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

    Best results for Sailing

    Showing 505-528 of 770 results
    Sunset Sail on San Juan Bay
    San Juan, San Juan

    Sunset Sail on San Juan Bay

    Sail San Juan Bay at sunset with views of Old San Juan and Cataño

    Sail San Juan Bay at sunset with views of Old San Juan and Cataño
    4.6 • 597 reviews
    $118/ person
    3-Hour Private Sailing Cruise in Little River
    Little River, SC

    3-Hour Private Sailing Cruise in Little River

    Customize a private sail with hands-on options and coastal views

    Customize a private sail with hands-on options and coastal views
    5.0 • 71 reviews
    $737
    Santa Barbara Harbor Private Sailing Charter
    Santa Barbara, CA

    Santa Barbara Harbor Private Sailing Charter

    Sail Santa Barbara’s harbor and waterfront with coastal views and onboard narration

    Sail Santa Barbara’s harbor and waterfront with coastal views and onboard narration
    5.0 • 68 reviews
    $411& up
    Private Morning Sailing Charter in Newport
    Newport, RI

    Private Morning Sailing Charter in Newport

    Sail Newport’s coast from Fort Adams to Brenton Point

    Sail Newport’s coast from Fort Adams to Brenton Point
    $901
    Afternoon Sailing Charter in Newport
    Newport, RI

    Afternoon Sailing Charter in Newport

    Private sailing with shaded lounging, hidden-cove swims and Newport coastal views

    Private sailing with shaded lounging, hidden-cove swims and Newport coastal views
    $1,219
    Seattle Day Sailing Adventure
    Seattle, WA

    Seattle Day Sailing Adventure

    Build day-sailing skills on a skipper-led voyage beyond the bay

    Build day-sailing skills on a skipper-led voyage beyond the bay
    4.6 • 1.6K reviews
    $140/ person
    Camden Sunset Sail on Penobscot Bay
    Camden, ME

    Camden Sunset Sail on Penobscot Bay

    Watch sunset colors unfold across Penobscot Bay aboard the Schooner Surprise

    Watch sunset colors unfold across Penobscot Bay aboard the Schooner Surprise
    $72/ person
    New Bern Sunset Sailing Charter
    New Bern, NC

    New Bern Sunset Sailing Charter

    Sail the Neuse River as the sky changes color at sunset

    Sail the Neuse River as the sky changes color at sunset
    $619/ boat
    2-Hour Private Sailing Charter in Oceanside
    Oceanside, CA

    2-Hour Private Sailing Charter in Oceanside

    Take the helm and scan the water for marine life

    Take the helm and scan the water for marine life
    $318
    Hands-On Harbor Sailing Tour in Grand Marais
    Grand Marais, MN

    Hands-On Harbor Sailing Tour in Grand Marais

    Share the sails on a social outing along the Grand Marais shoreline

    Share the sails on a social outing along the Grand Marais shoreline
    $64/ person
    Soufriere Rum & Chocolate Tasting Cruise
    Gros Islet, Saint Lucia

    Soufriere Rum & Chocolate Tasting Cruise

    Sail to Soufriere for rum and chocolate tastings

    Sail to Soufriere for rum and chocolate tastings
    4.7 • 293 reviews
    $200/ person
    Sunset Sail on Seneca Lake
    Watkins Glen, NY

    Sunset Sail on Seneca Lake

    An evening aboard a schooner as the light fades over Seneca Lake

    An evening aboard a schooner as the light fades over Seneca Lake
    4.8 • 19 reviews
    $90/ person
    Sunset Sailing Cruise in Camden
    Camden, ME

    Sunset Sailing Cruise in Camden

    Help raise sail as sunset views unfold across Penobscot Bay

    Help raise sail as sunset views unfold across Penobscot Bay
    $106/ person
    Coffee Sail Charter in Oceanside
    Oceanside, CA

    Coffee Sail Charter in Oceanside

    Hold your next work meeting on the water with ocean views

    Hold your next work meeting on the water with ocean views
    $318
    Vineyard Haven Brunch Cruise
    Tisbury, MA

    Vineyard Haven Brunch Cruise

    Sail Vineyard Haven Harbor with brunch bites, mimosas, and live jazz

    Sail Vineyard Haven Harbor with brunch bites, mimosas, and live jazz
    4.9 • 26 reviews
    $249
    Private Sea of Cortez Sailing Charter
    Cabo San Lucas, Baja California Sur

    Private Sea of Cortez Sailing Charter

    Sail Cabo San Lucas’ shoreline with your private group

    Sail Cabo San Lucas’ shoreline with your private group
    $5,088/ boat
    2-Hour Schooner Sail in Port Jefferson
    Port Jefferson, NY

    2-Hour Schooner Sail in Port Jefferson

    Help raise the sails or take the helm aboard a traditional tall ship

    Help raise the sails or take the helm aboard a traditional tall ship
    5.0 • 19 reviews
    $63/ person
    Salem 2-Hour Sunset Sail
    Salem, MA

    Salem 2-Hour Sunset Sail

    Sunset sailing aboard John Alden's racing yacht

    Sunset sailing aboard John Alden's racing yacht
    5.0 • 180 reviews
    $62
    2-Hour Camden Sailing Cruise
    Camden, ME

    2-Hour Camden Sailing Cruise

    Coastal views and local insight past Curtis Island Lighthouse

    Coastal views and local insight past Curtis Island Lighthouse
    $106/ person
    2.5-Hour Private Sailing Charter in San Diego Bay
    Gardnerville, NV

    2.5-Hour Private Sailing Charter in San Diego Bay

    Sail, swim, and toast aboard a private yacht

    Sail, swim, and toast aboard a private yacht
    $1,018
    4-Hour Sailing Charter in San Diego
    Gardnerville, NV

    4-Hour Sailing Charter in San Diego

    Sail the coastline, swim in a calm bay, and relax on the water

    Sail the coastline, swim in a calm bay, and relax on the water
    $1,479
    San Diego 2.5-Hour Sailing Charter
    Gardnerville, NV

    San Diego 2.5-Hour Sailing Charter

    Share a relaxed yacht sail with coastal views and a group toast

    Share a relaxed yacht sail with coastal views and a group toast
    $253/ person
    Sunset Sailing Charter in Seattle
    Seattle, WA

    Sunset Sailing Charter in Seattle

    Choose your level of participation on an evening Puget Sound sail

    Choose your level of participation on an evening Puget Sound sail
    4.6 • 1.6K reviews
    $47/ person
    4-Hour Sailing & Snorkeling Charter in Oranjestad
    Oranjestad, Aruba

    4-Hour Sailing & Snorkeling Charter in Oranjestad

    Sail, snorkel, and enjoy a barbecue meal with an open bar

    Sail, snorkel, and enjoy a barbecue meal with an open bar
    4.7 • 539 reviews
    $153/ person
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