Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,467 Reviews)

Page 15 of 41 • 964 listings

Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

5.0
$195/hour
Private Charter with Crew | Sail the Legendary Wind of Howe Sound | Squamish, BC
Sailing in Squamish · 12 guests

Private Charter with Crew | Sail the Legendary Wind of Howe Sound | Squamish, BC

5.0
$285/hour
Chaparral 256 Family Cabin Cruiser
Powerboats in Jersey City · 9 guests

Chaparral 256 Family Cabin Cruiser

5.0
$275/hour
Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!
Powerboats in Miami · 10 guests

Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!

4.3
$100+/hour
44' Luxury Catamaran Private Sailing Adventure
Sailing in Zona Hotelera Norte · 25 guests

44' Luxury Catamaran Private Sailing Adventure

5.0
$376/hour
🎉 Miches All Stars Cruise All Inclusive Luxury Yacht entertainment
Powerboats in Dominican Republic · 150 guests

🎉 Miches All Stars Cruise All Inclusive Luxury Yacht entertainment

5.0
Superowner
Best of 2026
$17/hour
Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC
Sailing in Squamish · 10 guests

Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC

5.0
$32/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

4.0
Superowner
Best of 2026
$350/hour
60' Sailing Party Catamaran in Miami Florida
Sailing in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida

4.6
$1,300/hour
35' Cruising Catamaran on San Francisco Bay
Sailing in Oakland · 10 guests

35' Cruising Catamaran on San Francisco Bay

4.9
$225/hour
62ft Lagoon 620 Catamaran – Private Cruise Experience in Newport, RI
Sailing in Newport · 12 guests

62ft Lagoon 620 Catamaran – Private Cruise Experience in Newport, RI

5.0
$1,500/hour
Shopping Tour to Isla Mujeres, Everyday 12:30 (Shared Basis)
Sailing in Isla Mujeres · 30 guests

Shopping Tour to Isla Mujeres, Everyday 12:30 (Shared Basis)

5.0
Superowner
$395/hour
Let’s Go Sailing On This Beautiful Private Catalina 350 Yacht From San Francisco
Sailing in San Francisco · 6 guests

Let’s Go Sailing On This Beautiful Private Catalina 350 Yacht From San Francisco

5.0
$300/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!
Events in Chicago · 13 guests

Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

5.0
$1,190/hour
4-Hour Sailing Catamaran for Rent in Punta Sam, Cancun
Sailing in Isla Mujeres · 12 guests

4-Hour Sailing Catamaran for Rent in Punta Sam, Cancun

5.0
Superowner
$221/hour
Lagoon 42´ Catamaran - All Inclusive In Tulum
Sailing in Tulum · 30 guests

Lagoon 42´ Catamaran - All Inclusive In Tulum

5.0
Superowner
$550+/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
Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests
Sailing in Cancún · 25 guests

Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests

4.4
Superowner
$157+/hour
Costa Rica Catamaran: Private Morning Tour with Snorkel & Drinks
Sailing in Guanacaste Province · 20 guests

Costa Rica Catamaran: Private Morning Tour with Snorkel & Drinks

5.0
$430/hour
Nicest Certified Sailing Yacht on the West Coast for 15 People Package
Sailing in San Francisco · 15 guests

Nicest Certified Sailing Yacht on the West Coast for 15 People Package

5.0
Superowner
$650+/hour
Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste
Sailing in Coco · 10 guests

Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

5.0
$165/hour
Private 37ft Catamaran Charter in Cancún for up to 25 Guests
Sailing in Cancún · 25 guests

Private 37ft Catamaran Charter in Cancún for up to 25 Guests

5.0
Superowner
$157+/hour
49-Passenger Sailing Charter Catamaran at Navy Pier Marina
Sailing in Chicago · 49 guests

49-Passenger Sailing Charter Catamaran at Navy Pier Marina

New
$900/hour

Sailing Reviews in United States

  1. RW

    Richard

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Rob will do everything he can to make your cruise one of the best ever!!

  2. LF

    Lena

    Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

    Amazing trip! Eric was fantastic. He asked us what we wanted to do, and he took us to his favorite spots. We went swimming and jumped off rocks. He told us very interesting stories and was extremely friendly. He made the whole experience better. He made us feel like the boat was our own. Great time, amazing boat. I’d definitely book him again!

  3. Kelly

    Kelly

    Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

    Eric was very prompt, accommodating and took great care of us on our last minute booking. He actually timed everything perfectly for a late afternoon, cruise out into the gulf, searching for dolphins, and wayward pirates, caught the sunset perfectly as we were returning to the marina. We all had a blast, great conversation, and just a good time with great people.

  4. Natalie

    Natalie

    44' Luxury Catamaran Private Sailing Adventure

    Our best day on the island! Our group of 17 people enjoyed snorkeling and play time at el cielo which was beautiful! The crew on the boat was amazing - great service and super friendly. The ceviche they prepared for lunch was the best I have had in a long time - over all a great boat and a great experience.

  5. JA

    Jem

    Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC

    If I could give 10/5 stars, I would. We had an engagement shoot and David and Alison exceeded all our expectations. They were fun, friendly, and professional. They made us feel at ease during the sail. Super knowledgeable. They toured us around and knew exactly where to take photos. We had an exceptional time and are already thinking of our next sail with them two. We highly recommend David and Alison for all your sailing needs. Definitely the BEST Captain and Crew out there!

  6. ab

    abby

    Sailing Tour | Sail the Legendary Wind of Howe Sound | Squamish, BC

    My friends and I had an incredible time and we absolutely loved the whole sailing boat experience. The views are breathtaking on the Sea to Sky shore. We will definitely go back for another sailing trip. Thank you David and Harli for giving us an unforgivable trip