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

    Best results for Sailing

    Showing 241-264 of 510 results
    Kayak Rental in Hilton Head
    Kayaking Tours

    Kayak Rental in Hilton Head

    Rent a kayak by the hour and paddle Hilton Head waterways

    Rent a kayak by the hour and paddle Hilton Head waterways
    4.7 • 237 reviews
    $27/ kayak
    Explore Hilton Head by Stand-Up Paddleboard Rental
    Stand Up Paddle Boarding

    Explore Hilton Head by Stand-Up Paddleboard Rental

    Rent a stand-up paddleboard by the hour in Hilton Head

    Rent a stand-up paddleboard by the hour in Hilton Head
    4.7 • 237 reviews
    $27& up
    Sail a Private Sunset Charter in Maui
    Yacht Charters

    Sail a Private Sunset Charter in Maui

    Cruise Ma’alaea Bay on a private sunset sail for up to 6

    Cruise Ma’alaea Bay on a private sunset sail for up to 6
    $1,637
    Sail a 24' Sloop Rental at Old Fisherman's Wharf
    Boat RentalsUp to 5

    Sail a 24' Sloop Rental at Old Fisherman's Wharf

    Rent a classic 24-foot wooden sloop from Old Fisherman’s Wharf

    Rent a classic 24-foot wooden sloop from Old Fisherman’s Wharf
    4.9 • 229 reviews
    $313/ boat
    Private Sailboat Charter on the Maine Coast
    Private Boat ChartersUp to 6

    Private Sailboat Charter on the Maine Coast

    Experience Acadia’s wildlife and scenery with an expert captain and a trip tailored to you

    Experience Acadia’s wildlife and scenery with an expert captain and a trip tailored to you
    5.0 • 391 reviews
    $417& up
    Rent a Pontoon Boat in Pensacola Beach
    Boat RentalsUp to 11

    Rent a Pontoon Boat in Pensacola Beach

    Cruise Pensacola Beach on a deluxe pontoon boat with half-day or full-day timeslots

    Cruise Pensacola Beach on a deluxe pontoon boat with half-day or full-day timeslots
    4.7 • 603 reviews
    $349/ boat
    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
    4.9 • 5.6K reviews
    $684& up
    Comfort Neck Dry Suit Rental In Port Gamble
    Equipment Rental

    Comfort Neck Dry Suit Rental In Port Gamble

    Rent a comfort neck dry suit for up to 24 hours in Port Gamble

    Rent a comfort neck dry suit for up to 24 hours in Port Gamble
    4.7 • 209 reviews
    $83
    Dry Suit Rental in Port Gamble Up to 24 Hours
    Equipment Rental

    Dry Suit Rental in Port Gamble Up to 24 Hours

    Rent a dry suit for up to 24 hours with a traditional latex neck gasket

    Rent a dry suit for up to 24 hours with a traditional latex neck gasket
    4.7 • 209 reviews
    $83
    Culinary Snorkel & Dolphin Watch Sail In Key West
    Snorkeling

    Culinary Snorkel & Dolphin Watch Sail In Key West

    Snorkel the Key West reef with an onboard seafood boil and open bar

    Snorkel the Key West reef with an onboard seafood boil and open bar
    4.7 • 8K reviews
    $81/ person
    Sail, Paddle & Snorkel Tour in Wailea
    Canoeing

    Sail, Paddle & Snorkel Tour in Wailea

    Sail and snorkel the Wailea coast by Hawaiian outrigger canoe

    Sail and snorkel the Wailea coast by Hawaiian outrigger canoe
    5.0 • 67 reviews
    $196/ person
    Kayak, Guided Snorkel & Morning Sail in Key West
    Snorkeling

    Kayak, Guided Snorkel & Morning Sail in Key West

    Paddle the mangroves and snorkel with a small group in the Key West National Wildlife Refuge

    Paddle the mangroves and snorkel with a small group in the Key West National Wildlife Refuge
    4.9 • 1.4K reviews
    $135/ person
    Cruise Matanzas River on a Pirate Treasure Hunt
    Boat Tours

    Cruise Matanzas River on a Pirate Treasure Hunt

    Sail on the Black Raven for a 1.5-hour pirate treasure hunt

    Sail on the Black Raven for a 1.5-hour pirate treasure hunt
    4.4 • 1.2K reviews
    $64/ 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.
    5.0 • 740 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 • 22.4K reviews
    $98/ person
    Watch a 2-Hour Sunset Cruise in Haleiwa
    Sunrise and Sunset Tours

    Watch a 2-Hour Sunset Cruise in Haleiwa

    Sail into a North Shore sunset from Haleiwa Harbor

    Sail into a North Shore sunset from Haleiwa Harbor
    4.7 • 383 reviews
    $101/ person
    Morning Sail & Snorkel Cruise From Haleiwa
    Snorkeling

    Morning Sail & Snorkel Cruise From Haleiwa

    Sail the North Shore and snorkel near Waimea Bay with a small group

    Sail the North Shore and snorkel near Waimea Bay with a small group
    4.7 • 383 reviews
    $160/ person
    Waikiki Turtle Canyon Snorkel Sail With Lunch
    Snorkeling

    Waikiki Turtle Canyon Snorkel Sail With Lunch

    Sail and snorkel Turtle Canyon with lunch and drinks

    Sail and snorkel Turtle Canyon with lunch and drinks
    $172/ person
    2-Hour Waikiki Sail & Snorkel Catamaran Cruise
    Snorkeling

    2-Hour Waikiki Sail & Snorkel Catamaran Cruise

    Sail and snorkel off Diamond Head on a 40-foot catamaran

    Sail and snorkel off Diamond Head on a 40-foot catamaran
    4.8 • 142 reviews
    $95/ person
    Guided 1.5-Hour Skull Creek Kayaking Tour
    Kayaking Tours

    Guided 1.5-Hour Skull Creek Kayaking Tour

    Paddle Skull Creek marshes on a 1.5-hour guided kayak tour

    Paddle Skull Creek marshes on a 1.5-hour guided kayak tour
    4.7 • 237 reviews
    $42/ kayak
    West Maui 4-Hour Snorkel Sail
    Snorkeling

    West Maui 4-Hour Snorkel Sail

    Sail and snorkel West Maui with breakfast, lunch, and an open bar

    Sail and snorkel West Maui with breakfast, lunch, and an open bar
    4.9 • 2.4K reviews
    $177/ person
    Cruise the Southern California Coast on a 3-Hour Charter
    Yacht Charters

    Cruise the Southern California Coast on a 3-Hour Charter

    Charter a 42-foot Lagoon catamaran with staterooms, paddle boards, and lounge space

    Charter a 42-foot Lagoon catamaran with staterooms, paddle boards, and lounge space
    $1,352
    Sail Monterey Bay on a 30' Hunter Sailboat Rental
    Boat Rentals

    Sail Monterey Bay on a 30' Hunter Sailboat Rental

    Rent the 30' Hunter Willow and sail Monterey Bay your way

    Rent the 30' Hunter Willow and sail Monterey Bay your way
    4.9 • 229 reviews
    $360/ boat
    Kealakekua Bay Snorkel and Sail
    Snorkeling

    Kealakekua Bay Snorkel and Sail

    Sail the Kona Coast and snorkel Kealakekua Bay with gear, breakfast, and lunch included

    Sail the Kona Coast and snorkel Kealakekua Bay with gear, breakfast, and lunch included
    4.9 • 729 reviews
    $207/ person
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