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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,481 Reviews)

Page 12 of 40 • 940 listings

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
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
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
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
🛥🤩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
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
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
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
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
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
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
Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica
Sailing in Tamarindo · 16 guests

Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica

5.0
$320/hour
Sailing Sloop Hunter 40 in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Sailing Sloop Hunter 40 in Puerto Vallarta

4.7
Superowner
$145/hour
Cancun Party Yacht 46ft Sea Ray Flybridge
Tours in Cancún · 15 guests

Cancun Party Yacht 46ft Sea Ray Flybridge

5.0
$260/hour
Instant Book
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
Lux Catamaran Fountaine Pajot 40ft
Sailing in Leeward Settlement · 10 guests

Lux Catamaran Fountaine Pajot 40ft

New
$714+/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
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
Private Sailboat Beneteau 42ft in Cabo, All-Inclusive
Sailing in Marina · 12 guests

Private Sailboat Beneteau 42ft in Cabo, All-Inclusive

5.0
$320/hour
Catmania Sailing Catamarans in Playa Mujeres, Cancun, Mexico.
Sailing in Isla Mujeres · 38 guests

Catmania Sailing Catamarans in Playa Mujeres, Cancun, Mexico.

5.0
Superowner
$262/hour
Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran
Sailing in Chicago · 13 guests

Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

5.0
$440/hour
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
Sailing in Whitehall · 6 guests

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

5.0
$140/hour
Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach
Sailing in West Palm Beach · 6 guests

Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach

5.0
$300/hour

Sailing Reviews in United States

  1. Casi

    Casi

    Sailing Catamaran Yacht for up to 20 Guests in Aruba

    Thanks for sharing the best parts of Aruba.. Highly grateful for this experience. Hands down the best boating experience I've ever participated in.. I will do the same exact thing next visit. Thank you !!!

  2. CA

    Caroline

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

    Beautiful boat with a professional and thoughtful team. We had a wonderful sail.

  3. M

    Mark

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

    Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.

  4. S

    Sandra

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

    Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.

  5. J

    Jeff

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

    What a WONDERFUL experience!! Capt. Russell was truly amazing, our 2 hour cruise Friday could not have been better! His attention to detail, coupled with a strong focus on safety didn't go unnoticed. We had 1 person in our party that was a little nervous about being on the open water. The Capt. was able to sooth their apprehension with his vast knowledge of sailing, peppered with humor...it was the needed medicine. We will be back soon, next time we'll book a 4 hour cruise, 2 hours was clearly not enough time. 5 star recommendation, only because 6 stars was not an option.

  6. 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❤️