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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,366 Reviews)

Page 7 of 39923 listings

Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB
Sailing in Charleston · 6 guests

Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB

5.0
Superowner
$240/hour
50' Azimut All-Inclusive Yacht Charter in Playa del Carmen.
Events in Playa del Carmen · 20 guests

50' Azimut All-Inclusive Yacht Charter in Playa del Carmen.

4.9
Superowner
Best of 2026
$420/hour
42 Sailing Monohull Tours in Sausalito
Sailing in Sausalito · 6 guests

42 Sailing Monohull Tours in Sausalito

5.0
Superowner
$200/hour
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
$700+/hour
35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands
Sailing in Vancouver · 6 guests

35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands

5.0
$130/hour
Limited Availability
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
Limited Availability
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
$110+/hour
Premium Sunset Sailing on a True WestSail 43ft Yacht
Sailing in San Diego · 6 guests

Premium Sunset Sailing on a True WestSail 43ft Yacht

5.0
$200/hour
Exclusive Sailing Boat
Sailing in Marina Vallarta · 15 guests

Exclusive Sailing Boat

5.0
Superowner
Best of 2026
$80+/hour
Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California
Sailing in Marina del Rey · 12 guests

Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California

5.0
Superowner
$650/hour
🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina
Sailing in Folly Beach · 6 guests

🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina

5.0
Superowner
$300/hour
60ft AIcon Yacht – Perfect for Luxury Day Trips
Events in Miami · 13 guests

60ft AIcon Yacht – Perfect for Luxury Day Trips

4.8
$350/hour
All Electric Powered Eco-Friendly San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

All Electric Powered Eco-Friendly San Diego Bay Sailing Experience

5.0
$300/hour
Incredible 36' Cruiser For Rent
Powerboats in Long Beach · 10 guests

Incredible 36' Cruiser For Rent

5.0
$149/hour
High Demand
Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch
Events in Sausalito · 30 guests

Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

4.9
Superowner
Best of 2026
$650/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
Full Day Sailing Potrero Guanacaste Province, Costa Rica
Sailing in Potrero · 12 guests

Full Day Sailing Potrero Guanacaste Province, Costa Rica

5.0
$200/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/hour
Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
Sailing in Cartagena · 45 guests

Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

4.9
Superowner
$1,000/day
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
Instant Book
Curacao Private Romantic Sunset Tour 2p
Sailing in Santa Barbara Plantation · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Beneteau 36’ Cruising Monohull in Redondo Beach
Sailing in Redondo Beach · 6 guests

Beneteau 36’ Cruising Monohull in Redondo Beach

5.0
$125/hour
Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL
Sailing in Stuart · 13 guests

Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

5.0
$354/hour

Sailing Reviews in United States

  1. UL

    Urs

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

    Matt is a competent sailor, who knows is boat and the local waters and conditions very well. Everyone felt safe on board with him. We had a great afternoon, a beautiful pacific sun set and overall a lovely experience. If we ever come back to LA we know who to call.

  2. AP

    Anna

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

    We had an amazing boat trip with Matthew and couldn’t have asked for a better captain! We were running late, and he was incredibly kind and patient to wait for us, which we really appreciated. From the moment we arrived, he made us feel welcome and ensured we had a fantastic experience. The trip was relaxing, fun, and perfectly organized, with beautiful views and a great atmosphere throughout. Matthew is professional, friendly, and truly goes above and beyond for his guests. We would absolutely book with him again and highly recommend him to anyone looking for an unforgettable day on the water!

  3. EM

    Erik

    35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands

    We had a great trip with James, he was very knowledgeable about the area and suggested several trip options depending on what we were looking to do and how long we wanted to be out. He was great to talk to while sailing and was completely flexible while on the trip. Our son loved getting to sail the boat. If we come back, would definitely look to setup another (maybe longer) trip. Thanks!

  4. CP

    Cheri

    42 Sailing Monohull Tours in Sausalito

    We had the perfect day with Rick! We loved his boat and were very confident in his seamanship. He’s also a fun guy to hang out with with!

  5. AG

    Aj

    Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

    Couldn’t say enough good things about our time with Erinn. We had 9 people 5 of which were young kids and Erinn not only showed us an amazing day on the water snorkeling sailing and having a great time . She was incredible great with our kids. 10 stars across the board if I could! The boat was amazing as well

  6. DP

    David

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

    This is a great experience. Matthew is a great captain and provides a wonderful itinerary. He knows his ship and the waters well and explains his vessel and how to sail.