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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,447 Reviews)

Page 12 of 40 • 951 listings

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$225+/hour
Instant Book
Sailing Catamaran Yacht for up to 20 Guests in Aruba
Sailing in Oranjestad-West · 24 guests

Sailing Catamaran Yacht for up to 20 Guests in Aruba

4.7
Superowner
$675/hour
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120/hour
NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA
Sailing in Los Angeles · 12 guests

NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA

5.0
Superowner
$169+/hour
Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain
Sailing in Chicago · 6 guests

Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain

5.0
$450/hour
Experience premier service: NYC’s longest-running private sailing charter
Sailing in Manhattan · 6 guests

Experience premier service: NYC’s longest-running private sailing charter

5.0
$395/hour
⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
$700+/hour
🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.
Events in Sosúa · 150 guests

🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.

4.4
$300/hour
Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo CR - Up to 16
Sailing in Tamarindo · 16 guests

Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo CR - Up to 16

5.0
$387/hour
Instant Book
36' Private Catamaran Charter in Cozumel | Perfect for Cruise Passengers
Sailing in San Miguel de Cozumel · 15 guests

36' Private Catamaran Charter in Cozumel | Perfect for Cruise Passengers

5.0
$310/hour
Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina
Sailing in Little River · 6 guests

Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina

5.0
$150/hour
41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0
$450/hour
Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!
Sailing in Clear Lake Shores · 6 guests

Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!

5.0
$180/hour
Cancun Party Yacht 46ft Sea Ray Flybridge
Tours in Cancún · 15 guests

Cancun Party Yacht 46ft Sea Ray Flybridge

5.0
$260/hour
Sailing Sloop Hunter 40 in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Sailing Sloop Hunter 40 in Puerto Vallarta

4.7
Superowner
$165/hour
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

5.0
$175+/hour
Safe & solid sailing catamaran - Green power! Stunning beauty & great location!
Sailing in Richmond · 6 guests

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

5.0
$162+/hour
Open Bar Escape: 40ft Catamaran Charter in Cancún for up to 30 Guests
Sailing in Cancún · 30 guests

Open Bar Escape: 40ft Catamaran Charter in Cancún for up to 30 Guests

New
Superowner
$300/hour
Available in Puerto Plata  Private Yacht Experience: Beautiful Views book now
Powerboats in Puerto Plata · 100 guests

Available in Puerto Plata Private Yacht Experience: Beautiful Views book now

New
Superowner
Best of 2026
$50/hour
Epic 42ft Party Catamaran for Rent in Cabo San Lucas
Events in Marina · 30 guests

Epic 42ft Party Catamaran for Rent in Cabo San Lucas

5.0
$550/hour
6 passengers:  San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor
Sailing in San Diego · 6 guests

6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

5.0
$220/hour
Luxury Sailing Experience on Robertson & Caine Leopard 40
Sailing in Saint Petersburg · 12 guests

Luxury Sailing Experience on Robertson & Caine Leopard 40

5.0
Superowner
$799+/hour
37' Sailing Yacht in Marina Del Rey: Sail into a deep, Relaxed State
Sailing in Marina del Rey · 6 guests

37' Sailing Yacht in Marina Del Rey: Sail into a deep, Relaxed State

5.0
$200/hour
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$199+/hour

Sailing Reviews in United States

  1. ZC

    Zach

    Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

    We really enjoyed our sailing on 9/12 with Jan’s crew. The boat was beautiful and everyone on board was extremely friendly and attentive!

  2. Tal

    Tal

    Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

    From the moment we stepped aboard, it was clear this yacht was something special. Impeccably maintained with every detail thoughtfully cared for, the vessel was not only stunning but also incredibly comfortable and inviting. What truly set this experience apart was our captain. An absolute gem- professional, patient, and genuinely kind. John’s calm demeanor and warm personality created an atmosphere of ease and enjoyment throughout the entire time. Whether it was navigating the waters flawlessly or ensuring everyone felt safe and cared for, this captain went above and beyond. This was more than just a ride—it was a luxury experience wrapped in beauty, serenity, and top-tier hospitality. Highly recommend for anyone looking to create lasting memories on the water. We will definitely be back❤️

  3. GE

    Glenda

    Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

    This charter was the perfect little getaway—a mini vacation on the water that left us completely refreshed. The boat was exactly as described: clean, comfortable, and clearly cared for with pride. Every moment felt relaxing and easy, from the smooth ride to the peaceful surroundings. It was the kind of experience that makes you forget about everything else for a while—in the best way. Highly recommend for anyone needing a short but sweet escape.

  4. MT

    Michelle

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    We had the absolute best time with Gerald. From the moment we stepped on the boat, we were treated like family. His kindness, generosity, and genuine spirit made the entire experience feel so special. What stood out most was not only how much fun we had, but how it truly felt like we made a new friend. Gerald’s knowledge of the area is expert level, and he shared so many great insights that made the day even more enjoyable. This was such a memorable experience for our group, and we cannot recommend him enough. We will absolutely be back.

  5. AK

    ALEXANDER

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    Excellent experience from first contact until and beyond offboarding. Very family friendly. Definitely 5* experience. Will book again next time. The trip from the pier to the Atlantic is a great experience by itself. Sailing on the ocean is a dream come true. Enjoy!

  6. ED

    Eric

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    We had an incredible time on the water from the get-go. Started off cruising the intercostal waterway and even got off the dock in time to catch an earlier bridge to avoid low tide. We cruised south past Singer Island and Palm Beach. We stopped in the ICW near Palm Beach to put our feet in the water and take in the scenery in peace and quiet. The wind was amenable to sailing so we tacked south for a while then sailed back past Singer Island to make the bridge opening to get us home on time. All in all, couldn’t change a thing about the experience. The vessel was clean, well-equipped and lots of space to relax. There was ample space for beverages and food that we brought onboard and a clean restroom. Definitely would love to sail again with Gerald in the future!