Key West Weekend Guide

Paradise is located just off the coast of mainland Florida -- and it's called Key West.
By: Erica Walsh

Paradise is located just off the coast of mainland Florida -- and it's called Key West. As Jimmy Buffet crooned, Key West is the original changer of latitudes and attitudes, and one weekend here proves he knew exactly what he was talking about.

KEY WEST, FLORIDA USA - JUNE 26, 2014: A typical Key West street in the historical district with neighborhood restaurants and retail stores.

KEY WEST, FLORIDA USA - JUNE 26, 2014: A typical Key West street in the historical district with neighborhood restaurants and retail stores.

Photo by: Raul Rodriguez

Raul Rodriguez

 Where to Stay

A boutique hotel with 17 suites spread out over an acre of tropical gardens, The Garden Hotel is that rare, centrally located oasis. Once a private residence, The Garden Hotel is on Angela Street near bustling Duval Street. In the center of the courtyard, guests are free to lounge in the pool and order cocktails from the tiki bar. The suites feature hardwood floors, brass and iron beds, and marble baths stocked with Aveda products.

Located in the heart of Key West's Old Town, The Mermaid and the Alligator is a 1904 Victorian home turned bed and breakfast. While each room features a different decorative theme, they all exude casual elegance and impeccable taste. Guests can mingle at the Outdoor Pavilion where complimentary breakfast is served poolside each morning (make sure to try the home-baked muffins). After a day of exploring vibrant Key West, return to the Mermaid and the Alligator for a complimentary glass of wine in the beautiful garden.

The Wicker Guesthouse is located near Duval Street's art galleries, bars, boutiques and restaurants, but its grounds offer the solace of a relaxing island vacation. The property's 6 guesthouses span the length of an entire city block and surround a centrally located pool and garden. Many of their rooms have private balconies or porches overlooking or bordering one of the city's largest landscaped gardens. Family-friendly and reasonably priced, this B&B has also been voted one of Key West's best in the local People's Choice Awards.

 Where to Eat

For some authentic Cuban, head to El Siboney in Old Town. Located just off Duval at the intersection of Catherine and Margaret Streets, its clientele consists primarily of locals and those in the know. For lunch, order the Cuban mix sandwich and remember, if you want to feast on the mouthwatering Paella Valenciana, call one hour ahead to place your order.


At 915, diners feast on global tapas and an extensive wine list. Located in a magnificently restored Victorian house, you can't beat the atmosphere of 915 for relaxed Key West dinner. A fusion of Mediterranean and New American, their signature dish is the Tuna Dome featuring fresh Dungeness crab and finely diced Granny Smith apples in a lemon miso dressing wrapped with ahi tuna.

For fresh seafood and cold drinks, Half Shell Raw Bar is the best choice. Bringing to mind Hemingway's Key West, the seafood is here simple, traditional and tasty; garlic oysters, steamed clams, stone crab claws and jumbo shrimp are found daily on the menu.

 What to See & Do

This state park is one of Florida's most beautiful, with wide stretches of sugary sand and tranquil waters. Visitors can rent snorkel gear or a 2-person glass-bottomed kayak from the concession area. We highly recommend a bike ride through this scenic protected reserve. A single bike path winds beside the Key West shipping channel, around the fort, through a rocky secluded beach and countless picnic spots. Those with a thirst for knowledge can take a guided tour of Fort Zachary Taylor.

To see Key West as rum runners and pirates did, book a tour with Danger Charters. The full-day sail includes snorkeling through a live reef, navigating mangroves in kayaks, and food and drink on a private island. Wine lovers will also love the sunset Wind and Wine tour featuring 8 different wines from around the world.

Pay homage to one of America's most honored and beloved authors. The Hemingway House and Museum, located on Whitehead Street, is where Hemingway lived and wrote for more than 10 years. Guests are welcome to tour the house in addition to the lush grounds and gardens that inspired the Nobel Prize winner.

 After Dark

After visiting Hemingway's home, enjoy a cold one at Captain Tony's, rumored to be one of his favorite haunts. The smoky joint is full of regulars with "back-in-the-day" and "remember-when" stories. There's a friendly, yet heated, rivalry between Captain Tony's and Sloppy Joe's as to which bar was Hemingway's home away from home. However, Sloppy Joe's can't compete with Captain Tony's immortal mentioning in Jimmy Buffet's "Last Mango in Paradise."

On the other side of the Hemingway debate, is Sloppy Joe's. The bar opens at 9:00 a.m. when mimosas and Bloody Marys are served with breakfast, making it a great place to start your day in Key West in addition to favored after-dark spot. Live entertainment is served with lunch and these good vibes continue through the late afternoon and long past sunset.

Travel Channel Insider's Tip:

Unless you're taking part in the good-spirited debauchery of Fantasy Fest, avoid Key West during late October and early November when the influx of villains, vixens and vampires cause hotel prices to skyrocket.

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