Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,367 Reviews)

Page 16 of 39925 listings

26ft Beneteau Flyer 8 Sundeck
Powerboats in Marina del Rey · 8 guests

26ft Beneteau Flyer 8 Sundeck

New
$200/hour
Private Sail from Brooklyn Bridge Park
Sailing in Manhattan · 6 guests

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
41ft Sailing Charters from Costa Mujeres, Cancun
Sailing in Isla Mujeres · 32 guests

41ft Sailing Charters from Costa Mujeres, Cancun

5.0
Superowner
$248/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
$315+/hour
All-Inclusive Luxury Catamaran in Puerto Vallarta
Sailing in Nuevo Vallarta · 14 guests

All-Inclusive Luxury Catamaran in Puerto Vallarta

5.0
$918/hour
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0
$499+/hour
Luxury Lagoon 450 Sailing Catamaran in Oceanside
Sailing in Oceanside · 6 guests

Luxury Lagoon 450 Sailing Catamaran in Oceanside

5.0
$250/hour
No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
Sailing in Chicago · 12 guests

No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

4.8
$245/hour
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/hour
Negril Private Catamaran Cruise with Snorkeling & Drinks
Sailing in West End · 120 guests

Negril Private Catamaran Cruise with Snorkeling & Drinks

New
$509/hour
Private Luxury Sunset Sailing Cruise in Cozumel, Mexico
Sailing in San Miguel de Cozumel · 35 guests

Private Luxury Sunset Sailing Cruise in Cozumel, Mexico

5.0
$473/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 12 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained
Sailing in Alameda · 6 guests

Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained

5.0
$300/hour
44' Leopard Catamaran All-Inclusive Charter in Tulum Beach.
Sailing in Tulum · 35 guests

44' Leopard Catamaran All-Inclusive Charter in Tulum Beach.

4.5
Superowner
Best of 2026
$520/hour
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour
Private 44ft Catamaran Charter for Up to 45 Guests
Sailing in Cancún · 45 guests

Private 44ft Catamaran Charter for Up to 45 Guests

5.0
Superowner
$343+/hour
Now available: 53" Carver Yacht for spring and summer sunset & day cruises
Events in Galveston · 12 guests

Now available: 53" Carver Yacht for spring and summer sunset & day cruises

5.0
$400/hour
40ft Catamaran Private Charter / Capacity 30 people
Sailing in Cancún · 30 guests

40ft Catamaran Private Charter / Capacity 30 people

5.0
Superowner
$275+/hour
Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/hour
20ft Bayliner VR5 Boat in Rockville, IN
Powerboats in Indiana · 6 guests

20ft Bayliner VR5 Boat in Rockville, IN

5.0
$510/day
Boat for Groups of up to 60 People in Cancún, Quintana Roo
Events in Cancún · 61 guests

Boat for Groups of up to 60 People in Cancún, Quintana Roo

5.0
$207/hour
San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat
Sailing in San Diego · 8 guests

San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat

5.0
$300/hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$450/hour

Sailing Reviews in United States

  1. CL

    Cathy

    Private Sail from Brooklyn Bridge Park

    Ian was a great captain. Very fun to sail with and he made us feel very comfortable. Celebrated my 30th and couldn’t recommend this experience, esp with Ian, more.

  2. CS

    Cait

    Private Sail from Brooklyn Bridge Park

    We had the best time on the boat trip. Michael was a great captain who was helpful and friendly. I would highly recommend this boat tour.

  3. NG

    Nicole

    Private Sail from Brooklyn Bridge Park

    We had such a great evening sailing around NYC! Andrew was a wonderful host and captain and even went out of his way to help one of our group struggling with motion sickness. We enjoyed the route and putting up the sail in the harbor! Overall, it was an awesome experience, and I would definitely recommend booking for a fun and memorable experience!

  4. ME

    Malky

    Private Sail from Brooklyn Bridge Park

    Sailing with this boat was a truly beautiful and magical experience!! It was comfortable and looked fresh too. We had a wonderful captain and he was very experienced and smooth! Ian was very responsive and accommodated us with our specific timing at sunset. My husband and I really enjoyed our night on the water!

  5. FS

    FRANCI

    Private Sail from Brooklyn Bridge Park

    Ian provided us with a fantastic sailing experience for our wedding anniversary. It was absolutely lovely—truly beyond our expectations. His communication and instructions were clear and outstanding from start to finish. On the day of our sail, Ian even reached out to offer an earlier time slot when one became available, which we appreciated. The boat was perfect, and we had an unforgettable time on the water. Thank you, Ian, for making our special day even more memorable!

  6. VL

    Van

    Private Sail from Brooklyn Bridge Park

    It's a bit windy but we all enjoyed the view and how friendly and professional Andrew is. He was very kind in helping my friend who has sea sickness. I had a wonderful birthday today on the boat even though it was cold. Also, they kindly waited for me to arrive due to unexpected traffic jam.