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Postcards from the Keys

Our mission was as shallow as the water in Biscayne Bay. After the winter of 2014 — arguably the harshest in memory, with higher-than-average snowfall and lower-than-average temperatures — we were impatient for summer. A posse of friends since college, on the hunt for sun and fun, we set our sights on a springtime, island-hopping tour of the iconic watering holes of the Florida Keys.

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Miami, our jumping-off point, proved a quick and convenient flight from most anywhere. “People used to chartering in the Caribbean are surprised at how much easier it is to come here,” said Travis Lund, base manager for The Moorings, which maintains a range of power- and sailboats for charter at the stylish Miami Beach Marina. Ours was a Moorings 393 PC with twin 110-hp Yanmar diesels, air conditioning and a fully outfitted galley. “The weather here is good year-round. We have the third-largest barrier reef in the world, and our fishing and snorkeling are excellent. It’s a great destination, with the added advantage of all the services of a metropolitan area — data and cell coverage, fuel and services, top-notch restaurants. We have it all.”

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That includes bars. Ever since tourists discovered the Keys in the 1950s, a cornucopia of taverns and night spots has spilled across these slivers of sand. And we planned to shimmy and shake the chill away at as many tiki bars as possible.

Holiday Isle was our first bar stop. Its original Tiki Bar is where the rum runner drink was invented 40 years ago, according to our bartender. She offered us a tray of adult slushies, as colorful as the Solo cups they were served in. From there we moved to the newer Rum Runner Bar on the other side of the resort. If the Swiss Family Robinson were to build a tavern, this is what it would look like. We added our graffiti to the scrawl along the walls and pillars and watched the setting sun paint the sky.

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Next up was colorful Wahoo’s Bar and Grill over the bridge. It appeared to be an anglers’ hangout, so we paced ourselves with delicious seafood hors d’oeuvres. Then we taxied to Lorelei’s Cabana Bar a few miles south. Local talent performs nightly, so we danced barefoot in the sand beneath branches strung with party lights before calling it a day.

The Florida Keys are part of a coral archipelago that sweeps 130 nautical miles from Miami to Key West. We knew we couldn’t cover the entire length during our charter, but we pilgrims were determined to get to Eric Stone’s Dockside Tropical Café in Marathon. Stone is a singer, songwriter and seadog, and we wanted to catch a live performance.

However, we awoke to a small craft advisory the next morning. Our concern wasn’t the 30-nautical-mile passage to Marathon — it was the return trip. Winds were expected to build the following day — heaven forbid we should be stranded at a bar.

By midday we were on the road in our Thrifty rental car, with the Margaritaville satellite radio station cranked up and Bob and his bevy of wahines singing along. Our first stop was at Bass Pro Shops, where a replica of Ernest Hemingway’s fishing boat Pilar is the focal point of the 25,000-square-foot store. We clambered aboard Pilar and sat in the author’s chair, as if we could soak up his talent and aura.


We were hungry, so our next stop was the Island Fish Company, where Eve declared her cocktail “the best pina colada ever.” The atmosphere was casual, but a helicopter pad on the grounds tipped us off that it’s a hot spot for jet-setters. It also offers 35 sizable slips for visiting boaters.

“Authentic Florida Keys” is what Stone and his wife, Kim, were aiming for when they bought and refurbished the Dockside Tropical Café, an open-air bar and restaurant between Sombrero Key and Vaca Key. The place has an everybody-knows-your-name kind of friendliness. As if on cue, a patron known as “Alabama Tim” bought us a round.

A steady night wind heralded a choppy morning. Even so, we opted to stick our nose into the Atlantic and attempt a dip at John Pennekamp Coral Reef State Park. The Hen and Chickens sanctuary is just three miles offshore and reported to be an excellent snorkeling spot. Despite the large seas, the intrepid crew jumped in. We snorkeled for half an hour, awed by the variety of fish, corals and fans in the crystalline aquarium below.

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Backtracking toward Miami, I was much more comfortable using the Raymarine HybridTouch plotter, which made navigation a breeze. Our destination was 23 nautical miles away: Gilbert’s Marina, with the mother of all tiki bars in a massive high-beamed thatched-roof building. Our side-tie there, on narrow Jewfish Creek, was a great spot for both people- and boat-watching.

The city of Miami sparkled and grew as we neared. We had traveled about 120 nautical miles in five days and could have used another five. But we were pleased with our pilgrimage, our comfortable boat, the fun destinations and our new friends. And we still had one night left. South Beach was jumpin’, so we took off in search of just one more tiki bar.

February 2015 issue