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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,472 Reviews)

Page 3 of 41 • 968 listings

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
43' Belize Catamaran Yacht Charter in Cabo San Lucas Baja, California Sur
Sailing in Marina · 20 guests

43' Belize Catamaran Yacht Charter in Cabo San Lucas Baja, California Sur

5.0
$544+/hour
Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!
Sailing in Marina · 70 guests

Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!

5.0
$423+/hour
Instant Book
Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.9
Superowner
$700+/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 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

5.0
$225/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat

5.0
$100+/hour
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
Best of 2026
$220/hour
All-Inclusive Private 42’ Trimaran in Los Cabos
Sailing in Marina · 50 guests

All-Inclusive Private 42’ Trimaran in Los Cabos

4.8
Superowner
Best of 2026
$379/hour
Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta
Sailing in Marina Vallarta · 13 guests

Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta

4.7
$122/hour
Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo
Sailing in Tamarindo · 20 guests

Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

5.0
$2,190/day
Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia
Sailing in Cartagena · 16 guests

Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia

4.8
Superowner
$870/day
Spacious, fast 80 foot sailboat
Events in Nuevo Vallarta · 40 guests

Spacious, fast 80 foot sailboat

5.0
$275/hour
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 2026
$420/hour
Cancun Private 44ft Catamaran - Isla Mujeres | Open Bar, Lunch – Groups & Events
Sailing in Cancún · 40 guests

Cancun Private 44ft Catamaran - Isla Mujeres | Open Bar, Lunch – Groups & Events

5.0
Superowner
$300/hour
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
Superowner
$325/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.9
$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
40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.
Sailing in Puerto Aventuras · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.

4.9
Superowner
Best of 2026
$450/hour
48ft Maui Catamaran for Island, Sunsets and Night Events
Sailing in Cartagena · 40 guests

48ft Maui Catamaran for Island, Sunsets and Night Events

5.0
Superowner
$999/day
Safe & solid sailing catamaran - Green power! Stunning beauty & great location!
Sailing in Richmond · 6 guests

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

5.0
$162+/hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
High End Catamaran, Luxury Private Party in Cabo San Lucas. Captain &  crew inc
Powerboats in Marina · 50 guests

High End Catamaran, Luxury Private Party in Cabo San Lucas. Captain & crew inc

5.0
Superowner
$600/hour
North Lake Tahoe 33ft Hobie Yacht 3 Hour Sailing Experience
Sailing in Placer County · 6 guests

North Lake Tahoe 33ft Hobie Yacht 3 Hour Sailing Experience

4.9
$233/hour

Sailing Reviews in United States

  1. AH

    Amit

    Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

    Jan was an excellent captain, he helped plan a surprise proposal and was a big reason why the day turned out so well. He’s very professional, easy to work with. The boat is quite nice as well, with space to comfortably sit in front and truly take in the sites that the bay has to offer. Could not recommend Captain Jan and his boat enough

  2. JY

    Jonathan

    Cancun Private 44ft Catamaran - Isla Mujeres | Open Bar, Lunch – Groups & Events

    I was celebrating my 50th birthday and I originally booked the 44 foot catamaran for 20 of us and 15 were able to go on the boat. We rented the boat on Tuesday October 13, 2026. The entire booking process with Joe was very easy. Joe responded to all my inquiries and messages in a timely manner. The staff on the boat was led by Victor and they were professional, attentive and fun. We snorkeled around a shipwreck for about 15 minutes. The wreck was pretty neat and there were a lot of fish to be seen. We had about 45 minutes of water time near Isla Mujeres where we could chill on the lily pad, swim in the water and dive off the boat. We had a very nice buffet lunch on Isla Mujeres and had the option to walk around the main tourist area or get beach side massages. Our entire group had an amazing time and I would not hesitate to book the boat again. Once again, my sincerest thanks to Joe and to Victor and the boat crew. Jon

  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. PH

    Paul

    Cancun Private 44ft Catamaran - Isla Mujeres | Open Bar, Lunch – Groups & Events

    Joe was great at communicating with me for our 37 person birthday party catamaran cruise. We had a terrific time and we’ll come back next year and use him and his team again. Thank you!

  5. Jen

    Jen

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    My sister and I had a wonderful time with Captain Allan and we had perfect weather all day. He was very knowledgable about the local area and a very skilled captain, making us feel comfortable throughout the whole experience. We played music and had such a great time talking with him. Would absolutely recommend and definitely use Captain Allan again.

  6. SP

    Sawkia

    48ft Maui Catamaran for Island, Sunsets and Night Events

    The staff tending to us on the boat was awesome and the communication leading up to the boat was great! The communication about the itinerary could have been better! All in all great day despite the mix up. Thank you and will book again!