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Browse Connecticut Boat Rentals.

Page 1 of 490 listings

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
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
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
28' Bertram around islands in Norwalk
Events in Norwalk · 12 guests

28' Bertram around islands in Norwalk

4.8
$195/hour
52’ Maxum FlyBridge Yacht - NY & NJ Pick up Available
Events in Montauk · 12 guests

52’ Maxum FlyBridge Yacht - NY & NJ Pick up Available

5.0
$400+/hour
Slide Pontoon on Candlewood Lake
Powerboats in New Fairfield · 8 guests

Slide Pontoon on Candlewood Lake

5.0
$165+/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
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
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
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
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
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
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' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

5.0
$300/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
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
Instant Book
53 ft. Luxury yacht for Day Charters on the East End of Long Island
Events in Sag Harbor · 10 guests

53 ft. Luxury yacht for Day Charters on the East End of Long Island

5.0
$995/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
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
$240+/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
36' 2025 De Antonio + Seabob Yacht Rental in Sag Harbor, New York
Events in Sag Harbor · 12 guests

36' 2025 De Antonio + Seabob Yacht Rental in Sag Harbor, New York

New
$1,063/hour
Brand New 50' Pardo Motor Yacht in The Hamptons
Events in Montauk · 12 guests

Brand New 50' Pardo Motor Yacht in The Hamptons

New
$940+/hour

Top Destinations Nearby

Connecticut Reviews

  1. KH

    Katy

    42' Catalina Sailing Yacht in the Hamptons

    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!

  2. JS

    Josh

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

    Matt was Great! went out with my 8 year-old son, girlfriend and a friend for a three hour trip on the boat. Checked out the beautiful coastline and a couple of awesome swimming holes spent some time on the paddleboard.. such an awesome day. Can’t wait to take another trip out with Matt. Beautiful boat, very professional.!

  3. MP

    Merritt

    Cruisers 420 Express Cruiser Rental in Long Island Sound

    Captain Dirk and his boat made our Fourth of July one to remember! From the moment we stepped on board, Dirk was the picture of professionalism—warm, respectful, and incredibly knowledgeable. I’m 39 weeks pregnant and felt completely safe and cared for the entire time. The boat itself was pristine, spacious, and so comfortable—perfect for taking in the fireworks in style. Dirk went above and beyond to make sure everyone had a great time. Truly one of the best boating experiences I’ve ever had. Can’t recommend him enough!

  4. CS

    Courtney

    52’ Maxum FlyBridge Yacht - NY & NJ Pick up Available

    Glenn and his crew are truly amazing hosts. The trip was everything we wanted and more. Leading up to the trip, Glenn was super responsive, accommodating, and flexible when I needed to change the date and time of the booking. The day of, they took us on a beautiful ride, including a wonderful swimming excursion with floats. It was everything I wanted for my birthday and I would definitely book with Glenn again!

  5. MM

    Molly

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

    Captain Alan and his boat are incredible!! We brought a group of girls for a bachelorette trip and spending the day out on the water was SO much fun. Captain Alan was so communicative and helpful throughout the process and leading up to the day of our charter. He had everything we could have needed on board and was so helpful the whole trip!! His deckie was also so incredibly helpful - we could not have asked for a better time!!! He even had floats and a paddleboard to use which was awesome. Highly recommend to anyone looking for a fun day on the water!! 10/10, no notes!!

  6. SM

    Shannon

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

    Brian was amazing! From the booking to our trip, he was great to work with. Professional and fun. We would recommend him to anyone. Thanks Brian!!