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All listings in Connecticut

Incredible sailboat rentals in Connecticut, United States.

Page 1 of 116 listings

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
$700+/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
$85/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
Best of 2025
$200+/hour
Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person
Sailing in Norwalk · 12 guests

Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person

4.7
Superowner
$200/hour
42' Catalina Sailing Yacht in the Hamptons
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons

5.0
$312+/hour
A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups
Sailing in Sag Harbor · 25 guests

A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups

5.0
$850/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
Sailing Tours Boat Charter - A Beneteau 36.7 Yacht in Connecticut
Sailing in Stonington · 6 guests

Sailing Tours Boat Charter - A Beneteau 36.7 Yacht in Connecticut

New
$200+/hour
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
$225/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
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
$160/hour
Large and Luxuriously Appointed Schooner for Private Daysails, Swims and Sunsets
Sailing in Sag Harbor · 41 guests

Large and Luxuriously Appointed Schooner for Private Daysails, Swims and Sunsets

5.0
$1,250/hour
Sail on a classy and fast Sailing Yacht in the Hamptons, New York
Sailing in East Hampton · 6 guests

Sail on a classy and fast Sailing Yacht in the Hamptons, New York

5.0
$300+/hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour
Captained sail on a beautiful and comfortable 50' wooden ketch
Sailing in East Marion · 6 guests

Captained sail on a beautiful and comfortable 50' wooden ketch

New
$475/hour
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200+/hour

Top Destinations Nearby

Sailing Reviews in Connecticut

  1. RA

    Reyoof

    Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person

    We had an amazing time! Mark was so professional and caring, and did everything he could so we can have the best time. Definitely going again!

  2. MB

    Mark

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

    Extraordinary experience on a comfortable and beautiful catamaran, with an excellent itinerary from Sag Harbor to Shelter Island for lunch and back. Captain Brian was super professional as was first Mate Erin in implementing and serving our extensive wines and hors d’oeuvres. The vibe of the team was fun, efficient but still chill. I highly recommend this as one of my best summer experiences and I’ve been in here my whole life and I’m in the hospitality business as a boutique hotel owner.

  3. SB

    Scott

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

    What a day on the water! Our Group of 7 people had an awesome time Captain Brian & Erin. The Catamaran was huge! The sun deck and the interior were clean and full of amenities. The Sailing around Sag Harbor and Shelter Island was something that we will never forget.

  4. NS

    Nicholas

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco was a wonderful captain and we had a great time watching fireworks from Todd's Point on the water. He piloted the ship safely and got us "front row seats" for the show. He also was mindful of other boaters in the area and got us out before the show ended so we weren't stuck or in danger. This was a surprise for my partner and Marco made it so worth the wait to reveal that we were going on an adventure in this beautifully renovated, fully equipped and well maintained ship. Would do this trip over 100 times! I highly recommend Marco for anyone that wants a safe, comfortable, and truly special time on the water.

  5. BS

    Bonnie

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco is the perfect captain. Extremely knowledgeable about boats, navigates the waterways with great confidence, and truly loves what he does. The boat is very clean, maintained beautifully, and the day was perfect. I would definitely sail with Marco again. Great experience!

  6. EC

    Erica

    Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person

    Mark was absolutely fantastic! He was in great communication with me for the planning, was extremely flexible with the departure time given the weather forecast within the days before, and overall made it the best sailing experience possible! The boat was in incredible condition and surpassed what is even pictured. I couldn’t recommend him more and we will definitely be sailing with him again