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All listings in Connecticut

Incredible sailboat rentals in Connecticut, United States.

Page 1 of 114 listings

Limited Availability
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$750+/hour
Instant Book
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
Limited Availability
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Westport · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York

5.0
$310+/hour
Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran

5.0
$900+/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience
Sailing in Sag Harbor · 41 guests

Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

5.0
$1,100+/hour
Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York

New
$249/hour
A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6
Sailing in Sag Harbor · 6 guests

A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6

New
$1,000+/hour
Captained sail on a beautiful and comfortable 50' wooden ketch
Sailing in Greenport · 6 guests

Captained sail on a beautiful and comfortable 50' wooden ketch

New
$475/hour
Sail the glamorous Hamptons in a 58ft Catana luxury catamaran
Sailing in Sag Harbor · 12 guests

Sail the glamorous Hamptons in a 58ft Catana luxury catamaran

New
$900/hour
Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
Snoozed - Active 17 Sep 2026
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
Snoozed - Active 17 Sep 2026

Sailing Reviews in Connecticut

  1. ST

    Sabrina

    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

    This was actually the best day of my life. I had my bachelorette and the boat was so incredible, Brian and his partner are amazing hosts and their boat is so gorgeous and special. They were flexible with the hours and very accommodating. Would love to rebook !!

  2. LT

    Louis

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    We had a great cruise on the sound. Marco was very personable and made sure everyone was comfortable and safe. I would highly recommend his boat. It is very well maintained and in excellent condition.

  3. CF

    Carlos

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Captain Marco was absolutely amazing! He was incredibly attentive to our entire group throughout our birthday party celebration and truly went above and beyond. His energy and hospitality made it such a special and memorable day for all of us. We would definitely recommend him to anyone looking for a perfect day on the water and we are already planning our future boat adventures with him!

  4. Jon

    Jon

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco was a gracious host. The boat is beautiful, clean, and in great shape. We had a fantastic day on the water. I highly recommend!

  5. AM

    Anna

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    We had a wonderful experience on the water with Captain Marco. He was incredibly friendly, knowledgeable, and made our family feel welcome from the moment we stepped aboard. Our children had a fantastic time, and Marco did a great job engaging with them and making the experience memorable. It was the perfect way to celebrate a special occasion as a family. Highly recommend!

  6. BA

    Brianne

    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

    We had the the most beautiful sunset cruise with Brian and their catamaran. Beyond accommodating, easy to communicate with, and a beautiful space. We had a group of 12 girls, and we felt more than comfortable relaxing, being silly- and not to mention the endless photos we asked to take. Everything you need on board with freedom to bring what you like. I could not suggest booking with Brian more!