...
Alison C. recommends Gypsy Soul Tours
Mark review as helpful
You found this review helpful
  Jonathan Flaks Captain replied
Read more
  • Settings