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    All listings in the United States

    Awesome sailboat rentals in United States.

    4.9
    (8,226 Reviews)

    Page 23 of 40 • 938 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington
    Tours in Anacortes · 6 guests

    Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

    5.0
    $200/hour
    Private Sunset Catamaran Cruise Cabo San Lucas for 50 Guests
    Sailing in Ildefonso Green · 50 guests

    Private Sunset Catamaran Cruise Cabo San Lucas for 50 Guests

    New
    $890/hour
    Family Friendly Sailing Catamaran | Explore San Diego Bay!
    Sailing in San Diego · 6 guests

    Family Friendly Sailing Catamaran | Explore San Diego Bay!

    New
    $250/hour
    Costa Rica Catamaran Private Sunset Tour with Drinks
    Sailing in Tamarindo · 20 guests

    Costa Rica Catamaran Private Sunset Tour with Drinks

    New
    $515/hour
    Bali 4.5 Luxury Catamaran Charter to the Islands of Loreto
    Sailing in Baja California Sur · 12 guests

    Bali 4.5 Luxury Catamaran Charter to the Islands of Loreto

    New
    $350/hour
    Ultra luxe Full Day Yacht Charter to Negril!
    Events in Montego Bay · 10 guests

    Ultra luxe Full Day Yacht Charter to Negril!

    New
    Superowner
    $1,625/hour
    Cabo Private Sail & Snorkel Tour Arch & Open Bar
    Sailing in Marina · 8 guests

    Cabo Private Sail & Snorkel Tour Arch & Open Bar

    New
    $200/hour
    Isla Mujeres Eco Catamaran Experience with Snorkeling & Beach Club
    Sailing in Cancún · 30 guests

    Isla Mujeres Eco Catamaran Experience with Snorkeling & Beach Club

    New
    Superowner
    Best of 2026
    $75/hour
    Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience
    Events in Sosúa · 25 guests

    Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience

    New
    $135/hour
    Catalina 27 Sailboat Rental in Olga, Washington
    Sailing in Anacortes · 6 guests

    Catalina 27 Sailboat Rental in Olga, Washington

    5.0
    $90+/hour
    Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena
    Sailing in Cartagena · 14 guests

    Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena

    New
    Superowner
    $200/hour
    Sailing in Cancun and Isla Mujeres
    Sailing in Cancún · 45 guests

    Sailing in Cancun and Isla Mujeres

    New
    $290+/hour
    65 People - All inclusive service aboard the 65ft Power Catamaran
    Events in Marina · 65 guests

    65 People - All inclusive service aboard the 65ft Power Catamaran

    New
    $548/hour
    Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York
    Sailing in Sag Harbor · 6 guests

    Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York

    New
    $249/hour
    Ocho Rios Private Sunset Catamaran with Dinner & Open Bar
    Powerboats in Ocho Rios · 100 guests

    Ocho Rios Private Sunset Catamaran with Dinner & Open Bar

    New
    $817/hour
    Dunn’s River Falls Private Catamaran Cruise – Ocho Rios
    Powerboats in Ocho Rios · 100 guests

    Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

    New
    $654/hour
    Custom 40ft Sail Boat Rental in Cozumel
    Sailing in Centro · 12 guests

    Custom 40ft Sail Boat Rental in Cozumel

    New
    $181+/hour
    Luxury Catamaran Party Lagoon 50 in Fort Lauderdale, Florida
    Sailing in Fort Lauderdale · 12 guests

    Luxury Catamaran Party Lagoon 50 in Fort Lauderdale, Florida

    New
    $300/hour
    2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey
    Sailing in Island Heights · 6 guests

    2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey

    5.0
    $120/hour
    Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia
    Sailing in Cartagena · 80 guests

    Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

    New
    Superowner
    $5,000/day
    An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena
    Sailing in Cartagena · 23 guests

    An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

    New
    Superowner
    $231/hour
    Sail into your Deep, Relaxed State
    Sailing in Marina del Rey · 6 guests

    Sail into your Deep, Relaxed State

    New
    $155+/hour
    Sail from Boynton Beach to Lake Boca
    Sailing in Boynton Beach · 12 guests

    Sail from Boynton Beach to Lake Boca

    New
    Superowner
    $126+/hour
    Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling
    Sailing in Montego Bay · 60 guests

    Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

    New
    $1,176/hour

    Top Destinations Nearby

    Sailing Reviews in United States

    1. Rachel

      Rachel

      Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

      What a fun day sailing around the orcas . Nat was an amazing sailing instructor and we loved learning about sailing and checking out the islands by water . Would highly recommend doing this - highlight of the trip .

    2. MS

      Michelle

      Catalina 27 Sailboat Rental in Olga, Washington

      Lots to learn of you're new at sailing. Great teacher. Guess over it until you get it. Did a wonderful job explaining everything. The who what when where and why's. Also gave us a great dinner ideas.

    3. KJ

      Kyle

      2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey

      Fantastic trip with a great captain. Captain Mike was very experienced and was able to easily navigate us on a windy day. We had a great time and would book with him again.

    4. Caitlin

      Caitlin

      2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey

      Such a great time with captain Mike! So easy going, fun and a smooth process!

    5. Jessenia

      Jessenia

      2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey

      Good experience , everything nice good captain and great service

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