Inside Key West Music Festivals

Key West boasts a live music scene that is sometimes said to rival those of Nashville and New Orleans. The island is home to many talented musicians, and many more visit each year. Local artists and world class acts alike can be found on stage any day of the year in a multitude of venues. From the blues to calypso, country-western, hip hop, jazz, reggae, retro, or the Keys’ own trop rock, something is always happening around town.

For the lucky folks who will be in Key West the week of May 3-11, and those who love outdoor music in tropical settings enough to make sure they will be there, the best musical happening in the Keys is set to go off. The week will kick off at 5 pm on Saturday, May 3rd, with the second annual Keystock Festival bringing rock legends The Doobie Brothers and local favorite Howard Livingston to the Truman Waterfront on the end of Southard Street in Key West.  Maybe we are showing our age here, but for those who may actually not know the Doobies, they are old school rockers with 40 years, 4 Grammys, and international hits including “China Grove,” “Black Water”, “Listen to the Music”, “Long Train Runnin”, and “What a Fool Believes” under their belts. To open the show, Howard Livingston and the Mile Marker 24 Band will break out their outboard motor-powered margarita blender and apropos tunes like “Blame It On the Margaritas” and “Livin’ On Key West Time”.

Keystock is the latest addition to an already great Key West music scene, and it is the creation of a collaborative effort by Alabama native Joe Cleghorn, owner of the Lazy Lakes RV Resort on Sugarloaf Key, musician Howard Livingston, Cleghorn’s business partner Dave McGlathery, and the staff of Lazy Lakes. For several years, Cleghorn and crew had been putting on concerts at the RV park, bringing in artists such as Jerry Jeff Walker, Mac McAnally, and Blood Sweat & Tears, along with hundreds of music lovers to enjoy sunshine, good tunes, and good times in the quaint setting of Lazy Lakes.

As the crowds grew, ideas about bigger venues and larger objectives began bubbling, including forming the non-profit Homes For Veterans, Inc., and using a music festival to raise the funds to award a paid-in-full home to a selected military veteran. With some inspiration from country music star Cowboy Troy of Big and Rich, and some Nashville connections, Keystock was born in 2013 when Livingston and the Mile Marker 24 Band opened for Three Dog Night and thousands of fans at the Truman Waterfront.  Now, what is already being called the greatest concert series in the Keys is set to bring it again, and do it for a good cause, with The Doobie Brothers in town with the kind of showmanship that has sold over 40 million albums.

The bands play on from May 7-11 when fans and performers from across the country hit town for the Key West Songwriter’s Festival. The Festival is by far the largest musical event held in Key West, with 5 days of performances and special events on tap. The biggest songwriter festival in the US, organized by BMI Nashville, America’s largest music rights organization and a major incubator of new talent and new music, the Key West festival pulls in many of America’s finest songwriters from Nashville and elsewhere. Over 150 artists will entertain fans from afternoon to evening. The event features many special shows including studio performances, sunset cruises, shows at the historic San Carlos Institute and Tropic Cinema, pool parties, a champagne brunch performance, a dinner show, and free street concerts. There is something here for every live music fan, and it is a chance to meet the artists behind some of your favorite songs.

If you love live music, and want to see some great bands in a tropical outdoor festival setting, the first week in May is the time to come down to Key West. Make plans now and don’t miss two great Key West Music Festivals.

Inside Five Brothers: The Old Key West Corner Store

No visit to Key West is complete without a stop at the Five Brothers corner store for a Cuban café con leche and maybe a mixto sandwich as well. This classic little neighborhood grocery occupies a vintage building at Southard and Grinnell (930 Southard St.) in the heart of town, and locals and tourists alike have been dropping in for 23 years to grab coffees, sandwiches or lunch plates, groceries and sundries, and hand-rolled Cuban seed cigars. People drop by Five Brothers to catch up on town gossip and soak up the atmosphere as their Key West neighbors chat in Spanish and grab cups of the strong, sweet coffee brewed fresh from the 24 pounds of beans the store goes through every day.

