From swimming with dolphins to marking time in Mallory Square, enjoy the best of the Florida Keys with this four-day itinerary.
Credit: Douglas Merriam

April 2005

Enveloped by the Atlantic Ocean and the Gulf of Mexico, the800-plus islands of the Florida Keys were once havens for piratesand conquistadores. Today, visitors from all over the world come insearch of sun, sea, and fresh seafood, mixed with a satisfying doseof history and culture.

From its beginning at Key Largo to Key West at the southernmostpoint, U.S. Highway 1 (aka Overseas Highway) and 42 vaulted bridgestether the inhabited islands. Addresses here refer to small greenmile markers and usually indicate whether you should look to theocean- or bayside of the main artery for your off-roaddestination.

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

Day One: The Upper Keys

Home to pods of bottle-nosed dolphins, the Florida Keys supportfive dolphin research and education facilities. Start your day inthe waters of Key Largo swimming with these graceful, curiousmammals at Dolphins Plus (31 Corinne Place; 866-860-7946). Wearing maskand snorkel, you�ll swim with them as if you wereone of the pod, allowing the dolphins to set the pace as youobserve 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 byfishermen directly to the back door. Try the locals' favorite, thefish matecumbe, a sizzling plate of yellowtail snapper or groupertopped with tomatoes, shallots, capers, fresh basil, olive oil, andlemon juice.

Back on the Overseas Highway, look bayside for the heron statuethat 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 whicha menagerie of injured and orphaned shorebirds recovers andresides.

Satisfy shopping urges at Islamorada's Rain Barrel Village of Artists and Craftspeople (MM 86.7Bayside; 305-852-3084), a maze of galleries, studios, and shops,where working artists make clay and raku pottery, create glassobjects, and paint on canvas, cloth, or stone. Even if you're notan angler, stop at World Wide Sportsman (MM 81.5 Bayside; 305-664-4615). Areplica of Hemingway's sport fishing boat Pilár and a 6,000-gallon saltwater aquarium dominatethe center of this massive fishing emporium.

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

Where to stay: Spend the night at Casa Morada (MM 82.2Bayside, Islamorada; 888-881-3030, A privatesecluded, yet accessible, island is just offshore. (In-seasonrates―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 toppedwith 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, awooden boardwalk meanders a half-mile through the mangroves atwater's edge. Stop at one of the thatched tiki huts, and enjoy yourbreakfast 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 toLittle Arsnicker Key. April is the last month to see hundreds ofwhite pelicans, whose black-tipped wings span 10 feet, that winterhere 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 35thStreet, Marathon; 305-743-4353). Then spend the afternoon inhistoric Pigeon Key (MM 47 Oceanside, Mara-thon; 305-743-5999), whereearly-1900s cottages once inhabited by railroad workers have beenrestored as mini museums. Pigeon Key was a construction andmaintenance site for Henry Flagler's Florida East Coast RailroadExtension from 1912 until a hurricane flooded the key in 1935.

Drive across the Seven Mile Bridge on your last stretch of roadto 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 thebanana 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,,your abode for the next couple of days. The eight guest rooms ofthis former U.S. Navy weather station will provide a sanctuary fromthe bustle of Duval Street two blocks away. A short path links theinn 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 firstorder of the day―ham, eggs, toasted Cuban bread, a side ofplantains, and, of course, café Cubano. Cuban exiles have beena major influence on the culture and cuisine of the islands sincethey 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 greatesttreasures of the Florida Keys―the only living coral reef inthe continental United States. You don't need previous divingexperience or certification for Snuba. A comfortable harnesstethered to the raft at the surface via a long air hose allows youto breathe and glide easily among the coral formations and schoolsof tropical fish.

Back in town, walk the length of Duval Street―whichstretches from the Gulf to the Atlantic―to Louie's Backyard (700 Waddell Ave.; 305-294-1061), a popularrestaurant situated in a 19th-century, revival-style home. Sit onthe 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 ofthe "Walking and Biking Guide to Key West," compiled by Keyspreservationist Sharon Wells. Choose from 14 self-guidedtours―literary landmarks, graveyard ramble, and vernaculararchitecture―and stroll the island. Or rent a conch cruiserfrom 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 dailytradition that starts a couple of hours before sunset. Tightropewalkers, jugglers, street players, and magicians compete with thesetting sun for your attention―and your dollar bills.

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

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

Day Four: Key West

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

Kayak through the Great White Heron National Wildlife Refuge with DownwindKayak Tours (305-797-7245). You can look for aquatic wildlifethrough 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 metamorphosedinto a marina lined with shops and restaurants. Stop for lunch atthe Conch Republic Seafood Company (305-294-4403), which boaststhe largest rum bar between Cuba and Miami. Start with a mojito,and try all things conch. Fritters and chowder have been staples ofKey West cuisine since the 1700s.

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

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

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

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