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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,466 Reviews)

Page 2 of 41 • 964 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
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$180/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
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
$401/hour
40' Luxury Catamaran in Cozumel -
Sailing in San Miguel de Cozumel · 22 guests

40' Luxury Catamaran in Cozumel -

5.0
Superowner
$249+/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
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
Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!
Sailing in San Diego · 6 guests

Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!

5.0
$225/hour
30ft Sailing Yatch. Real & Unique Sailing in Mazatlán
Sailing in Marina Mazatlán · 8 guests

30ft Sailing Yatch. Real & Unique Sailing in Mazatlán

5.0
$2,000/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
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
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
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
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
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
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
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

5.0
$225/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
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

Sailing Reviews in United States

  1. TW

    Toree

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

    From start to finish this experience was incredible. If we are ever back we will be booking with Tanya, no doubts. She was quick in responding, added lots of personal touches to our experience making it so unique and exciting. The crew on board was incredible. I had written their names down just because they were so awesome I wanted to give them a shout out, but I seem to have lost it. Vicky our host on the boat was perfect. Our captain was so personal and went above to make our trip special. And don’t get us started on the food our chef cooked up- the best. The young man helping was always attentive and helpful. All together the four of them made this boat trip one to remember. Thank you Tanya and team. Looking forward to seeing you guys again (hopefully)

  2. 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!

  3. 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.

  4. Bernardita

    Bernardita

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    Gustavo was courteous, informative and made sure to explain safety and was a pleasure to have as a captain. We thoroughly enjoyed our day on the water. I hope to hire him again! Thank you, Gustavo!

  5. TP

    Tripp

    Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!

    Max was a fantastic captain! I used this booking to propose to my girlfriend and Max helped insure it went smoothly. The boat was gorgeous and we had a relaxing sail through the bay! Highly recommend!

  6. 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