Best results for Sailing

    Showing 169-192 of 222 results

    NYC Harbor Day Sail on Clipper City Tall Ship

    Sail past the Statue of Liberty and skyline aboard NYC's only passenger tall ship

    4.5 699 reviews
    $79/ person

    Evening Wine and Jazz Concert Sail on Clipper City

    Sail past the NYC skyline with live jazz and two glasses of wine on a summer evening

    4.5 699 reviews

    Sunset Sail on Presque Isle Bay and Lake Erie

    Relax on a 2-hour sail with captain, crew, and complimentary drinks as Lake Erie glows at sunset

    5.0 146 reviews
    $201/ person

    Learn To Sail On A Hobie Catamaran

    Sail with an instructor for an easy, first-time-friendly session on calm Soundside waters

    4.9 66 reviews
    $106/ person

    Ocean Spirit Adult Sunset Sail

    Sail into the sunset on an adults-only catamaran cruise with pupus and island-style music

    4.7 2.5K reviews
    $149/ person

    Private 2-Hour Day Sail In Port Townsend Bay

    Enjoy a private sail with a licensed captain and choose a relaxed or more thrilling ride

    5.0 28 reviews

    Ka'anapali Wild Dolphin Sail

    Sail 2.5 hours to watch wild dolphins with expert commentary and refreshments

    4.9 1.9K reviews
    $126/ person

    Private Yacht Charter in Kailua Kona for 35

    Enjoy exclusive use of the Kibou for a 1–3 hour cruise with up to 35 guests.

    4.9 1.1K reviews
    $3,500

    Private Lake Erie Sunset Sail in Sandusky

    Glide across Lake Erie at dusk on a private sailboat led by an experienced captain.

    5.0 34 reviews

    Private Sailboat Charter on the Maine Coast

    Experience Acadia’s wildlife and scenery with an expert captain and a trip tailored to you

    5.0 391 reviews
    $417& up

    Cape Lookout Private Cruise on 45ft Catamaran

    Cruise to Cape Lookout for two stops with catered lunch, swimming, and lighthouse views on a 45-foot catamaran

    5.0 1.1K reviews
    $6,095

    Hilton Head Kayak Rentals

    Hourly rentals for all experience levels on scenic Lowcountry waterways

    4.7 228 reviews

    Dolphin Sightseeing Sail Aboard the Footloose Catamaran

    Fun Dolphin Sightseeing & Complimentary Beverage

    4.9 2.7K reviews
    $42/ person

    Na Pali Coast Deluxe Morning Power Catamaran Tour

    Glide along the Na Pali Coast on a fast catamaran with calmer morning seas and chances to spot dolphins

    $275/ person

    3-Hour Head Boat Bay Fishing Trip

    Fish calm, sheltered bay waters with crew support and more time with lines in than riding

    4.8 248 reviews
    $40/ person

    Private 3-Hour Fishing Or Party Cruise

    Rent the whole boat for your group and cruise the bay day or night

    4.8 248 reviews

    Historic Boston Harbor Sail with Landmark Views

    Sail an 80-foot classic schooner and admire Boston Harbor landmarks

    4.7 1.5K reviews
    $82/ person

    2-Hour Sunset Sail in Provincetown Harbor

    Enjoy a relaxing two-hour cruise as daylight fades over the water

    5.0 35 reviews
    $74/ person

    Salem Harbor Sunset Sail on 1812 Schooner

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

    5.0 535 reviews
    $49/ person

    Half-Day Coastal Sail in Saco, Maine

    See islands, beaches, and the Saco River on a half-day coastal sail

    5.0 376 reviews
    $256/ person

    Saco Bay Lighthouse Sail & Guided Tower Tour

    Sail Saco Bay to a restored island lighthouse with a guided tower tour

    5.0 376 reviews
    $395/ person

    Hoist Sails & Fire Cannons on Pirate Cruise

    Join a kid-friendly schooner cruise to hoist sails, fire the cannon, and earn your pirate stripes

    4.7 1.9K reviews
    $61/ person

    North Shore Sunset Sail from Haleiwa Harbor

    Sail along Oahu's North Shore for a peaceful two-hour voyage and watch vibrant sunset colors from the deck

    4.6 305 reviews
    $101/ person

    West Oahu Sunset Sail with Drinks & Appetizers

    Unwind on a West O‘ahu sunset cruise with panoramic views, drinks, and light bites included

    4.6 1.4K reviews
    $115/ person
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