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    All listings in the United States

    Awesome sailboat rentals in United States.

    4.9
    (8,087 Reviews)

    Page 22 of 39 • 920 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Standart Trip Luxury Catamaran in Gulf of Papagayo & Water Activities
    Sailing in Playa Hermosa · 25 guests

    Standart Trip Luxury Catamaran in Gulf of Papagayo & Water Activities

    New
    $650/hour
    Beautiful Catalina Marina Del Rey
    Sailing in Marina del Rey · 8 guests

    Beautiful Catalina Marina Del Rey

    New
    $125/hour
    Sail on a classy and fast Sailing Yacht in the Hamptons, New York
    Sailing in East Hampton · 6 guests

    Sail on a classy and fast Sailing Yacht in the Hamptons, New York

    5.0
    $340/hour
    Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises
    Events in Miami · 14 guests

    Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises

    New
    $250/hour
    Crewed Charter 42' Lagoon Sailing Catamaran from Playa del Carmen
    Sailing in Playa del Carmen · 20 guests

    Crewed Charter 42' Lagoon Sailing Catamaran from Playa del Carmen

    5.0
    $750/hour
    45' Lagoon Luxury Catamaran Charter in Riviera Maya
    Sailing in Puerto Aventuras · 30 guests

    45' Lagoon Luxury Catamaran Charter in Riviera Maya

    5.0
    $381+/hour
    Shared Party Boat Sail w/Bar: Charleston Harbor - Perfect for Bach or Birthday
    Sailing in Mount Pleasant · 100 guests

    Shared Party Boat Sail w/Bar: Charleston Harbor - Perfect for Bach or Birthday

    5.0
    $375/hour
    Luxury Catamaran 44 in Puerto Vallarta, Banderas Bay
    Sailing in Marina Vallarta · 12 guests

    Luxury Catamaran 44 in Puerto Vallarta, Banderas Bay

    New
    Superowner
    $459/hour
    Sailing live aboard Charter in Montego Bay, Jamaica
    Sailing in Montego Bay · 15 guests

    Sailing live aboard Charter in Montego Bay, Jamaica

    5.0
    $950/day
    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami
    Events in Miami · 13 guests

    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami

    New
    $250/hour
    Charter a Beautiful Lagoon Catamaran 400 S 2 for 17 people
    Sailing in Cartagena · 17 guests

    Charter a Beautiful Lagoon Catamaran 400 S 2 for 17 people

    New
    $180/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
    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    5.0
    $150+/hour
    45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay
    Sailing in San Diego · 6 guests

    45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

    5.0
    $550+/hour
    Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts
    Sailing in Salem · 6 guests

    Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

    5.0
    $550/hour
    Sailing Adventure on Bay in Miami on Tartan Sailboat!
    Sailing in Key Biscayne · 6 guests

    Sailing Adventure on Bay in Miami on Tartan Sailboat!

    5.0
    $100/hour
    Experience Maine on 65ft Classic Schooner Yacht
    Sailing in Rockport · 30 guests

    Experience Maine on 65ft Classic Schooner Yacht

    5.0
    $500/hour
    Newport Private Day Sail onboard 28' Sabre Yacht Serenity
    Sailing in Newport · 4 guests

    Newport Private Day Sail onboard 28' Sabre Yacht Serenity

    New
    $150/hour
    Cruising Catamaran Rental in Puerto Plata, Puerto Plata
    Sailing in Barrio Las Yaguitas · 80 guests

    Cruising Catamaran Rental in Puerto Plata, Puerto Plata

    1.0
    Superowner
    Best of 2026
    $183/hour
    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
    Sailing Lessons with Chicago's #1 Rated Sailing School
    Tours in Chicago · 6 guests

    Sailing Lessons with Chicago's #1 Rated Sailing School

    New
    $175+/hour
    Maxicat 65ft Private Party Catamaran in Cartagena
    Sailing in Cartagena · 80 guests

    Maxicat 65ft Private Party Catamaran in Cartagena

    New
    Superowner
    $838/hour
    Clear Kayak Mangrove Cay Eco Venture 2-hour tour
    Adventures in Leeward Settlement · 10 guests

    Clear Kayak Mangrove Cay Eco Venture 2-hour tour

    New
    $200/hour
    36ft Sailing Catamaran Charter for Up to 20 People in Cancún
    Sailing in Cancún · 20 guests

    36ft Sailing Catamaran Charter for Up to 20 People in Cancún

    New
    Superowner
    $129+/hour

    Top Destinations Nearby

    Sailing Reviews in United States

    1. AA

      Adam

      45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

      What can I say except a big thank you for the best experience I’ve had before! It’s been an adventure holiday and for me personally, an awakening. You gave it your all for me and it's been totally great. Your new friend, Adam.

    2. 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 .

    3. BD

      Brian

      Crewed Charter 42' Lagoon Sailing Catamaran from Playa del Carmen

      Highly recommend the service. Everything was handled and taken care of. Had no issues with pickup, communication, timing, crew was great, shuttle drivers were great.

    4. MH

      Madeline

      Experience Maine on 65ft Classic Schooner Yacht

      It was an absolutely beautiful sail! The captain and crew were so personable, sweet and accommodating! Gorgeous day and a BREATHTAKING boat! 10000/10 would recommend

    5. LT

      Lloyd

      43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

      Davis was our captain, he was great . Very informative and knowledgeable . We went on a 31/2 hour sail in the Chesapeake bay. Would definitely do it again

    6. Sreenivasan

      Sreenivasan

      Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

      Excellent sail boat and amazing crew. We had an unforgettable experience. The When & If… is a beauty! Thank you Capt. Seth & team of pirates :)..

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