A true family operation, Five Brothers is now run by the son of one of the original namesake 5 whose pictures make up the logo for the store. Be prepared to find a line of local working people and visitors when you drop in to sample the creations of owner Heriberto Paez Jr. and his family members. These hometown folks work six days a week to turn out the delicious coffees and authentic Cuban bread sandwiches like egg and cheese, fried grouper, mixed meat, palomilla steak, and roast pork. Besides sandwiches that have earned a solid reputation with everyone from Key West police and firemen, construction and utility crews, to retired millionaires and visiting celebrities, Five Brothers puts on daily lunch plate specials with treats like beef stew, chicken fricassee, picadillo, ropa vieja, and empanadas.

Prices are reasonable and with no tables, everything is grab and go, so this is the perfect place to pick up a picnic snack and head over to Mallory Square, down to the waterfront, or into the nearby historic cemetery. I find that the Cuban mix sandwiches do live up to their reputation as some of the best around, and the Fried Grouper and BBQ Pork sandwiches are also local favorites. And because this store caters to everyone, there’s even a veggie burger that is pretty good. The food and coffee are well worth the wait if you happen to catch the line during the morning or lunch rush.

After placing your order, take a minute to browse the eclectic selection of groceries and dry goods that capture the Cuban flavor of Key West with items like votive candles, chorizo, domino sets, spices, guava paste, beans and rice, violet cologne, and wines from the screw-top to the fine. Or just stand in line and eavesdrop on the local gossip because this place is a real crossroads of island society. Like many others, you will probably find yourself returning multiple times because each visit is an interesting treat that goes beyond the great-tasting coffee and lunch. However, if you want to catch lunch by the pool or in your room, Five Brothers delivers from 7:00 am to 2:30 pm.

Enjoy the Cuban/Key West cross-cultural mix in the neighborhoods of Old Town with a stop at Five Brothers. Chances are you will put this little corner store on your must-visit list for every trip you make to the island.

Inside the Conch Republic Independence Celebration

“Dedicated to the fundamentally American spirit of a people unafraid to stand up to ‘government gone mad with power’ that embodied the founding of the Conch Republic in 1982. As the world’s first fifth world nation, a sovereign state of mind seeking only to bring more humor, warmth and respect to a world in sore need of all three, the Conch Republic remains the country who seceded where others failed.” Sir Peter Anderson, Secretary General of the Conch Republic

In early 1982, citing concerns over increased human and drug smuggling activity in the Florida Keys, the United States Border Patrol set up a blockade and check point on US Highway 1 at Florida City, the first major town on the Florida mainland north of the Keys. Agents began stopping and searching cars and questioning drivers, with the most immediate result being a seventeen-mile long traffic jam on the only road leading to and from the Keys.

When the alarming news of a border checkpoint located deep within United States’ territory spread across the nation and the world, the developing Keys tourist industry felt the first impacts. Reservations were canceled, hotels emptied, deliveries delayed, and commerce and tourism in Key West effectively shut down. Key West Mayor Dennis Wardlow and community leaders gathered to formulate a response to the threat to the island’s nascent tourist industry. As a first step, Mayor Wardlow, Commissioner Ed Swift, and Attorney David Paul Horan flew to Miami to file an injunction in federal court. Despite Horan’s brilliant argument, the court refused to order the Border Patrol to cease roadblock operations.

As the Key Westers left the courthouse, members of the media demanded to know what Mayor Wardlow’s next response would be. On the advice of Counselor Horan, the Mayor announced that Key West would be seceding from the Union. When the Mayor’s party returned to Key West, announcements were made and preparations for secession were begun. The city was divided and emotions ran high, because many citizens were loath to see the American flag struck in favor of the new Conch Republic banner. Others were afraid of Central Government reaction as blue-suited Federal Agents began to pour into town.

Fears of mass arrest and martial law were very real when Mayor Wardlow and several staunch Keys loyalists assembled on the back of a flatbed truck parked in front of the Old Customs building in Clinton square and delivered a Proclamation of Secession on April 23, 1982. Following the Proclamation, the new Prime Minister and other members of the new government symbolically attacked the US by breaking a loaf of stale Cuban bread over the head of a US Navy sailor.

