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    Best results for Sailing

    Showing 145-168 of 302 results
    North Shore Sunset Sail from Haleiwa Harbor
    Sailing

    North Shore Sunset Sail from Haleiwa Harbor

    Sail along Oahu's North Shore for a peaceful two-hour voyage and watch vibrant sunset colors from the deck

    Sail along Oahu's North Shore for a peaceful two-hour voyage and watch vibrant sunset colors from the deck
    4.6 • 305 reviews
    $101/ person
    Diamond Head Views & Coastal Sail from Waikiki
    Sailing

    Diamond Head Views & Coastal Sail from Waikiki

    Glide along Oahu's coast on a breezy afternoon sail for panoramic views of Diamond Head, Waikiki beaches, and distant Molokai.

    Glide along Oahu's coast on a breezy afternoon sail for panoramic views of Diamond Head, Waikiki beaches, and distant Molokai.
    4.9 • 638 reviews
    $280/ person
    Sunset Catamaran Sail in Honolulu with Drinks
    Sailing

    Sunset Catamaran Sail in Honolulu with Drinks

    Toast the day aboard a catamaran as you watch the sun sink beneath the Oahu horizon.

    Toast the day aboard a catamaran as you watch the sun sink beneath the Oahu horizon.
    4.9 • 638 reviews
    $90/ person
    Diamond Head Sail with Marine Life & Views
    Sailing

    Diamond Head Sail with Marine Life & Views

    See marine life and Waikiki views on a one-hour Diamond Head sail

    See marine life and Waikiki views on a one-hour Diamond Head sail
    4.7 • 181 reviews
    $58/ person
    Waikiki Sunset Sail with Diamond Head Views
    Sailing

    Waikiki Sunset Sail with Diamond Head Views

    Unwind on a Waikiki sunset catamaran with views of Diamond Head, drinks and light bites included

    Unwind on a Waikiki sunset catamaran with views of Diamond Head, drinks and light bites included
    4.6 • 1.4K reviews
    $115/ person
    West Oahu Sunset Sail with Drinks & Appetizers
    Sailing

    West Oahu Sunset Sail with Drinks & Appetizers

    Unwind on a West O‘ahu sunset cruise with panoramic views, drinks, and light bites included

    Unwind on a West O‘ahu sunset cruise with panoramic views, drinks, and light bites included
    4.6 • 1.4K reviews
    $115/ person
    Beaufort Sunset Sail with Complimentary Drinks
    Sailing

    Beaufort Sunset Sail with Complimentary Drinks

    Unwind on a 90-minute evening cruise with coastal views and complimentary beverages

    Unwind on a 90-minute evening cruise with coastal views and complimentary beverages
    5.0 • 1.1K reviews
    $73/ person
    Small Group Sailing: Historic St. Augustine Bay
    Sailing

    Small Group Sailing: Historic St. Augustine Bay

    Sail past historic St. Augustine landmarks with a friendly crew

    Sail past historic St. Augustine landmarks with a friendly crew
    4.9 • 697 reviews
    $168/ person
    Waikīkī BYOB Sunset Sail & Swim
    Sailing

    Waikīkī BYOB Sunset Sail & Swim

    Sail Waikīkī at sunset with a swim stop on a spacious BYOB trimaran

    Sail Waikīkī at sunset with a swim stop on a spacious BYOB trimaran
    4.9 • 638 reviews
    $81/ person
    Waikiki Sunset Sail and Pupu
    Sailing

    Waikiki Sunset Sail and Pupu

    Sail off Waikiki at sunset with skyline views and a pupu platter on a comfortable catamaran.

    Sail off Waikiki at sunset with skyline views and a pupu platter on a comfortable catamaran.
    4.7 • 304 reviews
    $95/ person
    Friday Night Waikiki Fireworks Cruise
    Sailing

    Friday Night Waikiki Fireworks Cruise

    Sail off Waikiki for Friday fireworks with skyline views and drinks available to purchase

    Sail off Waikiki for Friday fireworks with skyline views and drinks available to purchase
    5.0 • 3.9K reviews
    $69/ person
    Adventure Sunset Sail
    Sailing

    Adventure Sunset Sail

    Sail South Maui at golden hour with live music, open bar, and a sparkling wine toast

