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    Best results for Sailing

    Showing 49-72 of 403 results
    Private Sailing Charter on Calibogue Sound, Hilton Head
    Sailing

    Private Sailing Charter on Calibogue Sound, Hilton Head

    Private captained sail on Calibogue Sound with room for your snacks and drinks

    Private captained sail on Calibogue Sound with room for your snacks and drinks
    4.7 • 972 reviews
    $345
    Private 1.5-Hour Sailing Cruise on the Delaware River
    Sailing

    Private 1.5-Hour Sailing Cruise on the Delaware River

    Private Delaware River day sail for up to six guests

    Private Delaware River day sail for up to six guests
    $424/ boat
    City Lights Sailing Cruise in New York City
    Sailing

    City Lights Sailing Cruise in New York City

    Sail past NYC’s lit-up skyline on the Clipper City at night

    Sail past NYC’s lit-up skyline on the Clipper City at night
    4.5 • 699 reviews
    $90/ person
    2-Hour Private Sailing Charter in Provincetown
    Sailing

    2-Hour Private Sailing Charter in Provincetown

    Sail Provincetown Harbor on a private, captained 2-hour charter for up to six guests

    Sail Provincetown Harbor on a private, captained 2-hour charter for up to six guests
    $913
    2-Hour Private Sunset Sailing Cruise in Narragansett Bay
    Sailing

    2-Hour Private Sunset Sailing Cruise in Narragansett Bay

    Private sunset sail for up to 4 on Narragansett Bay

    Private sunset sail for up to 4 on Narragansett Bay
    4.9 • 66 reviews
    $159
    Happy Hour Sailing Cruise in Traverse City
    Sailing

    Happy Hour Sailing Cruise in Traverse City

    Sail West Grand Traverse Bay on a 2-hour happy hour cruise

    Sail West Grand Traverse Bay on a 2-hour happy hour cruise
    4.8 • 1.2K reviews
    $71/ person
    Full-Day Private Sailing Charter to Waimea Bay
    Sailing

    Full-Day Private Sailing Charter to Waimea Bay

    Private 6-hour sail to Waimea Bay for up to 6 people

    Private 6-hour sail to Waimea Bay for up to 6 people
    5.0 • 56 reviews
    $1,937
    Sunset Sailing Cruise in Olympia
    Sailing

    Sunset Sailing Cruise in Olympia

    Sail at sunset on a classic schooner with cocktails or mocktails

    Sail at sunset on a classic schooner with cocktails or mocktails
    5.0 • 73 reviews
    $430
    Sunset Sailing Cruise From Ma'alaea
    Sailing

    Sunset Sailing Cruise From Ma'alaea

    Sail into the evening with pupus, island-style music, and sunset views

    Sail into the evening with pupus, island-style music, and sunset views
    $149/ person
    Midday Sailing Cruise in Kennebunkport
    Sailing

    Midday Sailing Cruise in Kennebunkport

    Sail Kennebunkport at midday with a local captain, public or private

    Sail Kennebunkport at midday with a local captain, public or private
    4.9 • 254 reviews
    $113/ person
    1.5-Hour Morning Sailing Cruise in Kennebunkport
    Sailing

    1.5-Hour Morning Sailing Cruise in Kennebunkport

    Sail Kennebunkport with options to relax or take the helm

    Sail Kennebunkport with options to relax or take the helm
    4.9 • 254 reviews
    $101/ person
    Sunset Catamaran Sailing Cruise in Monterey
    Sailing

    Sunset Catamaran Sailing Cruise in Monterey

    Sail Monterey Bay at sunset with a drink and snacks included

    Sail Monterey Bay at sunset with a drink and snacks included
    4.9 • 228 reviews
    $94/ person
    2-Hour Sailing Lesson in Monterey
    Sailing

    2-Hour Sailing Lesson in Monterey

    Learn sailing basics in a 2-hour class from Old Fisherman’s Wharf

    Learn sailing basics in a 2-hour class from Old Fisherman’s Wharf
    4.9 • 228 reviews
    $169/ person
    Birthday Sailing Charter in San Diego
    Sailing

    Birthday Sailing Charter in San Diego

    Celebrate your birthday with a private sail on San Diego Bay

    Celebrate your birthday with a private sail on San Diego Bay
    5.0 • 811 reviews
    $631& up
    3-Hour Private Sunset Sailing Cruise in San Diego
    Sailing

    3-Hour Private Sunset Sailing Cruise in San Diego

    Sail the San Diego coast at sunset with complimentary drinks and snacks

    Sail the San Diego coast at sunset with complimentary drinks and snacks
    5.0 • 811 reviews
    $631
    Bottomless Mimosa Sailing Cruise in San Diego
    Sailing

    Bottomless Mimosa Sailing Cruise in San Diego

    Sail San Diego Bay with bottomless mimosas on a 2-hour morning cruise

    Sail San Diego Bay with bottomless mimosas on a 2-hour morning cruise
    5.0 • 811 reviews
    $80/ person
    3-Hour Private Midday Sailing Cruise in San Diego
    Sailing

    3-Hour Private Midday Sailing Cruise in San Diego

    Sail San Diego on a private 3-hour midday cruise with complimentary drinks and snacks

    Sail San Diego on a private 3-hour midday cruise with complimentary drinks and snacks
    5.0 • 811 reviews
    $631
    Private 6-Hour Sailing Charter in San Diego
    Sailing

    Private 6-Hour Sailing Charter in San Diego

    Sail San Diego Bay on a private 6-hour charter for up to 12 guests

    Sail San Diego Bay on a private 6-hour charter for up to 12 guests
    5.0 • 811 reviews
    $954& up
    3-Hour Midday Sailing Cruise In San Diego
    Sailing

    3-Hour Midday Sailing Cruise In San Diego

    Midday sail in San Diego with drinks and snacks included

    Midday sail in San Diego with drinks and snacks included
    5.0 • 811 reviews
    $116/ person
    Take a 2-Hour Morning Sailing Tour in San Diego
    Sailing

    Take a 2-Hour Morning Sailing Tour in San Diego

    2-hour morning sail with complimentary drinks and snacks

    2-hour morning sail with complimentary drinks and snacks
    5.0 • 811 reviews
    $94/ person
    2-Hour Private Morning Sailing Cruise in San Diego
    Sailing

    2-Hour Private Morning Sailing Cruise in San Diego

    Private 2-hour morning sail with complimentary drinks and snacks

    Private 2-hour morning sail with complimentary drinks and snacks
    5.0 • 811 reviews
    $477& up
    Learn Basic Keelboat Sailing in Savannah
    Sailing

    Learn Basic Keelboat Sailing in Savannah

    Take a 2-day keelboat sailing course with a small group

    Take a 2-day keelboat sailing course with a small group
    4.9 • 103 reviews
    $631/ person
    Captain-Chartered Catalina 420 Sailing Charter in San Diego
    Sailing

    Captain-Chartered Catalina 420 Sailing Charter in San Diego

    Sail a spacious Catalina 420 with your group of up to 12

    Sail a spacious Catalina 420 with your group of up to 12
    $1,050& up
    Earn ASA 103 & 104 Sailing Certifications in San Diego
    Sailing

    Earn ASA 103 & 104 Sailing Certifications in San Diego

    Take an advanced 3-day ASA 103/104 sailing course with optional live-aboard

    Take an advanced 3-day ASA 103/104 sailing course with optional live-aboard
    $1,600/ person
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