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All listings in Connecticut

Incredible sailboat rentals in Connecticut, United States.

Page 1 of 118 listings

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
$225+/hour
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
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
Enjoy the Hamptons waters on wonderful and unique Classic Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic Mahogany Trimaran

5.0
$750+/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
36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
Sailing in Stonington · 6 guests

36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

5.0
$220+/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
$1,100+/hour
Private Sailing Charter – Explore the Hamptons from Sag Harbor Aboard a Beneteau
Sailing in Sag Harbor · 6 guests

Private Sailing Charter – Explore the Hamptons from Sag Harbor Aboard a Beneteau

New
$230+/hour
A large and luxurious French Sailing Yacht for up to 6
Sailing in Sag Harbor · 6 guests

A large and luxurious French Sailing Yacht for up to 6

New
$750+/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
$1,200/hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/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
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
Snoozed - Active 02 Jun 2026
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
Snoozed - Active 17 Jun 2026

Sailing Reviews in Connecticut

  1. Irene

    Irene

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

    Nina is a fantastic person, fantastic captain and a fantastic company. 2 of us and a doggie went on a short adventure with her and it couldn’t have been a better experience. We had so much fun, laughter and comfort with her on her boat that i can barely put this in words. We will definitely do this over and over again. Highly recommend!

  2. KF

    Karly

    36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

    We booked a 2 hour boat trip to celebrate my parents retirement and Francisco was amazing! The boat was beautiful, clean and exactly as listed. He was an incredibly gracious host and took us on a lovely sail! Will definitely be back!

  3. LE

    Lara

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

    My girlfriends and I had the best time celebrating a bachelorette party with Captain Brian and his beautiful boat! From the very start Brian had quick communication and was helpful answering our questions. The actual boat was so nice, with a rustic charm. It comfortably fit all 10 girls. Brian made the day extra special - he’s so kind and fun. Would definitely recommend to this others and even hope to do another trip again!

  4. EC

    Emily

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

    Nate and Jaime were the absolute best from start to finish! Super great communication and excellent service - loved the swimming spot and how knowledgeable Nate was about the area and other boats. Exceeded our expectations, will definitely book with Nate again!

  5. MR

    Madeleine

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Such a fun evening on the water with Marco. A very comfortable boat, easy to access and a beautiful cruise! Highly recommend and we look forward to going out again.

  6. KH

    Katy

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

    We are so happy we chose to book with Nate! The communication was clear and concise, we knew exactly where to go when our trip came! Nate and crew were beyond accommodating and the boat is so charming! This made our trip so special!