It’s almost here! The weekend that Nashville moves to Key West! April 28 – May 2, The Key West Songwriters Festival will return to Key West for its 15th annual event. Every year, it gets bigger and better. For those in the know, this unassuming festival has become one of Key West’s signature events, with the ranks of dedicated followers vying for the best rooms in town far in advance.
This year’s festival features over 100 songwriters performing their own material at venues all over Old Town, many outdoors and most free of charge. Live music and salt air is a naturally intoxicating combination, but when it’s infused with the exuberance of the songwriters themselves, sharing their creations as they were conceived — straight from the heart — Key West takes on an energy that’s hard to describe. These are the lyrics you hear on the radio, intimately presented with all the passion that inspired them. Sounds sexy, doesn’t it? It is.
Come join us for a long, mellow weekend of sun, song, tropical breezes, and free-flowing libations. The Tropical Inn is sold out except for one room. Be the lucky one to nab it.
Just like Key West, there is “something for everyone”, from funky coconut bowling to fine wine tastings designed to curl the pinkie finger of the most discriminating connoisseur.
The Southernmost Elves have been hard at work, cooking up a festive holiday season to banish the ghosts of all Christmases Past!
If you were lucky enough to be spending the Thanksgiving holidays in Key West, you perhaps joined the festivities to kick off the 2009 holiday season with the lighting of the Key West “Harbor Walk of Lights” at what we locals call “The Bight” and may appear on your map as “Historic Seaport”. The switch was flipped on thousands of holiday lights lining the Historic Seaport Harbor Walk, which runs for four blocks along the waterfront where Green, William, Margaret, and Grinnell Streets meet the Gulf of Mexico. The lights will sparkle on the water every night through New Years night.
Shortly after sunset, the Harbor Walk of Lights will become complete with the lighting of four Southernmost Christmas Trees, one located at each plaza along the Harbor Walk and one in the Key West Ferry Terminal. The smell of natural pines mingling with the tang of salty sea breeze is unique to a Caribbean Christmas.
If you’re “of a certain age”, you probably grumble about how much more meaningful Christmas used to be. You know, before TV commercials and internet ads moved the gifting frenzy to late summer. Back when everyone in town turned out to see the local high school band march down Main Street in the annual Christmas parade.
Sunday, December 6: Schooner Wharf Tree Trimming Party 5 PM
Saturday, December 12: Annual Lighted Boat Parade
Friday & Saturday, December 18 & 19: Holiday Historic Inn Tour 5:30 to 8PM
At the stroke of midnight, take your pick: the countdown lowering of the Giant Conch Shell at Sloppy Joe’s, the drop of the Pirate Wench from a 110-foot sailboat mast at Schooner Wharf, or the descent of local drag queen, Sushi, in the Red High Heel, in the 700 block of Duval Street. No matter the venue, don’t be surprised to see CNN cameras hovering! Key West has in recent years become a media darling, vying with New york’s Times Square, as Old Year meets New in the Conch Republic. 
Oh, my gosh! Only ten days left until Goombay, the kickoff weekend of our annual extravaganza, Fantasy Fest! Like Mardi Gras in New Orleans and Carnival in Rio, it’s a legendary 10-day party that no lifetime should go without experiencing! To paraphrase a local saying, “If you haven’t done Key West for Fantasy Fest, you haven’t done Key West!”
Each year, the celebration grows, bringing tens of thousands of visitors to Duval Street for the grand finale parade. Coinciding with Halloween night this year, it promises to be an even more exciting time than usual. Leading up to it is a 10-day party, with increasingly elaborate and high-energy events, building in excitement by the day. Click
On Saturday night, we enjoy the grand finale parade by treating our guests to a complimentary open bar of top-shelf libations and a gourmet buffet (no need to scramble for that mass-produced street food for dinner!), which starts early and remains available throughout the parade. Each is assured an uncrowded place on the Duval Street porches for parade viewing, from which they revel in being an integral part of the extravaganza, caught up in the pulsing, vibrant atmosphere. The upstairs veranda is especially popular, with guests throwing and receiving airborne strings of beads with each parade entry as it passes by, ”close enough to touch”. All the while, they have the convenience of their rooms near at hand and the ability to freshen their drinks and take in the festivities just above the crush of the crowd.
Thirty-seven years ago, Phil Peterson came up with the idea of a poker run to boost the motorcycle business, and the Key West tourist trade during the slow September season. What started with 46 riders has grown to become South Florida’s biggest motorcycle party weekend of the year. Today, more than 10,000 riders from all over the U.S. enjoy this event. They rumble from Miami to Key West, enjoying the sunshine, ocean breezes, and riding on the many bridges that cross over the beautiful turquoise water.
Along the way, they make five stops and draw a card at each stop. The winner is the lucky rider who draws the best hand. This year, if you draw one of the top ten hands, you get a chance to play one round of Texas Hold’em at The Guy Harvey Bar & Grill, located on Greene Street, across from Sloppy Joes. The Round will begin Saturday Night at 11:00 p.m., featuring a winner take all, a brand new Sportster 883 Custom! The City of Key West blocks off an eight-block area of Duval Street. A bike show is held in front of Rick’s/ Durty Harry’s and Sloppy Joe’s Bar on Saturday. Locals, tourists, and bikers all enjoy the sights and sounds of this mini-Mardi Gras with its carnival atmosphere, music, food, cold Budweiser, and Cola-Cola.
Everyone benefits, because over the years, these bikers have brought millions of dollars to the Key West economy and charities like the Diabetes Research Foundation, and the Key West Sunrise Rotary Club, who have collected hundreds of thousands of dollars for their worthy causes. If motorcycles ever had a bad reputation with some people, this long-time charity event has gone a long way to giving riders credibility and respect.