Sailo
Boat rental & yacht charters worldwide
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Sailo
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Monroe County, NY, USA
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200 boat rentals in Monroe County, NY
Create memories on the North Fork!
Greenport, New York • Captain Included
31 feet • 6 guests • Bertram • Flybridge • 1973
$1,600
per 4 hours
Sail NYC's skyline aboard a classic sailboat!
5.0
(41)
New York, New York • Captain Included
42 feet • 6 guests • Tayana • Tayana 37 • 1983
$655
per 2 hours
Enjoy a private charter of the classic sailing yacht Ventura
5.0
(5)
New York, New York • Captain Included
72 feet • 30 guests • Herreshoff • Custom • 1921
$3,900
per 2 hours
New 2021 Aquila 362 SEABOB in MONTAUK
5.0
(1)
Montauk, New York • Captain Available
36 feet • 12 guests • Aquila • 36 • 2021
$4,149
per 4 hours
2023 50′ Pardo | Fast, Beautiful, and Made for Long Days on the Water
5.0
(1)
Montauk, New York • Captain Included
50 feet • 12 guests • Pardo • 50 Pardo • 2023
$6,500
per 4 hours
Glide the Waves with us!
Sag Harbor, New York • Captain Available
27 feet • 12 guests • Sea Ray • SDX • 2024
$2,675
per 4 hours
Elevate Your Escape: The 2025 De Antonio D29
Sag Harbor, New York • Captain Available
29 feet • 10 guests • De Antonio • D29 • 2025
$2,910
per 4 hours
Set Sail on Beautiful Long Island Sound!
5.0
(3)
Port Washington, New York • Captain Included
47 feet • 6 guests • Beneteau • Oceanis 473 • 2006
$617
per 2 hours
Enjoy luxury and comfort aboard this beautiful 50' motor yacht in New York
Sag Harbor, New York • Captain Available
50 feet • 13 guests • AZIMUT • ATLANTIS • 2022
$7,697
per 4 hours
Get ready to spend great time aboard 62′ Pershing in New York
Sag Harbor, New York • Captain Available
62 feet • 13 guests • Pershing • 62 • 2017
$11,860
per 4 hours
Climb on board PARDO 43 to explore amazing New York
Sag Harbor, New York • Captain Available
43 feet • 13 guests • PARDO • 43 • 2021
$5,923
per 4 hours
Corporate Team Building on a Sailboat!
Oyster Bay, New York • Captain Included
40 feet • 6 guests • Match • 40s • 2000
$2,000
per 8 hours
Built for Long Summer Days on the Water
Montauk, New York • Captain Included
80 feet • 12 guests • pershing • 80 GTX • 2025
$14,000
per 4 hours
Brand New Convertible Riva 76 Bahamas
Sag Harbor, New York • Captain Included
76 feet • 12 guests • Riva • Bahamas • 2021
$13,500
per 4 hours
47 ft Luxury yacht NYC
4.8
(6)
Brooklyn, New York • Captain Available
47 feet • 12 guests • meridian • 441 • 2015
$1,200
per 2 hours
Fishing Charter in New York City
5.0
(1)
Bergen Beach, New York • Captain Included
22 feet • 3 guests • Cape Craft • 22' bay • 2005
$550
per 8 hours
85' SUNSEEKER LUXURY YACHT in the Hamptons
Sag Harbor, New York • Captain Included
85 feet • 12 guests • Sunseeker • 85 • 2005
$10,650
per 4 hours
Cruise Montauk on this pontoon boat with toys
Montauk, New York • Captain Included
40 feet • 33 guests • Custom • Custom • 1996
$800
per 2 hours
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