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

    Best results for Sailing

    Showing 97-120 of 404 results
    Evening Wine and Jazz Concert Sail on Clipper City
    New York, NY

    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

    Sail past the NYC skyline with live jazz and two glasses of wine on a summer evening
    4.5 • 703 reviews
    $161
    Sail a Private Sunset Cruise in Monterey
    Monterey, CA

    Sail a Private Sunset Cruise in Monterey

    Private keelboat sailing for up to 6 from Old Fisherman’s Wharf

    Private keelboat sailing for up to 6 from Old Fisherman’s Wharf
    4.9 • 229 reviews
    $996
    Sail a Private Catamaran Cruise in Manteo
    Manteo, NC

    Sail a Private Catamaran Cruise in Manteo

    Private 2.5–3 hour catamaran sail from Manteo for up to 6

    Private 2.5–3 hour catamaran sail from Manteo for up to 6
    4.7 • 470 reviews
    $543
    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 • 67 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 • 146 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 • 146 reviews
    $201/ person
    Sunset Sail Cruise on the Philadelphia Waterfront
    Philadelphia, PA

    Sunset Sail Cruise on the Philadelphia Waterfront

    Sail the Delaware River at sunset with a USCG-licensed captain

    Sail the Delaware River at sunset with a USCG-licensed captain
    $113/ 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 • 813 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 • 813 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 • 813 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 • 136 reviews
    $170/ person
    Sail York River on a 1.5-Hour Yorktown Cruise
    Yorktown, VA

    Sail York River on a 1.5-Hour Yorktown Cruise

    Cruise the York River on a 1.5-hour tall-ship day sail

    Cruise the York River on a 1.5-hour tall-ship day sail
    4.8 • 465 reviews
    $61/ 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 • 360 reviews
    $80/ 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 • 534 reviews
    $160/ person
    Hobie Cat Sailing Ride in St. Thomas
    St.Thomas, USVI

    Hobie Cat Sailing Ride in St. Thomas

    Sail Margaritaville Bay with a Hobie Cat captain in 30 or 60 minutes

    Sail Margaritaville Bay with a Hobie Cat captain in 30 or 60 minutes
    4.7 • 322 reviews
    $49/ 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
    4.7 • 322 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 • 534 reviews
    $115/ 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 • 534 reviews
    $92/ 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 • 5.6K 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
    4.8 • 1.7K 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 • 5.6K reviews
    $542& up
    Sunset Sail in the Heart of the Gorge
    Cascade Locks, OR

    Sunset Sail in the Heart of the Gorge

    Sail into a Gorge sunset on a romantic 2-hour cruise aboard Wy'East

    Sail into a Gorge sunset on a romantic 2-hour cruise aboard Wy'East
    5.0 • 49 reviews
    $143/ person
    2-Hour Sunset Sail in Charleston Harbor
    Charleston, SC

    2-Hour Sunset Sail in Charleston Harbor

    Sail the 84-foot Schooner Pride at sunset in Charleston Harbor

    Sail the 84-foot Schooner Pride at sunset in Charleston Harbor
    4.7 • 4.9K reviews
    $100/ person
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