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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,496 Reviews)

Page 40 of 40 • 951 listings

Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 17 May 2027
Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
Snoozed - Active 02 Nov 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
Efoiling at deer creek reservoir
Adventures in Salt Lake City · 1 guest

Efoiling at deer creek reservoir

5.0
Snoozed - Active 15 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
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
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
The Gallivanders Ultimate Sailing Adventure
Sailing in Nassau · 12 guests

The Gallivanders Ultimate Sailing Adventure

New
Snoozed - Active 03 Jan 2027
Lagoon 420 Hybrid Eco Friendly Electric Catamaran
Sailing in Guna Yala Comarca · 4 guests

Lagoon 420 Hybrid Eco Friendly Electric Catamaran

New
Snoozed - Active 27 Mar 2027

Sailing Reviews in United States

  1. 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.

  2. 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!

  3. 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.

  4. KD

    Katherine

    Sail in downtown Toronto

    We had an amazing time sailing with Dom! The views of the Toronto skyline were incredible, and we learned so much about the Toronto Islands and about sailing along the way. What we especially appreciated was Dom’s ability to make sailing feel accessible and unintimidating—he cuts through the insider language and conventions and focuses on the practical knowledge that really matters when you’re getting started. It made sailing feel much more approachable and feasible for complete beginners like us. Dom was an incredibly warm and welcoming host, and the whole experience was relaxed, fun, and genuinely informative. We also loved how easy it was to bring our own snacks and drinks. Highly recommend!

  5. GK

    Galina

    Sail in downtown Toronto

    Dom is a great and hospitable captain. He was very kind, he offered drinks, always checked with what we would like to see and was ready to offer alternatives. I would highly recommend his services!

  6. HC

    Hazel

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

    Bob and his wife Gabby are amazing. We had so much fun with them. The boat is gorgeous and Bob is clearly a seasoned captain. Thanks again!