A waterfront table under a thatched roof; a chilled drink and island music carried by a soft sea breeze. This is what many seek when they head to the Florida Keys, and they soon find it in the open-air tiki bars scattered across this drive-to chain of islands. There are many to choose from, but for purists, the best feature direct water views, a unique atmosphere and a colorful cast of patrons. Here are ten that shouldn’t be missed, so designate a driver and follow along as we count down the mileposts on U.S. Highway One on our way to Key West.
Skipper’s Dockside, Mile Marker 100, Key Largo
Before setting out on the final hundred miles of America’s southernmost highway, pull in for a refresher under the thatched roof of this revitalized Key Largo landmark formerly known as Coconuts. The elevated canal side deck provides a front row seat for the comings and goings of fishing charters and dive boats in the adjacent marina. But there’s more to the story than a new name and new ownership, as the kitchen now turns out meals that are as memorable as the views.
Skipper’s Dockside is perched on the wharf above Key Largo’s busiest marina. When fishermen and divers return from a day on the water, this is often their first stop. Photo: Skipper’s Dockside
Tiki Bar at the Postcard Inn, Mile Marker 84, Islamorada
This open air bar overlooking Whale Harbor has sated thirsty patrons since the 1950s, and is known as the home of the Rum Runner cocktail. Many locals still refer to the hotel and marina complex where the bar is located as “Holiday Isle,” but new ownership in 2014 resulted in a name change and some major upgrades to the vintage hotel rooms. But the resort’s Tiki Bar was spared gentrification, and continues to serve up its signature cocktails in an unabashed atmosphere of island-style revelry.
The longstanding landmark property now known as the Postcard Inn is still home to Islamorada’s famous Tiki Bar, which has hosted generations of revelers. Photo: Craig Denis/Postcard Inn
Lorelei Cabana Bar, Mile Marker 82, Islamorada
Look to the right as you cruise through the fishing village of Islamorada and you’ll know you’ve arrived when the giant mermaid signboard comes into view. If you’ve timed it right, you’ll score a table on the water a bit before sunset. It’s a daily ritual for fishing guides, happy hour locals and in-the- know travelers, who gather for the evening light show set against the backdrop of Florida Bay. Sit back; order some fish dip and a key lime piña colada, and then watch for the fabled green flash as the last rays of the sun sink below the horizon.
Spectacular sunsets, drink specials and live entertainment provide a trifecta of enticements for patrons at Islamorada’s Lorelei Cabana Bar. Photo: Tom Lynch/Lorelei
Island Fish Company Tiki Bar, Mile Marker 54, Marathon
As you move south through the middle Keys, the town of Marathon provides a trifecta of tiki bars that kicks off with a stop at Mile Marker 54, where the longest open air bar in the keys perches on a sand spit that juts into turquoise waters. It’s a popular stop, and bar stools are often filled by midday. But libations aren’t the only attraction, as the kitchen turns out some excellent seafood fare, and the atmosphere is lively yet still family friendly.
Marathon’s Island Fish Company boasts the longest tiki bar in the Florida Keys, but it is more than just a waterfront watering hole, as it is also known for good food and entertainment. Photo: Island Fish Company
Chiki Tiki Bar & Grille at Burdines Waterfront, Mile Marker 49.5, Marathon
For a taste of Marathon’s local maritime vibe, get off U.S. 1 at 15th Street and make your way to the boatyard at Burdines Waterfront. Set in a working waterfront of lobster traps and dry-docked workboats is a second-story tavern that enjoys big views across the anchorage of Boot Key Harbor. A steady stream of dinghies come and go from moored boats, and crews climb the stairs of the Chiki Tiki to enjoy reasonably priced food and drinks in a relaxed atmosphere that is missed by tourists who remain on the highway.
