Key West has always marched to the beat of its own drummer. First inhabited by the Europeans DGF-KeyWest_copyin 1521, Key West has grown over the centuries to become a place for America’s creative minds to let go and be themselves. Ernest Hemingway lived for nearly a decade in Key West, as did a number of other prominent historical figures, such as President Harry Truman. You probably won’t find such a laid-back atmosphere anywhere else in Florida. If you get the chance to come down to Key West, you’ll wonder why you didn’t visit earlier. Let me tell you about the things to see and do here in the town the locals call “The Conch Republic.”


Key West is located 129 miles southwest of Miami. The two cities are connected by U.S. Highway 1. There is also bus service that connects Key West with Miami.

Key West International Airport serves most major airports in South and Central Florida. American Eagle flies daily to and from Miami, Cape Air flies between Key West and Fort Myers, Silver Airways flies to and from Fort Lauderdale, Fort Myers and Tampa, and Southwest Airlines flies to and from Tampa and Orlando.

There is also a rapid ferry, the Key West Express, that connects Key West with Fort Myers. For more information, visit


The Island House Key West is a local institution, having been open for decades and having won slews of “best accommodations” awards from all over the world. The all-male gay resort offers so much, like clothing-optional pools and jacuzzis, a 24-hour cafe and adjoining bar, an erotic video lounge, and rooms decorated in the Ernest Hemingway style. If you want to make DGF-KeyWest_AlexanderGuestHousenew friends right away, you can’t go wrong with staying at the Island House. (1129 Fleming St., 305-294-6284)

Alexander’s Guesthouse (actually three houses) dates from 1902, and all of the beautiful restoration work has landed the buildings in the National Historic Register. Enjoy your tastefully-decorated guest room until it’s time to sun yourself at the pool. Make friends during the complimentary happy hour and then pick one of the three available sun decks on which you’ll lay out and relax. (The upper two are clothing optional!) (1118 Fleming St., 305-294-9919)

The New Orleans House describes itself as being the only all-male guesthouse right on Duval Street. There are a dozen rooms available, each with a different comfort level and price tag, appealing to everyone. There is an area for nude sunbathing, as well as a pool and jacuzzi that are clothing-optional and open to men only. Most of the guest rooms are above a gay club, and there are two restaurants on-site, so you don’t have to venture far to meet most of your vacation needs! (724 Duval St., 305-293-9800)


The Key West gay nightlife scene isn’t as big as other cities in the state, but it is very vibrant. Big DGF-KeyWest_KeyWestPrideevents on the Key West social calendar each year include Key West Pride in June (; Tropical Heat, a sexy event for gay men held in August (; and Fantasy Fest, a ten-day event celebrating Halloween and fun costumes (or the lack thereof!), held in October (

Aqua Nightclub (711 Duval St.) is a fun, chic bar and nightclub combo, featuring drag shows, karaoke and live entertainment. Bourbon Street Pub (724 Duval St.) and 801 Bourbon (801 Duval St.) bring the feeling of New Orleans’ French Quarter to Key West, with high-energy parties entertaining crowds until the very wee hours of the morning. Saloon One (801 Duval St.) is just behind 801 Bourbon and caters to the leather crowd. La Te Da (1125 Duval St.) is a complex that consists of three bars, a cabaret room and a restaurant. Garden of Eden (224 Duval St.) is for the more adventurous among us — it’s Key West’s only clothing-optional bar. Bobby’s Monkey Bar (900 Simonton St.) is one of the city’s best-kept secrets; it’s a bar very popular with the local gay community and it’s a great place for tourists to meet new friends.


Duval Street is where so much of the action happens here in Key West. It runs a mile in length DGF-KeyWest_SouthernBuoyfrom the Gulf to the Atlantic. At the southern end, there is the Southernmost Point buoy, which famously informs tourists and locals alike that they are standing on the southernmost point in the continental United States, and that Cuba is only 90 miles away. At the northern end, there’s Mallory Square, which plays host to the daily “Sunset Celebration,” where tourists come to watch street performers and hear live music as the sun sets on the Gulf.

Also near Mallory Square are the Key West Shipwreck Museum and the Old Post Office and DGF-KeyWest_ShipwreckMuseumCustoms House. The shipwreck museum uses real-life actors, film footage and artifacts to tell the story of 400 years of marine history through shipwreck rescues that have been conducted off the coast of Key West over the years. The Old Post Office and Customs House now serves as the city’s museum of art and history, and there are a number of exhibits featuring works from local artists, and a particularly well-researched exhibit on the life of Ernest Hemingway.

Speaking of Hemingway, the Ernest Hemingway House on Whitehead Street is now a DGF-KeyWest_HemmingwayHousemuseum, focusing on his life in the Keys and his literary works. There are a number of six and seven-toed cats who live on the property and they are famous in their own right. The Key West Lighthouse was a working lighthouse between the years of 1848 and 1969; now people can walk to the top of the lighthouse themselves and see how the lighthouse keepers lived.

The Harry S. Truman Little White House was a place for then-President Harry S. Truman to rest and keep up his health during a trying time in his presidency. Since then, a number of presidents have used the house for their own vacations, and it opened as a museum in 1991. Fort Zachary Taylor State Park is the southernmost state park in the lower 48 states, and was once a fort that defended the city from the British and Union Naval forces during the Civil War. Now it is open for exploration, and the landmark tells the story of Key West during the war between the states.

For more information on Key West, visit the Keys’ tourism website at For more information on Gay Key West, visit