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Browse Connecticut Boat Rentals.

Page 1 of 487 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 · 6 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
$200+/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
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
28' Bertram around islands in Norwalk
Events in Norwalk · 12 guests

28' Bertram around islands in Norwalk

4.8
$195/hour
30ft 2022 Pontoon w/ Slide - Stamford, CT!
Powerboats in Stamford · 10 guests

30ft 2022 Pontoon w/ Slide - Stamford, CT!

5.0
$450/hour
Instant Book
Slide Pontoon on Candlewood Lake
Powerboats in New Fairfield · 8 guests

Slide Pontoon on Candlewood Lake

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

32' Luxurious Yacht Certified Express Cruiser

5.0
$300/hour
42' Catalina Sailing Yacht in the Hamptons - 4 Hours
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 4 Hours

5.0
$325/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
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
$325/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
 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
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
$300/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
Instant Book
North Fork Land & Sea: Perfect Southwind 2400SD for Sun, Sea and Harbor Hopping!
Powerboats in Greenport West · 10 guests

North Fork Land & Sea: Perfect Southwind 2400SD for Sun, Sea and Harbor Hopping!

5.0
$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
 Welcome aboard embark on our 38ft charter relax, and enjoy Sunsets Cruises
Events in Norwalk · 6 guests

Welcome aboard embark on our 38ft charter relax, and enjoy Sunsets Cruises

5.0
$285+/hour
Instant Book
Luxury Cruiser 25ft Four Winns Vista
Powerboats in Stratford · 6 guests

Luxury Cruiser 25ft Four Winns Vista

5.0
$125/hour
Instant Book
Fun on Candlewood Lake 2022 G23 Wakeboarding, Surfing, Lake Cruise
Powerboats in New Milford · 8 guests

Fun on Candlewood Lake 2022 G23 Wakeboarding, Surfing, Lake Cruise

5.0
$179+/hour
Instant Book
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

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Connecticut Reviews

  1. SA

    Stefana

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

    Beautiful boat and our Capitan Hagen was amazing! We travelled from out of town and will definitely book again next time we come to town. 10/10 overall aesthetic and vibes!

  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