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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,388 Reviews)

Page 1 of 38912 listings

Limited Availability
35' Private Catamaran Charters in Belize
Sailing in San Pedro · 16 guests

35' Private Catamaran Charters in Belize

5.0
$130/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
$110+/hour
30ft Catalina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catalina Sailboat Charter in Alameda CA

5.0
$95/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
$600/hour
Cancun Private Catamaran Isla Mujeres - Open Bar, Snorkeling Lunch & Fun
Sailing in Cancún · 15 guests

Cancun Private Catamaran Isla Mujeres - Open Bar, Snorkeling Lunch & Fun

5.0
Superowner
$169/hour
Limited Availability
Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel
Sailing in West Bay · 20 guests

Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel

5.0
$400/hour
FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr
Sailing in Folly Beach · 6 guests

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

5.0
$200/hour
Private 30’ Catalina Luxury Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Private 30’ Catalina Luxury Sailing Yacht in Mazatlan Bays & Islands

5.0
$2,500/hour
New in the bay! Lagoon 42' Sailing Catamaran in La Cruz
Sailing in La Cruz de Huanacaxtle · 20 guests

New in the bay! Lagoon 42' Sailing Catamaran in La Cruz

5.0
Superowner
Best of 2026
$250+/hour
Instant Book
Limited Availability
Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch
Sailing in Annapolis · 6 guests

Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

5.0
$200+/hour
Lagoon 450F Catamaran
Sailing in George Town · 30 guests

Lagoon 450F Catamaran

5.0
$500/hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2026
$213+/hour
Private 40ft Lagoon Catamaran -  Isla Mujeres | Open Bar, Snorkeling & Lunch
Sailing in Cancún · 30 guests

Private 40ft Lagoon Catamaran - Isla Mujeres | Open Bar, Snorkeling & Lunch

5.0
Superowner
$249/hour
William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience
Sailing in Seattle · 8 guests

William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience

5.0
$150/hour
Crown 34' Sailboat - Private Coastal Sailing - Los Angeles
Sailing in Marina del Rey · 4 guests

Crown 34' Sailboat - Private Coastal Sailing - Los Angeles

4.9
$110/hour
46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included

5.0
Superowner
Best of 2026
$599/hour
Lagoon 40 Yacht Catamaran in Puerto Vallarta
Sailing in Marina Vallarta · 15 guests

Lagoon 40 Yacht Catamaran in Puerto Vallarta

5.0
Superowner
Best of 2026
$225+/hour
Instant Book
23’ Bayliner Beautiful Boat In Miami
Sailing in Miami · 9 guests

23’ Bayliner Beautiful Boat In Miami

4.9
$90/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
Superowner
$355/hour
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.7
$59/hour
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

5.0
$320/hour
All-Inclusive Sunset Cruise in Cabo San Lucas
Tours in Marina · 45 guests

All-Inclusive Sunset Cruise in Cabo San Lucas

5.0
Superowner
Best of 2026
$350/hour
Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
Sailing in Shalimar · 6 guests

Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

5.0
$150/hour
Manhattan Luxury Sailboat - 40' Hinckley Sailboat
Sailing in Manhattan · 6 guests

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

5.0
$300/hour

Sailing Reviews in United States

  1. Kasheena

    Kasheena

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    Yesterday’s sailing experience was simply amazing. The captain and crew went above and beyond to take care of our family and make sure all of our needs were met. Even when we were caught up in the moment, they made sure to point out the incredible sights and beauty of the Vineyard so we would not miss a thing. Their kindness, attention to detail, and genuine care made the whole experience unforgettable. We had such a wonderful time and will definitely charter with them again when we return.

  2. KG

    Kathleen

    Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

    Highly highly recommend booking with Stephen! We had friends coming to visit from out of town and we had the most wonderful charter. Stephen was an excellent captain and very kind host. The boat itself is very cool, with plenty of room to hang on the bow (and a clean bathroom!). Can’t say enough about what a great time we had!!

  3. Phil

    Phil

    35' Private Catamaran Charters in Belize

    Great find! We were looking for a private sunset cruise for our anniversary and this trip did not disappoint. The crew (Ana and Charlie) were hilarious, friendly and professional. The itinerary and playlists were catered to what we wanted. Doing a little snorkeling along the reef was an awesome experience. The drinks and food included were delicious. Don’t hesitate to book!

  4. RB

    Richard

    Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

    Not sure I can say enough about how absolutely incredible our experience was with Steve. Boat was perfect. Communication was perfect. But the experience was incredible! He took my wife, two sons and I out to the Wednesday night races in Annapolis, and we got to engage right into the races, feel the speed of the boats, see the tight turns, and it’s an experience my sons will not forget. Can’t recommend highly enough.

  5. 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!

  6. LF

    Linda

    Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

    Stephen was wonderful! A few days before our sailing trip, the weather forecast looked questionable, but he stayed in touch the entire time, offering to start earlier or even reschedule for a different day if needed. He was incredibly flexible and genuinely wanted to make sure we had the best possible experience. Thanks to his communication and commitment, we had a fantastic trip. I highly recommend sailing with Stephen!