Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Browse Connecticut Boat Rentals.

Page 1 of 493 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
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
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
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
28' Bertram around islands in Norwalk
Events in Norwalk · 12 guests

28' Bertram around islands in Norwalk

4.8
$195/hour
31’ Bertram Classic with captain. Greenport NY
Events in Greenport · 6 guests

31’ Bertram Classic with captain. Greenport NY

5.0
$250/hour
36ft Vintage Yacht Marlinspike Charter in Sag Harbor, New York
Events in Sag Harbor · 6 guests

36ft Vintage Yacht Marlinspike Charter in Sag Harbor, New York

5.0
$375/hour
Experience the Candlewood Lake in CT
Powerboats in Brookfield · 6 guests

Experience the Candlewood Lake in CT

5.0
$175/hour
Sunset, 3-6 Hour Cruises on Spacious Cruiser - Norwalk, Westport, Rowayton CT
Events in Norwalk · 6 guests

Sunset, 3-6 Hour Cruises on Spacious Cruiser - Norwalk, Westport, Rowayton CT

5.0
$350+/hour
Slide Pontoon on Candlewood Lake
Powerboats in New Fairfield · 8 guests

Slide Pontoon on Candlewood Lake

5.0
$165+/hour
24ft Cobia: Center Console Versatility- Captain Optional! 3000+ Charters
Powerboats in Stamford · 8 guests

24ft Cobia: Center Console Versatility- Captain Optional! 3000+ Charters

5.0
$200/hour
Tour Gold Coast of Connecticut, fishing, or have a boat party and swim
Powerboats in Westport · 12 guests

Tour Gold Coast of Connecticut, fishing, or have a boat party and swim

5.0
$195/hour
Cruisers 420 Express Cruiser Rental in Long Island Sound
Events in Greenwich · 6 guests

Cruisers 420 Express Cruiser Rental in Long Island Sound

4.8
$425+/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
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
Spend sunset on Long Island sound | 28ft Bertram Sportfisher Yacht
Fishing in Fairfield · 12 guests

Spend sunset on Long Island sound | 28ft Bertram Sportfisher Yacht

5.0
$195/hour
32' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

5.0
$300/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
30ft 2022 Pontoon w/ Slide- Stamford, CT! Charter Specialists. Over 3000+ Trips
Powerboats in Stamford · 10 guests

30ft 2022 Pontoon w/ Slide- Stamford, CT! Charter Specialists. Over 3000+ Trips

5.0
$300/hour
Classic Motor Yacht in Hampton's, Long Island
Powerboats in Sag Harbor · 12 guests

Classic Motor Yacht in Hampton's, Long Island

5.0
$750/hour
 32' 2020 Sundancer + Seabob Yacht Rental in Sag Harbor, New York
Events in Sag Harbor · 12 guests

32' 2020 Sundancer + Seabob Yacht Rental in Sag Harbor, New York

5.0
$1,063/hour
Tubing and Water Fun on Candlewood Lake
Powerboats in New Fairfield · 10 guests

Tubing and Water Fun on Candlewood Lake

5.0
$185/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
 18' 2025 Small Fun Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 12 guests

18' 2025 Small Fun Boat Rental in Sag Harbor, New York

New
$545/hour

Connecticut Reviews

  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. 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!

  3. 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.

  4. 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.

  5. 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!

  6. Ilona

    Ilona

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

    We had a great day out on the water with Nate! He was very flexible with starting a bit later due to the weather and had great communication overall. He and his crew are very kind and professional. The boat is great and this is a must-do while you are in the Hamptons!