The Road to Key West

From swimming with dolphins to marking time in Mallory Square, enjoy the best of the Florida Keys with this four-day itinerary.
By Victoria Shearer

April 2005

Enveloped by the Atlantic Ocean and the Gulf of Mexico, the 800-plus islands of the Florida Keys were once havens for pirates and conquistadores. Today, visitors from all over the world come in search of sun, sea, and fresh seafood, mixed with a satisfying dose of history and culture.

From its beginning at Key Largo to Key West at the southernmost point, U.S. Highway 1 (aka Overseas Highway) and 42 vaulted bridges tether the inhabited islands. Addresses here refer to small green mile markers and usually indicate whether you should look to the ocean- or bayside of the main artery for your off-road destination.

April temperatures are warm and inviting, a good time for a long weekend break. Rent a car, roll down the windows so you can taste and smell the salty air, and coast along a stretch that has drawn the likes of notables from Jimmy Buffett to Ernest Hemingway: the road to Key West.

Day One: The Upper Keys

Home to pods of bottle-nosed dolphins, the Florida Keys support five dolphin research and education facilities. Start your day in the waters of Key Largo swimming with these graceful, curious mammals at Dolphins Plus (31 Corinne Place; 866-860-7946). Wearing mask and snorkel, you�ll swim with them as if you were one of the pod, allowing the dolphins to set the pace as you observe them. Afterward, stop for lunch at The Fish House (Mile Marker 102.4 Oceanside; 305-451-4665), a campy little roadhouse featuring fresh seafood delivered by fishermen directly to the back door. Try the locals' favorite, the fish matecumbe, a sizzling plate of yellowtail snapper or grouper topped with tomatoes, shallots, capers, fresh basil, olive oil, and lemon juice.

Back on the Overseas Highway, look bayside for the heron statue that heralds the entrance to the Florida Keys Wild Bird Center (MM 93.6 Bayside, Tavernier; 305-852-4486). Walk the shady boardwalk to Florida Bay, along which a menagerie of injured and orphaned shorebirds recovers and resides.

Satisfy shopping urges at Islamorada's Rain Barrel Village of Artists and Craftspeople (MM 86.7 Bayside; 305-852-3084), a maze of galleries, studios, and shops, where working artists make clay and raku pottery, create glass objects, and paint on canvas, cloth, or stone. Even if you're not an angler, stop at World Wide Sportsman (MM 81.5 Bayside; 305-664-4615). A replica of Hemingway's sport fishing boat Pilár and a 6,000-gallon saltwater aquarium dominate the center of this massive fishing emporium.

Follow the footpath to Morada Bay Restaurant (MM 81.6 Bayside; 305-664-0604). Order the house specialty drink, M.O.B. (Man Overboard), then put your toes in the sand, drop into an Adirondack chair, and watch the sun set as you enjoy seafood tapas and live music.

Where to stay: Spend the night at Casa Morada (MM 82.2 Bayside, Islamorada; 888-881-3030, www.casamorada.com). A private secluded, yet accessible, island is just offshore. (In-season rates―from December 20 to April 30―start at $289.)

Day Two: Middle and Lower Keys

Pick up a cup of coffee and an oversized cinnamon bun topped with cream cheese at the Islamorada Restaurant and Bakery (MM 81.6 Bayside; 305-664-8363), and take a short drive down the Overseas Highway to Anne's Beach (MM 73.5, Oceanside, Islamorada). Here, a wooden boardwalk meanders a half-mile through the mangroves at water's edge. Stop at one of the thatched tiki huts, and enjoy your breakfast by the water.

Afterward, board Skimmer Charters' (MM 61 Oceanside, Duck Key; 305-743-7436) shallow-draft boat for a seven-mile run through Florida's waters to Little Arsnicker Key. April is the last month to see hundreds of white pelicans, whose black-tipped wings span 10 feet, that winter here before heading back to their northern habitats.

Once back on terra firma, order stone crabs for lunch at Keys Fisheries Market and Marina (MM 49 Bayside, end of 35th Street, Marathon; 305-743-4353). Then spend the afternoon in historic Pigeon Key (MM 47 Oceanside, Mara-thon; 305-743-5999), where early-1900s cottages once inhabited by railroad workers have been restored as mini museums. Pigeon Key was a construction and maintenance site for Henry Flagler's Florida East Coast Railroad Extension from 1912 until a hurricane flooded the key in 1935.