Tucked into Marathon’s working waterfront, the Chiki Tiki Bar & Grille is a favorite with local boat crews, who come ashore for signature items such as fried key lime pie. Photo: Chiki Tiki Bar
Sunset Grille & Raw Bar, Mile Marker 47, Marathon
Since opening in 2010, this final stop before the Key’s famous Seven Mile Bridge has quickly become a favorite hangout for the bare feet and bathing suit crowd, thanks to the oceanfront pool and palm shaded sands that flank the thatch-roofed bar. Patrons are welcome to settle in for an afternoon of swimming and sunning in a beach party atmosphere. The sunset is always a big draw, and those who come to dine can choose from a broad array of offerings that includes sushi, fresh fish, every manner of shellfish and even a Caribbean paella entree.
Patrons at Marathon’s Sunset Grille & Raw Bar can watch the sun sink low over the famous Seven Mile Bridge, and can also enjoy a quick dip in the on- site pool. Photo: Sunset Grille
Sugarloaf Lodge Tiki Bar, Mile Marker 17, Sugarloaf Key
Travelers on the Overseas Highway often breeze right past the Sugarloaf Lodge in their eagerness to reach Key West. Those who do pull in to this old school fishing lodge will discover a thatch-roofed waterfront bar, where happy hour stretches into an all-day affair, and nightly entertainment draws a laid-back local crowd. The drinks are stout and reasonably priced, as are the burgers and pizza. Though most of the business is local folk and lodge guests, the atmosphere is welcoming to all.
Though just a stone’s throw from the Overseas Highway, the Sugarloaf Lodge Tiki Bar is missed by most travelers. Those who do stop discover an inviting local atmosphere. Photo: Sugarloaf Lodge
The Fish Camp at Geiger Key Marina, Mile Marker 10.5, Big Coppitt Key
A GPS or a stop for directions may be needed to find this hidden gem, formerly known as the Geiger Key Smokehouse and Tiki Bar, which is tucked away in a small marina and RV park, well off the main drag. The entrance sign proclaims “on the backside of paradise,” and the quiet setting is certainly reminiscent of an earlier era. The kitchen opens early to accommodate a fishing crowd who come for hearty breakfast favorites such as fish and grits. Many will return after a day on the water to enjoy fresh seafood favorites, tall drinks and live entertainment. The Sunday afternoon barbecue is always a big draw.
Anglers often begin their day with breakfast at the Fish Camp, and tie up at the tiki bar’s dock after a day on the water to celebrate their catch. Photo: Geiger Key Marina
Hogfish Bar and Grill, Mile Marker 5, Stock Island
Another out-of-the-way find on the outskirts of Key West delivers an authentic serving of local flavors, both on the menu and with the views. A tasty local species is the signature ingredient in the bar’s most famous offering, the Killer Hogfish Sandwich. Picnic tables set under the palm-thatch roof of a large chickee hut look out over a working waterfront where shrimp boats unload fresh catches. Opt for a table by the water and you can keep the kids amused by tossing scraps and shrimp tails to resident schools of fish that swarm in anticipation of a handout.
Seafood served at Stock Island’s Hogfish Bar and Grill often come fresh from the boat, as this local landmark sits in the heart of the town’s commercial fishing district. Photo: Hogfish Bar
Sunset Tiki Bar, Mile Marker almost 0, Key West
True to its catch phrase, “where the boardwalk ends and the sunset begins,” the waterfront bar at the Galleon Resort delivers unobstructed westward sight lines from a prime overwater location. Purists might suggest that the bar’s tin roof precludes tiki status, as there is no palm thatching in sight. But any such quibbles are soon overshadowed by expansive water views and a tempting collection of signature libations. In recognition of Key West’s party town atmosphere, the Sunset Tiki offers not only an evening happy hour, but also two-for-one specials on Bloody Marys from ten till noon.
The Sunset Tiki Bar perches on the western tip of Key West. As the name promises, the over-water sunsets are spectacular, but patrons also come for morning-after libations. Photo: Sunset Tiki Bar