    Sail South Maui at golden hour with live music, open bar, and a sparkling wine toast
    4.9 • 2.7K reviews
    $216/ person
    Premium Sunset Dinner Cruise from Ka'anapali
    Sailing

    Premium Sunset Dinner Cruise from Ka'anapali

    Savor a buffet dinner and open bar aboard a luxury catamaran at sunset

    Savor a buffet dinner and open bar aboard a luxury catamaran at sunset
    4.9 • 2.1K reviews
    $155/ person
    Holo Holo Sunset Cocktail Sail in Maui
    Sailing

    Holo Holo Sunset Cocktail Sail in Maui

    Sip cocktails as the sun sets on a 2-hour West Maui sail with open bar and appetizers

    Sip cocktails as the sun sets on a 2-hour West Maui sail with open bar and appetizers
    4.9 • 1.9K reviews
    $143/ person
    West Maui Adventure Snorkel Sail
    Sailing

    West Maui Adventure Snorkel Sail

    Sail Kaanapali and snorkel top West Maui reefs with breakfast, lunch, and open bar

    Sail Kaanapali and snorkel top West Maui reefs with breakfast, lunch, and open bar
    4.9 • 1.9K reviews
    $177/ person
    Santa Rosa Island Adventure
    Sailing

    Santa Rosa Island Adventure

    Sail with a licensed captain to swim, snorkel, and unwind—perfect for families and groups up to six

    Sail with a licensed captain to swim, snorkel, and unwind—perfect for families and groups up to six
    5.0 • 58 reviews
    $482& up
    Sunrise Catamaran Sail in Destin
    Sailing

    Sunrise Catamaran Sail in Destin

    Catch sunrise views over Choctawhatchee Bay with a private captain

    Catch sunrise views over Choctawhatchee Bay with a private captain
    5.0 • 58 reviews
    $345
    Pensacola Beach Sunset Sail on the Jolly Mon
    Sailing

    Pensacola Beach Sunset Sail on the Jolly Mon

    Unwind on a 2-hour sail with cushioned seating, drinks, and chances to spot dolphins

    Unwind on a 2-hour sail with cushioned seating, drinks, and chances to spot dolphins
    5.0 • 1.8K reviews
    $120& up
    Evening Sunset Sail on the Footloose Catamaran
    Sailing

    Evening Sunset Sail on the Footloose Catamaran

    Relax on a 40-foot sunset catamaran with tropical music, dolphin sightings, and a complimentary drink

    Relax on a 40-foot sunset catamaran with tropical music, dolphin sightings, and a complimentary drink
    4.9 • 2.7K reviews
    $47/ person
    Snorkel, Swim & Dolphin Sail on the Daydreams Sailboat
    Sailing

    Snorkel, Swim & Dolphin Sail on the Daydreams Sailboat

    Sail to Shell Island for snorkeling, then cruise the Gulf for dolphin sightings with a captain and first mate.

    Sail to Shell Island for snorkeling, then cruise the Gulf for dolphin sightings with a captain and first mate.
    4.9 • 2.7K reviews
    $132/ person
    Sunset & Dolphin Sightseeing on the Daydreams Sailboat
    Sailing

    Sunset & Dolphin Sightseeing on the Daydreams Sailboat

    Unwind on a scenic sunset sail with dolphin spotting and complimentary drinks

    Unwind on a scenic sunset sail with dolphin spotting and complimentary drinks
    4.9 • 2.7K reviews
    $114/ person
    The Locals Island Charter
    Sailing

    The Locals Island Charter

    Sail to a secluded beach near Fort McRee for swimming, paddleboarding, and lunch on a private 6-hour charter

    Sail to a secluded beach near Fort McRee for swimming, paddleboarding, and lunch on a private 6-hour charter
    5.0 • 16 reviews
    $1,344
    San Diego Bay Afternoon Sail Aboard A Classic Yacht
    Sailing

    San Diego Bay Afternoon Sail Aboard A Classic Yacht

    Sip craft beer and wine as you sail San Diego Bay on an intimate six-passenger classic yacht

    Sip craft beer and wine as you sail San Diego Bay on an intimate six-passenger classic yacht
    5.0 • 94 reviews
    $125/ person
    San Diego Bay Sunset Sail on a Classic Yacht
    Sailing

    San Diego Bay Sunset Sail on a Classic Yacht

    Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht

    Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht
    5.0 • 94 reviews
    $125/ person
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