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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,220 Reviews)

Page 11 of 40939 listings

NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA
Sailing in Los Angeles · 12 guests

NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA

5.0
Superowner
$169+/hour
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.
Sailing in Tulum · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.

5.0
Superowner
Best of 2026
$450/hour
Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.
Sailing in Nassau · 12 guests

Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.

4.7
$252+/hour
Amazing Sailing Catamaran for Charter in Cabo San Lucas, Mexico
Sailing in Ildefonso Green · 10 guests

Amazing Sailing Catamaran for Charter in Cabo San Lucas, Mexico

5.0
$550/hour
Fountaine Pajot 41' Sailing Catamaran In Nuevo Vallarta, Mexico
Sailing in Nuevo Vallarta · 15 guests

Fountaine Pajot 41' Sailing Catamaran In Nuevo Vallarta, Mexico

5.0
$160+/hour
Instant Book
Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers
Events in San Francisco · 49 guests

Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

5.0
Superowner
$1,467/hour
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2026
$50/hour
Epic 42ft Party Catamaran for Rent in Cabo San Lucas
Events in Marina · 30 guests

Epic 42ft Party Catamaran for Rent in Cabo San Lucas

5.0
$550/hour
Luxury Sail into a Deep, Relaxed State
Sailing in Marina del Rey · 6 guests

Luxury Sail into a Deep, Relaxed State

5.0
$200/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
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120/hour
28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!
Sailing in Marina del Rey · 8 guests

28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!

4.8
$250+/hour
Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

5.0
$225/hour
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/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
$750+/hour
Enjoy an Excursion in Cabo San Lucas, Mexico on this Sailing Catamaran
Sailing in Ildefonso Green · 12 guests

Enjoy an Excursion in Cabo San Lucas, Mexico on this Sailing Catamaran

5.0
$325+/hour
⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
$700+/hour
🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.
Events in Sosúa · 150 guests

🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.

4.4
$300/hour
🎉 Miches All Stars Cruise All Inclusive Luxury Yacht
Powerboats in Dominican Republic · 150 guests

🎉 Miches All Stars Cruise All Inclusive Luxury Yacht

5.0
Superowner
Best of 2026
$17/hour
The nicest Charter Sailing Yacht in the West - Downtown San Francisco
Sailing in San Francisco · 20 guests

The nicest Charter Sailing Yacht in the West - Downtown San Francisco

4.9
$750+/hour
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$225+/hour
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0
$100/hour

Sailing Reviews in United States

  1. AH

    Aileenka

    Beneteau 36’ Cruising Monohull in Redondo Beach

    Booked Brasher and his boat for my 30th birthday and it did not disappoint! From the very beginning he had excellent communication and assured me I would have a great time. I definitely did! He had a cooler aboard for drinks, he took us to a lovely anchorage spot to swim and inflated the cube. I would 100% book this trip again.

  2. LD

    Lucy

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

    We had a beautiful day on the bay with Drew and Garrett who are both accomplished sailors and considerate hosts. Everyone felt comfortable and taken care of and I would highly recommend them to anyone looking for a day on the water with local experts. It was a gorgeous day and reminded us why we are so lucky to live here!

  3. OA

    Omar

    Beneteau 36’ Cruising Monohull in Redondo Beach

    We had an absolutely wonderful Mother’s Day sail today, and our captain made the entire experience unforgettable. From the moment we stepped aboard, he was professional, relaxed, knowledgeable, and incredibly accommodating. He made everyone feel comfortable and safe while still keeping the trip fun and memorable. The boat was beautiful, the sailing was smooth, and he knew exactly how to create the perfect atmosphere for a special family day on the water. You can tell he genuinely loves what he does, and that energy made all the difference. Highly recommend to anyone looking for a relaxing, first-class sailing experience. We’ll definitely be back. Thank you again for making Mother’s Day so special!

  4. MT

    Michelle

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    We had the absolute best time with Gerald. From the moment we stepped on the boat, we were treated like family. His kindness, generosity, and genuine spirit made the entire experience feel so special. What stood out most was not only how much fun we had, but how it truly felt like we made a new friend. Gerald’s knowledge of the area is expert level, and he shared so many great insights that made the day even more enjoyable. This was such a memorable experience for our group, and we cannot recommend him enough. We will absolutely be back.

  5. jj

    joy

    Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

    stellar experience overall, great memories with my family and learned a little history about oyster Bay.

  6. MM

    Monica

    Sailing Adventure Aboard 44' Hunter Sailboat

    I cannot rave more about how AMAZING our experience was with Geoff! 1000 stars! It was absolutely beautiful and he made sure we had the best view of the sunset. We booked with him for an engagement photoshoot and he was super professional, fun, and incredibly helpful throughout helping us get the perfect shots. I’d recommend booking with Geoff for any occasion. I will definitely book again! Thanks Geoff!