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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,466 Reviews)

Page 40 of 41 • 964 listings

SAILING THE GULF OF NICOYA ON A LUXURY 37" YACHT
Sailing in Punta Arenas · 4 guests

SAILING THE GULF OF NICOYA ON A LUXURY 37" YACHT

New
$100/hour
Sail into adventure in Costa Rica, playa Flamingo
Sailing in Playa Flamingo · 12 guests

Sail into adventure in Costa Rica, playa Flamingo

New
$2,640/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
Bayliner Deck Boat Rental at Lake wallenpaupack!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Lake wallenpaupack!

New
$115/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
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
Seattle Sailing Adventure – Wicked Wind Catalina 275 Sport
Sailing in Seattle · 4 guests

Seattle Sailing Adventure – Wicked Wind Catalina 275 Sport

New
$80/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
William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience
Sailing in Seattle · 8 guests

William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience

5.0
Snoozed - Active 02 Feb 2027
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
43' Beneteau Sailboat with Captain for 6 People in Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Beneteau Sailboat with Captain for 6 People in Bristol RI & Beyond

5.0
Snoozed - Active 01 May 2027
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
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
Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida
Sailing in West Palm Beach · 12 guests

Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida

5.0
Snoozed - Active 02 Feb 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. 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.

  3. 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!

  4. 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!

  5. LT

    Luc

    William Garden 39ft Ketch Sailboat Bar Hop Seattle Experience

    Shiva was an incredible captain! Super knowledgeable about sailing, and he made the entire experience super special for my wife and I. He’ll tailor the experience to your preferences — whether you want to stay on the water to dock to drink some wine and explore! Don’t hesitate to book with him and his beautiful sailboat.

  6. Kim

    Kim

    Sail in downtown Toronto

    Dominic was incredible! He was so chill and so kind with our family. It was a perfect day out sailing on the water. He taught us so much, shared stories, local history and was genuinely so sweet with our family, taking pictures and showing us points of interest! A PERFECT EXPERIENCE AND A PERFECT DAY!