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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,051 Reviews)

Page 12 of 39920 listings

33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$199+/hour
Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica
Sailing in Tamarindo · 16 guests

Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica

5.0
$320/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
Beautiful 57' Lagoon Sailing Catamaran
Sailing in Seattle · 12 guests

Beautiful 57' Lagoon Sailing Catamaran

5.0
$900/hour
Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina
Sailing in Little River · 6 guests

Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina

5.0
$150/hour
41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0
$450/hour
Fort Lauderdale - Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale - Bahamas Sailing Charters

5.0
$130+/hour
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
$159+/hour
San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event
Sailing in San Diego · 30 guests

San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

5.0
$600+/hour
Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!
Events in Cabarete · 100 guests

Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!

New
Superowner
Best of 2026
$45/hour
Chicago's Largest Chartered Catamaran!
Sailing in Chicago · 13 guests

Chicago's Largest Chartered Catamaran!

5.0
$375+/hour
Limited Availability
Hudson 58ft Sailing Vessel - Enjoy The Classic Sailing Experience With Us!
Sailing in Marina del Rey · 12 guests

Hudson 58ft Sailing Vessel - Enjoy The Classic Sailing Experience With Us!

4.8
$275+/hour
Up to 7 person Private Sailing Catamaran Charter with Captain included
Sailing in Chicago · 6 guests

Up to 7 person Private Sailing Catamaran Charter with Captain included

5.0
$450/hour
Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste
Sailing in Coco · 10 guests

Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

5.0
$165/hour
46' Lagoon 450 Sailing Catamaran - 12 Guests - Kemah Boardwalk Marina, Galv Bay
Sailing in Kemah · 12 guests

46' Lagoon 450 Sailing Catamaran - 12 Guests - Kemah Boardwalk Marina, Galv Bay

5.0
$279+/hour
Shared Catamaran Sailing Tour To Passion Island (9am to 2pm)
Sailing in Zona Hotelera Norte · 35 guests

Shared Catamaran Sailing Tour To Passion Island (9am to 2pm)

5.0
$74/hour
Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico
Sailing in Marina · 15 guests

Private Charter on a 38ft Cruising Catamaran for Up to 15 People in Cabo, Mexico

5.0
$420/hour
Negril Private Catamaran Cruise with Snorkeling & Drinks
Sailing in West End · 120 guests

Negril Private Catamaran Cruise with Snorkeling & Drinks

New
$509/hour
Enjoy a small group Shared Sunset Sailing Cruise in Cabo San Lucas
Sailing in Marina · 14 guests

Enjoy a small group Shared Sunset Sailing Cruise in Cabo San Lucas

5.0
Superowner
Best of 2026
$60/hour
Chaparral 256 Family Cabin Cruiser
Powerboats in Jersey City · 9 guests

Chaparral 256 Family Cabin Cruiser

5.0
$275/hour
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 4 guests

★ 28' Classic Schooner in Rockland, Maine ★

5.0
$175/hour
38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.
Sailing in Tulum · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.

5.0
Superowner
Best of 2026
$420/hour
Limited Availability
55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!
Sailing in Marina del Rey · 12 guests

55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

4.9
Superowner
Best of 2026
$185+/hour
San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp
Sailing in San Diego · 6 guests

San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

5.0
$54/hour

Sailing Reviews in United States

  1. MH

    Madeline

    Hudson 58ft Sailing Vessel - Enjoy The Classic Sailing Experience With Us!

    Perfect sailboat experience for a large group!! I booked this for a group of photographers and I, and it was seriously everything we could've hoped for! The boat is gorgeous above and below deck and our captain was excellent! He was so helpful in helping us navigate where to spend the most of our time since it was pretty rough waters outside of the marina, and helped to make sure the seasick ones in our group felt comfortable & no one ended up getting too sick! Would book again in a heartbeat :)

  2. AS

    Andrew

    San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

    Our birthday celebration aboard the Jada was nothing short of exceptional. The yacht is stunning, the atmosphere was perfect, and the crew delivered a flawless experience - attentive, welcoming, and effortlessly on point throughout the entire day. Every moment felt seamless and elevated. It was one of those days you wish you could relive again and again. We’ll absolutely be back.

  3. YF

    Yosi

    55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

    We had an incredible time on our three‑hour boat trip. The ride itself was beautiful—calm water, great views, and the perfect mix of relaxation and adventure—but what truly made the experience stand out was the captain. He was an absolute pleasure to be with: friendly, knowledgeable, and genuinely invested in making sure everyone on board felt comfortable and had a great time. His easygoing personality and passion for what he does turned a simple outing into a memorable experience. I’d happily sail with him again.

  4. BC

    Breck

    Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

    This is by far the best catamaran experience I’ve ever had! The whole trip, the hospitality, the food, the atmosphere, everything about the entire time spent with Clem and crew was truly incredible. I wholeheartedly recommend this experience to everyone I talk to.

  5. JF

    Joshua

    Chaparral 256 Family Cabin Cruiser

    we highly recommend eli as a captain - he was very accommodating & easy communication, great boat and enjoyable experience! 5+ star!

  6. GL

    Gregoire