After a one-minute rebellion, Prime Minister Wardlow surrendered to the Admiral in charge of the Key West Naval Station, and immediately demanded billions in foreign aid and war relief funding from the United States Government. Although no official response to the secession was ever forthcoming from the central government in Washington DC, in terms of aid money or otherwise, proud citizens of the Conch Republic continue to obtain passports and government information from the official Conch Republic web portal.

More importantly, the week-long Conch Republic Independence Celebration held each year from April 18-27 is one of the best parties in the Keys! The 2014 extravaganza begins at High Noon on Friday, April 18th with the raising of the colors at Fort Taylor, followed by a 7:00 pm kick-off party at the Schooner Wharf Bar. The celebration continues with special events and parties throughout the week, leading up to the Conch Republic Naval Parade & Great Battle for the Conch Republic in Key West Harbor at 7:00 pm on Friday, April 25th, and a final weekend of fun highlighted by The Conch Crawl – The World’s Longest Bar Stroll from the Atlantic to the Gulf, followed at 7:00 pm by the Pirate’s Ball & Pig Roast at the Schooner Wharf Bar. The Independence Celebration is a wonderful time to come on down and take part in the Key West state of mind.


Inside Key West Spring Break

Depending on your personal perspective and proclivities, this post may be taken as either an invitation or a warning, so read and heed or disregard at your own risk. For better or worse, the Spring Break season opens in Key West (and Florida in general) in early March. Although Spring Break is a nation-wide phenomenon, some useful Florida-specific kickoff dates include March 3 for the University of Florida, the University of Central Florida, Florida Memorial University, Florida Southern College, and Florida Gulf Coast University. Florida State University, the University of Miami, and the University of South Florida all let out on March 10, while Florida Keys Community College goes on break March 24.

There it is – a solid month of hyped-up college students hitting the island looking for sun, sand, sex, and altered states of consciousness, in no particular order. Once considered too isolated to compete with traditional northern Florida Spring Break sites like Daytona Beach, Fort Lauderdale, and Fort Meyers, Key West has drawn today’s more travel-ready Spring Breakers for a number of years already. It doesn’t hurt that Key West knows how to party no matter what the season, prompting some to observe that “It’s always Spring Break in Key West.” Fortunately (or unfortunately?) the period between March and May is the best time to visit Key West. Winter crowds thin out, hotel rates go down, and the weather is still very nicely set in the 70s and 80s. Skies are generally clear, and the temperature trend is upward. Whether you are a college student or not, spring is an inviting time to be in the Keys.

If you are a member of the Spring Break set, here are a few general Key West tips to help guide your planning. First of all, Key West is known for its quirky and fun-loving sensibility and tolerance for diversity, as well as for boisterous good times. It is no problem to bust loose a bit, as long as you get along with the locals. Try to pick up on the vibe and fit in rather than taking over. The place is laid back and chill is the way to play it. There will be plenty of opportunities to turn up the craziness as the night goes on, and there are crowds of locals who are ready, willing, and able to party with the best of them if you find the right spots.

Next, there are a couple of beaches that are the best places for large groups of people to fit in, hang out, play games, and get in the water safely. Smathers Beach draws the majority of Breakers, and the beach party goes on until the sun goes down. Vendors on the beach can supply everything needed for a good time, from beer to lemonade, jet skis to parasails, and more. Smather’s Beach is free and located directly across from the airport and the Sheraton Suites, a Key West hotel popular with students. A mellower beach spot is Fort Zachary Taylor, a State Park and picnic grounds located in Old Town Key West. There is a small admission fee, but reentry is allowed, and the natural setting and scenic beauty of the beach make it ideal for a relaxing day in the warm sun and soothing water after a hard night out.

Something to be aware of with all Key West beaches is the fact that open containers are not allowed, and the city will issue tickets for infractions. Also, there are no nude beaches in Key West, and there are often families with children around, so it is best to keep minimally covered. Finally, the beaches close at 11 pm and they are regularly patrolled, so it is a good idea to pack up shortly after sunset and take the party to Duval Street, where you can check out a mile and a quarter of shops, boutiques, galleries and a huge selection of bars and nightclubs.

