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    Best results for Sailing

    Showing 25-48 of 302 results
    Daytime Sailing on Presque Isle Bay
    Sailing

    Daytime Sailing on Presque Isle Bay

    Enjoy a 2-hour captain-led sail with two included drinks

    Enjoy a 2-hour captain-led sail with two included drinks
    5.0 • 146 reviews
    $170/ person
    Sunset Sail on Presque Isle Bay and Lake Erie
    Sailing

    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

    Relax on a 2-hour sail with captain, crew, and complimentary drinks as Lake Erie glows at sunset
    5.0 • 146 reviews
    $201/ person
    Private Sunset Sailing Cruise in Destin
    Private Boat ChartersUp to 6

    Private Sunset Sailing Cruise in Destin

    Savor Gulf Coast views on a quiet private sail with licensed crew and complimentary water and sodas

    Savor Gulf Coast views on a quiet private sail with licensed crew and complimentary water and sodas
    5.0 • 219 reviews
    $542& up
    3-Hour Guided Sailing Cruise in Kennebunkport
    Sailing

    3-Hour Guided Sailing Cruise in Kennebunkport

    Sail the Saco River and Saco Bay in a small group

    Sail the Saco River and Saco Bay in a small group
    Contact for pricing
    Private 2-Hour Sunset Sailing Charter in Kennebunkport
    Sailing

    Private 2-Hour Sunset Sailing Charter in Kennebunkport

    Reserve a private 2-hour sunset sail for up to 6 guests

    Reserve a private 2-hour sunset sail for up to 6 guests
    Contact for pricing
    4-Hour Private Sailing Lesson in Kennebunkport
    Sailing

    4-Hour Private Sailing Lesson in Kennebunkport

    Learn to sail with a private instructor on a 42-foot boat

    Learn to sail with a private instructor on a 42-foot boat
    Contact for pricing
    6-Hour Private Sailing Charter in Kennebunkport
    Sailing

    6-Hour Private Sailing Charter in Kennebunkport

    Sail for 6 hours with your private group of up to 6

    Sail for 6 hours with your private group of up to 6
    Contact for pricing
    Private 4-Hour Sailing Charter in Kennebunkport
    Sailing

    Private 4-Hour Sailing Charter in Kennebunkport

    Sail Saco Bay for 4 hours with your private group of up to 6

    Sail Saco Bay for 4 hours with your private group of up to 6
    Contact for pricing
    3-Hour Puget Sound Sailing Charter in Seattle
    Sailing

    3-Hour Puget Sound Sailing Charter in Seattle

    Sail Puget Sound on a private 3-hour charter for up to 6

    Sail Puget Sound on a private 3-hour charter for up to 6
    Contact for pricing
    Sunset Sailing Charter on Puget Sound in Seattle
    Sailing

    Sunset Sailing Charter on Puget Sound in Seattle

    Private 3-hour sunset sail with views of Seattle and the Olympic Mountains

    Private 3-hour sunset sail with views of Seattle and the Olympic Mountains
    Contact for pricing
    Private 1.5-Hour Schooner Sailing Charter in Key West
    Sailing

    Private 1.5-Hour Schooner Sailing Charter in Key West

    Charter a private historic schooner sail with drinks and snacks included

    Charter a private historic schooner sail with drinks and snacks included
    Contact for pricing
    Private Key West Sunset Sailing Charter
    Sailing

    Private Key West Sunset Sailing Charter

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included
    Contact for pricing
    Proposal & Anniversary Sailing Cruise in Fort Walton Beach
    Sailing

    Proposal & Anniversary Sailing Cruise in Fort Walton Beach

    Sail with a licensed captain for a proposal or anniversary cruise

    Sail with a licensed captain for a proposal or anniversary cruise
    Contact for pricing
    Private Sailing Charter In Key West
    Sailing

    Private Sailing Charter In Key West

    Charter a sailboat in Key West for up to 42 guests

    Charter a sailboat in Key West for up to 42 guests
    Contact for pricing
    Sunset Sailing Cruise on San Francisco Bay
    Sailing

    Sunset Sailing Cruise on San Francisco Bay

    Sail past Alcatraz and under the Golden Gate on a sunset catamaran cruise

    Sail past Alcatraz and under the Golden Gate on a sunset catamaran cruise
    Contact for pricing
    San Francisco Bay Day Sailing Cruise From PIER 39
    Sailing

    San Francisco Bay Day Sailing Cruise From PIER 39

    Sail past Alcatraz and under the Golden Gate Bridge from PIER 39

    Sail past Alcatraz and under the Golden Gate Bridge from PIER 39
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    6-Hour Provincetown Private Sailing Charter
    Sailing

    6-Hour Provincetown Private Sailing Charter

    Sail Provincetown Harbor and Cape Cod Bay on a private 6-hour charter

    Sail Provincetown Harbor and Cape Cod Bay on a private 6-hour charter
    Contact for pricing
    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
    Contact for pricing
    1-Hour Toddler Sailing Lesson at Jetties Beach
    Sailing

    1-Hour Toddler Sailing Lesson at Jetties Beach

    Introduce your toddler to sailing with a 1-hour instructor-led lesson

    Introduce your toddler to sailing with a 1-hour instructor-led lesson
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    Private Sailing Lesson & Coastal Cruise in Savannah
    Private Boat ChartersUp to 6

    Private Sailing Lesson & Coastal Cruise in Savannah

    Savor coastal views and learn to handle the sails on an exclusive 2-hour voyage for up to six.

    Savor coastal views and learn to handle the sails on an exclusive 2-hour voyage for up to six.
    4.9 • 98 reviews
    $423
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