The month of September welcomes one of the most fantastic, largest festivals of its kind in Southwest Florida. Island Hopper Songwriter Fest is a 10 day event with performances (mostly free) scheduled on Sanibel Island, Captiva Island, Fort Myers and Fort Myers Beach.
Previously known as....
Key West Suds Run
Key West celebrates this annual St. Patrick's Day Event every March 17th.
10th Annual Key West BrewFest
August 29 - September 2, 2020
The last 8 Key West BrewFest events have been so much fun and an amazing success for the local charities, the committee is teaming up to bring it to you again! Between 150 and 200 beers and micro-brews are on tap at this "tasty" annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic.
The festival is to feature nearly 200 beers and ales including unique microbrews. They are showcased at beer dinners, brunches, happy hours, pool parties, late-night after parties, and of course, the oceanfront Signature Tasting Event.
Located on Key West’s famous Duval Street, Irish Kevin’s is one of the most popular bars in all of Key West.
Parrotheads of the world unite, it’s time to go Back to the Island!! The Westin Resort and Marina Key West has become the Margaritaville Key West Resort and Marina. This 170+ room resort is the epitome of Key West and now with Jimmy Buffett lending his name to it, only backs up that claim.
This AAA Four Diamond waterfront resort is just steps from Mallory Square, home of the nightly Sunset Celebration. Hundreds come out every night to watch the sun slowly set into to the emerald waters off Key West. Street vendors and performers also gather to hawk their wares and put on a show that only Key West could pull together (you might even see Spiderman or Darth Vader). The resort is also just a block from the famous Duval Street. Lined with some of the best restaurants, waterholes, shopping and art galleries that you’ll find anywhere. The marina is also home to one of three cruise ports on the island, welcoming people from around the world.
For the gourmet in all of us, the resort is home to three fantastic restaurants. Bistro 245 is a casual, indoor dining experience, with gorgeous views of Key West’s One Particular Harbor. Castaways is the classic pool side bar, for all you Beautiful Swimmers, which features a minimalists, no nonsense menu. From appetizers, salads to burgers and other sandwiches, not to mention a cocktails to die for. Lastly, is the Sunset Deck. As the name proclaims, you will have a panoramic view of the harbor and of the Key West sunsets, as you’re sipping on that fresh Boat Drink.
If you want to try something a bit different and get some of that Island Fever, then hop on the island ferry that will take you to Sunset Key, just across the harbor. This private island has all the amenities that you could desire.
So, on your next escape, grab your Brown Eyed Girl or Lost Boy, not forgetting your shaker of salt, while making another Trip Around the Sun and head to the namesake, Margaritaville Key West Resort and Marina.
What is the first bar that comes to mind when you think Key West? Most likely Sloppy Joe’s, the famous watering hole of Ernest Hemingway is a Key West tradition steeped in history. Founded on the very day prohibition was repealed, December 5, 1933. The bar actually went through a of couple name changes before Sloppy Joe’s was chosen with encouragement from the infamous Ernest Hemingway.
Fearless rum runner/bootlegger & speakeasy operator Joe “Josey” Russell and his friend, customer and fishing companion Hemingway formed a special bond during the writer’s residency on the island. After the inevitable failure of “Operation Dry America” Russell found himself on the up & up as a genuine saloon keeper and business owner of a dump called the “Blind Pig” which cost him a whopping three dollars a week to lease the building. The pig was located around the corner where Capt. Tony’s Saloon still stands. (Fascinating history there too!) http://www.capttonyssaloon.com/ Built in 1852 the building served 2 important purposes. It was an ice house (very important due to the heat in Key West) and the city morgue (also very important due to the heat in Key West).
Thought to be haunted, the bar now houses the “hanging tree” where 16 pirates and a woman who took a knife to her husband and 2 children met their maker. Known as The Lady in Blue, (nicknamed for the color of her dress during the hideous killing spree and the color she turned during the ….)
In 1898 a telegraph was housed in the same building. Famous for informing the world during the Spanish–American War that the battleship Maine was destroyed, when the news came from Havana to Key West.
Over the following decades it housed speakeasies, a bordello, a cigar factory and an early gay bar. The Navy forbade their men from patronizing the establishment which was ultimately forced to close and remain empty for quite some time until Anthony Tarracino opened its doors in 1958 as Captain Tony’s.
Not long after Joe Russell attained the Blind Pig in 1931, the ratty ramshackle establishment added a dance floor and changed its name to the "Silver Slipper" where in addition to gambling, gossip and ten cent shots patrons could now kick up their wobbly heels.
An Old Havana bar and fish market where Joe “Josie” Russell and Hemingway spent considerable time while in Cuba was owned by another friend, Jose Garcia Rio. Joe’s Cuban bar was ridiculed as being sloppy due to constantly melting ice that made a big mess of the floors….. Hence Havana’s aptly monikered “Sloppy Joe's”. One thing led to another….. and one drink led to another…. and the Silver Slipper became the now famous Sloppy Joe’s at the urging of Hemingway!
Roadside diners, vintage drive-ins and out-of-the-way "dives" are enjoying a come-back of hipness. Host Guy Fieri travels the country in search of the best greasy spoons. The restaurants he visits are well-known among locals and visitors looking for authentic area food joints and mom and pop kitchen’s. While at the locations, Guy interacts with customers and staff as well as the chef’s. The first episode aired on April 23, 2007 and the show has grown continuously in popularity.
Who doesn’t love a diner, drive in or dive. Steeped in tradition, aged with consistency and slathered in warm nostalgic sentiment these are a binding ingredient in communities across the nation.
Dixie Roadhouse is a fantasic place to go with friends or to make new ones!
Indulge in some of Southwest Florida’s Exciting Gaming, Entertainment, Luxurious Accommodations, and Decadent Dining at one of the area’s top vacation holiday destinations - Seminole Casino.
Not sure what you want for lunch, dinner or in-between? WineDine Key West is a month long event between mid September and the middle of October celebrating fine dining at an affordable price. If you're looking for a great Key West excursion, in the cooler months, but aren't quite ready for Fantasy Fest. Well, this just may be for you.
Legendary Key West restaurants offer up three-course prix-fixe menus specially priced for you to experience what makes this islands food so special. Want to know who's making what, when and where? Head on over to their Facebook page, below, and find out all of the info you'll need.