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Fairfield, Connecticut Boat Rentals

Page 1 of 124 listings

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

28' Bertram around islands in Norwalk

4.8
$195/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
Welcome aboard on our 33ft charter have fun, relax & enjoy Sunset Cruises.
Events in Norwalk · 6 guests

Welcome aboard on our 33ft charter have fun, relax & enjoy Sunset Cruises.

New
$265+/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
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
Robalo 207 Center Console for Rent in Norwalk
Powerboats in Norwalk · 6 guests

Robalo 207 Center Console for Rent in Norwalk

5.0
$200/hour
24ft Cobia: Center Console Versatility- Captain Optional! 3000+ Charters
Powerboats in Stamford · 8 guests

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

New
$200/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
32' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

5.0
$300/hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour
Customized Boating Adventure on the Sound | 25ft Seacraft Pacific Center Console
Powerboats in Stamford · 6 guests

Customized Boating Adventure on the Sound | 25ft Seacraft Pacific Center Console

New
Snoozed - Active 02 Oct 2025
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
Custom Boating Adventure in Stamford, Connecticut.
Powerboats in Stamford · 5 guests

Custom Boating Adventure in Stamford, Connecticut.

5.0
Snoozed - Active 02 Aug 2025
Chartered 48' 459 Meridian Motor Yacht Package
Events in Port Jefferson · 12 guests

Chartered 48' 459 Meridian Motor Yacht Package

New
$750/hour
SPECIAL EVENT? It's A Night Club On The Water! Invite up to 29 people.
Powerboats in Port Jefferson · 30 guests

SPECIAL EVENT? It's A Night Club On The Water! Invite up to 29 people.

New
$750/hour
Tiki Boat Booze Cruise Tour in Port Jefferson, New York
Events in Port Jefferson · 29 guests

Tiki Boat Booze Cruise Tour in Port Jefferson, New York

New
$69/hour
2021 22’ Deck Boat in Northport, Long Island, New York
Powerboats in Northport · 6 guests

2021 22’ Deck Boat in Northport, Long Island, New York

4.9
$185+/hour
Instant Book
Be a Sea Pro for a Day onboard 24ft Center Console
Powerboats in Northport · 11 guests

Be a Sea Pro for a Day onboard 24ft Center Console

New
$125/hour
''Over The Top'' Malibu 24mxz Bowrider Rental in Northport, New York
Powerboats in Northport · 6 guests

''Over The Top'' Malibu 24mxz Bowrider Rental in Northport, New York

New
$541/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
Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

4.8
Superowner
$150/hour
Beautiful & Modern 35 Foot Express Cruiser!!
Events in Huntington · 6 guests

Beautiful & Modern 35 Foot Express Cruiser!!

5.0
$215+/hour
Instant Book

Fairfield Reviews

  1. CH

    Cynthia

    Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

    We had the absolute best day celebrating my birthday thanks to Captain Mark! From the moment we stepped on board, he made sure every detail was perfect. He had snacks and drinks ready for us, made sure everyone was comfortable, and truly went above and beyond to make the day special. He was so friendly and easygoing — he got along with everyone effortlessly and made us all feel welcome. One of the most memorable moments was when he pulled out his guitar and sang me “Happy Birthday.” It was such a thoughtful, personal touch that made the day feel even more magical. Throughout the entire experience, Mark paid incredible attention to detail, always checking in to make sure we were having a great time and had everything we needed. He was a great communicator leading up to the day, extremely accommodating to all of our requests, and even followed up after to make sure everything went smoothly. He also made safety a priority and got us back to shore safe and sound without a hitch. Captain Mark is not only a fantastic captain but a genuinely kind and thoughtful person. I couldn’t have asked for a better birthday or a better host. Highly, highly recommend!

  2. 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!

  3. 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.!

  4. Aden

    Aden

    Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

    Mark was super cool, and we had a great time overall. The only issue was that the zodiac boat at the front was blocking access to the bow, so we couldn’t use that part of the boat. We also wanted to swim, but there was probably a miscommunication — we ended up eating during the time we should’ve been swimming, and later Mark said it was too late. That was a bit disappointing, as we didn’t get to swim at all during our 4-hour trip. Everything felt safe and nice overall. Mark let us play any music we wanted, and everything was clean. A longer trip with more time would definitely be a better option next time.

  5. RL

    Ricky

    Beautiful & Modern 35 Foot Express Cruiser!!

    We had an amazing time with Captain Steve watching the sunset. The scenery was breathtaking, and the calmness of being out on the water made it truly unforgettable. Captain Steve was friendly, approachable, and kept the experience fun from start to finish. Highly recommend for a relaxing and memorable family outing!

  6. Tf

    Tom

    Beautiful & Modern 35 Foot Express Cruiser!!

    Steve was fantastic from start to finish through this experience. He was extremely flexible and accommodating and provided a fantastic trip for our family. We will be using him again soon