For visitors who are not in Spring Break mode, the best advice is to either reschedule your trip or go with the flow and enjoy the lively, youthful atmosphere. It is actually not that bad, or anyway not that much different than most of the other exuberant, festive occasions encountered in Key West. In fact, Spring Break on the island has actually calmed down a bit, as indicated in a Miami Herald article that noted efforts by Key West City Commissioners to bring back Spring Break Court. Canceled in recent years due to diminishing need for its services, the court had been convened annually from 1991 to 2007 in order to provide an alternative venue for dealing efficiently with minor offenses such as underage drinking, using false ID, and public urination.

Young or old, student or drop-out, gay or straight, no matter what your thing is, it is always going to be more fun to do your thing in Key West. So the best advice for Spring Break season is to come on down, get in the island groove, and join the party that only Key West can put on.

Inside the One Race Cuban-American Art Exchange

Next weekend, the Key West art community will celebrate a historic Cuban-American art exchange that will bridge a 50-year gap between Key West and it’s 90-mile distant neighboring island. Thursday through Saturday, February 20-22, eleven of Cuba’s leading contemporary artists will be in Key West to make and install original pieces at a variety of local venues in a show entitled “One Race, The Human Race / Una Raza, La Raza Humana”.

The event kicked off in Havana on January 17 when Cuba’s prestigious Museo Nacional de Bellas Artes mounted a solo exhibition of work by Cuban-American folk artist Mario Sanchez (1908-2005).  The museum offered 30 intaglio prints by Sanchez, a second-generation American who was best known for producing painted bas-relief carvings that captured his views of Key West life in the early 1900s. Sanchez’s work celebrated the relatively harmonious gender, race, and religious relations that prevailed on the island, and themes of diversity, openness, and humor personify his work.

The visiting artists will show contemporary work generated from inspirations provided by these same themes. Nearly 120 pieces will be presented in a series of unveilings and other events scheduled for 5 different Old Town Key West venues. Participating partners and organizations include the Ernest Hemingway Home & Museum, the Florida Keys Council of the Arts, the Mel Fisher Maritime Museum, and the Oldest House & Garden Museum.

The Key West portions of the event will open on Tuesday, February 18 at the Tropic Cinema with a 6:30 pm screening and discussion of Unfinished Spaces, a film about Cuba’s famous National Art Schools. The following Thursday, February 20, The Studios of Key West at 600 White Street will present the work of Manual Mendive, a world-renowned sculptor and painter born in Havana in 1944 and one of Cuba’s most acclaimed artists. Mendive will debut performance art featuring body-painted dancers at 7 pm.

Also showing at The Studios will be the work of Roberto Fabelo, Sandra Ramos, and Rocio Garcia. Fabelo was born in 1950 in Guáimaro, Camagüey, and is highly regarded as a prolific painter, sculptor, and illustrator, particularly of the works of Gabriel Garcia Marquez. Ramos (Havana, 1969) was among the first artists to expose the harsh realities of Cuban life, using paintings and drawings to address issues of racism, poverty, and mass migration. Rocio Garcia (Santa Clara, Las Villas, 1955) produces courageous and provocative cartoon-inspired work that builds stories around issues of human intimacy and sexuality.

On Friday the 21st, the Florida Keys Council of the Arts, in the Gato Building at 1100 Simonton Street, will host Rubén Alpízar and Reinerio Tamayo. Alpizar (Santiago de Cuba, 1965) is a sculptor who makes paintings and sculpture based on historical references to, and sometimes including, figures such as Hieronymous Bosch, Leonardo da Vinci, John Lennon, and Andy Warhol. Reynerio Tamayo (Niquero, 1968) is a contemporary caricaturist who uses painting and sculpture to offer pointed and comic commentary on art and politics. Tamayo is also known for work inspired by baseball, a favorite sport in both Cuba and Key West.

