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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,360 Reviews)

Page 21 of 39915 listings

Private Full-Day Catamaran Charter in Playa Flamingo
Sailing in Playa Flamingo · 40 guests

Private Full-Day Catamaran Charter in Playa Flamingo

New
$800/hour
Private 42-Foot Sailing Catamaran Charter in Bocas del Toro
Sailing in Bocas del Toro Province · 22 guests

Private 42-Foot Sailing Catamaran Charter in Bocas del Toro

New
$420/hour
MAXIMA Powerboat 38ft in Cartagena de Indias
Powerboats in Cartagena · 20 guests

MAXIMA Powerboat 38ft in Cartagena de Indias

4.0
$830/day
Rosario Islands Private Cruise – 40ft Catamaran from Cartagena
Powerboats in Cartagena · 40 guests

Rosario Islands Private Cruise – 40ft Catamaran from Cartagena

New
$750/hour
Limited Availability
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
45ft  Luxury Catamaran Private Charter / Capacity 38 people
Sailing in Cancún · 40 guests

45ft Luxury Catamaran Private Charter / Capacity 38 people

New
Superowner
$572+/hour
Experience the Gulf Star 41' Sailing and Dining in Guanacaste
Sailing in Guanacaste Province · 12 guests

Experience the Gulf Star 41' Sailing and Dining in Guanacaste

5.0
$200/hour
Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht
Sailing in Philadelphia · 6 guests

Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht

5.0
$350/hour
46ft Sailing Catamaran Private Charter / Capacity 45 people
Sailing in Cancún · 45 guests

46ft Sailing Catamaran Private Charter / Capacity 45 people

3.3
Superowner
$343+/hour
Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica
Sailing in Playa Flamingo · 45 guests

Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica

5.0
$750/hour
Classic Rainbow Hobie Cat Racing or Day Sailor
Sailing in Des Moines · 4 guests

Classic Rainbow Hobie Cat Racing or Day Sailor

New
$150/hour
50Ft Sunseeker Yacht Perfect for your Party 🎉
Events in Marina · 10 guests

50Ft Sunseeker Yacht Perfect for your Party 🎉

New
$270/hour
🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️
Sailing in Barrio Las Yaguitas · 18 guests

🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️

New
Superowner
Best of 2026
$75/hour
3-Hour Morning Sail | Private 50ft Luxury Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

3-Hour Morning Sail | Private 50ft Luxury Sailing Yacht in Charleston

New
$250/hour
Foilborne Power Catamaran 40´Party Boat For Your Next Adventure!
Sailing in Herradura · 35 guests

Foilborne Power Catamaran 40´Party Boat For Your Next Adventure!

5.0
$500/hour
Rent our 25ft Sailboat in Kemah, Texas
Sailing in Seabrook · 4 guests

Rent our 25ft Sailboat in Kemah, Texas

5.0
$54/hour
30 Persons 46' Cruising LEOPARD Sailing Catamaran in Cancún, For Charter
Sailing in Cancún · 30 guests

30 Persons 46' Cruising LEOPARD Sailing Catamaran in Cancún, For Charter

New
$540/hour
40' Catamaran - Sail away
Sailing in Marina del Rey · 6 guests

40' Catamaran - Sail away

5.0
$400/hour
Sunset Cruise in Myrtle Beach, South Carolina
Sailing in Little River · 6 guests

Sunset Cruise in Myrtle Beach, South Carolina

5.0
$450/hour
42ft Catamaran Charter in Cancun for up to 30 Guests
Sailing in Cancún · 30 guests

42ft Catamaran Charter in Cancun for up to 30 Guests

New
Superowner
$275+/hour
Sail from Delray Beach to Lake Boca
Sailing in Delray Beach · 12 guests

Sail from Delray Beach to Lake Boca

1.0
Superowner
$125+/hour
Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch
Powerboats in Sosúa · 70 guests

Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch

New
$242/hour
42' Luxury Catamaran Sailboat
Sailing in Miami · 6 guests

42' Luxury Catamaran Sailboat

New
$285/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
$178/hour

Sailing Reviews in United States

  1. AA

    ADOLFO

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

    This was an amazing boat! It’s HUGE!! Captain Lester was a true professional who catered to all are requests. This was the best day of our summer. I would highly recommend this boat! Truly great!

  2. Joanne

    Joanne

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

    awesome relaxing, listened to what we wanted to do an then didn't question things while we relaxed

  3. LC

    Louis

    Experience the Gulf Star 41' Sailing and Dining in Guanacaste

    Incredible sailing experience, look no further and book. From start to finish Hugo and the fellow two crew members were incredible guides, and the itinerary they drafted was spectacular. Great value and every step of the way was incredible. Food and drinks very good as well, and a very safe experience. Also compared to other options the best value in Guanacaste. Will be back!!

  4. DF

    Dina

    Rent our 25ft Sailboat in Kemah, Texas

    Loved the sailing experience on the 25 foot sailboat. Eventhough it was an old sailboat form the 80's, David, our captain, was in control of every detail. He is a great captain. He is very paused and confident and easy to get along with. Recommend David with closed eyes. Lucy and the rest of the gals at the office are great people.

  5. 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!

  6. 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!