Key West Guide

###A Weekend in Key West

In the 19th century, a large percentage of Key West’s residents were Bahamian immigrants known as “Conchs.” Today, the term is applied to anybody who’s born on this tiny but lively island off the coast of Florida. “Freshwater Conchs” are transplants who’ve lived here seven years or more. After experiencing Key West’s sunny beaches, warm temperatures, and fun-loving atmosphere, you might be tempted to make the move yourself (you certainly wouldn’t be the first). But it’s probably best to try it out for a weekend before calling the realtor. Here’s a suggested itinerary to get you started:

Day 1

Start your visit by getting to know Key West on the fun (though slightly cheesy) Conch Tour Train, a narrated, history-filled 90-minute ride on a yellow tram car. Then hit the beach. That’s why you’re here, isn’t it? Smathers Beach is a good choice—it’s a half-mile long and there are places to rent gear for windsurfing and jet-skiing. After a day in the sun, check out the famous Sloppy Joe’s Bar, a Key West staple that opened on the day Prohibition was repealed in 1933.

Day 2

In the mid-20th century, Key West became a favorite vacation spot for literary celebrities, including playwright Tennessee Williams, poet James Merrill, and novelist Ernest Hemingway. Be sure to plan a visit to the Ernest Hemingway Home & Museum, where the author lived for several years and wrote For Whom the Bell Tolls. Descendents of Hemingway’s six-toed cats still roam the property today. Later, spend the afternoon shopping on Duval Street, then party the night away at The Green Parrot, a bar that’s been around since 1880. Expect strong drinks and wildly uneven live music.

What to Eat

Two words for you: Cuban and seafood. Key West is only about 90 miles from Cuba, so it should come as no surprise that some of the best Cuban food in the United States can be found here. Wait in line with locals for marinated pork at El Siboney, then slurp down oysters and steamed beer shrimp at Alonzo’s Oyster Bar on Front Street.

Where to Stay

  • Marquesa Key Hotel: a small, award-winning boutique hotel in the heart of Key West’s historic district; it dates back to 1884
  • Casa Marina, A Waldorf Astoria Resort: Built in the 1920s, this luxury resort is listed on the National Register of Historic Places. The hotel has its own stretch of private beach near the shops on Duval Street.
  • La Te Da Hotel: a quaint and quiet B&B on the southern end of Duval Street; this hotel offers hearty breakfasts and a peaceful garden with a small pool
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