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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,248 Reviews)

Page 12 of 40948 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
Instant Book
BOOK 6 hrs and  GET 1 hr free! GREAT DEAL YACHT IN CANCUN  35FT REGAL
Events in Cancún · 8 guests

BOOK 6 hrs and GET 1 hr free! GREAT DEAL YACHT IN CANCUN 35FT REGAL

4.5
$174+/hour
Instant Book
Sail into your Deep, Relaxed State
Sailing in Marina del Rey · 6 guests

Sail into your Deep, Relaxed State

New
$155+/hour
Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

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

4.6
$199+/hour
Day Sailing Trip in San Pedro Aboard 42' Polynesian Catamaran
Sailing in San Pedro · 24 guests

Day Sailing Trip in San Pedro Aboard 42' Polynesian Catamaran

5.0
$400/hour
Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast
Sailing in Friendship · 6 guests

Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

5.0
$125/hour
LAGOON 42´ CATAMARAN - ALL INCLUSIVE IN TULUM
Sailing in Tulum · 30 guests

LAGOON 42´ CATAMARAN - ALL INCLUSIVE IN TULUM

5.0
Superowner
$543/hour
Enjoy an Excursion in Cabo San Lucas, Mexico on this Sailing Catamaran
Sailing in Ildefonso Green · 12 guests

Enjoy an Excursion in Cabo San Lucas, Mexico on this Sailing Catamaran

5.0
$450/hour
Private Catmaran With Fun Crew up to 55 People Open Bar Unlimited Drinks
Sailing in Cancún · 55 guests

Private Catmaran With Fun Crew up to 55 People Open Bar Unlimited Drinks

5.0
$466+/hour
Private Catamaran Charter – Swim, Sail & Explore San Diego – Up to 12 Guests
Sailing in San Diego · 12 guests

Private Catamaran Charter – Swim, Sail & Explore San Diego – Up to 12 Guests

5.0
$350+/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
Private Yacht Sea Ray 46ft Cancun - Isla Mujeres just for 4 hours
Tours in Cancún · 15 guests

Private Yacht Sea Ray 46ft Cancun - Isla Mujeres just for 4 hours

5.0
$155/hour
Instant Book
Luxury Italian Sailing Yacht on the Puget Sound — Seattle
Sailing in Seattle · 6 guests

Luxury Italian Sailing Yacht on the Puget Sound — Seattle

5.0
$374+/hour
Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica
Sailing in Tamarindo · 22 guests

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

5.0
$300/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
SHARED Catamaran sailing tour to Passion Island (10 am to 3pm)
Sailing in Zona Hotelera Norte · 20 guests

SHARED Catamaran sailing tour to Passion Island (10 am to 3pm)

5.0
$70/hour
Private Luxury Sunset Sailing Cruise in Cozumel, Mexico
Sailing in San Miguel de Cozumel · 30 guests

Private Luxury Sunset Sailing Cruise in Cozumel, Mexico

5.0
$500/hour
Enjoy the Hamptons waters on wonderful and unique Classic Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic Mahogany Trimaran

5.0
$750+/hour
ELEGANCE CATAMARAN LAGOON  45 IN PUERTO VALLARTA-NUEVO NAYARIT
Sailing in Isla Iguana · 30 guests

ELEGANCE CATAMARAN LAGOON 45 IN PUERTO VALLARTA-NUEVO NAYARIT

New
$250+/hour
Instant Book
44ft Helia Fountinae Pajot Catamaran for sailing in Turks and Caicos
Sailing in Leeward Settlement · 18 guests

44ft Helia Fountinae Pajot Catamaran for sailing in Turks and Caicos

5.0
$999+/hour
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
$199/hour
Nice Sailing vessel 41ft for cruising and explore PV.
Sailing in Marina Vallarta · 12 guests

Nice Sailing vessel 41ft for cruising and explore PV.

5.0
$130/hour
35' Seawind Sailing Catamaran  - Cabo
Sailing in Marina · 7 guests

35' Seawind Sailing Catamaran - Cabo

5.0
$350/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

5.0
Superowner
Best of 2025
$244/hour
Instant Book

Sailing Reviews in United States

  1. cC

    chris

    43' Sailboat, Bristol RI & Beyond

    This was an incredible sail. We had to cancel our initial trip due to very bad storms with 65 knot winds and flooding rains early in the season. We rebooked and had a fabulous, relaxing time. The Capt' is both entertaining and a wealth of information and just makes the entire experience what you would want.....sublime.

  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. AH

    Anne

    43' Sailboat, Bristol RI & Beyond

    Four of us had a great sail with Captain Francis. He struck the right balance between chatting with us and letting us talk amongst ourselves. We wanted to sail by a specific area and he graciously complied. I thought the value for the sailing experience was great. Highly recommend.

  4. BB

    Bryan

    43' Sailboat, Bristol RI & Beyond

    Table for Two and Captain Francis make for a great sail. We have sailed with him multiple times and will continue to do so yearly for our family sailing vacation. Safety, value, and his knowledge of sailing globally make it a great time and experience we return back to every year. I highly recommend his services.

  5. BE

    Bill

    43' Sailboat, Bristol RI & Beyond

    We had a delightful afternoon sail with Captain Francis! He was skilled and easygoing and his boat was very well equipped. Two of us were experienced sailors and he graciously allowed us to help crew and take the helm as much as we wished. We all shared stories of past adventures and had a wonderful day in Bristol and Narragansett Bay. Highly recommended!

  6. DW

    David

    43' Sailboat, Bristol RI & Beyond

    We had a wonderufl afternoon sailing on the bay with Captain Francis! Our kids had some prior sailing experience, and he was kind enough to let them crew a bit. He was personable and knowledgeable, we had a great time, and would definitely book through him again!