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Greenwich, Connecticut Boat Rentals

Page 1 of 124 listings

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
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
$250/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
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour
32' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

5.0
$300/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
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
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour
Sit Back, Relax and Enjoy on a Formula 260 SS!!!
Powerboats in Bronx · 6 guests

Sit Back, Relax and Enjoy on a Formula 260 SS!!!

New
$175+/hour
Fun in the Sun with Manhattan skyline in the background
Sailing in Bronx · 6 guests

Fun in the Sun with Manhattan skyline in the background

New
$150/hour
Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!
Sailing in Bronx · 6 guests

Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!

New
$150/hour
ASA practice sailing exercizes
Tours in Bronx · 6 guests

ASA practice sailing exercizes

New
$150/hour
Enjoy Oysterbay on a speed boat
Powerboats in Oyster Bay · 6 guests

Enjoy Oysterbay on a speed boat

New
Best of 2025
$150/hour
50’ Yacht in Oysterbay, Cruise, Paddleboard, Kayak, Tubing
Events in Oyster Bay · 12 guests

50’ Yacht in Oysterbay, Cruise, Paddleboard, Kayak, Tubing

5.0
Best of 2025
$499+/hour
Its "Play Time", Lets go have some fun on the water.
Powerboats in Oyster Bay · 12 guests

Its "Play Time", Lets go have some fun on the water.

5.0
Best of 2025
$365+/hour
45ft Sundeck Motor Yacht in Glen Cove
Events in Glen Cove · 12 guests

45ft Sundeck Motor Yacht in Glen Cove

New
Best of 2025
$395/hour
Okean 52’ Luxury Yacht – One of Only 3 in North America – NYC & LI Charters
Events in Glen Cove · 12 guests

Okean 52’ Luxury Yacht – One of Only 3 in North America – NYC & LI Charters

New
$770+/hour
40ft Formula 400 SSC-Western Long Island, Connecticut, Westchester, NYC
Events in Glen Cove · 6 guests

40ft Formula 400 SSC-Western Long Island, Connecticut, Westchester, NYC

New
$750+/hour
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$190+/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
 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
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
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
Hudson River Tours: West Point, Statue of Liberty, Sleepy Hollow Lighthouse.
Tours in Tarrytown · 6 guests

Hudson River Tours: West Point, Statue of Liberty, Sleepy Hollow Lighthouse.

5.0
$315+/hour

Greenwich Reviews

  1. 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!

  2. MJ

    Marc and

    Cruisers 420 Express Cruiser Rental in Long Island Sound

    Captain Dirk is by far the best Captain around! He was extremely flexible and polite. Family and kid friendly. He invited my kids to learn about the boat, pointed out the sites around and made us feel like we were "apart of his crew." His boat was immaculate, very well taken care of. To date, he is the only Captain I've charted with who wore the full captains uniform. I was highly impressed and would recommend and use him again in the future! THANK YOU CAPTAIN DIRK! My family had a fabulous time!

  3. Helen

    Helen

    32' Luxurious Yacht Certified Express Cruiser

    Joseph’s boat was incredibly clean and comfortable, and Joseph was super responsive and accommodating the entire time leading up to our trip. We had a great time swimming at Peanut Island and cruising along the Intercoastal. Would highly recommend to anyone!

  4. BV

    Betsy

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

    Excellent experience, and this was my first time using this service to rent a boat. Luke was very helpful in coordinating everything and even in watching the weather. Chip was our captain and he was super knowledgeable and accommodating to my family. We enjoyed our time on the pontoon, felt very safe going down the slide, and we had so much fun! Will book again soon!

  5. PP

    PARNAZ

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Captan Rick's boat trip was an incredible experience that I highly recommend ! The planning was flawless, offering a perfect blend of activities. Captan Rick excellent communication and warm demeanor made the journey even more enjoyable. This boat trip is a must-do for anyone looking for an unforgettable day on the water!

  6. KB

    Keisha

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    The boat is large enough to comfortably fit a group of 10. We learned some new terms and had a sailing lesson. Capt Rick is a great vibe and fits right in with the group from kids to adult, the experience was one of a kind. Boat is very well kept and has lots of lounging areas inside and outside.