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
(8,056 Reviews)

Page 4 of 39922 listings

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
Suncatcher 22ft Family Pontoon!
Powerboats in Montana · 8 guests

Suncatcher 22ft Family Pontoon!

5.0
$65/hour
55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.
Sailing in Marina del Rey · 12 guests

55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.

5.0
Superowner
Best of 2026
$185+/hour
Sailing Charter On 35' Ericson Sloop In Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 8 guests

Sailing Charter On 35' Ericson Sloop In Puerto Vallarta, Mexico

5.0
Superowner
$119+/hour
Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
$220/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
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
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
Sailing is unique in Puerto Vallarta on board the Catalina 42 Sailing Yacht!
Sailing in Marina Vallarta · 12 guests

Sailing is unique in Puerto Vallarta on board the Catalina 42 Sailing Yacht!

5.0
Superowner
$145/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
Beautiful Classic Sailboat in Marina Del Rey
Sailing in Marina del Rey · 10 guests

Beautiful Classic Sailboat in Marina Del Rey

5.0
$200+/hour
Luxury 42ft Catamaran Sailing Charter in Charleston Harbor
Sailing in Mount Pleasant · 6 guests

Luxury 42ft Catamaran Sailing Charter in Charleston Harbor

5.0
Superowner
$225+/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
$173/hour
2019 Lagoon 450F Sailing Catamaran Yacht in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 17 guests

2019 Lagoon 450F Sailing Catamaran Yacht in Puerto Vallarta, Mexico

5.0
$370+/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.8
$150/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
50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys
Sailing in Marina · 40 guests

50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys

New
$720/hour
Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL
Sailing in West Palm Beach · 12 guests

Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL

4.3
Superowner
$125+/hour
High Demand
SINGLAR PLUS BITCOIN LIMITED EDITION
Powerboats in Cartagena · 10 guests

SINGLAR PLUS BITCOIN LIMITED EDITION

4.8
$550/day
Yacht Party 42' Sea RaySundancer Free 1-way pick up transportation Hotel Marina
Events in Cancún · 8 guests

Yacht Party 42' Sea RaySundancer Free 1-way pick up transportation Hotel Marina

5.0
$180/hour
Instant Book
40' Leopard Luxury Catamaran All-Inclusive Charter in Playa del Carmen.
Sailing in Playa del Carmen · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Playa del Carmen.

5.0
Superowner
Best of 2026
$450/hour
52ft Custom Motor Yacht for Charter in Cabo San Lucas
Events in Marina · 18 guests

52ft Custom Motor Yacht for Charter in Cabo San Lucas

4.8
$350/hour
Beautiful Jeanneau 58' Sailboat in San Diego
Sailing in San Diego · 8 guests

Beautiful Jeanneau 58' Sailboat in San Diego

4.8
$400/hour
Wild Cat 35 Sailing Catamaran Charter starting fare up to 12 people.
Sailing in Isla Mujeres · 26 guests

Wild Cat 35 Sailing Catamaran Charter starting fare up to 12 people.

4.9
Superowner
$169+/hour

Sailing Reviews in United States

  1. GM

    Gagan

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

    I had a great time on board with Captain Fred and James who were taking over for Jan while he was away. Jan reached out to me via phone call and gave me a great run down of expectations and what I wanted the itinerary to be. He also followed with an orientation email and introduced me to Fred. Fred was great and was really passionate about sailing. He even let us drive for a good while. It was an incredible experience and we likely will be back with more people!!

  2. DB

    David

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

    Our Host & Captain were amazing. They gave our family a great tour on the water with our own private swimming area, a scenic sunset cruise and checking out all the majestic cliffs and caves. We'll definitely rent from them again.

  3. DH

    Debbi

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

    This boat is as advertised. It’s a floating living room. It’s very comfortable and easy to get into and out of the water. It’s not set up to deal with large waves or long periods on the open ocean so you are limited in where you can go. But it is a very nice time and exactly as I expected. The staff was amazing…beyond friendly and helpful. The guacamole is delicious (more matcha!). I would definitely do this again.

  4. GK

    George

    Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL

    Capt Mark is not just a skilled boatman, he is a gentleman of many talents. What a delight to spend the day on his Naked Truth (thankfully, Capt stayed fully clothed!). This was a sailing experience even staying in the intracoastal. You made our day memorable! I look forward to our next voyage.

  5. BP

    Billie Jo

    Luxury Leopard 38 Catamaran located in Downtown Miami

    Captain Aaron is wonderful and the experience exceeded our expectations

  6. GM

    George

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

    If you’re in the Bay Area, going with Jan and the Hokahey is a no brainer. Excellent communication from booking to boarding. Great conversation and knowledge of the area. Beautiful boat with room indoors for a warm setting out of the breeze, and plenty of room to spread out and sit up high and see the views or lay on the trampoline mesh up front to listen to the waves. Excellent experience, would recommend to anyone.