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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,469 Reviews)

Page 39 of 39933 listings

 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
Best of 2026
Snoozed - Active 02 Oct 2026
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
Snoozed - Active 17 Sep 2026
Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!
Sailing in New Orleans · 6 guests

Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

5.0
Snoozed - Active 02 Jan 2027
52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

5.0
Snoozed - Active 02 Jan 2027
Efoiling at deer creek reservoir
Adventures in Salt Lake City · 1 guest

Efoiling at deer creek reservoir

5.0
Snoozed - Active 15 Jan 2027
Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

5.0
Snoozed - Active 02 Jan 2027
SeaDoo Switch Sport *5 ADULTS*
Powerboats in Texas · 9 guests

SeaDoo Switch Sport *5 ADULTS*

5.0
Snoozed - Active 02 Oct 2026
Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.
Sailing in Brooklyn · 6 guests

Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.

5.0
Snoozed - Active 02 Jan 2027
Bali 43 Complete comfort Catamaran
Sailing in Marina del Rey · 12 guests

Bali 43 Complete comfort Catamaran

5.0
Snoozed - Active 14 Sep 2026
51ft Bavaria Cruiser – Shelter Island San Diego Luxury Ocean Charter
Sailing in San Diego · 12 guests

51ft Bavaria Cruiser – Shelter Island San Diego Luxury Ocean Charter

New
Snoozed - Active 02 Jan 2027
46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica
Sailing in Playa Flamingo · 40 guests

46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica

5.0
Snoozed - Active 02 Nov 2026
Islander 36 - The Perfect Sailing Yacht for San Francisco Bay
Sailing in Sausalito · 6 guests

Islander 36 - The Perfect Sailing Yacht for San Francisco Bay

5.0
Snoozed - Active 02 Jan 2027
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
Snoozed - Active 17 Sep 2026
Sausalito: 41ft Jeanneau 410 Sun Odyssey Sailing Charter for Up to 10 Guests
Sailing in Sausalito · 10 guests

Sausalito: 41ft Jeanneau 410 Sun Odyssey Sailing Charter for Up to 10 Guests

New
Snoozed - Active 23 Sep 2026
40' Luxury Cruising Sailboat – Private Charters for 8 Guests
Sailing in Richmond · 8 guests

40' Luxury Cruising Sailboat – Private Charters for 8 Guests

New
Snoozed - Active 23 Sep 2026
The Gallivanders Ultimate Sailing Adventure
Sailing in Nassau · 12 guests

The Gallivanders Ultimate Sailing Adventure

New
Snoozed - Active 03 Jan 2027
42' Luxury Catamaran – Private San Francisco Bay Charters for 12 - Oakland
Sailing in Oakland · 12 guests

42' Luxury Catamaran – Private San Francisco Bay Charters for 12 - Oakland

New
Snoozed - Active 23 Sep 2026
Lagoon 420 Hybrid Eco Friendly Electric Catamaran
Sailing in Guna Yala Comarca · 4 guests

Lagoon 420 Hybrid Eco Friendly Electric Catamaran

New
Snoozed - Active 27 Mar 2027
Luxury Bay Sailing Experience – Private 42' Yacht, Comfortably Seats 10 Guests
Sailing in Oakland · 10 guests

Luxury Bay Sailing Experience – Private 42' Yacht, Comfortably Seats 10 Guests

New
Snoozed - Active 23 Sep 2026
Catalina Capri 22 Daysailer - Simple to Sail in Seattle
Sailing in Seattle · 5 guests

Catalina Capri 22 Daysailer - Simple to Sail in Seattle

New
Snoozed - Active 11 Sep 2026
Seattle Sailing Adventure – Wicked Wind Catalina 275 Sport
Sailing in Seattle · 4 guests

Seattle Sailing Adventure – Wicked Wind Catalina 275 Sport

New
Snoozed - Active 11 Sep 2026

Sailing Reviews in United States

  1. MC

    Marco

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian is a great captain. You can truly see he loves to sail. The best way to be lead on an adventure is by someone who is passionate. He has a lot of knowledge regarding the cityscapes the surround our rivers here in NYC. I have seen the city from the sky during heli rides and can say sailing was so much better. Will definitely bring more visiting family and friends to sail with him.

  2. RA

    Rosette

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Captain Ian was professional, knowledgeable, and created a relaxed, welcoming atmosphere from the moment we stepped aboard. The boat was beautiful, the views of the Manhattan skyline were incredible, and the entire experience felt both peaceful and memorable. Captain Ian made sure everyone was comfortable while sharing interesting insights along the way. If you’re looking for a private sailing experience on the Hudson that’s both scenic and personal, I highly recommend booking with Captain Ian. We can’t wait to sail again!

  3. PS

    Pierangela

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    We had an amazing time on the boat! Ian was incredibly attentive, friendly, and made sure we were comfortable throughout the entire trip. The boat was beautiful, very clean, and well maintained. The cruise itself was absolutely incredible relaxing, scenic, and a perfect experience from start to finish. We would definitely recommend this tour to anyone looking for a memorable day on the water. Thank you, Ian!

  4. JK

    Junghun Jemma

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    With Ian, our special 250th July 4th celebration became even more unforgettable. From the marina, we enjoyed spectacular views of the fireworks. What made the evening truly exceptional was Ian's personalized dock tour—something only possible because of his close relationship with the marina. It gave us experiences we never expected, including seeing the historic tall ships, watching the special boats on the river, and getting a close look at the Macy's fireworks barges as they prepared for the show. Ian went out of his way to make sure our family had a remarkable experience. Seeing my granddaughter dancing on the deck of his romantic sailboat to the music Ian thoughtfully selected, with the fireworks lighting up the sky in front of her, is a memory we will cherish forever. Thank you, Ian, for making our Independence Day celebration so magical. We will definitely be back on your sailboat for another special occasion soon!

  5. Andrew

    Andrew

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian is a wonderful host! We had a romantic evening on his boat, getting to see the sunset and the city. Ian is very responsive, professional, and gracious, we definitely recommend him!

  6. MM

    Mordechai

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian is an incredible host that is super passionate about his work. Every detail is thought out from the onset. He is very inviting and chilled yet extremely professional. Ian guided us through everything we would like to know about and gave many of his experienced recommendations. We had an incredible time out at sea, and are looking forward to booking our next voyage!