Drive across the Seven Mile Bridge on your last stretch of road to Key West. Stop at the colorful, Caribbean-style roadhouse Mangrove Mama's (MM 20 Bayside, Sugarloaf Key; 305-745-3030), and dine on tropical seafood bouillabaisse, sautéed hogfish, and key lime pie while sitting beneath the banana trees in the funky garden out back.

Where to stay: Check into Key West's Weatherstation Inn (57 Front St., Key West; 800-815-2707, www.weatherstationinn.com), your abode for the next couple of days. The eight guest rooms of this former U.S. Navy weather station will provide a sanctuary from the bustle of Duval Street two blocks away. A short path links the inn to the beach at Fort Zachary Taylor. (In-season rates start at $215.)

Day Three: Key West

A traditional Cuban breakfast at Jose's Cantina (800 White St.; 305-296-4366) is the first order of the day―ham, eggs, toasted Cuban bread, a side of plantains, and, of course, café Cubano. Cuban exiles have been a major influence on the culture and cuisine of the islands since they began settling here in the 1800s.

Then, with the help of a guide from SNUBA of Key West (305-292-4616), visit one of the greatest treasures of the Florida Keys―the only living coral reef in the continental United States. You don't need previous diving experience or certification for Snuba. A comfortable harness tethered to the raft at the surface via a long air hose allows you to breathe and glide easily among the coral formations and schools of tropical fish.

Back in town, walk the length of Duval Street―which stretches from the Gulf to the Atlantic―to Louie's Backyard (700 Waddell Ave.; 305-294-1061), a popular restaurant situated in a 19th-century, revival-style home. Sit on the veranda, order lunch, and drink in the view of Louie's "backyard," the sparkling ocean.

Discover Old Town this afternoon. At KW Light Gallery (534 Fleming St.), pick up a free copy of the "Walking and Biking Guide to Key West," compiled by Keys preservationist Sharon Wells. Choose from 14 self-guided tours―literary landmarks, graveyard ramble, and vernacular architecture―and stroll the island. Or rent a conch cruiser from one of the many bicycle kiosks, and pedal the paths.

Celebrate day's end at the famous Mallory Square Sunset Celebration, a 20-year-old daily tradition that starts a couple of hours before sunset. Tightrope walkers, jugglers, street players, and magicians compete with the setting sun for your attention―and your dollar bills.

Dine at Pisces (1007 Simonton St.; 305-294-7100), formerly known as Café des Artistes, where chef Andrew Berman's classic French cuisine endures. Save room for the chocolate mousse smothered with white chocolate and raspberries, a local favorite.

Burn those dessert calories with a walk to the north end of William Street for the Stargazer Cruise (Key West Historic Seaport; 305-292-1766) aboard the historic schooner Western Union. You'll learn the history and mythology of the constellations as you sail the waters off Key West.

Day Four: Key West

For an unusual breakfast, Camille's Restaurant (1202 Simonton St.; 305-296-4811) is renowned for lobster and shrimp omelets and banana-pecan pancakes the size of dinner plates. Indulge yourself, then prepare to get physical.

Kayak through the Great White Heron National Wildlife Refuge with Downwind Kayak Tours (305-797-7245). You can look for aquatic wildlife through the kayak's glass-bottom viewer. Bring your binoculars; you'll find world-class birding here, too.

Back on dry land, wander the boardwalk at Key West Historic Seaport (at the foot of Front Street). Once seedy commercial fishing docks, the Seaport has metamorphosed into a marina lined with shops and restaurants. Stop for lunch at the Conch Republic Seafood Company (305-294-4403), which boasts the largest rum bar between Cuba and Miami. Start with a mojito, and try all things conch. Fritters and chowder have been staples of Key West cuisine since the 1700s.

Now that you've changed latitude and attitude, discover Jimmy Buffett's Key West with Trails of Margaritaville (meet at Captain Tony's Saloon, 428 Greene St.; 305-292-2040). You'll visit the venues at which the songster played in the 1970s and the studio where he still records. You'll imbibe a few margaritas at the stops along the way, as well.

In the evening, dine at Mangia Mangia (900 Southard St.; 305-294-2469). The chefs here work their magic in plain view, and the pasta is homemade. Try the jumbo shrimp with rigatoni, a Mediterranean treatment topped with a lemony mix of greens, including arugula, radicchio, and endive.

For your grand finale in paradise, follow those who came before you in a Key West tradition: the Duval Crawl. The exercise is simple: Sample libations from as many Duval Street nightspots as you care to. Then crawl into bed, relaxed and ready to plan your next Keys getaway.

Victoria Shearer is a writer in Duck Key, Florida. She is the author of the Insider's Guide to Key West.