Also on Friday, the work of The Merger will appear at the Ernest Hemingway Home & Museum. The Merger is a collective of sculptors (Mario Gonzalez, Havana, 1969; Niels Moleiro, Havana, 1970; Alain Pino, Camagüey, 1974) who use Plexiglass, neon, stainless steel, and other materials to produce large-scale, pop-art inspired objects with a satirical edge.

On Saturday, February 22nd, the Oldest House & Garden Museum at 322 Duval will present a project by Miami-based Cuban-American artist Xavier Cortada. Cortada produces work that addresses themes of multiculturalism and the environment. For the Oldest House, Cortada will reference Cuba and Key West’s shared heritage via the native flowers which Spanish explorer Ponce de Leon would have encountered on his expedition to the region he would name “La Floridita”. Visitors may send a drawing or message to a child in Cuba, and take home packets of native seeds to create flower gardens dedicated to them.

Saturday will also bring the conclusion of this cultural celebration with the 6 pm debut of Sandra Ramos’ massive sculpture “The Bridge” at the Mel Fisher Maritime Museum. Large enough for people to walk across, the sculpture represents the Florida Straits crossing from Cuba to Key West. The debut will include multicultural dance performances incorporating the piece and symbolically reconnecting the two islands and their cultures.

Inside the Harry S. Truman Little White House

American history buffs and anyone interested in the lives of US presidents or tales of old Key West will want to spend an afternoon visiting the Harry S. Truman Little White House at 111 Front Street in Key West. Originally constructed in 1890 on the island’s western shoreline, the building was the first officer’s quarters on the Key West Naval Station. As the years went by, the building hosted many interesting visitors and important events. Now, it has been restored to appear as it was in 1949 when President Harry S. Truman was using it as an escape from the pressures of Washington DC, much as US presidents now use the Camp David retreat.

The house was sited directly on the waterfront when it was built, but subsequent creation of more land by filling to the seaward, and construction of more buildings on the seaward side resulted in the building’s setting as it appears today. It began life as a wooden duplex that housed two dwelling spaces: Quarters A for the Naval base commandant and Quarters B for the paymaster. In 1911, the building was converted into a single-family dwelling dedicated solely as housing for the commandant, and fill was added to extend the land in front of the house.

William Howard Taft became the first president to visit the house when he arrived in Key West in 1912 via Henry Flagler’s Overseas Railroad en route to inspecting ongoing construction at the Panama Canal. A few years later, during World War 1, Thomas Edison came down to Key West to give his service to the war effort, and lived in the house for six months while completing 41 new weapons. The house continued to serve as US Command Headquarters through World War II.

After the close of World War Two, in November of 1946, President Harry S Truman had spent 19 months in office, all of it during wartime, and was physically exhausted. Ordered by presidential doctor Wallace Graham to take a rest in a warm place, Truman immediately headed for Key West, arriving on November 17th. After resting for a week, he left on the 23rd, promising to return whenever he needed to rest. It was not long before he did return, from March 12th to the 19th in the spring of 1947. This was the beginning of a pattern that lead to 9 more visits to the island, always around November-December and March-April.

When technological advances made it possible for the President to communicate with multiple world or political leaders at one time, or summon staff from Washington in a matter of only 3 hours by air, Truman recognized that wherever the President was, the White House was. Cabinet members and foreign officials were regular visitors for fishing trips and poker games during Truman’s visits. President Truman also conducted many important items of presidential business in Key West, and documents issued from the Little White House bore the letterhead of The White House, US Naval Station, Key West, Florida. In the end, Truman visited Key West 11 times while in office and spent 175 days of his presidency in the house.

Later presidents including Dwight D. Eisenhower, John F. Kennedy, Jimmy Carter, and Bill Clinton also made use of the Little White House, and the house stayed in service as the Naval Station commandant’s quarters until the submarine base closed in March of 1974 when the Navy made the transition from diesel to nuclear submarines. The Little White House was added to the National Register of Historic Places on February 12 of 1974, and today, the building is a small museum and tourist destination filled with original furnishings and presidential memorabilia from the Truman era. The Little White House is Florida’s only presidential site, and after undergoing a $1 million dollar restoration completed in 2009 for the celebration of Truman’s 125th birthday, it is definitely one Key West’s must-see museums.


