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    All listings in the United States

    Awesome sailboat rentals in United States.

    4.9
    (8,341 Reviews)

    Page 9 of 39 • 915 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Charter a 31' Pearson Cruising Sloop, Chicago
    Sailing in Chicago · 6 guests

    Charter a 31' Pearson Cruising Sloop, Chicago

    4.5
    $200+/hour
    Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
    Sailing in Mayo · 6 guests

    Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

    5.0
    $150+/hour
    High Demand
    Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
    Sailing in Manhattan · 6 guests

    Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

    5.0
    $317/hour
    Limited Availability
    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey
    Sailing in Marina del Rey · 6 guests

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    5.0
    Superowner
    Best of 2026
    $150/hour
    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
    Sailing in Mamaroneck · 10 guests

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    5.0
    $50/hour
    LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE
    Sailing in Isla Iguana · 15 guests

    LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE

    5.0
    $265/hour
    Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers
    Events in San Francisco · 49 guests

    Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

    5.0
    Superowner
    $1,467/hour
    Limited Availability
    38-ft Hunter 376 Sailing Adventure in Annapolis
    Sailing in Annapolis · 6 guests

    38-ft Hunter 376 Sailing Adventure in Annapolis

    5.0
    Superowner
    $100+/hour
    Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat
    Sailing in Marina Mazatlán · 8 guests

    Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat

    5.0
    $2,500/hour
    Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
    Sailing in George Town · 20 guests

    Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

    5.0
    $425/hour
    38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.
    Sailing in Playa del Carmen · 15 guests

    38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

    4.7
    Superowner
    Best of 2026
    $420/hour
    Limited Availability
    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
    Sailing in Sag Harbor · 12 guests

    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

    5.0
    $750+/hour
    28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!
    Sailing in Marina del Rey · 8 guests

    28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!

    4.8
    $250+/hour
    Luxury Italian Sailing Yacht on the Puget Sound — Seattle
    Sailing in Seattle · 6 guests

    Luxury Italian Sailing Yacht on the Puget Sound — Seattle

    5.0
    $349+/hour
    Shared Snorkeling & Sailing in Cabo San Lucas
    Sailing in Marina · 12 guests

    Shared Snorkeling & Sailing in Cabo San Lucas

    5.0
    Superowner
    Best of 2026
    $40/hour
    BEST IN CLASS All Inclusive Catamaran Charters
    Sailing in Nassau · 20 guests

    BEST IN CLASS All Inclusive Catamaran Charters

    5.0
    $1,080/hour
    Gorgeous Luxurious 50ft Sailing Catamaran in Cancún & Isla Mujeres - Open Bar
    Sailing in Cancún · 30 guests

    Gorgeous Luxurious 50ft Sailing Catamaran in Cancún & Isla Mujeres - Open Bar

    5.0
    $323/hour
    🥂AMAZING PRIVATE YACHT🥂
    Powerboats in La Romana · 50 guests

    🥂AMAZING PRIVATE YACHT🥂

    5.0
    Superowner
    Best of 2026
    $50/hour
    🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
    Events in Sosúa · 150 guests

    🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

    5.0
    $425/hour
    Sailing in Cancun and Isla Mujeres
    Sailing in Cancún · 45 guests

    Sailing in Cancun and Isla Mujeres

    New
    $287+/hour
    Available in Puerto Plata Private Yacht Experience: Beautiful Views book now
    Powerboats in Puerto Plata · 100 guests

    Available in Puerto Plata Private Yacht Experience: Beautiful Views book now

    New
    Superowner
    Best of 2026
    $50/hour
    San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp
    Sailing in San Diego · 6 guests

    San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

    5.0
    $54/hour
    34' Hunter Cruising Monohull In Rock Hall, Maryland United States
    Sailing in Rock Hall · 4 guests

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    4.6
    $275+/night
    Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
    Sailing in Prince Edward · 12 guests

    Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

    4.9
    $320/hour

    Top Destinations Nearby

    Sailing Reviews in United States

    1. SF

      Sierra

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Captain Alberto and Grace were incredibly welcoming and accommodating during our time on their boat. Captain Alberto taught us all about sailing and we really enjoyed being involved with helping sail the boat. My friend group had such a great time; would recommend! We will definitely be back!

    2. TJ

      Tushar

      Luxury Italian Sailing Yacht on the Puget Sound — Seattle

      Everything was perfect, Matt and JB made sure we had the perfect day! They made our day even more special, and were super accommodating and helpful, the perfect crew to sail with. As for the boat, Serafina is hands down the best boat on GetMyBoat, it is beautiful and very unique, it’s classy and we had a great time sailing.

    3. RM

      Richard

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Capt. Alberto and his wife were awesome hosts! They were totally flexible about our schedule and it was great to hear about his prior sailing experiences. It was great to be with such an experienced host! We will definitely book with them in the future!!

    4. MK

      Michael

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Capt Alberto is great. Very knowledgeable and very pleasant. He lets you participate in manning the boat as much as you want and is especially good and introducing new sailors to the glorious activity. Highly recommend!

    5. MB

      Maya

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Capt Alberto and his wife were SO AMAZING!! They taught us how to sail and we sailed across the Chesapeake. Their boat is beautiful and their company is great. I highly recommend everyone book if they are looking to sail in the Annapolis area for a few hours, learn about sailing, and have a relaxing time.

    6. Cindy

      Cindy

      38-ft Hunter 376 Sailing Adventure in Annapolis

      We had a wonderful time on the water with Captain Alberto and Grace! Their wealth of sailing knowledge of the bay and beyond was quite entertaining and impressive. Thanks for sharing your lovely boat with us.

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