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    Best results for Sailing

    Showing 97-120 of 302 results
    Golden Hour Cocktail Sail in New York City
    Sailing

    Golden Hour Cocktail Sail in New York City

    Sail past the Statue of Liberty with a welcome cocktail at golden hour

    Sail past the Statue of Liberty with a welcome cocktail at golden hour
    Contact for pricing
    Cruise West Grand Traverse Bay at Noon in Traverse City
    Sailing

    Cruise West Grand Traverse Bay at Noon in Traverse City

    Relax on a 2-hour noon catamaran cruise on West Grand Traverse Bay

    Relax on a 2-hour noon catamaran cruise on West Grand Traverse Bay
    Contact for pricing
    Ko Olina Sunset Sail with Tasting Menu
    Dinner Cruises

    Ko Olina Sunset Sail with Tasting Menu

    Savor island pupu dishes and open-bar drinks while cruising past Oahu’s coast on an intimate six-guest sunset sail.

    Savor island pupu dishes and open-bar drinks while cruising past Oahu’s coast on an intimate six-guest sunset sail.
    5.0 • 341 reviews
    $252/ person
    Full-Day Snorkel & Sail Catamaran Charter in Maui
    Private Yacht ChartersUp to 6

    Full-Day Snorkel & Sail Catamaran Charter in Maui

    Customize a 7-hour private sail in Maalaea Bay with guided snorkeling and flexible stops for your group of up to six

    Customize a 7-hour private sail in Maalaea Bay with guided snorkeling and flexible stops for your group of up to six
    5.0 • 141 reviews
    $9,552
    Full-Day Snorkel & Sail Charter in Maalaea Harbor
    Private Boat ChartersUp to 6

    Full-Day Snorkel & Sail Charter in Maalaea Harbor

    Sail Maalaea Bay with snorkel stops, guided in-water tour, and meals included

    Sail Maalaea Bay with snorkel stops, guided in-water tour, and meals included
    5.0 • 141 reviews
    $5,731
    San Diego Whale Watching Tour on 138ft Yacht
    Whale Watching

    San Diego Whale Watching Tour on 138ft Yacht

    Sail on a stable 138-foot yacht to spot migrating whales off San Diego

    Sail on a stable 138-foot yacht to spot migrating whales off San Diego
    4.8 • 433 reviews
    $91/ person
    Sail From Historic Charleston to Kiawah Island, South Carolina
    Yacht Charters

    Sail From Historic Charleston to Kiawah Island, South Carolina

    Sail offshore with licensed captains to Charleston's barrier islands on a full-day adventure

    Sail offshore with licensed captains to Charleston's barrier islands on a full-day adventure
    4.9 • 216 reviews
    $1,712& up
    Kona Luxury Dolphin Snorkel Sail with Lunch
    Snorkeling

    Kona Luxury Dolphin Snorkel Sail with Lunch

    Sail Kona’s coast on a luxury catamaran, snorkel top reefs, spot dolphins, and enjoy lunch

    Sail Kona’s coast on a luxury catamaran, snorkel top reefs, spot dolphins, and enjoy lunch
    4.8 • 498 reviews
    $455/ person
    Private Sunset Sailing Charter in St. Augustine
    Private Boat ChartersUp to 6

    Private Sunset Sailing Charter in St. Augustine

    Savor a chef-prepared four-course meal with drinks aboard a private luxury yacht at sunset

    Savor a chef-prepared four-course meal with drinks aboard a private luxury yacht at sunset
    4.9 • 697 reviews
    $1,862& up
    Private 3-Hour Whale Watching Cruise in Maui
    Whale Watching

    Private 3-Hour Whale Watching Cruise in Maui

    Sail a private catamaran whale watch from Ma‘alaea Harbor with hydrophone listening

    Sail a private catamaran whale watch from Ma‘alaea Harbor with hydrophone listening
    Contact for pricing
    4.5-Hour Sail, Snorkel & Kayak Tour in Key West
    Snorkeling

    4.5-Hour Sail, Snorkel & Kayak Tour in Key West

    Sail, snorkel, and kayak on a historic schooner with drinks and snacks included

    Sail, snorkel, and kayak on a historic schooner with drinks and snacks included
    Contact for pricing
    Private Catamaran Sail with Captain & Crew
    Private Boat Charters2 to 3

    Private Catamaran Sail with Captain & Crew

    Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.

    Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.
    5.0 • 437 reviews
    $2,511
    Half Day Tour of Annapolis
    City Tours

    Half Day Tour of Annapolis

    Explore historic Annapolis and Navy heritage with a licensed guide and luxury transport

    Explore historic Annapolis and Navy heritage with a licensed guide and luxury transport
    5.0 • 29 reviews
    $1,547
    Private Sunset Sail on Catamaran Artemis
    Private Boat ChartersUp to 6

    Private Sunset Sail on Catamaran Artemis

    Sail Ma’alaea Bay at sunset with crew, light appetizers, and soft drinks on a private catamaran

    Sail Ma’alaea Bay at sunset with crew, light appetizers, and soft drinks on a private catamaran
    5.0 • 141 reviews
    $2,729
    Ka'anapali Wild Dolphin Sail
    Dolphin Watching

    Ka'anapali Wild Dolphin Sail

    Sail 2.5 hours to watch wild dolphins with expert commentary and refreshments

    Sail 2.5 hours to watch wild dolphins with expert commentary and refreshments
    4.9 • 1.9K reviews
    $126/ person
    Turtle Canyon Snorkeling Tour from Waikiki
    Snorkeling

    Turtle Canyon Snorkeling Tour from Waikiki

    Snorkel with Hawaiian green sea turtles at Turtle Canyon and cruise Waikiki aboard a comfortable catamaran

    Snorkel with Hawaiian green sea turtles at Turtle Canyon and cruise Waikiki aboard a comfortable catamaran
    4.8 • 4K reviews
    $90
    Honolulu Private Catamaran Sail & Snorkel
    Private Boat ChartersUp to 12

    Honolulu Private Catamaran Sail & Snorkel

    Sail a modern 40' catamaran from Kewalo Basin with spacious lounges and snorkel gear

    Sail a modern 40' catamaran from Kewalo Basin with spacious lounges and snorkel gear
    5.0 • 186 reviews
    $664& up
    Swim with Turtles & Sail Past Diamond Head
    Snorkeling

    Swim with Turtles & Sail Past Diamond Head

    Snorkel with sea turtles and sail past Diamond Head on a 2-hour Waikiki cruise

    Snorkel with sea turtles and sail past Diamond Head on a 2-hour Waikiki cruise
    4.9 • 638 reviews
    $116/ person
    24' Sailboat Rental in Monterey Bay
    Boat RentalsUp to 5

    24' Sailboat Rental in Monterey Bay

    Sail a classic wooden sloop with simple controls, perfect for relaxed family outings

    Sail a classic wooden sloop with simple controls, perfect for relaxed family outings
    $313
    Sail & Swim Private Charter in Destin
    Yacht Charters

    Sail & Swim Private Charter in Destin

    Sail Destin Harbor, then swim and snorkel from your private yacht

    Sail Destin Harbor, then swim and snorkel from your private yacht
    Contact for pricing
    Sail on a Private Maui Whale Watching Cruise
    Whale Watching

    Sail on a Private Maui Whale Watching Cruise

    Private sailboat whale watch from Ma‘alaea Harbor (Jan–Apr), with hydrophone listening

    Private sailboat whale watch from Ma‘alaea Harbor (Jan–Apr), with hydrophone listening
    Contact for pricing
    St. Augustine Pirate Ship Battle & Treasure Hunt
    Boat Tours

    St. Augustine Pirate Ship Battle & Treasure Hunt

    Experience pirate battles, sea shanties, and treasure hunting fun for all ages.

    Experience pirate battles, sea shanties, and treasure hunting fun for all ages.
    4.3 • 1.1K reviews
    $51/ person
    St. Augustine Sunset Cruise with Wine Pairings
    Dinner Cruises

    St. Augustine Sunset Cruise with Wine Pairings

    Savor expertly paired wines and seasonal appetizers as you sail past St. Augustine’s scenic coastline at sunset.

    Savor expertly paired wines and seasonal appetizers as you sail past St. Augustine’s scenic coastline at sunset.
    4.9 • 697 reviews
    $336/ person
    Key West Sunset Catamaran Cruise with Open Bar
    Dinner Cruises

    Key West Sunset Catamaran Cruise with Open Bar

    Enjoy unlimited drinks, appetizers, and live music aboard a catamaran while you watch the famous Key West sunset.

    Enjoy unlimited drinks, appetizers, and live music aboard a catamaran while you watch the famous Key West sunset.
    4.8 • 20.8K reviews
    $102/ person
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