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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,476 Reviews)

Page 39 of 40 • 938 listings

Bayliner Deck Boat Rental at Lake wallenpaupack!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Lake wallenpaupack!

New
$115/hour
Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan
Sailing in Holland · 6 guests

Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan

New
$150/hour
22ft SeaSwirl Striper Center Console
Fishing in Los Angeles · 8 guests

22ft SeaSwirl Striper Center Console

New
$175/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
Stay Warm and dry, year-round cruising San Juan’s and Seattle charters
Sailing in Seattle · 6 guests

Stay Warm and dry, year-round cruising San Juan’s and Seattle charters

New
$350+/hour
Unwind in Sunlit Luxury: Experience 360° Views Aboard This One-of-a-Kind Yacht!
Sailing in Stock Island · 12 guests

Unwind in Sunlit Luxury: Experience 360° Views Aboard This One-of-a-Kind Yacht!

New
$325+/hour
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/hour
Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
Sailing in Gloucester · 60 guests

Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

New
$1,200+/hour
 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
Best of 2026
Snoozed - Active 02 Oct 2026
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 17 May 2027
Limited Availability
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
Snoozed - Active 05 Oct 2026
Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!
Sailing in New Orleans · 6 guests

Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

5.0
Snoozed - Active 02 Jan 2027
52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

5.0
Snoozed - Active 02 Jan 2027
Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

5.0
Snoozed - Active 02 Jan 2027
SeaDoo Switch Sport *5 ADULTS*
Powerboats in Texas · 9 guests

SeaDoo Switch Sport *5 ADULTS*

5.0
Snoozed - Active 02 Oct 2026
Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC
Sailing in Manhattan · 6 guests

Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

5.0
Snoozed - Active 28 Sep 2026
Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.
Sailing in Brooklyn · 6 guests

Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.

5.0
Snoozed - Active 02 Jan 2027
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
Snoozed - Active 12 Oct 2026
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
Sailing in Chicago · 6 guests

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

5.0
Snoozed - Active 14 Jun 2027
Bali 43 Complete comfort Catamaran
Sailing in Marina del Rey · 12 guests

Bali 43 Complete comfort Catamaran

5.0
Snoozed - Active 09 Oct 2026
All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter
Sailing in Nassau · 24 guests

All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter

5.0
Snoozed - Active 02 Nov 2026
46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica
Sailing in Playa Flamingo · 40 guests

46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica

5.0
Snoozed - Active 02 Nov 2026
Islander 36 - The Perfect Sailing Yacht for San Francisco Bay
Sailing in Sausalito · 6 guests

Islander 36 - The Perfect Sailing Yacht for San Francisco Bay

5.0
Snoozed - Active 02 Jan 2027
51ft Bavaria Cruiser – Shelter Island San Diego Luxury Ocean Charter
Sailing in San Diego · 12 guests

51ft Bavaria Cruiser – Shelter Island San Diego Luxury Ocean Charter

New
Snoozed - Active 02 Jan 2027

Sailing Reviews in United States

  1. Jen

    Jen

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    My sister and I had a wonderful time with Captain Allan and we had perfect weather all day. He was very knowledgable about the local area and a very skilled captain, making us feel comfortable throughout the whole experience. We played music and had such a great time talking with him. Would absolutely recommend and definitely use Captain Allan again.

  2. MC

    Marco

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian is a great captain. You can truly see he loves to sail. The best way to be lead on an adventure is by someone who is passionate. He has a lot of knowledge regarding the cityscapes the surround our rivers here in NYC. I have seen the city from the sky during heli rides and can say sailing was so much better. Will definitely bring more visiting family and friends to sail with him.

  3. RA

    Rosette

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Captain Ian was professional, knowledgeable, and created a relaxed, welcoming atmosphere from the moment we stepped aboard. The boat was beautiful, the views of the Manhattan skyline were incredible, and the entire experience felt both peaceful and memorable. Captain Ian made sure everyone was comfortable while sharing interesting insights along the way. If you’re looking for a private sailing experience on the Hudson that’s both scenic and personal, I highly recommend booking with Captain Ian. We can’t wait to sail again!

  4. TF

    Todd

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.

  5. AF

    Allison

    All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter

    What a day! That’s the best way I can describe this incredible experience. True Story is a true gem. Our crew, Steven our captain and Cecilia and Bianca made this a trip to remember. From the moment we boarded to the moment we left. We booked this trip for my mom’s 80th birthday. We had ages 21-80 and everyone fully enjoyed. From relaxing in the sun, to snorkeling, jet skiing, paddle boarding, walking on private beaches, and we even had a few try the E-Foil. It was constant fun! And I can’t say enough about the food. Beautiful, healthy and super yummy. We did not leave hungry. This was truly an experience of a lifetime and again, it would not have been the same without this incredible crew. We hope to be back to the Bahamas and we would 100% book this again. Thank you from the bottom of our hearts, True Story crew!

  6. AB

    Alan

    Sail in downtown Toronto

    Dom was a great host. He went above and beyond. We have nothing but good things to say about our experience. Ot was a great experience and we would definitely recommend it for anyone visiting the area or locals just wanting to get out on the water and enjoy the beautiful views.