Upcoming Events 
Key West, Florida

Upcoming Events near Key West, Florida

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Looking for something extra to do to make your stay in Key West, Florida the best vacation ever? Check out our list of the top events coming up in 2021.

Festivals & Celebrations

Celebrations, Parties and Festivals are a big part of Key West because they bring people of different cultures and diversities together to have fun.  Many of these festivals celebrate the heritage and history of Key West, while the participants enjoy the party atmosphere Key West is so known for. They have become  part of the fabric and tradition that has personified Key West.  Learn about the heritage and harmony of Key West by attending any of our famous festivals.

If you've already missed some of this year's festivals, you may be able to catch one next year as most of them occur annually!

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January 26-30

Food and Wine Festival

Taste vintage, local wines and fine foods at the Food and Wine Festival.
According to Travel Magazine April 2020: "Shining a spotlight on local chefs, indigenous Florida Keys ingredients, and premium spirits is the overarching goal of this hugely popular wine and food themed event, which has been running for over a decade. Hosted by passionate culinary and beverage producers, the festival features waterfront tastings, winemaker/chef collaborations, and several other quirky events. Among the major highlights each year is "Duval Uncorked", which sees masses of wine lovers descend on Key West's famous Duval Street for a tantalising (sic) mile-long wine tasting, with many of the street's chic boutiques, funky shops and galleries participating by offering wines from around the world."
Forbes said: "Along with its unapologetically offbeat ambience and burgeoning allure for luxury travelers, Key West is steadily adding another distinction to its dossier: a paradise for serious foodies. 

April 16-25

Conch Republic Independence Celebration

Celebrate the creation of the Conch Republic, a micronation, born on April 23, 1982 as a stand against a blockade placed at The Last Chance Saloon in Florida City by the U.S. Border Patrol.
Since the United States insisted on treating the Keys like a foreign country, Mayor Dennis Wardlow seceded from Union. Today we stand proudly as a community of who have "Sovereign State Of Mind" and as the "People who seceded where others have failed"
On April 23rd, the Conch Republic flag was raised over city hall and the Schooner Western Union, under command of Captain John Kraus, went forth into the harbor and attacked the US Coast Guard Cutter DILIGENCE with water balloons, Conch fritters and stale Cuban bread. The DILIGENCE fought back with fire hoses and thus commenced the Great Battle of the Conch Republic. The road block was quietly removed and the glorious Conch Republic was born.

Janauary 25-29

 Mile 0 Festival

Listen to some of Key West's best performers and try foods from the city's various vendors.
Line Up:

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Mile 0 Fest

Mile 0 Fest Line Up 2022


May 4-9

Songwriters Festival

The Key West Songwriters Festival - the largest festival of its kind in the world. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs!
Staged at an array of the island's most popular Beaches, Boats, Bars, Resorts and Historic Theatres.
Most of the Festival shows are FREE to enter.
100+ Performers
Last Year's Performers: (2022 Performers will be announced in March)
Lee Brice, Brandy Clark, Lori McKenna, Robert Randolph, Chuck Cannon,Bob DiPero,Dean Dillon,Steve Cooper,Liz Rose, Jeffrey Steele, Bobby Pinson, Scotty Emerick, Adam Craig, Clint Daniels, Luke Laird, Ben Burgess,Shane Minor,Erik Dylan,Ronnie Bowman,Trent Tomlinson,Shy Carter,Barry Dean, Tyler Reeve,Ashland Craft, Rob Snyder, Channing Wilson, Lewis Brice, Emily Shakelton,Anthony Smith,Katie Pruitt, Rebecca Lynn Howard, and Many more

July 21-23

Hemingway Days

Pulitzer Prize–winning author Ernest Hemingway left a powerful legacy in Key West. His party life-style, along with zest for life and literary accomplishments are legendary in Key West. Hemingway's had an enduring affection for the island he called home during the 1930s, where thousands of visitors line up to get a peek at his magnificent home on Whitehead Street. This jewel is just a short walk from Caribbean House. And all of this is to be celebrated Tuesday through Sunday, July 21-26, with the annual Hemingway Days festivities.
See if you can find the closest match to Ernest Hemingway at the Hemingway Look-Alike Contest at Sloppy Joe's bar and send the lookalikes off at the "Running of the Bulls" on Duval Street.

Aug. 11-14

Lobsterfest

For a diver in South Florida, spiny lobster mini season is considered a special time. The purpose of the two-day mini-season is to allow recreational divers the opportunity to harvest spiny lobster before the commercial season begins
Florida lobsters, sometimes called spiny lobsters, are known for their sweet, tender meat. Unlike their northern cousins, the spiny specimens have no claws.
Purists savor them steamed, with each bite dipped in melted butter. Every year, at the beginning of August, just before the opening of commercial lobster season, lobster lovers from all over the world come to Key West to celebrate lobster with free concerts, great food, and the biggest party of the summer.
The culmination of Key West Lobsterfest is the Street Fair, set for noon through 11 p.m. Saturday, Aug. 12, in the 100 through 500 blocks of Duval. Enjoy delicious lobster, cold drinks and diverse music.

Sept. 2-6

BrewFest

Join us over Labor Day weekend to celebrate BEER! Happening from September 2nd to September 6th, 2021. Events from beer dinners, brunches, happy hours, pool parties, late-night after parties, and of course, the Signature Tasting Event are just some of the fun events we have on tap for you! You won't want to miss your chance to taste over 150 beers in one weekend!
Stay close to all the fun and brews at Caribbean House!
Saturday, September 4th 5pm-8pm: Grand Tasting Event on South Beach featuring over 150 beers
Drink beers and cocktails like a local. Relax at the Hangover Brunch and then play bingo.

