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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,463 Reviews)

Page 14 of 39932 listings

Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12
Sailing in San Francisco · 12 guests

Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12

5.0
$876+/hour
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 4 guests

★ 28' Classic Schooner in Rockland, Maine ★

5.0
$175/hour
!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic
Events in La Romana · 100 guests

!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic

5.0
Superowner
Best of 2026
$60/hour
Limited Availability
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
46' Lagoon 450 Sailing Catamaran - 12 Guests - Kemah Boardwalk Marina, Galv Bay
Sailing in Kemah · 12 guests

46' Lagoon 450 Sailing Catamaran - 12 Guests - Kemah Boardwalk Marina, Galv Bay

5.0
$512+/hour
Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

5.0
$195/hour
Yacht 46ft Sea Ray, Free pick up transporation Hotel Marina One way
Tours in Cancún · 15 guests

Yacht 46ft Sea Ray, Free pick up transporation Hotel Marina One way

5.0
$210/hour
🎉 Miches All Stars Cruise All Inclusive Luxury Yacht entertainment
Powerboats in Dominican Republic · 150 guests

🎉 Miches All Stars Cruise All Inclusive Luxury Yacht entertainment

5.0
Superowner
Best of 2026
$17/hour
50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle
Sailing in Seattle · 47 guests

50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle

4.9
$1,050/hour
Curacao Private Sunset Tour Deluxe
Sailing in Santa Barbara Plantation · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/hour
Chaparral 256 Family Cabin Cruiser
Powerboats in Jersey City · 9 guests

Chaparral 256 Family Cabin Cruiser

5.0
$275/hour
No Rush Sailing Tours
Sailing in San Pedro · 16 guests

No Rush Sailing Tours

5.0
$125/day
Leopard 53 Power Catamaran (25-ft wide deck space)
Powerboats in Fort Lauderdale · 13 guests

Leopard 53 Power Catamaran (25-ft wide deck space)

New
$400+/hour
Luxury Catamaran Lagoon ' Capacity up to 18
Powerboats in Cartagena · 18 guests

Luxury Catamaran Lagoon ' Capacity up to 18

5.0
Superowner
$180/hour
44' Luxury Catamaran Private Sailing Adventure
Sailing in Zona Hotelera Norte · 25 guests

44' Luxury Catamaran Private Sailing Adventure

5.0
$406/hour
Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!
Powerboats in Miami · 10 guests

Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!

4.3
$100+/hour
Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC
Sailing in Squamish · 10 guests

Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC

5.0
$32/hour
Exclusive Giant 60ft Sundancer Motor Yacht In Cancún, Quintana Roo
Events in Cancún · 18 guests

Exclusive Giant 60ft Sundancer Motor Yacht In Cancún, Quintana Roo

4.0
Superowner
Best of 2026
$350/hour
60' Sailing Party Catamaran in Miami Florida
Sailing in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida

4.6
$1,300/hour
Hawaiian Breeze in Marina del Rey
Sailing in Marina del Rey · 6 guests

Hawaiian Breeze in Marina del Rey

5.0
$150/hour
Shopping Tour to Isla Mujeres, Everyday 12:30 (Shared Basis)
Sailing in Isla Mujeres · 30 guests

Shopping Tour to Isla Mujeres, Everyday 12:30 (Shared Basis)

5.0
Superowner
$395/hour
62ft Lagoon 620 Catamaran – Private Cruise Experience in Newport, RI
Sailing in Newport · 12 guests

62ft Lagoon 620 Catamaran – Private Cruise Experience in Newport, RI

5.0
$1,500/hour
Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building
Sailing in Vancouver · 8 guests

Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

5.0
$179/hour
Hunter 45' - Largest Sailing Yacht in Central Texas, Lake Travis
Sailing in Lakeway · 18 guests

Hunter 45' - Largest Sailing Yacht in Central Texas, Lake Travis

5.0
$299+/hour

Sailing Reviews in United States

  1. SL

    Samantha

    Chaparral 256 Family Cabin Cruiser

    Eli was AMAZING! We had the best time for my friend’s 40th birthday and would recommend him to anyone in a heartbeat!

  2. MR

    Matthew

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

    We had a great time sailing out of Port Washington with Steven! Got to sail around the harbor to see some cool houses in Great Neck, the old lighthouse, and views of New York City in the distance. Steven was very communicative and a great captain for the morning! Would do again!

  3. KS

    Katherine

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

    Steven was an excellent host! He answered all of our questions up to the trip and met us on the dock when we got there. The boat was great and the trip was exciting, he even let us help sail! All the views were great and we loved the whole experience!

  4. JH

    John

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

    Four of us went out with Captain Steve for a 3 hour sunset sail. It was calm when we got on the boat. A light breeze picked up once we got underway. We sailed out of Manhasset Bay into the LI Sound. We first headed towards the Throgs Neck Bridge. When we got abreast of Kings Point and the Merchant Marine Academy, we turned around and headed back east. Steve pointed out the various islands (e.g., Hart Island) and lighthouses and coastal points (Connecticut, Larchmont, the Bronx, Whitestone and Throgs Neck Bridges, Merchant Marine Academy, Manhattan skyline in the distance, etc.) we saw, providing appropriate history and commentary along the way. He answered numerous questions. He was a most amiable host. The boat was in great shape, clean and well maintained. We recommend this experience most highly.

  5. LF

    Lena

    Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

    Amazing trip! Eric was fantastic. He asked us what we wanted to do, and he took us to his favorite spots. We went swimming and jumped off rocks. He told us very interesting stories and was extremely friendly. He made the whole experience better. He made us feel like the boat was our own. Great time, amazing boat. I’d definitely book him again!

  6. Kelly

    Kelly

    Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

    Eric was very prompt, accommodating and took great care of us on our last minute booking. He actually timed everything perfectly for a late afternoon, cruise out into the gulf, searching for dolphins, and wayward pirates, caught the sunset perfectly as we were returning to the marina. We all had a blast, great conversation, and just a good time with great people.