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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,358 Reviews)

Page 11 of 39914 listings

Limited Availability
Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

5.0
$225/hour
Limited Availability
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
The nicest Charter Sailing Yacht in the West - Downtown San Francisco
Sailing in San Francisco · 20 guests

The nicest Charter Sailing Yacht in the West - Downtown San Francisco

4.9
Superowner
$750+/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
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
Fountaine Pajot 41' Sailing Catamaran In Nuevo Vallarta, Mexico
Sailing in Nuevo Vallarta · 15 guests

Fountaine Pajot 41' Sailing Catamaran In Nuevo Vallarta, Mexico

5.0
$160+/hour
Instant Book
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
Limited Availability
Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

5.0
$250/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
All-Inclusive Private 42’ Trimaran in Los Cabos
Sailing in Marina · 50 guests

All-Inclusive Private 42’ Trimaran in Los Cabos

4.8
Superowner
Best of 2026
$379/hour
Limited Availability
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
Limited Availability
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
Stunning 56' Sailing Yacht in Nassau! Up to 26 guests.
Sailing in Nassau · 26 guests

Stunning 56' Sailing Yacht in Nassau! Up to 26 guests.

4.4
$607+/hour
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/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
ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
Sailing in Nassau · 40 guests

ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

5.0
$960/hour
Limited Availability
Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!
Sailing in Marina · 70 guests

Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!

5.0
$352/hour
Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included
Sailing in Saint Michaels · 6 guests

Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

New
$585/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
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
Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht
Sailing in Port Washington · 12 guests

Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht

4.8
Superowner
$219/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
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
Bachelorette Party in Trimaran at Cabo San Lucas💃🏼🎉🎶🍾⛵️
Sailing in Marina · 50 guests

Bachelorette Party in Trimaran at Cabo San Lucas💃🏼🎉🎶🍾⛵️

5.0
Superowner
Best of 2026
$359/hour

Sailing Reviews in United States

  1. RM

    Richard

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    The Amura was the highlight of our time in the Bahamas! The communication was clear, and time at sea was fantastic. The boat had all the toys that our family could want. Captain Dan and crew make for a really enjoyable day. Also the food was incredible, come hungry!

  2. Vince

    Vince

    Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

    Highly recommend, Planned a surprised engagement, and Ted and Christy were awesome. Super accommodating, friendly, and went out of their way to make the experience very personal and fun. I wouldn’t want to experience a charter any other way.

  3. 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 !!!

  4. NN

    Natalie

    All-Inclusive Private 42’ Trimaran in Los Cabos

    My group of 19 had so much fun on this private excursion! One thing that stood out what how extremely kind and attentive the staff was. The bartender, driver, coordinator, photographer, etc. were all so nice and made sure we were safe and having fun. However a tip from me would be to not party too hard the night before because half of our group was so hungover and seasick LOL. Despite that, we still had so much fun making memories in the water. Food and drinks were great! There is a photographer on board who was very kind but there is an additional charge for photos/drone footage which we unfortunately did not purchase because it was out of budget. There are also some jelly fish in the water that some of my friends got stung by. The staff was helpful to spray some unknown liquid on the stings to prevent it from getting worse. Overall through the hangover, I still had a great time thanks to Big Mike Adventures!!!

  5. AC

    Alyssa

    Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!

    Such a great experience! Danny, Rene and Marcos were incredible hosts for our group of 14. They were efficient, so welcoming and always made sure we had what we needed (and more!)

  6. Morgan

    Morgan

    Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

    Amazing! The captains were very knowledgeable and experienced. They took the extra step to accommodate a big party and we had such an awesome time! Highly recommend.