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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,434 Reviews)

Page 14 of 39928 listings

Limited Availability
55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!
Sailing in Marina del Rey · 12 guests

55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

4.9
Superowner
Best of 2026
$185+/hour
Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia
Sailing in Cartagena · 18 guests

Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

5.0
$1,700/day
🎉 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
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
★ 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
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
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
Chaparral 256 Family Cabin Cruiser
Powerboats in Jersey City · 9 guests

Chaparral 256 Family Cabin Cruiser

5.0
$275/hour
Curacao Private Sunset Tour Deluxe
Sailing in Santa Barbara Plantation · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/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 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
Leopard 53 Power Catamaran (25-ft wide deck space)
Powerboats in Fort Lauderdale · 12 guests

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

New
$400+/hour
No Rush Sailing Tours
Sailing in San Pedro · 16 guests

No Rush Sailing Tours

5.0
$125/day
Luxury Catamaran Lagoon ' Capacity up to 18
Powerboats in Cartagena · 18 guests

Luxury Catamaran Lagoon ' Capacity up to 18

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

44' Luxury Catamaran Private Sailing Adventure

5.0
$412/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
$33/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
Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste
Sailing in Coco · 10 guests

Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

5.0
$165/hour
BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!
Sailing in Marina del Rey · 12 guests

BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!

5.0
Superowner
$425/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
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
$181/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

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. Christie

    Christie

    BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!

    We had such a great evening sailing, swimming off the coast of Playa and cruising the Marina! Alex and Zach were amazing! Thank you!

  3. 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!

  4. TB

    Tom

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

    I rented this boat for my 40th birthday party with around 40 adults during Sea Fair and it was a great experience.

  5. YF

    Yosi

    55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

    We had an incredible time on our three‑hour boat trip. The ride itself was beautiful—calm water, great views, and the perfect mix of relaxation and adventure—but what truly made the experience stand out was the captain. He was an absolute pleasure to be with: friendly, knowledgeable, and genuinely invested in making sure everyone on board felt comfortable and had a great time. His easygoing personality and passion for what he does turned a simple outing into a memorable experience. I’d happily sail with him again.

  6. SA

    Sam

    55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

    A truly wonderful experience of a lifetime! The team was exceptionally professional and attentive throughout our 3-hour boat trip. They ensured continuous communication, prioritized safety at every step, and took great care of the kids, making the entire experience smooth, enjoyable, and worry-free. Highly recommended for families!