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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,681 Reviews)

Page 21 of 451,077 listings

4-Hour Private Charter in Destin, Florida! Crab Island, Snorkeling, Dolphins & More!
Sailing in Destin · 6 guests

4-Hour Private Charter in Destin, Florida! Crab Island, Snorkeling, Dolphins & More!

5.0
$150hour
2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale

5.0
$150hour
Samana catamaran SAILING & exclusive Wellness experience
Sailing in Samaná Province · 12 guests

Samana catamaran SAILING & exclusive Wellness experience

New
$297hour
Bahamas Sunset Sailing Cruise
Powerboats in Nassau · 8 guests

Bahamas Sunset Sailing Cruise

New
$325hour
🤩VIP🛥PRIVATE BOAT FOR SMALL OR BIG GROUPS-BACHELORETE-FAMILY Trip Río San Juan
Events in Rio San Juan · 150 guests

🤩VIP🛥PRIVATE BOAT FOR SMALL OR BIG GROUPS-BACHELORETE-FAMILY Trip Río San Juan

New
Superowner
$59person
''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl
Events in Cape Canaveral · 11 guests

''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl

5.0
$382hour
80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

80' Sailing Schooner Charter In Key West, Florida

5.0
$475-$950hour
1978 Classic Explorer 45' Bluewater Sailboat for Charter in Oceanside, CA
Sailing in Oceanside · 7 guests

1978 Classic Explorer 45' Bluewater Sailboat for Charter in Oceanside, CA

5.0
$170hour
Luxury Experience on a new 2020 Catamaran in Baja California Sur, Mexico
Sailing in La Paz · 14 guests

Luxury Experience on a new 2020 Catamaran in Baja California Sur, Mexico

5.0
$406hour
Center Console Private Bahamas Boat Charter
Powerboats in Nassau · 14 guests

Center Console Private Bahamas Boat Charter

New
$325-$375hour
50' Sailing Catamaran Charter in Noord, Aruba
Sailing in Oranjestad-West · 50 guests

50' Sailing Catamaran Charter in Noord, Aruba

5.0
$700hour
Experience premiere service: NYC’s longest-running private sailing charter
Sailing in Manhattan · 6 guests

Experience premiere service: NYC’s longest-running private sailing charter

5.0
$370hour
Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC
Sailing in Wilmington · 6 guests

Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC

5.0
$350hour
Vintage-style sailboat Ketch 50 ft
Sailing in Marina Vallarta · 14 guests

Vintage-style sailboat Ketch 50 ft

New
Superowner
Best of 2023
$135hour
Sail from Delray Beach to Lake Boca - $150/Hr - $30/Person
Sailing in Delray Beach · 10 guests

Sail from Delray Beach to Lake Boca - $150/Hr - $30/Person

New
Superowner
Best of 2023
$30person
Lagoon 42 Elegance, Modernity & Space Freedom
Sailing in La Cruz de Huanacaxtle · 20 guests

Lagoon 42 Elegance, Modernity & Space Freedom

New
Superowner
$315-$470hour
Beneteau 50 Elegance, Pleasure & Sailing Performance, Puerto Vallarta Jalisco
Sailing in Marina Vallarta · 10 guests

Beneteau 50 Elegance, Pleasure & Sailing Performance, Puerto Vallarta Jalisco

New
Superowner
$275-$300hour
Sailing live aboard  Charter in Montego Bay, Jamaica
Sailing in Montego Bay · 15 guests

Sailing live aboard Charter in Montego Bay, Jamaica

5.0
$135person
ENJOY CANCUN IN 43FT CRANCHI FOR 12 PEOPLE!!!
Events in Cancún · 12 guests

ENJOY CANCUN IN 43FT CRANCHI FOR 12 PEOPLE!!!

New
$175-$240hour
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia
Sailing in Cartagena · 60 guests

Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia

5.0
$3,500day
Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington
Tours in Anacortes · 6 guests

Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

5.0
$166-$200hour
78ft Catamaran Private Charter / Capacity 100 people in Cancún, Quintana Roo
Sailing in Cancún · 100 guests

78ft Catamaran Private Charter / Capacity 100 people in Cancún, Quintana Roo

5.0
$685-$893hour
A timeless journey sailing the California coast!
Sailing in Marina del Rey · 10 guests

A timeless journey sailing the California coast!

5.0
$400hour

Sailing Reviews in United States

  1. MM

    Mike

    4-Hour Private Charter in Destin, Florida! Crab Island, Snorkeling, Dolphins & More!

    Tracy & Ladd are true professionals, and a generally good time. The offering was exactly as presented and they catered to the specific requests we had. The boat is great and their knowledge of the area helped make this a fantastic afternoon on the water. I would highly recommend you book this if you are looking for a private charter in the Destin, FL area!

  2. Richard

    Richard

    1978 Classic Explorer 45' Bluewater Sailboat for Charter in Oceanside, CA

    Captain Eric and his First Mate, Nate, showed us a wonderful time sailing out of Oceanside Harbor. We highly recommend the Captain and his classic sailing ship! My family & I chartered the boat primarily to disperse my mother's ashes. Although this was a somewhat sad experience for us, Captain Eric could not have been more helpful and empathetic. He even provided a bucket for that purpose. Nate's hors d'oeuvres and the champagne were top notch quality and most appreciated. (Not one of the seven in our party experienced motion sickness.) We also appreciated the Captain's willingness to take pictures of our group. He had shared lots of interesting "sea stories. His love for his boat, and the care he devotes to it, really shines through. All in all, our morning was a relaxing & pleasant experience thanks to Captain Eric & Nate!

  3. Jason

    Jason

    1978 Classic Explorer 45' Bluewater Sailboat for Charter in Oceanside, CA

    I can’t say enough great things about Eric and the experience. The boat is a classic beauty sure to impress just about anyone. The captain has the right mix of professionalism and know-how while keeping things comfy and fun. Have no doubt when booking. This is the perfect sailing adventure you’ve envisioned.

  4. Justin

    Justin

    50' Sailing Catamaran Charter in Noord, Aruba

    The best time in Aruba with the best crew!! 21 of us came to Aruba for my Husbands 50th this was definitely a must!! The food and drink were great as were the snorkel spots!!! I added on a charcuterie board and fruit platter for a small charge. All my guest were so happy I planned this excursion. I will definitely be back!!!

  5. MA

    Megan

    Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC

    James was so accommodating for our elopement on his sailboat. He was always quick to respond and great at communicating with us. We really enjoyed our trip on the water and James made it easy for us to be comfortable and sit and relax. It was perfect!

  6. BM

    Breana

    A timeless journey sailing the California coast!

    I have one word to describe the way we felt aboard the Mayan Star — special. It really was an experience, including the vibe that they have curated to fit. It won’t be hard to convince my husband to allow us to book more trips in the future!