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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,509 Reviews)

Page 2 of 40 • 952 listings

Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
Sailing in Shalimar · 6 guests

Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

5.0
$150/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Westport · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Sailing in Tisbury · 6 guests

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

5.0
Superowner
$355/hour
40' Luxury Catamaran in Cozumel -
Sailing in San Miguel de Cozumel · 22 guests

40' Luxury Catamaran in Cozumel -

5.0
Superowner
$252+/hour
Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak
Sailing in Cancún · 25 guests

Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak

5.0
$406/hour
Limited Availability
Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

5.0
$238+/hour
Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
$85/hour
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$750+/hour
#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages

5.0
Superowner
$300/hour
Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

5.0
$250/hour
Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!
Powerboats in South Carolina · 10 guests

Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

5.0
$57/hour
Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey
Sailing in Marina del Rey · 6 guests

Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

5.0
Superowner
Best of 2026
$150/hour
Sunset Cruise on Classic 1975 Sailboat
Sailing in Marina del Rey · 2 guests

Sunset Cruise on Classic 1975 Sailboat

5.0
$65/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
Superowner
$300+/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

5.0
$225/hour
Private Catamaran Fun from Isla Mujeres | Open Bar & Snorkeling
Sailing in Centro - Supmza. 001 · 15 guests

Private Catamaran Fun from Isla Mujeres | Open Bar & Snorkeling

4.9
Superowner
$188/hour
Avalon Harbor's Only Sailing Charter
Sailing in Avalon · 6 guests

Avalon Harbor's Only Sailing Charter

5.0
$275+/hour
Enjoy cruising the Montego Bay coastline  In a 46  feet Searay yacht
Events in Montego Bay · 16 guests

Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

4.9
Superowner
Best of 2026
$599/hour
⛵️ Catamaran Party Boat 50' (49-Person)
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 50' (49-Person)

5.0
Superowner
$700+/hour
Beautiful Catalina 42 Sailboat In Puerto Vallarta, México
Sailing in Marina Vallarta · 12 guests

Beautiful Catalina 42 Sailboat In Puerto Vallarta, México

5.0
$130+/hour
La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California
Sailing in Oceanside · 6 guests

La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California

5.0
$150/hour

Sailing Reviews in United States

  1. KM

    Kimberly

    Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

    This boat was seriously so amazing and was the highlight of our trip to Charleston! The boat is fully stocked with ice, cups, and non alcoholic drinks. The inside area was super comfy and a great place to get some shade. The outside area of the boat was super spacious and had plenty of room. Highlight was seeing so many dolphins!

  2. EB

    Emily

    38-ft Hunter 376 Sailing Adventure in Annapolis

    A wonderful experience start to finish! Alberto and his wife were so wonderful; we had a great time learning some sailing basics, enjoying the day on the water, and chatting about life. We hope we get to do another trip with them soon.

  3. SP

    Susan

    Sunset Cruise on Classic 1975 Sailboat

    We had the most spectacular sunset sail aboard the Hot Tamale with Captain Karl! He was a very skilled and knowledgeable sailer, allowed us to help raise the sail, and we were so impressed with how he restored this beautiful ship. We were lucky enough to have a warm evening, gentle waves, and clear skies. A pod of dolphins joined us just at sunset which was such a fun bonus. What a perfect way to celebrate my boyfriend’s birthday. We will absolutely be booking another sail sometime soon.

  4. NB

    Nicole

    Beautiful Catalina 42 Sailboat In Puerto Vallarta, México

    The staff of this boat were amazing super attentive. They were always offering help, making sure our kids were safe and helping us. The boat was fantastic and their guacamole was amazing! Thanks again for this experience

  5. DH

    Dianne

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    Booked for our Anniversary with my 2 kids and OMG it was an experience we will never ever forget! I wish we coulve stayed longer. It was spectacular, amazing beyond words! Gustavo made sure we are safe especially the kids! He is a gentle soul, very patient and welcoming. The boat was very clean and well equipped. Truly an experience everyone must try once in their life! Haha! I can’t get over it!!

  6. SL

    Saskia

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Captain Alberto and his wife provided a lovely sailing experience for myself and my elderly parents, and were so kind to help both of my parents on and off the boat with great care-- even assisting them to get back to our car. We really enjoyed our time out on the bay