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

    Best results for Sailing

    Showing 97-120 of 496 results
    Sail Wrightsville Beach on a 2-Hour Afternoon Cruise
    Chapel Hill, NC

    Sail Wrightsville Beach on a 2-Hour Afternoon Cruise

    Sail across Masonboro Inlet on a 2-hour afternoon cruise

    Sail across Masonboro Inlet on a 2-hour afternoon cruise
    $106/ person
    Brunch Sailing Cruise in Wrightsville Beach
    Wrightsville Beach, NC

    Brunch Sailing Cruise in Wrightsville Beach

    Sip coffee and mimosas on a 2-hour brunch sail

    Sip coffee and mimosas on a 2-hour brunch sail
    4.9 • 68 reviews
    $159/ person
    2-Hour Daytime Sailing Cruise in Presque Isle Bay
    Erie, PA

    2-Hour Daytime Sailing Cruise in Presque Isle Bay

    Sail Presque Isle Bay with a captain and crew, plus two complimentary drinks

    Sail Presque Isle Bay with a captain and crew, plus two complimentary drinks
    5.0 • 153 reviews
    $170/ person
    2-Hour Sunset Sailing Cruise in Presque Isle Bay
    Erie, PA

    2-Hour Sunset Sailing Cruise in Presque Isle Bay

    Sail Presque Isle Bay at sunset with wine and crew included

    Sail Presque Isle Bay at sunset with wine and crew included
    5.0 • 153 reviews
    $201/ person
    4-Hour Sailing Lesson on Narragansett Bay
    Barrington, RI

    4-Hour Sailing Lesson on Narragansett Bay

    Practice sailing skills with an instructor on Narragansett Bay

    Practice sailing skills with an instructor on Narragansett Bay
    4.9 • 70 reviews
    $201/ person
    2-Hour Daytime Charleston Harbor Shared Sail
    Mt. Pleasant, SC

    2-Hour Daytime Charleston Harbor Shared Sail

    Sail Charleston Harbor by day on a shared catamaran with shade, restrooms, and an onboard bar

    Sail Charleston Harbor by day on a shared catamaran with shade, restrooms, and an onboard bar
    5.0 • 1.1K reviews
    $54/ person
    Sunset Sail Cruise in Charleston Harbor
    Mt. Pleasant, SC

    Sunset Sail Cruise in Charleston Harbor

    Sail into sunset views with music and an onboard bar

    Sail into sunset views with music and an onboard bar
    5.0 • 1.1K reviews
    $54/ person
    2-Hour Charleston Harbor Party Sail
    Mt. Pleasant, SC

    2-Hour Charleston Harbor Party Sail

    Shared 2-hour Charleston Harbor party sail with an onboard bar (21+ only)

    Shared 2-hour Charleston Harbor party sail with an onboard bar (21+ only)
    5.0 • 1.1K reviews
    $54/ person
    Sail Lake Tahoe on a 2-Hour Catamaran Cruise
    Carnelian Bay, CA

    Sail Lake Tahoe on a 2-Hour Catamaran Cruise

    Cruise Lake Tahoe on a 55-foot catamaran with lakewide views

    Cruise Lake Tahoe on a 55-foot catamaran with lakewide views
    4.4 • 138 reviews
    $171/ person
    Sail a 2-Hour Sunset Cruise in Seattle
    Seattle, WA

    Sail a 2-Hour Sunset Cruise in Seattle

    Sail Seattle’s harbor at sunset with skyline views and an onboard bar

    Sail Seattle’s harbor at sunset with skyline views and an onboard bar
    4.8 • 386 reviews
    $80/ person
    2-Hour Brunch Sailing Cruise in Seattle
    Seattle, WA

    2-Hour Brunch Sailing Cruise in Seattle

    Sail Seattle’s harbor and enjoy a brunch buffet on a tall ship

    Sail Seattle’s harbor and enjoy a brunch buffet on a tall ship
    4.8 • 386 reviews
    $92/ person
    Waikoloa Signature Sunset Sail
    Kailua-Kona, HI