Inside Key West Aquarium

Key West is home to one of Florida’s oldest aquariums, the Key West Aquarium. The only public aquarium in Key West, it was built between 1932 and 1934 during the Great Depression. The original Key West Aquarium project was the vision of Dr. Robert O. Van Deusen, a marine biologist and director of Philadelphia’s Fairmount Park Aquarium. When the federal government took over the city’s charter during those hard economic times, Dr. Van Deusen was one of the promoters who helped convince the government of the idea that the island would make a good tourist destination. The Works Progress Administration undertook the building of the aquarium, along with many of the island’s other historic tourist attractions. These projects provided many much-needed jobs to Key West locals.

The Key West Aquarium was the first aquarium to use an open-air design that allowed natural sunlight into the concrete marine display pools. It was also one of the largest aquariums of its time. The project was completed in two years, and the aquarium opened to the public on February 18, 1935, with admission set at 15 cents for adults and 5 cents for children. It was hoped that the aquarium would draw thousands of visitors to Key West.

Unfortunately, only seven months after the opening, on Labor Day of 1935, a hurricane struck the middle keys and destroyed the Overseas Railroad. The railroad was the only way to reach Key West other than by boat, and with the tourist flow cut-off, there was no hope of success for the Key West Attraction. The aquarium was shut down, and on May 8, 1943 the US Government leased it to the Navy, Marine Corps, and Coast Guard for use as an indoor rifle range. For this purpose, all of the displays were torn down or filled in to make a level surface area. Three years later, in June of 1946, the government returned the aquarium to the city of Key West. Restored and reopened, it became one of the city’s most popular tourist attractions.

Now, as the oldest attraction on the island, the Key West Aquarium retains the small, intimate feel of a historic building, but offers a wide range of interesting displays. A roof has been added to cut down on algae growth in the tanks, and modern technology has replaced sunlight for providing illumination to the exhibits. A 50,000-gallon tank houses a variety of tropical fish and game fish, and the Atlantic Shores exhibit presents a view of a near-shore mangrove environment. Visitors can see barracuda, grouper, moray eels, parrotfish, tarpon, tropical fish, and much more. A touch tank allows children to interact with harmless creatures of the shallow waters and tide pools, and daily tours that highlight dramatic feedings of barracudas, sea turtles, sharks, and stingrays are an exciting attraction for all ages.

The Key West Aquarium, while modest in size, is truly one of the island’s treasures. It also plays an important role in the rescue of injured and stranded sea turtles, working with the Turtle Hospital and the state agencies, universities and marine parks that make up the Florida Sea Turtle Stranding Network.  The aquarium is an important resource in the efforts to protect the endangered marine ecosystems of the Florida Keys. It is interesting in many ways, and a visit is a very worthwhile and enjoyable experience for people of all ages.

Inside Key West Womenfest

Now is the time to start making plans to attend the annual Key West Womenfest, the island’s biggest gathering for lesbians and their friends. Scheduled for September 4th through the 7th, 2014, this cornucopia of celebration pulls people in from all over the world for 3 days and nights of female-only playing, partying, and outdoor adventures. Now in its 28th year, this festival offers a plethora of activities guaranteed to appeal to a broad range of interests.

The active and adventurous will go in for the wild clothing-optional pool parties, hot nightlife and dance club scene, sexy & competitive bull riding, and many types of female-only water sports excursions.  Or chill out and indulge in some culture with plentiful offerings of art, comedy, live music, poetry, and theatre, often set in venues that take advantage of the tropical setting and fine Key West fall weather.

The 2013 Womenfest, while a bit less crowded than past festivals, was special because world-record setting distance swimmer and out lesbian Diana Nyad walked ashore September 3rd on a Key West beach having completed the first swim between the U.S. and Cuba without a shark cage. Nyad, age 64, battled powerful currents, sharks, and box jellyfish to finally best the difficult 110-mile crossing that had already defeated her 4 times previously. While Nyad was unable to stay in town for Womefest 2013 because of other commitments, her accomplishment was the talk of the town, and added an additional touch of excitement to the festival. The 2014 festival is sure to have its special moments as well, and is a great opportunity to simply enjoy being part of the pride and friendship that comes from thousands of gay women enjoying life and love, hanging out and about in Key West.

