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
(8,359 Reviews)

Page 14 of 39914 listings

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
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
No Rush Sailing Tours
Sailing in San Pedro · 16 guests

No Rush Sailing Tours

5.0
$125/day
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
44' Luxury Catamaran Private Sailing Adventure
Sailing in Zona Hotelera Norte · 25 guests

44' Luxury Catamaran Private Sailing Adventure

5.0
$407/hour
San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440
Sailing in Brisbane · 6 guests

San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440

5.0
$250/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

New
$225/hour
50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle
Sailing in Seattle · 47 guests

50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle

4.9
$1,050/hour
Negril Private Catamaran Cruise with Snorkeling & Drinks
Sailing in West End · 120 guests

Negril Private Catamaran Cruise with Snorkeling & Drinks

New
$509/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
2hr Day Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Day Sail from the port of South Haven Mi. on a Catalina 36

5.0
$175/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
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Sailing in Essex · 6 guests

Welcome Aboard Optimystic! Create a beautiful memory on the water.

5.0
$150/hour
Puerto Plata-private And Luxury VIP Party Yachts
Powerboats in Puerto Plata · 100 guests

Puerto Plata-private And Luxury VIP Party Yachts

New
Superowner
Best of 2026
$50/hour
EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝
Events in La Romana · 150 guests

EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝

New
Superowner
Best of 2026
$17/hour
BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!
Sailing in Marina del Rey · 12 guests

BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!

5.0
Superowner
$425/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
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
Lagoon 42´ Catamaran - All Inclusive In Tulum
Sailing in Tulum · 30 guests

Lagoon 42´ Catamaran - All Inclusive In Tulum

5.0
Superowner
$550+/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
High Demand
San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event
Sailing in San Diego · 30 guests

San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

5.0
$600+/hour
42' Trimaran Rental in Cabo San Lucas, Mexico
Events in Marina · 45 guests

42' Trimaran Rental in Cabo San Lucas, Mexico

5.0
$720/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
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

Sailing Reviews in United States

  1. Christie

    Christie

    BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!

    We had such a great evening sailing, swimming off the coast of Playa and cruising the Marina! Alex and Zach were amazing! Thank you!

  2. LM

    Liz

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

  3. TB

    Tom

    50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle

    I rented this boat for my 40th birthday party with around 40 adults during Sea Fair and it was a great experience.

  4. AW

    Avery

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

    SOOOOO much fun!!!!!!! We would do this many more times with this crew. So attentive and fun. Luna and Alex were great. Highly recommend.

  5. SF

    Serlena

  6. 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!