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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,464 Reviews)

Page 38 of 39931 listings

Standart Trip Luxury Catamaran in Gulf of Papagayo & Water Activities
Sailing in Playa Hermosa · 25 guests

Standart Trip Luxury Catamaran in Gulf of Papagayo & Water Activities

New
$750/hour
Romantic Sunset Sailing in La Boquilla, Bolívar
Sailing in La Boquilla · 4 guests

Romantic Sunset Sailing in La Boquilla, Bolívar

New
$260/hour
Aqua Catamaran 65ft | Private Group Cruises in Guanacaste
Sailing in Playa Hermosa · 46 guests

Aqua Catamaran 65ft | Private Group Cruises in Guanacaste

New
$895+/hour
44' LAGOON STANDARD CATAMARAN - RIVIERA MAYA
Sailing in Puerto Aventuras · 20 guests

44' LAGOON STANDARD CATAMARAN - RIVIERA MAYA

New
$333/hour
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
1986 22ft Catalina Sailboat in Holland, Michigan
Sailing in Holland · 6 guests

1986 22ft Catalina Sailboat in Holland, Michigan

New
$75+/hour
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
Sail A Proven World Circumnavigation Yacht | 30' Classic
Sailing in Vancouver · 4 guests

Sail A Proven World Circumnavigation Yacht | 30' Classic

New
$260/hour
St. Pete Sunset Sails - 34ft Sailboat
Sailing in Saint Petersburg · 4 guests

St. Pete Sunset Sails - 34ft Sailboat

New
$160/hour
Lagoon 46Ft - Your Private Luxury Escape on the Pacific
Events in Guanacaste Province · 30 guests

Lagoon 46Ft - Your Private Luxury Escape on the Pacific

New
$650+/hour
Gold Coast 65ft Catamaran in Playas del Coco
Sailing in Coco · 45 guests

Gold Coast 65ft Catamaran in Playas del Coco

New
$1,330+/hour
All Inclusive 45´ Luxury Catamaran in Baja California Sur
Sailing in Centro · 8 guests

All Inclusive 45´ Luxury Catamaran in Baja California Sur

New
$272/hour
SAILING THE GULF OF NICOYA ON A LUXURY 37" YACHT
Sailing in Punta Arenas · 4 guests

SAILING THE GULF OF NICOYA ON A LUXURY 37" YACHT

New
$150/hour
Sail into adventure in Costa Rica, playa Flamingo
Sailing in Playa Flamingo · 12 guests

Sail into adventure in Costa Rica, playa Flamingo

New
$2,640/hour
Bayliner Deck Boat Rental at Lake wallenpaupack!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Lake wallenpaupack!

New
$115/hour
Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan
Sailing in Holland · 6 guests

Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan

New
$150/hour
22ft SeaSwirl Striper Center Console
Fishing in Los Angeles · 8 guests

22ft SeaSwirl Striper Center Console

New
$175/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
Stay Warm and dry, year-round cruising San Juan’s and Seattle charters
Sailing in Seattle · 6 guests

Stay Warm and dry, year-round cruising San Juan’s and Seattle charters

New
$350+/hour
Luxury 47' Lagoon Catamaran Charter - Snorkel, Sunset, Overnight Stays
Sailing in Marina Vallarta · 25 guests

Luxury 47' Lagoon Catamaran Charter - Snorkel, Sunset, Overnight Stays

New
$237/hour
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/hour
Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
Sailing in Gloucester · 60 guests

Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

New
$1,200+/hour
Unwind in Sunlit Luxury: Experience 360° Views Aboard This One-of-a-Kind Yacht!
Sailing in Stock Island · 12 guests

Unwind in Sunlit Luxury: Experience 360° Views Aboard This One-of-a-Kind Yacht!

New
$325+/hour
 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

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!