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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,046 Reviews)

Page 11 of 39918 listings

Luxury Sail into a Deep, Relaxed State
Sailing in Marina del Rey · 6 guests

Luxury Sail into a Deep, Relaxed State

5.0
$200/hour
Set Sail with 36' Sailing Boat in Downtown, Chicago
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0
$225/hour
LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE
Sailing in Isla Iguana · 15 guests

LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE

5.0
$265/hour
Instant Book
28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!
Sailing in Marina del Rey · 8 guests

28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!

4.8
$250+/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
Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/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
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
$750+/hour
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0
$100/hour
36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
Sailing in Stonington · 6 guests

36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

5.0
$220+/hour
36' Private Catamaran Charter in Cozumel, Mexico
Sailing in San Miguel de Cozumel · 15 guests

36' Private Catamaran Charter in Cozumel, Mexico

5.0
$310/hour
Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers
Events in San Francisco · 49 guests

Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

5.0
Superowner
$1,467/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
Fountaine Pajot 41 Catamaran in Nuevo Vallarta, MX
Events in Nuevo Vallarta · 15 guests

Fountaine Pajot 41 Catamaran in Nuevo Vallarta, MX

5.0
$160+/hour
Instant Book
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
Private Boat Rental Turks & Caicos
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0
$200/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
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
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117+/hour
Sea Ray 350 Luxury Charter for Up to 10 Guests in Cabo, San Lucas
Events in Marina · 10 guests

Sea Ray 350 Luxury Charter for Up to 10 Guests in Cabo, San Lucas

5.0
$230/hour
Bali 43 Complete comfort Catamaran
Sailing in Marina del Rey · 12 guests

Bali 43 Complete comfort Catamaran

5.0
$400/hour
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
Montego Bay Private Champagne Sunset Catamaran Cruise
Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New
$1,896/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. JP

    Jeremy Pratt

    Fountaine Pajot 41 Catamaran in Nuevo Vallarta, MX

    We had an incredible experience on this catamaran trip. The boat itself was gorgeous—new, spotless, and spacious, with multiple bedrooms and bathrooms that made the journey comfortable and relaxing. The wildlife sightings were unforgettable. We watched whales slapping their fins, leaping out of the water, and even saw a mother with her baby right near the boat. The baby breached around 20 times, and the mother followed multiple times—truly a once-in-a-lifetime moment we’ll never forget. The crew was extremely attentive and kept everything tidy throughout the trip, and the captain navigated the catamaran with absolute skill and confidence. Overall, an extraordinary adventure that exceeded every expectation.

  2. Kenderick

    Kenderick

    Luxury Sail into a Deep, Relaxed State

    I had an amazing experience Sailing with Matthew! From start to finish, everything was smooth and easy. The boat was beautiful, clean, and comfortable, and the entire day out on the water in the Marina was absolutely perfect. Matthew was professional, welcoming, and made sure we had everything we needed to enjoy the trip. It was such a memorable and relaxing day, and I can’t wait to book again. Highly recommend!

  3. LA

    Lindsay

    Luxury Sail into a Deep, Relaxed State

    Sailing with Captain Mancini is a wonderful experience! He is thoughtful and informative, and he has a beautiful vessel perfect for a relaxing day on the water. We opted for a sunset sail this time, and it couldn’t have been more lovely. We will definitely book again!

  4. RH

    Ryan

    Luxury Sail into a Deep, Relaxed State

    We took a 4 hour cruise up to Malibu and back. The boat was excellent, and Captain Mancini was pleasant and professional. Snacks and drinks were delicious. Highlight of the trip, other than the beautiful weather, was the large pod of dolphins that swam right around the boat as they were feeding. Very cool.

  5. GD

    Gary

    Luxury Sail into a Deep, Relaxed State

    Captain Mathew led 7 of us safely, and expertly maneuvered the 35 foot sailboat on a bright sunny day with mild winds and mild seas. While regaling us with fascinating stories about exotic locations, he served delicious hors d’ oeuvres and entertained us speaking on several topics and pointing out items of interest. He took us slightly off-course to point out and follow a school of dolphins. It was a delightful sail.

  6. HD

    Helene Marie

    Luxury Sail into a Deep, Relaxed State

    I highly recommend Captain Matthew and any of his boats. We were on his sailboat, it was lovely, the voyage was so nice calm and peaceful. His hors d’oeuvres are delightful and healthy and delicious. He is sincerely a lovely person and we enjoyed spending some time with him!!!