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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,463 Reviews)

Page 15 of 39932 listings

62ft Lagoon 620 Catamaran – Private Cruise Experience in Newport, RI
Sailing in Newport · 12 guests

62ft Lagoon 620 Catamaran – Private Cruise Experience in Newport, RI

5.0
$1,500/hour
Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building
Sailing in Vancouver · 8 guests

Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

5.0
$179/hour
Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!
Sailing in San Diego · 6 guests

Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!

New
$225/hour
Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste
Sailing in Coco · 10 guests

Gemini 105M Private Catamaran Sailing & Snorkeling in Guanacaste

5.0
$165/hour
Lagoon 42´ Catamaran - All Inclusive In Tulum
Sailing in Tulum · 30 guests

Lagoon 42´ Catamaran - All Inclusive In Tulum

5.0
Superowner
$550+/hour
4-Hour Sailing Catamaran for Rent in Punta Sam, Cancun
Sailing in Isla Mujeres · 12 guests

4-Hour Sailing Catamaran for Rent in Punta Sam, Cancun

5.0
Superowner
$221/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
Limited Availability
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!
Events in Chicago · 13 guests

Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

5.0
$1,190/hour
Nicest Certified Sailing Yacht on the West Coast for 15 People Package
Sailing in San Francisco · 15 guests

Nicest Certified Sailing Yacht on the West Coast for 15 People Package

5.0
Superowner
$650+/hour
Instant Book
Let’s Go Sailing On This Beautiful Private Catalina 350 Yacht From San Francisco
Sailing in San Francisco · 6 guests

Let’s Go Sailing On This Beautiful Private Catalina 350 Yacht From San Francisco

5.0
$300/hour
Costa Rica Catamaran: Private Morning Tour with Snorkel & Drinks
Sailing in Guanacaste Province · 20 guests

Costa Rica Catamaran: Private Morning Tour with Snorkel & Drinks

5.0
$430/hour
Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests
Sailing in Cancún · 25 guests

Sail Away in Style: Private 37ft Catamaran Charter in Cancún for up to 25 Guests

4.4
Superowner
$157+/hour
EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝
Events in La Romana · 150 guests

EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝

New
Superowner
Best of 2026
$17/hour
Private 37ft Catamaran Charter in Cancún for up to 25 Guests
Sailing in Cancún · 25 guests

Private 37ft Catamaran Charter in Cancún for up to 25 Guests

5.0
Superowner
$157+/hour
Limited Availability
Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch
Events in Sausalito · 30 guests

Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

4.9
Superowner
Best of 2026
$650/hour
35' Cruising Catamaran on San Francisco Bay
Sailing in Oakland · 10 guests

35' Cruising Catamaran on San Francisco Bay

4.9
$225/hour
Lancer 36 Sailing Sloop for 8 Passenger in Puerto Vallarta
Sailing in Marina Vallarta · 8 guests

Lancer 36 Sailing Sloop for 8 Passenger in Puerto Vallarta

New
Superowner
$125/hour
San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440
Sailing in Brisbane · 6 guests

San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440

5.0
$250/hour
Romantic city lights trip on beanbags on 42 ft Bertram
Events in Long Beach · 6 guests

Romantic city lights trip on beanbags on 42 ft Bertram

5.0
$125/hour
Leopard 51 Flybridge Power Catamaran in Tulúm
Powerboats in Tulum · 25 guests

Leopard 51 Flybridge Power Catamaran in Tulúm

5.0
Superowner
$607+/hour
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0
$100/hour
No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
Sailing in Chicago · 12 guests

No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

4.8
$245/hour
Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California
Sailing in Newport Beach · 6 guests

Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

5.0
$160/hour

Sailing Reviews in United States

  1. EC

    Emily

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Had a group with me and they had a blast. Weather started as misty and then became wonderfully sunny along the way. Hoping to see some sea life but alas none waves were pretty choppy. Boat was wonderful.

  2. ST

    Shaddy

    56' SeaRay Yacht in New York!

    We had an incredible experience aboard Encore with Captain Max! I booked the boat for my engagement, and when rain threatened our original date, Max was extremely understanding and worked with me to move the reservation so the moment could still be everything I had planned. He was communicative, flexible, and genuinely invested in helping make the occasion special. The boat was beautiful, clean, comfortable, and exactly as advertised. Once we were aboard, Max made us feel completely at ease and gave us the perfect experience on the water. This was one of the most important and memorable days of our lives, and Max played a huge role in making it happen. I truly appreciate how accommodating he was throughout the entire process. I couldn’t recommend Captain Max and Encore more highly!

  3. Julia

    Julia

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    Paul is personable while also extremely professional. He is obviously very familiar with his boat and we felt very safe during our entire trip. He’s super adept at spotting whale blows and spotting wildlife in general, which allowed us to spot an entire orca family. Amazing experience overall, and I would especially recommend Paul if you’re looking to learn how to sail!

  4. AB

    Anthony

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    What a fantastic day! Paul is a very experienced sailor and made the trip both educational and extremely fun! Paul is a fantastic teacher and everyone had a chance to sail the boat and feel the wind in our hands. I would recommend Paul to anyone. Great for a corporate event, or a romantic day on the water with your significant other. Can't wait until next time!

  5. AW

    Andrea

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    We can’t say enough good things about our wonderful experience with Paul. From the first inquiry, his communication and responsiveness was outstanding. We encountered some challenges with our original plans and Paul went above and beyond to coordinate with us to make our trip possible. He brought the Radiance to pick up our group in a new location which required him to overnight in that location the evening before so that he could ensure that he would be able to meet us at the appropriate time. It was an extremely important and special trip for our family and he went to great lengths to make sure all went smoothly. It was a pleasure to spend our day with him and we are incredibly grateful for his expertise and outstanding customer service. We eagerly look forward to our next sail with Paul!

  6. JH

    Johnny

    Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

    Paul was excellent. Had a great day and did some fun sailing. Paul is very knowledgable and happy to teach as much or as little as you like. The boat was in great condition, very clean and organized. Paul was generous with his time and catered to exactly what we wanted to do for the day.