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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,454 Reviews)

Page 8 of 39932 listings

Beneteau 36’ Cruising Monohull in Redondo Beach
Sailing in Redondo Beach · 6 guests

Beneteau 36’ Cruising Monohull in Redondo Beach

5.0
$125/hour
Limited Availability
AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch
Sailing in Annapolis · 6 guests

AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

5.0
$200+/hour
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
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
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
ELEGANCE CATAMARAN LAGOON  45 IN PUERTO VALLARTA-NUEVO NAYARIT
Sailing in Isla Iguana · 30 guests

ELEGANCE CATAMARAN LAGOON 45 IN PUERTO VALLARTA-NUEVO NAYARIT

5.0
$250+/hour
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
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
Incredible 36' Cruiser For Rent
Powerboats in Long Beach · 10 guests

Incredible 36' Cruiser For Rent

5.0
$149/hour
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Puget Sound Sailing Adventure on 32' Hunter Sailboat
Sailing in Seattle · 6 guests

Puget Sound Sailing Adventure on 32' Hunter Sailboat

5.0
$180/hour
Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York

5.0
$310+/hour
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$317/hour
Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran
Sailing in San Miguel de Cozumel · 22 guests

Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran

5.0
Superowner
$270+/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
FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!
Sailing in San Francisco · 6 guests

FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!

5.0
Superowner
$300+/hour
Instant Book
42ft J Boat Sailing Yacht in Newport, Rhode Island
Sailing in Newport · 4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260/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
$129/hour
Add a SPARK to Your Special Event with a 65 ft Sailboat Cruise on the Bay
Sailing in San Francisco · 35 guests

Add a SPARK to Your Special Event with a 65 ft Sailboat Cruise on the Bay

4.9
$750/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
$200+/hour
Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package
Sailing in San Francisco · 20 guests

Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package

5.0
Superowner
$750+/hour
Instant Book
Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
$190/hour
Beautiful Sea Ray Flybridge 45ft Available In Cabo San Lucas,
Events in Marina · 12 guests

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

5.0
$350/hour
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour

Sailing Reviews in United States

  1. AB

    Alex

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

    Steve was an amazing host. His itinerary was punctual and we could tell he spent the time researching just how to make our experience just what we were looking for. Steve was a great captain and the boat is perfect for a few hours out on the bay. Can’t wait to ride with Steve the next time we come to Annapolis

  2. Peter

    Peter

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    My wife and I had a great time taking out Matt’s Sunfish sailboat! He was there to greet us and help prepare the boat, and he had great recommendations for where in the lake to find the best sailing conditions. His sunfish is well maintained and sailed great. I would love to rent his Sunfish again next summer!

  3. JM

    Jerry

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

    Stephen was great from the jump and the boat was as advertised. Great communication, super flexible with the itinerary. Made it super easy for our group to show up and be on our way.

  4. KG

    Kathleen

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' 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!!

  5. RB

    Richard

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' 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.

  6. Jessi

    Jessi

    Puget Sound Sailing Adventure on 32' Hunter Sailboat

    We had a great time on our sailing adventure! The boat was very nice and outfitted to protect us from the wind. We saw some wildlife and it was just a picturesque experience. The Captain was knowledgeable and engaging. Overall, we enjoyed our time on the water.