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Browse Connecticut Boat Rentals.

Page 1 of 489 listings

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
$600/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
$180+/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
Best of 2023
$33/person
Sunset & Lighthouse Cruises on Spacious Cruiser - Norwalk, Westport, Rowayton CT
Powerboats in Norwalk · 6 guests

Sunset & Lighthouse Cruises on Spacious Cruiser - Norwalk, Westport, Rowayton CT

5.0
$310+/hour
Enjoy 80ft Chris-craft In New York!!
Events in Sag Harbor · 40 guests

Enjoy 80ft Chris-craft In New York!!

New
Superowner
Best of 2023
$1,375+/hour
28' Bertram around islands in Norwalk
Events in Norwalk · 12 guests

28' Bertram around islands in Norwalk

4.8
$165/hour
Luxury Cruiser 25ft Four Winns Vista
Tours in Stratford · 6 guests

Luxury Cruiser 25ft Four Winns Vista

5.0
$125/hour
42' Catalina ailing Yacht - Two Hour Sailing Charter - Sunset Sail Available
Sailing in Sag Harbor · 6 guests

42' Catalina ailing Yacht - Two Hour Sailing Charter - Sunset Sail Available

New
$400/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
River Cruise, Sunset Cruise, Day party, Night Cruise
Tours in New Haven · 6 guests

River Cruise, Sunset Cruise, Day party, Night Cruise

5.0
$50/person
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
$165/hour
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
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
32' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

5.0
$300/hour
29' 2022 Sea Ray SDX Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 12 guests

29' 2022 Sea Ray SDX Boat Rental in Sag Harbor, New York

New
$743/hour
 18' 2025 Volt Electric Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 12 guests

18' 2025 Volt Electric Boat Rental in Sag Harbor, New York

New
$545/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
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
$165/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
Luxury 38 Express Cruiser - Sag Harbor, Greenport, Shelter Island, Southampton!
Events in Sag Harbor · 8 guests

Luxury 38 Express Cruiser - Sag Harbor, Greenport, Shelter Island, Southampton!

5.0
$495/hour
Slide Pontoon on Candlewood Lake
Powerboats in New Fairfield · 10 guests

Slide Pontoon on Candlewood Lake

5.0
$150/hour
51' 2022 Azimut Atlantis + 2 Seabobs Yacht Charter in East Hampton, New York
Events in East Hampton · 12 guests

51' 2022 Azimut Atlantis + 2 Seabobs Yacht Charter in East Hampton, New York

New
$1,632+/hour
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

Connecticut Reviews

  1. 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.

  2. Ashley

    Ashley

    Luxury 38 Express Cruiser - Sag Harbor, Greenport, Shelter Island, Southampton!

    The PERFECT summer day! Gary and Connie were absolutely wonderful and so accommodating. The vessel was perfect and in pristine condition! Wish I’d booked for much longer but can’t wait to run it back!

  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