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Sleepy Hollow, New York Boat Rentals & Yacht Charters

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
40ft Pirate Ship Themed Catamaran in Dobbs Ferry
Sailing in New York · 12 guests

40ft Pirate Ship Themed Catamaran in Dobbs Ferry

5.0
$289/hour
Luxury Miami Yacht Charter - 90' Pershing "Regal"
Events in New York · 12 guests

Luxury Miami Yacht Charter - 90' Pershing "Regal"

New
$1,500/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 · 8 guests

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

5.0
$190+/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
$575/hour
NYC Harbor Cruise out of Englewood NJ
Powerboats in Manhattan · 6 guests

NYC Harbor Cruise out of Englewood NJ

5.0
$300/hour
Enjoy the sun, Sunset/Nightfall, or summer night sky, or go for a swim.
Powerboats in Bronx · 7 guests

Enjoy the sun, Sunset/Nightfall, or summer night sky, or go for a swim.

New
$250/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
$300/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
$225+/hour
32' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

5.0
$300/hour
Luxurious 65' Sunseeker Manhattan serving NYC
Events in Port Washington · 12 guests

Luxurious 65' Sunseeker Manhattan serving NYC

New
$875+/hour
Beautiful 62' Sea Ray with Water Toys serving Long Island, NY
Powerboats in Port Washington · 12 guests

Beautiful 62' Sea Ray with Water Toys serving Long Island, NY

5.0
$850+/hour
53'Princess serving NYC, Sag Harbor, Connecticut, and more on Long Island.
Events in Port Washington · 12 guests

53'Princess serving NYC, Sag Harbor, Connecticut, and more on Long Island.

New
$750+/hour
59ft Sea Ray L590 Fly Bridge Yacht Charter from Port Washington, NY
Powerboats in Port Washington · 12 guests

59ft Sea Ray L590 Fly Bridge Yacht Charter from Port Washington, NY

New
$1,250/hour
Luxe 44ft Galeon w/ an Underwater Scooter & Paddleboard serving Northeastern US
Events in Port Washington · 10 guests

Luxe 44ft Galeon w/ an Underwater Scooter & Paddleboard serving Northeastern US

New
$680+/hour
46' Silverton Motor Yacht Charters in Port Washington, New York
Events in Port Washington · 6 guests

46' Silverton Motor Yacht Charters in Port Washington, New York

New
$538/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
Port washington, NY -  Private Yacht Charter - 43' Azimut Flybridge
Events in Port Washington · 12 guests

Port washington, NY - Private Yacht Charter - 43' Azimut Flybridge

4.9
$500/hour
Luxury Galeon 560 Fly Yacht |   Luxury Cruises & Swimming | Captain included
Events in Port Washington · 12 guests

Luxury Galeon 560 Fly Yacht | Luxury Cruises & Swimming | Captain included

New
$720+/hour
Luxurious 60ft Cruisers Cantius serving NYC, Sag Harbor and Montauk
Events in Glen Cove · 12 guests

Luxurious 60ft Cruisers Cantius serving NYC, Sag Harbor and Montauk

New
$738+/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
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht
Sailing in Port Washington · 12 guests

Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht

4.8
Superowner
$219/hour

Sleepy Hollow Reviews

  1. RV

    Renee

    Port washington, NY - Private Yacht Charter - 43' Azimut Flybridge

    Captain Scott was absolutely fantastic! Found us the perfect spots for swimming and helped ensure we had a great day at sea. The boat was everything we could ask for, great for groups! Would love to do that again!

  2. NR

    Naomi

    Port washington, NY - Private Yacht Charter - 43' Azimut Flybridge

    What a wonderful afternoon on the water! The boat is beautiful. We were a group of 11 and this boat was perfect size for us. Everything was super clean. The crew were helpful and were even able to help us arrange a swim. We had a great experience and would definitely do it again.

  3. Tara

    Tara

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

    I reached out to book this boat around 10am and connected with Capt Glenn who was the owner of the boat. After easy communication, I was on the boat with my 3 children at 1pm (3 hours later!) with Capt Brian and his first mate, Serena. They were both very kind and easy to be around. We just wanted a lazy day on the water that that is exactly what they gave us. The boat was clean and everything we had hoped for. Without hesitation, I highly recommended Glenn, his boat and his staff. Thank you, Glenn, Brian and Serena for an awesome afternoon.

  4. JP

    Jenny

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    I can’t say enough about how great this experience was! I celebrated my birthday, and it will definitely be one of the most memorable ones. The boat was beautiful, clean, and spacious. The best part was having Captain Rick on board. He was knowledgeable, kind, and made us feel very comfortable the entire time. He showed us around, shared interesting information, and made sure we had a smooth and relaxing sailing trip. Truly an unforgettable experience!

  5. PC

    Peter

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Had a GREAT day on the sound with Captain Rick. His boat is in excellent condition clean comfortable and so well maintained. Rick is a very experienced sailor with whom we always felt safe. He showed us all over Long Island Sound, which he knows so well. I highly recommend Rick for a great day on the water!!

  6. 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!