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04/20/2024  ± 1 day
All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,698 Reviews)

Page 1 of 451,073 listings

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey
Sailing in Marina del Rey · 4 guests

Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

5.0
Superowner
$105-$125hour
Privat 30’ Sailing Yacht in Mazatlan Bays & Islands
Sailing in Marina Mazatlán · 8 guests

Privat 30’ Sailing Yacht in Mazatlan Bays & Islands

5.0
$150hour
New  Catamaran Lagoon 450 Charter in Puerto Vallarta Mexico
Events in Marina Vallarta · 30 guests

New Catamaran Lagoon 450 Charter in Puerto Vallarta Mexico

4.9
Superowner
Best of 2023
$350hour
 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
$255-$285hour
Instant Book
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2023
$210-$325hour
Sailing Charters in Wilmington NC
Sailing in Wilmington · 6 guests

Sailing Charters in Wilmington NC

5.0
$89person
New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500hour
Privat Sunset  Sailing
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing

5.0
$120hour
Cabbage Key, Captiva Day Trip 1-6 people Captained
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained

5.0
$95-$119hour
Tour in Las Terrenas on 45ft Fountaine Pajot Sailing Catamaran
Sailing in Las Terrenas · 15 guests

Tour in Las Terrenas on 45ft Fountaine Pajot Sailing Catamaran

New
Best of 2023
$279hour
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Treasure Island · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
$225-$350hour
46 feet luxury yacht in Montego Bay with round trip transportation!
Powerboats in Montego Bay · 14 guests

46 feet luxury yacht in Montego Bay with round trip transportation!

5.0
Best of 2023
$699hour
38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.
Sailing in Puerto Aventuras · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Riviera Maya.

5.0
Superowner
Best of 2023
$420hour
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.8
Superowner
$49hour
40' Luxury Catamaran in Cozumel
Sailing in San Miguel de Cozumel · 20 guests

40' Luxury Catamaran in Cozumel

5.0
Superowner
$290hour
MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS
Sailing in Cartagena · 40 guests

MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS

5.0
Superowner
Best of 2023
$1,100day
😍Experience Peace and Tranquility 😍🍷🍾
Sailing in Coronado · 4 guests

😍Experience Peace and Tranquility 😍🍷🍾

5.0
$100-$150hour
50ft Catamaran Charter with Water Toys - Boca Raton, FL
Sailing in Boca Raton · 12 guests

50ft Catamaran Charter with Water Toys - Boca Raton, FL

5.0
$350hour
Private 35' Catamaran Sailing to Isla Mujeres
Sailing in Cancún · 15 guests

Private 35' Catamaran Sailing to Isla Mujeres

5.0
Superowner
$190hour
⛵ Lagoon 40 Yacht Catamaran in Puerto Vallarta
Sailing in Marina Vallarta · 15 guests

⛵ Lagoon 40 Yacht Catamaran in Puerto Vallarta

5.0
Superowner
Best of 2023
$238-$300hour
Beautiful sailboat hunter 40ft adventure sea breezes in Puerto Vallarta
Sailing in Marina Vallarta · 13 guests

Beautiful sailboat hunter 40ft adventure sea breezes in Puerto Vallarta

4.7
$96hour
Sail away in Montego Bay! 39ft Leopard Catamaran
Sailing in Montego Bay · 16 guests

Sail away in Montego Bay! 39ft Leopard Catamaran

5.0
Superowner
Best of 2023
$600hour
SINGLAR PLUS BITCOIN LIMITED EDITION
Powerboats in Cartagena · 10 guests

SINGLAR PLUS BITCOIN LIMITED EDITION

5.0
$550day
30ft Catlina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catlina Sailboat Charter in Alameda CA

5.0
$115hour

Sailing Reviews in United States

  1. BB

    Brendan

    Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

    Matthew was a true professional. Knowledgeable, friendly, and dedicated to his craft. We couldn't have felt more at ease with him and his boat Bronco. I'd highly recommend booking a trip with Matthew if you are considering an adventure on the seas.

  2. CC

    Christine

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    Richard was prompt and affordable. We really enjoyed our day out. There should be mention of the wear and tear on the boat and the fact that the depth finder was broken. Kind of an issue when navigation in such shallow water. Luckily we have experience with that but those who do not may have an issue.

  3. Janine

    Janine

    Privat 30’ Sailing Yacht in Mazatlan Bays & Islands

    This was the highlight of our whole trip! Jorge is an excellent, well known sailor in the area. He is so kind and knowledgeable, we felt like we already knew him. The boat was spotless and the lunch and drinks were perfect! The sights were breathtaking! Thanks again! We loved our day of sailing.

  4. OV

    Olivia

    Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

    We had the most fantastic photoshoot at sea. Matthew was an amazing captain and the boat is gorgeous. He took us on an amazing trip to capture the best shots, was so thoughtful, helpful, and funny. We felt like we were living in a JCrew ad - we can't wait to come back!

  5. AM

    Angela

    Amazing Private Sailing Charter on 36' Sailboat in Marina del Rey

    Excellent communication and professionalism from Matthew took the stress out of planning this excursion for my 7 year old's birthday trip to CA. The location was great with a nice Marina, wildlife spotting, and beautiful beaches! We really enjoyed our first sailing adventure!

  6. AZ

    Ann

    Beautiful sailboat hunter 40ft adventure sea breezes in Puerto Vallarta

    Super friendly and helpful staff (helped us bring food onboard, offered us food + drink multiple times including a beautiful fruit platter), quick communication before the trip, easy to find, convenient departure / drop-off location, would highly recommend!! Thanks!