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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,078 Reviews)

Page 8 of 39916 listings

Gorgeous Luxurious Catamaran Open Bar
Sailing in Cancún · 30 guests

Gorgeous Luxurious Catamaran Open Bar

5.0
$250/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 25 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour
2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
$995/hour
⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

4.8
Superowner
$700+/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
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Memorable Experience on this Leopard 47 Catamaran
Sailing in Isla Iguana · 25 guests

Memorable Experience on this Leopard 47 Catamaran

5.0
$325/hour
Limited Availability
60’ Premier Sailing Yacht in San Diego.
Sailing in San Diego · 35 guests

60’ Premier Sailing Yacht in San Diego.

5.0
$775/hour
Limited Availability
One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!
Events in Manhattan · 12 guests

One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!

5.0
$475/hour
38' Sailing catamaran for parties / events in Long Beach! DISCOUNT WEEK DAYS
Sailing in Long Beach · 12 guests

38' Sailing catamaran for parties / events in Long Beach! DISCOUNT WEEK DAYS

5.0
Superowner
$169+/hour
Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away
Sailing in Nuevo Vallarta · 18 guests

Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away

5.0
Superowner
Best of 2026
$263+/hour
Sailing Trips out of La Conner, Washington
Sailing in Anacortes · 8 guests

Sailing Trips out of La Conner, Washington

5.0
$500/day
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
Private Sail from Brooklyn Bridge Park
Sailing in Manhattan · 6 guests

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
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
44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.
Sailing in Playa del Carmen · 35 guests

44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.

5.0
Superowner
Best of 2026
$520/hour
Your own 42' Private Sailboat in Cabo
Sailing in Marina · 14 guests

Your own 42' Private Sailboat in Cabo

5.0
Superowner
Best of 2026
$363/hour
Beautiful Sea Ray Flybridge 45 ft Available In Cabo San Lucas,
Events in Marina · 12 guests

Beautiful Sea Ray Flybridge 45 ft Available In Cabo San Lucas,

5.0
$350/hour
37ft Sea Ray Sundancer Yacht for Charter  in Cabo San Lucas, Baja California Sur
Events in Marina · 8 guests

37ft Sea Ray Sundancer Yacht for Charter in Cabo San Lucas, Baja California Sur

5.0
$230/hour
Incredible 36' Cruiser For Rent
Powerboats in Long Beach · 10 guests

Incredible 36' Cruiser For Rent

5.0
$149/hour
Lagoon 42 Yacht Catamaran In Punta Mita
Sailing in Punta de Mita · 20 guests

Lagoon 42 Yacht Catamaran In Punta Mita

5.0
Superowner
Best of 2026
$309+/hour
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0
$225/hour
Marlowe Hunter 33’ Sailing In Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing In Fort Lauderdale

5.0
$90+/hour

Sailing Reviews in United States

  1. ML

    Michelle

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

    Excellent trip with Captain Joseph! He was so easy to plan the itinerary with beforehand and very fun on board. He made us feel safe and we had a wonderful time sailing around the bay with friends and our dogs! Would go out again with Captain Joseph soon! Definitely a wonderful trip and gorgeous and cozy boat.

  2. NH

    Nicole

    Private Sail from Brooklyn Bridge Park

    We loved getting up close to the statue of liberty ! Mike really showed us some beautiful sights! He was so great! Excellent experience top to bottom!

  3. DO

    Delia

    Incredible 36' Cruiser For Rent

    Captain Chris is very professional. We enjoyed the trip. The boat is clean as described and perfect size for my party of 7. Would love to book again with him.

  4. KI

    Keoni

    Incredible 36' Cruiser For Rent

    I want to start off thanking God for people like Captain Chris. I had the absolute pleasure of celebrating my 33rd birthday with Captain Chris, and I truly cannot recommend him enough. From start to finish, he exceeded every expectation. His boat was spotless, and his sailing was incredibly smooth—it honestly felt effortless and relaxing the entire time. What stood out the most was his professionalism and kindness. He was extremely accommodating, answered every call leading up to the trip, and made sure we had clear directions and everything we needed. He welcomed everything we brought onboard without any hesitation and never once made us feel uncomfortable or restricted—he simply allowed us to enjoy our time fully. Captain Chris has such a calm and respectful presence that at times we even forgot he was there, yet everything ran perfectly. That balance is rare, and he handled it beautifully. This experience meant more to us than just a birthday celebration. Our family had just experienced a loss, and this day gave us a moment to breathe, laugh, and reconnect. It truly felt like a healing escape, and Captain Chris played a huge role in creating that space for us. It felt like we were in a movie, and he was the one helping bring it all together behind the scenes. I’m beyond grateful for the experience and for his energy, professionalism, and generosity. If you’re thinking about booking—do it. You will not be disappointed. He is absolutely stellar. Thank you again, Captain Chris, for making my birthday unforgettable. 💛

  5. JH

    Jeremy

    Gorgeous Luxurious Catamaran Open Bar

    The Trip was amazing. Great Staff Great food, Great service. Would Highly recommend this charter and this Captain. All of my passengers loved every minute of this. A+++

  6. DG

    David

    Gorgeous Luxurious Catamaran Open Bar

    The experience was simply great! The crew was amazing, the boat just perfect! And the day wondefull! 100% recommended. Listen Tatyana recomendations, she almost beg us to upgrade the size of the boat for the amount of people we were. Best recomendation ever! Thanks