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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,137 Reviews)

Page 1 of 39934 listings

Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey
Sailing in Marina del Rey · 6 guests

Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

5.0
Superowner
Best of 2025
$150/hour
Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Privat 30’ Luxury Sailing Yacht in Mazatlan Bays & Islands

5.0
$134/hour
Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey
Sailing in Marina del Rey · 4 guests

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

5.0
$100+/hour
Sail away in Montego Bay! 39ft Leopard Catamaran
Sailing in Montego Bay · 16 guests

Sail away in Montego Bay! 39ft Leopard Catamaran

5.0
Superowner
Best of 2025
$600/hour
30ft Catalina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catalina Sailboat Charter in Alameda CA

5.0
$95/hour
Private Coastal Sailing - Los Angeles
Sailing in Marina del Rey · 4 guests

Private Coastal Sailing - Los Angeles

4.8
$90/hour
Sunset Sails: Explore the Open Waters of Tampa, Florida
Sailing in Tampa · 6 guests

Sunset Sails: Explore the Open Waters of Tampa, Florida

5.0
$225/hour
 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
Best of 2025
$240+/hour
35' Private Catamaran Charters in Belize
Sailing in San Pedro · 16 guests

35' Private Catamaran Charters in Belize

4.9
$130/hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2025
$200/hour
Private Catamaran - Sailing To Isla Mujeres
Sailing in Cancún · 15 guests

Private Catamaran - Sailing To Isla Mujeres

5.0
Superowner
Best of 2025
$169/hour
Instant Book
⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz
Sailing in La Cruz de Huanacaxtle · 20 guests

⛵New in the bay! Lagoon 42 Yacht Catamaran in La Cruz

5.0
Superowner
Best of 2025
$250+/hour
Instant Book
40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.
Sailing in Puerto Aventuras · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.

5.0
Superowner
$450/hour
46 feet luxury yacht in Montego Bay with round trip transportation!
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with round trip transportation!

5.0
Superowner
Best of 2025
$659/hour
38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.
Sailing in Puerto Aventuras · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.

5.0
Superowner
$420/hour
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Sailing in Tisbury · 6 guests

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

5.0
$250/hour
Instant Book
The Only 40ft Hinckley Sailboat in Manhattan
Sailing in Manhattan · 6 guests

The Only 40ft Hinckley Sailboat in Manhattan

5.0
$300/hour
Instant Book
Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta
Sailing in Marina Vallarta · 13 guests

Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta

4.7
Best of 2025
$122/hour
Spacious, fast 80 foot sailboat with a hot tub
Events in Marina Vallarta · 40 guests

Spacious, fast 80 foot sailboat with a hot tub

5.0
$275/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained

5.0
$95+/hour
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
Best of 2025
$180/hour
New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500/hour
40' Luxury Catamaran in Cozumel -
Sailing in San Miguel de Cozumel · 22 guests

40' Luxury Catamaran in Cozumel -

5.0
Superowner
$249+/hour
34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas
Events in Marina · 8 guests

34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas

5.0
$190/hour

Sailing Reviews in United States

  1. MH

    Melissa

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    We had a great trip with Kenny - highly recommend. Very prompt, communicative, and clear in departure directions. We had a great sail with beautiful conditions and Kenny is personable and knowledgeable. Highly recommend for a great time on the water, we’ll definitely go sailing with him again next time!

  2. SC

    Steven

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    This wasn’t just a sail—it was an adventure filled with stories, laughter, and the kind of peaceful moments you only find out on the water. I can’t recommend Kenneth highly enough if you’re looking for a memorable and truly enjoyable sailing experience. Highly recommend! 🚤⛵️

  3. Rodney

    Rodney

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    Highly recommend if you’re looking for something different to do than what all the other tourists are doing when visiting Martha’s Vineyard, you might want to consider contacting Mason for a peaceful & relaxing sailboat ride to see the beautiful coastline of MV that most don’t get to experience while on land. We’ll definitely be back next year to do another trip

  4. LX

    Linda

    The Only 40ft Hinckley Sailboat in Manhattan

    My group and I had an incredible experience with Captain Andy. He was warm, accommodating, and an excellent captain throughout the entire trip. He truly made the day unforgettable for all of us, and we can’t wait to set sail with him again. The sailboat, Nanette Marie, was stunning so comfortable and perfect for capturing beautiful photos.

  5. SC

    Stephanie

    Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

    My husband and I had a great time with Matthew! He was timely and professional. He let us both get behind the wheel to steer, which was really fun. We enjoyed hearing about his sailing experience and appreciated that he answered all of our questions. Highly recommend this trip!

  6. SP

    Shawna

    35' Private Catamaran Charters in Belize

    We had a trip making day on our private full day charter. Our family of 6 all agreed it was the highlight of our Belize trip. A few win… Charlie was a fun and warm captain. His lunch was literally the best meal we got in Belize! Pablo made this anxious mom feel safe on the snorkel portion of the day. Happy I could adventure with my teenagers and share the experience. He was incredibly knowledgeable about the area, the fish, nature and all things Belize. My family has traveled all over the world and this makes our top 5 list of best experiences!