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    Best results for Sailing

    Showing 265-288 of 302 results
    3-Hour Head Boat Bay Fishing Trip
    Fishing Charters

    3-Hour Head Boat Bay Fishing Trip

    Fish calm, sheltered bay waters with crew support and more time with lines in than riding

    Fish calm, sheltered bay waters with crew support and more time with lines in than riding
    4.8 • 248 reviews
    $40/ person
    3-Hour Private Fishing Charter in Ocean City
    Private Fishing ChartersUp to 32

    3-Hour Private Fishing Charter in Ocean City

    Rent the whole boat for your group and cruise the bay day or night

    Rent the whole boat for your group and cruise the bay day or night
    4.8 • 248 reviews
    $962
    2-Hour Sunset Sail in Provincetown Harbor
    Sailing

    2-Hour Sunset Sail in Provincetown Harbor

    Enjoy a relaxing two-hour cruise as daylight fades over the water

    Enjoy a relaxing two-hour cruise as daylight fades over the water
    5.0 • 35 reviews
    $74/ person
    Salem Harbor Sunset Sail on 1812 Schooner
    Sailing

    Salem Harbor Sunset Sail on 1812 Schooner

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.
    5.0 • 535 reviews
    $49/ person
    Saco Bay Lighthouse Sail & Guided Tower Tour
    Sailing

    Saco Bay Lighthouse Sail & Guided Tower Tour

    Sail Saco Bay to a restored island lighthouse with a guided tower tour

    Sail Saco Bay to a restored island lighthouse with a guided tower tour
    5.0 • 376 reviews
    $395/ person
    Hoist Sails & Fire Cannons on Pirate Cruise
    Sailing

    Hoist Sails & Fire Cannons on Pirate Cruise

    Join a kid-friendly schooner cruise to hoist sails, fire the cannon, and earn your pirate stripes

    Join a kid-friendly schooner cruise to hoist sails, fire the cannon, and earn your pirate stripes
    4.7 • 1.9K reviews
    $61/ person
    Waikiki Friday Fireworks Sunset Cruise
    Boat Tours

    Waikiki Friday Fireworks Sunset Cruise

    Catch Waikiki's Friday fireworks from the water with sunset views and included Mai Tais.

    Catch Waikiki's Friday fireworks from the water with sunset views and included Mai Tais.
    4.9 • 1.4K reviews
    $72/ person
    BYOB Sunset Cruise with Live Music or DJ in Waikiki
    Sailing

    BYOB Sunset Cruise with Live Music or DJ in Waikiki

    Sail Waikiki at sunset with live music or a DJ on a BYOB catamaran with appetizers

    Sail Waikiki at sunset with live music or a DJ on a BYOB catamaran with appetizers
    4.8 • 468 reviews
    $122/ person
    Afternoon Schooner Sail on Frenchman Bay
    Sailing

    Afternoon Schooner Sail on Frenchman Bay

    Ride afternoon breezes and watch for wildlife on a 1.5–2 hour cruise

    Ride afternoon breezes and watch for wildlife on a 1.5–2 hour cruise
    4.2 • 2.5K reviews
    $52/ person
    Maui Sunset Sail on a Floating Tiki Bar Catamaran
    Sailing

    Maui Sunset Sail on a Floating Tiki Bar Catamaran

    Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran

    Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran
    4.8 • 1K reviews
    $138/ person
    Dolphin Sightseeing Sail Aboard the Daydreams Sailboat
    Sailing

    Dolphin Sightseeing Sail Aboard the Daydreams Sailboat

    Sail Grand Lagoon and Shell Island with complimentary drinks while spotting dolphins

    Sail Grand Lagoon and Shell Island with complimentary drinks while spotting dolphins
    4.9 • 2.7K reviews
    $88/ person
    Live Music Sunset & Fireworks Sail
    Sailing

    Live Music Sunset & Fireworks Sail

    Enjoy live music, sunset views, and unobstructed fireworks with drinks and appetizers included

    Enjoy live music, sunset views, and unobstructed fireworks with drinks and appetizers included
    4.8 • 180 reviews
    $186/ person
    Chrissy Lobster Sloop Cruises
    Sailing

    Chrissy Lobster Sloop Cruises

    Small, intimate cruises available for private charter

    Small, intimate cruises available for private charter
    4.2 • 2.5K reviews
    $530
    Salem Sound Sail Aboard the Schooner Fame
    Sailing

    Salem Sound Sail Aboard the Schooner Fame

    Hands-on 1812-style sail with engaging crew and scenic Salem Sound views

    Hands-on 1812-style sail with engaging crew and scenic Salem Sound views
    5.0 • 535 reviews
    $37/ person
    Sail Repair and Sail Making Course
    Sailing

    Sail Repair and Sail Making Course

    Learn to design, build, and repair sails in a hands-on two-day class

    Learn to design, build, and repair sails in a hands-on two-day class
    4.9 • 51 reviews
    $625/ student
    Wind Dancer Signature Sunset Sail
    Sailing

    Wind Dancer Signature Sunset Sail

    Glide across West Bay at sunset as you savor local food and drinks

    Glide across West Bay at sunset as you savor local food and drinks
    4.9 • 328 reviews
    $256/ person
    Two-Hour Afternoon Sail
    Sailing

    Two-Hour Afternoon Sail

    Ride afternoon breezes across the inlet with a brief ocean sail when conditions allow

    Ride afternoon breezes across the inlet with a brief ocean sail when conditions allow
    5.0 • 278 reviews
    $106/ person
    Lake Tahoe Catamaran Cruise on the Sierra Cloud
    Sailing

    Lake Tahoe Catamaran Cruise on the Sierra Cloud

    Sail Lake Tahoe’s shores with panoramic views on a 2-hour cruise

    Sail Lake Tahoe’s shores with panoramic views on a 2-hour cruise
    $170/ person
    Alcatraz Tour and Bay Sail Combo
    Sailing

    Alcatraz Tour and Bay Sail Combo

    Book two separate trips: an Alcatraz visit plus a Bay sail on Adventure Cat

    Book two separate trips: an Alcatraz visit plus a Bay sail on Adventure Cat
    4.9 • 1K reviews
    $133/ person
    Sunset Sail in the Heart of the Gorge
    Sailing

    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
    $143/ person
    Wednesday Night Sunset Cruise With Live Music
    Sailing

    Wednesday Night Sunset Cruise With Live Music

    Sail Casco Bay at sunset with live music and a BYOB vibe

    Sail Casco Bay at sunset with live music and a BYOB vibe
    4.9 • 132 reviews
    $53/ person
    Bloodhound Daysail In Provincetown
    Sailing

    Bloodhound Daysail In Provincetown

    Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

    Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard
    $66/ person
    North Shore Massachusetts Two-Day Scenic Byway Tour
    Sailing

    North Shore Massachusetts Two-Day Scenic Byway Tour

    Spend two days exploring charming North Shore towns with a private sunset sail and landmark stops

    Spend two days exploring charming North Shore towns with a private sunset sail and landmark stops
    4.9 • 464 reviews
    $546
    Day Sail From Mackinac Island
    Sailing

    Day Sail From Mackinac Island

    Sail the Straits on a catamaran with time to relax, swim, and try stand-up paddleboarding

    Sail the Straits on a catamaran with time to relax, swim, and try stand-up paddleboarding
    $101/ person
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