Sailing in United States

50 boats available

The best out of 50 deals in United States - enter dates to check availability

Top Sailing in United States

  • 40 ft
    •
    up to 6
    4 Hour – Sailing Adventure
    You will cruise on the New River through downtown Ft Lauderdale to the Atlantic Ocean where we will set sail.We can take a maxium of 6 passengers.Sightseeing,ocean sailing and swimming.We have refrigeration on board so you can bring food and beverage.A clean bathroom on board as well.Your group will have a greaaaat fun and safe day on the water.
    Price for up to 6 people
    US $500
  • 37 ft
    •
    up to 6
    2 Hour – Boat Tour
    This IOR Raceboat is a classic restored 1973 Ranger 37 named Masquerade and intended for the sports enthusiast. This 37' yacht was known as "The Rocket" back in her day due to her lightning speed and innovative hull design. Much heavier than traditional boats today, Masquerade will provide a steady, smooth sail no matter what the conditions. The mythical Ranger 37 had a colorful racing history back in the 1970′s and continues to win offshore races to this day.
    Instant Confirmation
    Price for up to 6 people
    US $650
  • 32 ft
    •
    up to 6
    2 Hour – Sunset Funset
    Set sail into the golden hour with your favorite food and drinks in hand. Soak in a breathtaking sunset over the water while keeping an eye out for playful dolphins along the way!
    Instant Confirmation
    Price for up to 6 people
    US $350
  • 40 ft
    •
    up to 6
    4 Hour – Sail Aboard A Pirate Ship
    On our 4-hour sail, we cruise the Coast of Catalina Island searching for sea life, learning the history of the island as well as some maritime and pirate history, firing off the ship's cannons, and having an experience you'll never forget!
    Instant Confirmation
    Price for up to 6 people
    US $700
  • 36 ft
    •
    up to 6
    2 Hour Private Sailing Charter
    Sail Long Island's Gold Coast on WINDSWEPT, a beautifully kept Jeanneau 36i! Private sailing charters can accommodate up to 6 guests. Departure times are flexible - select a start time that works best for your group! Two-hour charters allow enough time to sail to the mouth of Oyster Bay Harbor and back. Perfect for catching a sunset or for touring the harbor, you'll have great views of the sandy bluffs and waterfront mansions that line the bay.
    Instant Confirmation
    Price for up to 4 people
    US $525
  • 42 ft
    •
    up to 6
    4 Hour – Sail Around The Bay
    This is a four-hour sail around the bay. This will allow ample time for a mix of sailing, swimming, exploring, and byob/food dining. We can cater to your desires and make a custom itinerary that works for you and your guests.
    Instant Confirmation
    Price for up to 6 people
    US $1,250
  • 45 ft
    •
    up to 6
    3 Hour – Sunset Sail
    Private captained sail through the protected waters of Boca Ciega Bay, with a beautiful view of the sun on an open Gulf Horizon! You're welcome to bring any of your own food or drinks to accompany you on the evening sail!
    Instant Confirmation
    Price for up to 6 people
    US $900
  • 43 ft
    •
    up to 12
    2 Hour – Sailing Adventure
    Enjoy a 2, 2.5, or a 3 hour sail adventure along San Diego's coastline. Relax onboard with cityscape ocean views and a fresh sea breeze, or enjoy snorkeling, paddleboards, and kayaks (by special request and seasonal). Keep an eye out for dolphins, sea lions or other wildlife along the way. Departure times are flexible, contact the captain to customize the trip, including sunset options depending on timing. Perfect for families, friends, or couples seeking a quick, unforgettable ocean experience.
    Instant Confirmation
    Price for up to 6 people
    US $475
  • 36 ft
    •
    up to 6
    2 Hour – Group Sunset Sail
    Come aboard for a private sunset sailing experience. The boat is all yours for you and your crew - no sharing the boat with strangers.
    Instant Confirmation
    Price for up to 6 people
    US $495
  • 29 ft
    •
    up to 6
    4 Hour – Daytime Charter
    The sailboat is captained by Geoffrey McIntire, a USCG-certified captain with round-the-world sailing experience. We work closely with you to make the best from hourly charters, half-day charters, sunset sails, and full moon sails. We also teach sailing lessons. The day and experience will be tailored to you to provide you with the happiest, most adventurous, and most fun day.
    Instant Confirmation
    Price for up to 6 people
    US $400

What boaters said about Sailing

  • 5.0
    /5
    (3 Hour Sunset Sail with a meal.)

    Awesome experience

    Captain Rick and Deb were wonderful hosts aboard the Artemis. It was a lovely day of sailing paired with a delicious lunch. Couldn’t have asked for a better experience!
    Amy A.
    Amy A.
    Reviewed on Sep 21, 2026
  • 5.0
    /5
    (4 Hour – Sail Around The Bay)

    Fun time with great people

    Captains Lynne and Mason were very engaging and willing to expertly answer all of our questions about sailing. thisnis a great experience!
    Peter M.
    Peter M.
    Reviewed on Sep 20, 2026
  • 5.0
    /5
    (4 Hr – Private Sailing Chicago)

    Perfect day in the water!

    The boat was amazing! So comfortable and well equipped. Plenty of shade if desired. Smooth sailing and comfortable. Captain Russ was awesome.
    Jennifer T.
    Jennifer T.
    Reviewed on Sep 8, 2026
  • 5.0
    /5
    (Sunset Sailing Experience)

    Perfect Evening

    Our family had so much fun together sailing Charleston harbor as the sun set. Captain Todd and Kathy went above and beyond to emsure our evening was very memorable. Highly recommend Everything Zen!
    Craig H.
    Craig H.
    Reviewed on Aug 24, 2026
  • 5.0
    /5
    (3 Hour – Sunset Sail)

    Amazing experience!

    My teen and I sailed at sunset with Mason and Lynn and they are amazing people with a passion for sailing. Mason helped my young budding sailor to understand more about the sport and also let her be at the helm under his supervision. The vessel is in great condition and has all the amenities. They made sure we got great photos and memories. I would sail with them again and again!
    Lisa K. H.
    Lisa K. H.
    Reviewed on Jul 29, 2026