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    Best results for Sailing

    Showing 169-192 of 403 results
    Dolphin Watch & Historic Harbor Cruise in St. Augustine
    Dolphin Watching

    Dolphin Watch & Historic Harbor Cruise in St. Augustine

    Cruise St. Augustine’s historic harbor and look for bottlenose dolphins by catamaran

    Cruise St. Augustine’s historic harbor and look for bottlenose dolphins by catamaran
    4.8 • 221 reviews
    $46/ person
    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
    4.9 • 5.7K reviews
    $135/ person
    Snorkel & Sunset Sail Cruise in Maui
    Snorkeling

    Snorkel & Sunset Sail Cruise in Maui

    Snorkel a reef, then sail into a Maui sunset with appetizers and a bring-your-own-drinks cooler

    Snorkel a reef, then sail into a Maui sunset with appetizers and a bring-your-own-drinks cooler
    $172/ person
    Sail Sarasota Bay on a Private Catamaran Charter
    Yacht Charters

    Sail Sarasota Bay on a Private Catamaran Charter

    Private 6–8 hour Bali 4.2 catamaran charter on Sarasota Bay

    Private 6–8 hour Bali 4.2 catamaran charter on Sarasota Bay
    5.0 • 488 reviews
    $3,584
    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 • 488 reviews
    $2,511
    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 • 2.3K reviews
    $126/ person
    2-Hour Turtle Canyon Snorkeling Cruise From Waikiki
    Snorkeling

    2-Hour Turtle Canyon Snorkeling Cruise From Waikiki

    Snorkel Turtle Canyon on a 2-hour catamaran sail with gear and light snacks included

    Snorkel Turtle Canyon on a 2-hour catamaran sail with gear and light snacks included
    4.8 • 4.9K reviews
    $90/ person
    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
    Snorkel Turtle Canyon on a Waikiki Sail Cruise
    Snorkeling

    Snorkel Turtle Canyon on a Waikiki Sail Cruise

    Sail off Waikiki and snorkel Turtle Canyon for tropical fish and sea turtles

    Sail off Waikiki and snorkel Turtle Canyon for tropical fish and sea turtles
    4.9 • 740 reviews
    $116/ person
    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
    5.0 • 153 reviews
    $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 • 228 reviews
    $313/ boat
    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
    $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
    5.0 • 219 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 • 208 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 • 208 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
    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
    $53/ 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 • 736 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 • 22K reviews
    $102/ 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
    4.8 • 652 reviews
    $172/ person
    Cape Lookout Private Cruise on 45ft Catamaran
    Private Boat ChartersUp to 37

    Cape Lookout Private Cruise on 45ft Catamaran

    Cruise to Cape Lookout for two stops with catered lunch, swimming, and lighthouse views on a 45-foot catamaran

    Cruise to Cape Lookout for two stops with catered lunch, swimming, and lighthouse views on a 45-foot catamaran
    5.0 • 1.1K reviews
    $7,702
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