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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,660 Reviews)

Page 21 of 451,071 listings

Private Catmaran With Fun Crew up to 55 People Open Bar Unlimited Drinks
Sailing in Cancún · 55 guests

Private Catmaran With Fun Crew up to 55 People Open Bar Unlimited Drinks

New
$40person
Sailing Trip on 35' Catamaran in Cozumel All Inclusive
Sailing in Zona Hotelera Norte · 15 guests

Sailing Trip on 35' Catamaran in Cozumel All Inclusive

5.0
Superowner
Best of 2023
$391hour
Bahamas Sunset Sailing Cruise
Powerboats in Nassau · 8 guests

Bahamas Sunset Sailing Cruise

New
$325hour
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
Private Cruise on 30' Magic-Sea-wind Sailing Catamaran Cancún Isla Mujeres Mexico
Sailing in Cancún · 20 guests

Private Cruise on 30' Magic-Sea-wind Sailing Catamaran Cancún Isla Mujeres Mexico

5.0
$159-$200hour
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
Hunter 170 Sailboat with Honda motor in Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Hunter 170 Sailboat with Honda motor in Sag Harbor, New York

New
$129hour
''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
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
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
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
Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht
Sailing in Philadelphia · 6 guests

Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht

5.0
$350hour
MAXIMA Powerboat 38ft in Cartagena de Indias
Powerboats in Cartagena · 20 guests

MAXIMA Powerboat 38ft in Cartagena de Indias

4.0
$784day
50' Sailing Catamaran Charter in Noord, Aruba
Sailing in Oranjestad-West · 50 guests

50' Sailing Catamaran Charter in Noord, Aruba

5.0
$700hour
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
ENJOY CANCUN IN 43FT CRANCHI FOR 12 PEOPLE!!!
Events in Cancún · 12 guests

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

New
$175-$240hour
Tripp 43 Cruiser Racer Sailing Yacht in Alameda, California
Sailing in Alameda · 6 guests

Tripp 43 Cruiser Racer Sailing Yacht in Alameda, California

New
$199hour
Beautiful 42Ft Express Cruiser yacht in Puerto Vallarta
Events in Isla Iguana · 15 guests

Beautiful 42Ft Express Cruiser yacht in Puerto Vallarta

New
Snoozed - Active 02 Jan 2025
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
Vintage-style sailboat Ketch 50 ft
Sailing in Marina Vallarta · 14 guests

Vintage-style sailboat Ketch 50 ft

New
Superowner
Best of 2023
$135hour
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
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
A timeless journey sailing the California coast!
Sailing in Marina del Rey · 10 guests

A timeless journey sailing the California coast!

5.0
$400hour
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 Reviews in United States

  1. 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!

  2. 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.

  3. Vidur

    Vidur

    Private Cruise on 30' Magic-Sea-wind Sailing Catamaran Cancún Isla Mujeres Mexico

    Boat and crew were absolutely top notch! Everyone was more than willing to create an itinerary based on my preferences, also the crew was always one step away to refill drinks. Highly recommend renting via Eduardo! Shoutout to Helen for getting the reservation turned around in less than 12 hours!

  4. 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!

  5. 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!!!

  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!