Womenfest 2014 will offer the same rich mix of events and activities as in years past, beginning when you first check in to the festival headquarters at the Gay Key West Visitor Center to pick up guides, maps, tickets, t-shirts, One Human Family Stickers, and other assorted swag. The party really kicks off with a no-cover launch party on September 3rd at Aqua night club, leading into an evening of shows and partying all night long with friends old and new.

Daily activities run the gamut from golf to sea kayaking, parades, photoshoots, watersports, yoga, and jet ski tours. Many of the local Key West tour operators put on special trips for womenfest attendees, allowing you to enjoy the experience of snorkeling, parasailing, sunning, swimming, snacking, and sunset cocktail cruising all in the comfortable company of like-minded companions. When you get off the water, prepare for evenings of happy hour specials, stand-up comedy performances, themed dance parties, all-girl bands, burlesque shows, and bikini competitions. And don’t forget to set an afternoon aside for the Gay Key West Trolley Tour to get an inside look at the history, architecture, and rich gay culture of the island.

If you want to experience the tolerance and diversity that Key West is famous for, a visit to Womenfest 2014 is the perfect way to do it. Plan now to visit Key West next fall and party with pride in a tropical paradise.

Inside Clothing-Optional Key West

Perhaps due to its history as a free-wheeling port city on a remote island, Key West has long been a place where tolerant, liberal attitudes set the tone for eccentric, creative lifestyle choices. The island has always hosted multiple racial and cultural groups, a mix of seafarers and landlubbers, travelers and permanent residents, fishermen and factory owners, businesspeople, pirates, smugglers, and rumrunners. In the modern era, Key West has been a magnet for artists, iconoclasts, hippies, gays, and lesbians since at least the late 1960’s.

As an accessory to or upshot of all of this, in Key West, naturist and clothing-optional facilities and activities are a big part of the urban scene. On many days in town, especially around the big festival dates like Fantasy Fest, it will be hard to move through the crowds without being “exposed” to various degrees and types of nudity. However, in general, things are not quite as “free” in Key West as one might think. There are, for example, no nude beaches on the island, and even topless sunbathing in the public realm is confined to a small section of Higgs Beach. The best bet for the naturist visiting Key West is to take advantage of the many private venues that support clothing-optional playing and partying.

Many of the most popular clothing-optional hotels in Key West are near Duval Street. If you are planning to visit one, it is mandatory to look into the details of the accommodation before booking. Some properties cater exclusively to males, others to females; some are primarily gay-oriented while others draw a mixed crowd; there are places that offer clothing-optional policies throughout the property, while others permit nudity around the pool area, or have a designated sundeck for clothes-free tanning. Here are some of the better-known of the Key West naturist hotels.

The Island House on Fleming Street is one of Key West’s most well-known all-male gay guest houses. The Island House is luxury-style clothing optional, has a fun pool area, a mist-cooled sun deck, and many other amenities. The staff is very attentive and the happy hour drinks are free. The location is good for accessing the Key West party scene, but many guests spend their entire visit on the Island House grounds.

Olivia by Duval on Olivia Street offers a good location within walking or biking distance of Mallory Square, Duval Street, and Zachary Taylor State Beach. It is a pet-friendly guest house, with some full-kitchen suites available. The outdoor swimming pool and sun deck are adults-only and clothing-optional.

The Pilot House is a restored Victorian-era mansion right in the middle of Old Town Key West on Simonton Street. Fourteen suites offer full-kitchen facilities, and clothing-optional policies are liberal around the lush and private tropical gardens, outdoor pool, and hot tub. Duval Street and several public beaches are within walking distance.

The La-Te-Da on Duval Street is a bar, restaurant, and hotel with a 30-year history as one of the most vibrant and iconic in Key West, and a clothing-optional sun deck. The resort features luxury surroundings and a choice of luxury, deluxe, or standard rooms. Amenities include an outdoor swimming pool, two bars and complimentary breakfast. South beach is within walking distance.

