Activities in Key West


Two-Hour Standup-Paddleboard Tour for Two, Four, Six, or Eight at SUP Key West (39% Off)

SUP Key West

Key West

Peaceful views of Key West and regional wildlife during two-hour guided tours atop standup paddleboards

$90 $55

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Seashell Hunt and Snorkel Adventure for Four or Six from Keys Huka Dive (Up to 57% Off)

Keys Huka Dive

Marathon

Guests snorkel and hunt for seashells in groups of four or six

$700 $300

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$169.99 for a Key West Helicopter Tour Package for Up to 3 from Air Adventures LLC (Up to $332 Value)

Air Adventures LLC

Key West

Helicopters soar over 10 miles of immaculate Key West shoreline for a bird’s-eye view of marine life and seascapes

$332 $169.99

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$160 for 90-Minute Harbor Day Sailing Tour for Up to Six from Sunset Sail Key West ($294 Value)

Sunset Sail Key West

Key West

Up to six passengers take to the Gulf of Mexico in a 33-foot sailboat with water, soft drinks, and cooler space for BYO drinks

$294 $160

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Two-Hour Sunset Sail for Two, Four, or Six from Florida Keys Sailing (Up to 52% Off)

Florida Keys Sailing

Florida Keys Sailing

On an air-conditioned boat, passengers can bring coolers of food or drinks and even take the helm, if they wish

$200 $99

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Hop-On, Hop-Off Trolley Tour for One, Two, or Four from City View Trolley Tours (36% Off)

City View Trolley Tours

Key West

Riders hop on and off at nine stops along a scenic route through the streets of Key West

$28 $19

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90-Minute Ghost Tour for Two, Four, or Six from The Original Ghost Tours Key West (Up to 52% Off)

The Original Ghost Tours Key West

Key West

Guides lead family-friendly walking tours of Key West, sharing stories of the city’s paranormal history and legendary spirits

$42 $20

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Select Local Merchants

Rum, spirits, music, sun, and food: the Key West Bacchanalia celebrates summer with all five. The festival pours out tastes of Puerto Rican rum cocktails and other select drinks, which guests sip while watching celebrity chefs whip up savory cuisine in the handheld form of burgers and barbecue. A portion of the event's proceeds benefit the Darrell Gwynn Foundation, an organization supporting individuals with paralysis.
202 Duval St.
Key West,
FL
US
For a mouthwatering collection of American classics, Boondocks Grille and Draft House serves traditional, no-frills fare. Boondocks Grille and Draft House is making food that everyone loves. Taking it back to the high-calorie basics. Boondocks Grille and Draft House's fully stocked bar is a perk for patrons who enjoy a fine wine (or more) with their meal. Go ahead and bring your rug rats with you — Boondocks Grille and Draft House has kid-friendly food and seating. The patio seating at Boondocks Grille and Draft House is perfect for those warm summer days. Boondocks Grille and Draft House is a suitable restaurant for both large and small groups. Show up in sneakers or a suit at Boondocks Grille and Draft House, where dining in comfort is of utmost importance. You can also grab your food to go. Boondocks Grille and Draft House makes bikers feel at ease with the multiple storage racks outside. Save your pennies for a rainy day — with prices generally under $15, you'll have plenty left over even after dining at Boondocks Grille and Draft House. Boondocks Grille and Draft House serves breakfast, lunch, and dinner, so stop by whenever is most convenient for you.
27205 Overseas Hwy
Summerland Key,
FL
US
Grab some friends and head on over to Green Parrot Bar for great pub grub. Health-crazed eaters may have to stick with water, though, as Green Parrot Bar offers delicious grub that s far as can be from low-fat fare. Complement your meal with a beer or wine from Green Parrot Bar's delightful drink menu. Don't miss out on the great happy hour deals at Green Parrot Bar. Green Parrot Bar caters to all party sizes, both large and small. Live musical acts often perform, and guests take advantage of the spacious dance floor. Those with sensitive ears may want to stay away from this restaurant, though, as it can get quite loud. The restaurant's "rush" is all weekend long, so diners should be prepared to wait for a table. Green Parrot Bar's dress code is casual — diners are welcome to dress up (or down) to their comfort level. Both street parking and lot parking are available near Green Parrot Bar. Taste the greatness Green Parrot Bar is serving up with meals around $30. Breakfast, lunch, and dinner are all on Green Parrot Bar's menu — you can stop by whenever the moment's right for you.
601 Whitehead St
Key West,
FL
US
To call the restoration of the High Tide a labor of love would be to greatly devalue the definition of "labor." The 33-foot sloop remained on land for almost a year and a half as a team, mostly volunteers, returned the 1978-construction vessel to like-new status. Now, with Captain Seth at its open cockpit, the High Tide dips its fiberglass hull back into the waters of Key West, unfurls its sails, and embarks for the horizon. Whether on trips to admire the sunset, snorkel in the Gulf of Mexico, or test a new brand of motion sickness medication, the sailboat provides noiseless passage, save for the flap of canvas on the breeze.
202 William Street
Key West,
FL
US
It?s not an energy drink, a crimson bovine, or even a particularly misguided spelling of ?bread bowl.? Rather, the Red Bull is a 26-foot-long, cherry-red Nordic tugboat, and it provides a unique way to rub metaphorical elbows with the Florida Key's aquatic wildlife and sea birds. Clients can charter the boat for a historic tour of the harbor, and get a watery glimpse at the seaport, Mallory Square, and the Sand Key lighthouse. Or, they can commission Captain Bob and his crew to chauffeur them on dolphin-spotting excursions. The Red Bull is also available for fishing trips, and is equipped with a state-of-the-art fish finder.
1102 Duval Street
Key West,
FL
US
On many windy, sun-drenched days in the Florida Keys, an electric catamaran flying the colors of the America Sailing & Diving Club can be seen escorting revelers across ocean waves. Formed in 1973, the club brings together boat owners as well as nonowners who can set sail on the club’s fleet of sailboats that range in size from 22 feet to 44 feet, each designed to keep the club’s carbon footprint to a minimum. The club also offers courses that teach landlubbers basic sailing techniques, such as knot-tying skills so they needn’t fear that their loose engagement ring will fall overboard.
12399 Overseas Highway
Marathon Key,
FL
US
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