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    1. Local experiences
    2. /All experiences
    3. /Sailing

    Best results for Sailing

    Showing 217-240 of 497 results
    Champagne Sunset Catamaran Cruise in Key West
    Key West, FL

    Champagne Sunset Catamaran Cruise in Key West

    Sail Key West at sunset with complimentary champagne and drinks

    Sail Key West at sunset with complimentary champagne and drinks
    4.7 • 8.1K reviews
    $58/ person
    Morning 2-Hour Sail in Wrightsville Beach
    Chapel Hill, NC

    Morning 2-Hour Sail in Wrightsville Beach

    Sail calm morning waters on the Intracoastal Waterway

    Sail calm morning waters on the Intracoastal Waterway
    $114/ person
    2-Hour Sunset Sailing Cruise in Wrightsville Beach
    Chapel Hill, NC

    2-Hour Sunset Sailing Cruise in Wrightsville Beach

    Sail at sunset off Wrightsville Beach and Masonboro Islands

    Sail at sunset off Wrightsville Beach and Masonboro Islands
    $122/ person
    2-Hour Performance Sailing in Wrightsville Beach
    Wrightsville Beach, NC

    2-Hour Performance Sailing in Wrightsville Beach

    Race-boat sailing with a certified captain near Wrightsville Beach

    Race-boat sailing with a certified captain near Wrightsville Beach
    4.9 • 68 reviews
    $95/ person
    Cruise Local Waterways on a 2-Hour Sunset Sail
    Wrightsville Beach, NC

    Cruise Local Waterways on a 2-Hour Sunset Sail

    Relax on Bella with cocktails and a sunset sail for up to 6 guests

    Relax on Bella with cocktails and a sunset sail for up to 6 guests
    4.9 • 68 reviews
    $159/ person
    4-Hour Private Catamaran Sail in Wrightsville Beach
    Wrightsville Beach, NC

    4-Hour Private Catamaran Sail in Wrightsville Beach

    Customize a private 44' catamaran sail to islands and local stops

    Customize a private 44' catamaran sail to islands and local stops
    4.9 • 68 reviews
    $1,272
    Learn Sailing After-Work at Soundside
    Wrightsville Beach, NC

    Learn Sailing After-Work at Soundside

    Learn basic sailing in two after-work classes at Soundside

    Learn basic sailing in two after-work classes at Soundside
    4.9 • 68 reviews
    $313/ person
    3-Hour Basic Keelboat Prep Class in St. Augustine
    St. Augustine, FL

    3-Hour Basic Keelboat Prep Class in St. Augustine

    Learn sailing basics with classroom and dockside instruction

    Learn sailing basics with classroom and dockside instruction
    5.0 • 762 reviews
    $275/ person
    2-Hour Intro Sailing Lesson in St. Augustine
    St. Augustine, FL

    2-Hour Intro Sailing Lesson in St. Augustine

    Learn sailing basics in a small group of 2–4 people

    Learn sailing basics in a small group of 2–4 people
    5.0 • 762 reviews
    $224/ person
    2-Hour Sailing Lesson in St. Augustine
    St. Augustine, FL

    2-Hour Sailing Lesson in St. Augustine

    Build sailing confidence with a beginner-friendly 2-hour coaching sail

    Build sailing confidence with a beginner-friendly 2-hour coaching sail
    5.0 • 762 reviews
    $224/ person
    Join A Sailing Book Club Cruise In St. Augustine
    St. Augustine, FL

    Join A Sailing Book Club Cruise In St. Augustine

    Sail St. Augustine and swap book club notes over tea

    Sail St. Augustine and swap book club notes over tea
    5.0 • 762 reviews
    $224/ person
    Learn Coastal Navigation Online in St. Augustine
    St. Augustine, FL

    Learn Coastal Navigation Online in St. Augustine

    Build coastal navigation skills with a self-paced ASA 105 online course

    Build coastal navigation skills with a self-paced ASA 105 online course
    5.0 • 762 reviews
    $795/ person
    Join a Sunday Sailing Lesson in St. Augustine
    St. Augustine, FL