    Waikoloa Signature Sunset Sail

    Unwind on a 1.5-hour coastal sunset sail with a full bar and light bites

    Unwind on a 1.5-hour coastal sunset sail with a full bar and light bites
    4.9 • 590 reviews
    $172/ person
    Sail a 2-Hour Champagne Sunset Cruise in St. Thomas
    St.Thomas, USVI

    Sail a 2-Hour Champagne Sunset Cruise in St. Thomas

    Sail St. Thomas at sunset with an open bar and appetizers

    Sail St. Thomas at sunset with an open bar and appetizers
    4.8 • 4.8K reviews
    $117/ person
    Kona Signature Sunset Sail
    Kailua-Kona, HI

    Kona Signature Sunset Sail

    Sail the Kona Coast at sunset with light bites and drinks included

    Sail the Kona Coast at sunset with light bites and drinks included
    4.9 • 590 reviews
    $123/ person
    Kona Tradewind Day Sail
    Kailua-Kona, HI

    Kona Tradewind Day Sail

    Glide along the Kona Coast on a 1.5-hour sailing catamaran with drinks and coastal views

    Glide along the Kona Coast on a 1.5-hour sailing catamaran with drinks and coastal views
    4.9 • 590 reviews
    $99/ person
    Sail a Private Daytime Cruise in Destin
    Destin, FL

    Sail a Private Daytime Cruise in Destin

    Private daytime sailing cruise with optional hands-on instruction

    Private daytime sailing cruise with optional hands-on instruction
    4.9 • 6.2K reviews
    $456& up
    Private Sunset Catamaran Cruise in Panama City Beach
    Panama City Beach, FL

    Private Sunset Catamaran Cruise in Panama City Beach

    Cruise Grand Lagoon, then sail toward the Gulf of Mexico for sunset views

    Cruise Grand Lagoon, then sail toward the Gulf of Mexico for sunset views
    4.9 • 4.9K reviews
    $4,162
    Private Sunset Sailing Cruise in Destin
    Destin, FL

    Private Sunset Sailing Cruise in Destin

    Sail into the Destin sunset on a private, quiet cruise

    Sail into the Destin sunset on a private, quiet cruise
    4.9 • 6.2K reviews
    $542& up
    Chicago Sunset Skyline Sail
    Chicago, IL

    Chicago Sunset Skyline Sail

    Sail Lake Michigan for views of Chicago’s shoreline and skyline

    Sail Lake Michigan for views of Chicago’s shoreline and skyline
    4.6 • 594 reviews
    $64/ person
    Chicago Blues Concert Sail
    Chicago, IL

    Chicago Blues Concert Sail

    Live blues, Lake Michigan sailing, and Chicago skyline views

    Live blues, Lake Michigan sailing, and Chicago skyline views
    4.6 • 594 reviews
    $76/ person
    Chicago Lakefront 3-Hour Sailing Cruise
    Chicago, IL

    Chicago Lakefront 3-Hour Sailing Cruise

    Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board

    Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board
    5.0 • 27 reviews
    $1,099
    4-Hour Sail & Swim Charter From Navy Pier
    Chicago, IL

    4-Hour Sail & Swim Charter From Navy Pier

    Private Lake Michigan sailing with swimming, snacks, and a certified captain

    Private Lake Michigan sailing with swimming, snacks, and a certified captain
    5.0 • 27 reviews
    $1,417
    Chicago Sunset Sailing Cruise
    Chicago, IL

    Chicago Sunset Sailing Cruise

    Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht

    Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
    5.0 • 27 reviews
    $993
    Chicago Sunset Skyline Sail
    Chicago, IL

    Chicago Sunset Skyline Sail

    See Chicago’s skyline from Lake Michigan on an evening sail

    See Chicago’s skyline from Lake Michigan on an evening sail
    4.6 • 594 reviews
    $17/ person
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