Beyond this brief sample list of Key West clothing-optional resorts, there are other options for the more adventurous naturist. The Garden of Eden is a Key West roof-top night club bar on the third floor of the Bull and Whistle Bar on Duval Street. When the music and dancing begin after dark, those who choose may enjoy the natural experience of the night air against exposed skin. There are also options for, shall we call it, “bare-boat” sailing. Enjoy sunbathing at sea, hedonistic cocktail cruises, and even swim with wild dolphins while wearing the same swimming suit that they do – skin. There are plenty of options, so come on down and expose yourself to unclothed Key West.

Inside Winter in Key West

Winter in Key West is the busy season as frozen northerners flock to the island for a tropical respite to tide them over until the spring thaw hits. With arctic blasts and record cold spells covering much of the continental US this winter, and even reaching down into Florida, there is more reason than ever to plan an escape to paradise. But good weather is not the only thing happening on the island in January. Several large-scale special events run through the latter part of January and offer Key West visitors a chance to add some special highlights to their island trip.

The 2014 Key West Food and Wine Festival runs from January 22 to the 26th, and is the event of the season for those who revel in excellent wine and delicious food. From the kickoff in the hospitality suite on the morning of the 21st, to the 20th annual Master Chef’s Classic on the afternoon of the 26th, this festival is nothing but 5 days of feasting, friends, and fun as you walk about, talk about, learn about, and enjoy great wine, amazing cuisine, and incredible vintners and chefs in the kind of party atmosphere that only Key West can put on. Wine, beer, and liquor tastings, gourmet food and wine seminars, competitions, parties, and feasts all vie for participants’ time in a packed schedule that fills each day from (not too early!) morning until late night. From barefoot beach parties to Cuban-style pig roasts, Key West shrimp boils, and Duval Street wine tasting crawls, this is a true tropical bacchanalia and is a perfect excuse to spend a week thawing out and unwinding in Key West.

Sailing fans and wannabe yachties alike can have a ball at the 27th annual Quantum Key West Regatta, in town from January 19 – 24.  Beginning with the skippers’ meeting and welcome reception on the 19th, the event features 5 days of racing with some of the most amazing yachts and crews in the world starting daily out of Key West harbor. The big 70-foot boats of the Mini-maxi class will inspire awe with their speed, power, and sheer size, while action will be fast and furious in the 52-foot class with an international fleet of 6 boats manned by some of the world’s top racing professionals.  This US SAILING-sanctioned event sponsored by high-performance sailmakers Quantum Sails includes the IRC 1, 2, and 3 classes along with the exciting J-classes, which draw some big fleets, like the 62-boat flotilla in the J/70 class, and promise some spectacular racing action. The racing will be conducted offshore under permit in the Florida Keys National Marine Sanctuary, but there are plenty of options for fans who cannot be out on the racecourse. Live twitter, blog, and video coverage will follow the action, and of course just being on the scene, checking out the boats and sponsors, and mingling with the crowds will offer some great nautical fun.

If you still have time in your Key West schedule, the Stock Island Marina Village King Mackerel Tournament runs from January 24th to the 26th. A fleet of elite anglers will go out after the big King Mackerel that migrate to Key West waters each winter, with each fisherman looking for the biggest fish and the $10,000 dollar purse that goes with it. Charter a boat and join the fun on an amateur basis, or follow the action at the daily weigh-ins and dockside parties. Non-fishermen may want to set aside January 25 – 26 for a visit to the 29th Annual Key West Craft Show. This free event features more than 100 jury-selected artisans and crafters who display the fruits of their talents in historic old Key West on lower Whitehead and Caroline Streets. Expect beautiful displays of pottery, fabric, glass, wood, jewelry and other colorful handmade works to be on display from 10 a.m. to 5 p.m. daily.

From wind to wine, fine arts, fair weather, friendly folk, and fishing fun, Key West has got it going on in the depths of winter. Come on down out of the chill and be a part of it all!