    Join a Sunday Sailing Lesson in St. Augustine

    Train as crew on Sunday sails with a USCG captain or ASA sailing instructor

    Train as crew on Sunday sails with a USCG captain or ASA sailing instructor
    5.0 • 762 reviews
    $309/ person
    Sunset Sailing Cruise in Key West With Live Music
    Key West, FL

    Sunset Sailing Cruise in Key West With Live Music

    Sip and sail into the Key West sunset with live music and an open well bar

    Sip and sail into the Key West sunset with live music and an open well bar
    4.8 • 23.2K reviews
    $65/ person
    Private 3-Hour Catamaran Sailing Tour in Key Largo
    Manteo, NC

    Private 3-Hour Catamaran Sailing Tour in Key Largo

    Sail Key Largo on a private 40-foot catamaran for up to 6 guests

    Sail Key Largo on a private 40-foot catamaran for up to 6 guests
    5.0 • 45 reviews
    $546
    Private Sunset Sailing Charter in Key Largo
    Manteo, NC

    Private Sunset Sailing Charter in Key Largo

    Sail Key Largo at sunset on a private 40-foot catamaran for up to 6 guests

    Sail Key Largo at sunset on a private 40-foot catamaran for up to 6 guests
    5.0 • 45 reviews
    $655
    Sunrise Coffee Sail in Ka'anapali
    Lahaina, HI

    Sunrise Coffee Sail in Ka'anapali

    Sip Maui coffee on a Kaʻanapali sunrise catamaran sail

    Sip Maui coffee on a Kaʻanapali sunrise catamaran sail
    4.9 • 2.5K reviews
    $87/ person
    2-Hour Sandbar Sailing Charter
    Marathon, FL

    2-Hour Sandbar Sailing Charter

    Sail a captained Hobie Cat to a local sandbar with complimentary beverages

    Sail a captained Hobie Cat to a local sandbar with complimentary beverages
    4.7 • 233 reviews
    $283
    Team Racing Sailing Series on Long Island Sound
    Oyster Bay, NY

    Team Racing Sailing Series on Long Island Sound

    Build team racing skills and strategy on Long Island Sound

    Build team racing skills and strategy on Long Island Sound
    4.5 • 62 reviews
    $53& up
    Private 5-Hour Power Island Sailing Cruise
    Traverse City, MI

    Private 5-Hour Power Island Sailing Cruise

    Cruise to Power Island on a 5-hour private sail for up to 6 people

    Cruise to Power Island on a 5-hour private sail for up to 6 people
    5.0 • 86 reviews
    $741
    Private 2-Hour Sunset Sailing Cruise on West Bay
    Traverse City, MI

    Private 2-Hour Sunset Sailing Cruise on West Bay

    Private 2-hour sunset sail on Grand Traverse West Bay for up to 6 people

    Private 2-hour sunset sail on Grand Traverse West Bay for up to 6 people
    5.0 • 86 reviews
    $345
    2-Hour Evening Sail Cruise in Traverse City
    Traverse City, MI

    2-Hour Evening Sail Cruise in Traverse City

    Sail Grand Traverse Bay at sunset and help raise Manitou’s sails

    Sail Grand Traverse Bay at sunset and help raise Manitou’s sails
    4.9 • 582 reviews
    $64/ person
    Sail Traverse City With Moomers Ice Cream
    Traverse City, MI

    Sail Traverse City With Moomers Ice Cream

    Sail Traverse City and enjoy two scoops of Moomers ice cream

    Sail Traverse City and enjoy two scoops of Moomers ice cream
    4.9 • 582 reviews
    $60/ person
    Brunch Cruise in Traverse City
    Traverse City, MI

    Brunch Cruise in Traverse City

    Sail the bay on a 2-hour brunch cruise with your first drink included

    Sail the bay on a 2-hour brunch cruise with your first drink included
    4.9 • 582 reviews
    $88/ person
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