Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,454 Reviews)

Page 3 of 39932 listings

Open Bar Escape: 40ft Catamaran Charter in Cancún for up to 30 Guests
Sailing in Cancún · 30 guests

Open Bar Escape: 40ft Catamaran Charter in Cancún for up to 30 Guests

New
Superowner
$300/hour
30ft Catalina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catalina Sailboat Charter in Alameda CA

5.0
$95/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
Luxury Catamaran Leopard 48 in Santa Marta Colombia
Sailing in Santa Marta · 10 guests

Luxury Catamaran Leopard 48 in Santa Marta Colombia

5.0
$150/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
2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

5.0
$200/hour
Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat
Sailing in Newport · 6 guests

Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat

5.0
$400/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
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
High Demand
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
Catalina 36 Sailing Yacht Charter Mazingon in Valle de Bravo
Sailing in Valle de Bravo · 16 guests

Catalina 36 Sailing Yacht Charter Mazingon in Valle de Bravo

5.0
$174/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
Sail Away Private Day Trip: all inclusive with Snorkelling and Island Hop!
Sailing in San Pedro · 24 guests

Sail Away Private Day Trip: all inclusive with Snorkelling and Island Hop!

4.9
$275+/hour
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
Private 44ft Trimaran in Los Cabos for 50 Guests
Sailing in Juárez · 50 guests

Private 44ft Trimaran in Los Cabos for 50 Guests

5.0
Superowner
Best of 2026
$250/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
$352/hour
Instant Book
Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México
Sailing in Marina Vallarta · 20 guests

Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México

5.0
$265/hour
Private Catamaran Charter in Los Cabos | 46ft Nautitech Sailing Yacht
Sailing in San José del Cabo · 12 guests

Private Catamaran Charter in Los Cabos | 46ft Nautitech Sailing Yacht

5.0
$500+/hour
Amazing Party Boats In Puerto Plata Make Your Reservation Now
Powerboats in Puerto Plata · 100 guests

Amazing Party Boats In Puerto Plata Make Your Reservation Now

5.0
Superowner
Best of 2026
$50/hour
All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas
Sailing in Marina · 50 guests

All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas

5.0
Superowner
Best of 2026
$367/hour
Schock 35' Cruiser Sailboat in San Francisco Bay
Sailing in Alameda · 6 guests

Schock 35' Cruiser Sailboat in San Francisco Bay

5.0
$99/hour
Private 38' Hunter Sailing boat in Cabo San Lucas
Sailing in Marina · 12 guests

Private 38' Hunter Sailing boat in Cabo San Lucas

4.9
Superowner
Best of 2026
$275/hour
Luxury Leopard 38 Catamaran located in Downtown Miami
Sailing in Miami · 12 guests

Luxury Leopard 38 Catamaran located in Downtown Miami

5.0
$219+/hour
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way
Sailing in Marina · 6 guests

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way

4.8
Superowner
$170/hour

Sailing Reviews in United States

  1. 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.

  2. 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!

  3. German

    German

    30ft Catalina Sailboat Charter in Alameda CA

    We had an absolutely fantastic time with Bradford! He was friendly, professional, knowledgeable, and made the whole experience very relaxed and enjoyable from start to finish. Sailing around San Francisco Bay was a great experience, and Bradford made it even better. We felt comfortable the entire time and really enjoyed spending the afternoon with him. Highly recommended — we would definitely book with Bradford again!

  4. AW

    Ariana

    Los Cabos Private Catamaran Cruise with Snorkeling & Open Bar!

    My group of 13 and I had an excellent time aboard! From the moment we got on the boat, the vibes were great! I chose this boat because it offered lunch in addition to an open bar. The food was good and the drinks were strong! I couldn't have asked for a better bachelorette party experience!

  5. JC

    Jon

    30ft Catalina Sailboat Charter in Alameda CA

    Our group of six had a wonderful time. Plenty of space for everyone to stretch out. The Marina was easy to find and had plenty of convenient parking. Communicating with Brad before our appointment time was easy. highly recommend.

  6. ZC

    Zach

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

    We really enjoyed our sailing on 9/12 with Jan’s crew. The boat was beautiful and everyone on board was extremely friendly and attentive!