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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,461 Reviews)

Page 16 of 41 • 962 listings

Lancer 36 Sailing Sloop for 8 Passenger in Puerto Vallarta
Sailing in Marina Vallarta · 8 guests

Lancer 36 Sailing Sloop for 8 Passenger in Puerto Vallarta

New
Superowner
$125/hour
Romantic city lights trip on beanbags on 42 ft Bertram
Events in Long Beach · 6 guests

Romantic city lights trip on beanbags on 42 ft Bertram

5.0
$125/hour
Cancun Shared Catamaran: Isla Mujeres, Snorkeling, Drinks & Buffet Lunch
Sailing in Cancún · 40 guests

Cancun Shared Catamaran: Isla Mujeres, Snorkeling, Drinks & Buffet Lunch

5.0
$60/day
Leopard 51 Flybridge Power Catamaran in Tulúm
Powerboats in Tulum · 25 guests

Leopard 51 Flybridge Power Catamaran in Tulúm

5.0
Superowner
$607+/hour
35' Sailing Yacht Charter in Sausalito
Sailing in Sausalito · 6 guests

35' Sailing Yacht Charter in Sausalito

5.0
$220/hour
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0
$100/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
Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California
Sailing in Newport Beach · 6 guests

Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

5.0
$160/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 this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco
Sailing in San Francisco · 6 guests

Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco

5.0
Superowner
$400+/hour
Private 53' Sailing Catamaran with Cool Crew - Up to 55 People, Open Bar
Sailing in Cancún · 55 guests

Private 53' Sailing Catamaran with Cool Crew - Up to 55 People, Open Bar

5.0
$460+/hour
40ft Private Catamaran in Riviera Maya – Up to 20 Guests
Sailing in Puerto Aventuras · 20 guests

40ft Private Catamaran in Riviera Maya – Up to 20 Guests

New
$465+/hour
Leopard 53 Power Catamaran (25-ft wide deck space)
Powerboats in Fort Lauderdale · 13 guests

Leopard 53 Power Catamaran (25-ft wide deck space)

New
$575+/hour
Catalina 30 sailboat  in Portland, Oregon
Sailing in Portland · 12 guests

Catalina 30 sailboat in Portland, Oregon

5.0
$199/hour
Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht
Sailing in New Bedford · 6 guests

Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht

5.0
$260+/hour
Luxury Lagoon 450 Sailing Catamaran in Oceanside
Sailing in Oceanside · 6 guests

Luxury Lagoon 450 Sailing Catamaran in Oceanside

5.0
$250/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
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
55ft Private Catamaran Charter for Up to 55 Guests in Cancún, Quintana Roo
Sailing in Cancún · 55 guests

55ft Private Catamaran Charter for Up to 55 Guests in Cancún, Quintana Roo

5.0
Superowner
$400+/hour
San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440
Sailing in Brisbane · 6 guests

San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440

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

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
$315+/hour
Cruising Monohull Charter in Samaná, Dominican Republic
Sailing in Samana · 10 guests

Cruising Monohull Charter in Samaná, Dominican Republic

4.0
$1,586/day
63' Catamaran - Newport, RI - Luxury Sailing For Large Groups!
Sailing in Newport · 40 guests

63' Catamaran - Newport, RI - Luxury Sailing For Large Groups!

5.0
$833/hour

Sailing Reviews in United States

  1. ME

    Megan

    35' Sailing Yacht Charter in Sausalito

    We had an absolutely beautiful time with Captain Kirk’s San Francisco Sailing!! My parents came to visit and I took them out on the bay for the afternoon. Our captain, Rowan, was a master boatman—friendly, helpful, encouraging, and hilarious. He truly took the time to ensure that we enjoyed ourselves. Captain Kirk runs a great operation; we had everything we could’ve needed on the boat and they made it very easy to find the boat and ensured we were well-prepared with all the info. It was also extremely well-priced. Overall, very happy with our experience and we will remember it forever!! Couldn’t recommend it enough. Thank you to Rowan and Captain Kirk!

  2. JS

    Janessa

    63' Catamaran - Newport, RI - Luxury Sailing For Large Groups!

    Thank you so much for having us last night! It was truly the BEST boat experience any of us had ! The Captaint and Kiki were the best hosts ! Super helpful and fun !! They exceeded our expectations and the boat was amazing ! Will definitely make this a yearly thing !!!

  3. RB

    Richard

    41' Morgan Classic Sloop in Muskegon, Michigan!!!

    This was our second time sailing with Jim My wife and I had a great time. Jim was easy to contact and responded very quickly to questions before the sail. We had to change our scheduled date and time because of weather, but Jim was very flexible and accommodating. We had a great conversation with him and heard some great stories about his sailing past. He even let me take the helm for a while, which i really enjoyed,

  4. MB

    Malinda

    41' Morgan Classic Sloop in Muskegon, Michigan!!!

    We had such a special day. Our captain was so attentive to everyone's comfort and went above and beyond for our member who was a first time sailor with motion sickness. His company was enjoyable and never intrusive and the day relaxing because he made sure no matter what each individual wanted to do, they got to do it. Thank you for your expertise and kindness Captain!!

  5. RB

    Richard

    41' Morgan Classic Sloop in Muskegon, Michigan!!!

    I gave 5 stars on everything. Would have given 6 if it were an option. Jim was Quick to respond to questions. He was very accommodating and flexible on everything before and during the sailing trip. He was very friendly and has a ton of sailing experience. It was an extremely enjoyable trip.

  6. KG

    Kevin

    41' Morgan Classic Sloop in Muskegon, Michigan!!!

    The trip was exactly as described. Very easy to find and go out for a couple of hours and learn about sailing and the sites to see. Communication was great, the boat was fantastic, and the captain was a great guy who will make sure you have an awesome time. We hope to do this again some day!