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Bahama Village Goombay Festival: October 22-24

A Family Friendly Event
This exuberant street party showcases island arts and crafts, music and food in the heart of Key West's historic Bahama Village neighborhood and right in front of Caribbean House! The festival's main entertainment stage is located at the corner of Petronia and Fort streets on Truman Annex, and features nonstop musical entertainment ranging from gospel to reggae. This family friendly street party continues on Saturday! Noon to midnight; FREE.
Start off Fantasy Fest with your family by enjoying musical entertainment and arts and crafts in the Bahama Village neighborhood.

Fantasy Fest: October 24-31
Think Mardi Gras! Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!
Don't miss the Headdress Ball, The Pet Masquerade, The Masquerade March The Street Fair or the famous Saturday night Fantasy Fest Parade, an event you won't soon forget!

Nov. 4

Parrotheads in Paradise: Meeting of the Minds

Who or what is a Parrot Head? The "Who" are responsible party-goers coming from all walks of life, ethnicity and span the girth of human age.
The "What" is a group with a deep admiration for the Florida Keys lifestyle, so poignantly coined in Jimmy Buffett's songs, fun loving Parrot Heads party with a purpose - responsibly.
However, there is far more to this group of music loving, parrot dressing people than a genuine appreciation for trop rock music. An important part of the Parrot Head culture is that they engage in a variety of charitable activities.
Parrot Head Clubs can be found almost everywhere. The United States is home to several hundred organizations while others have sprouted up around the world.
This once a year party theme is "Party At The End Of The World" and the events and revelry is all in good fun and is about all things Jimmy Buffet.

Nov. 7

Race World Offshore Key West Championships

This event brings race teams and fans to Key West for an amazing Offshore World Championship experience. Watch speed boats race across the water at this outdoor event. Then join the build-a-boat contest to see what you can do!
Opening Ceremony in the Truman Waterfront Park
Wednesday Race Truman Waterfront Cup and winners will be recognized with awards immediately after each race
Friday Race Southernmost Continental Champion and winners will be recognized with awards immediately after each race
Thursday & Saturday concert in Truman Waterfront Park (TBD)
Friday Parade of boats on water with Florida Powerboat Club
Online Registration for teams convenience
2nd Annual Build-A-Boat Contest
Build-A-Boat to include USCG, Fire, Police, Community & Race Teams
Online hospitality ticket sales for convenience
Water shuttle on race day for Outer Mole VIP guests – Easy walk from Duval (to be confirmed)
Sunday UIM World Champion Awards & Closing Ceremonies in TWP Amphitheater immediately following final Sunday race
Awards Ceremony to include public.

Dec. 1-Jan. 1

Christmas & New Years Eve

Christmas Events
Celebrate Christmas and New Years Eve with the locals.
Old Town Trolley's Holiday Lights Tour. Select nights from December 6th-23rd. Annual Key West Holiday Parade. Saturday, December 7th. ...
Historic Inns Holiday Tour. The Nutcracker Key West. Conch Tour Train Holiday Light Tours. ...
Annual Lighted Boat Parade. ...
New Year's Eve
Ball Drops and Parties
Lowering of the Pirate Wench at Schooner Wharf
Visit the Tall Ship America 2.0 and experience canon blasts that welcome in the New Year. See the Pirate Wench descend from the top of the ship while listening to some live music and enjoying the festivities at Schooner Wharf Bar.
Dropping of the Conch Shell at Sloppy Joe's
The wildest ball drop on Duval Street happens above Sloppy Joe's, the most famous bar in Key West. Thousands of spectators gather to catch a glimpse of this annual tradition. If you're not looking for a crowd, avoid this area at all costs because it's like a small version of Times Square.
The Red High Heel Drop Starring Sushi
From the balcony of the New Orleans House, Sushi descends in a giant red high heel shoe. VIP balcony tickets usually sell out within hours and Duval Street overflows with spectators who party into the wee hours.
TheChive Annual New Year's Eve Party
Join theChive crowd at The Porch for an unforgettable New Year's Eve celebration. They'll be dropping a Chive Unicorn at midnight and engaging in multitudes of tomfoolery throughout the evening.

Looking to view interesting art and learn about the culture and history of Key West? Check out the buildings under the care of the Art and Historical Society:

Custom House

A magnificent building, originally the Key West custom's office, post office & district courts, opened in 1891. It is four-story architectural feat built to keep up with the population growth and wealth coming from Key West's trade industry.
Typical of Federal Buildings of the 19th century, The Custom House is of Richardson Romanesque architecture. Located near the Naval Base, The Custom House was the site of the very famous inquiry regarding the sinking of the USS Maine in Havana Harbor in 1898. 
Transferred to the US Navy's possession in 1932, it became the Navy Headquarters, followed by it being abandoned for 20 years when it was no longer of use.
The Custom House is now in the hands of the State of Florida and leased to the Key West Art & Historical Society and is used as a museum.

Learn about soldiers, a railroad and local artwork. Gift shop available for interesting souvenirs. A 15-minute walk from our bed and breakfast. 
Local lore is that the roof was slanted as required by Federal mandate for the sleeting of snow from the roof.

Key West Lighthouse

Climb to the top of this maintained lighthouse and get spectacular views of Key West. The best time to visit is during a sunrise or sunset. A 5-minute walk from our B&B.

Fort East Martello Museum

After the Civil War ended, Fort East Martello was abandoned in its unfinished state by the Army.
Today, visitors can explore the collection of relics from the Civil War, learn about the wrecking and cigar-manufacturing industries which shaped Key West. For the ghost hunters, the Ghosts of East Martello, including the infamous Robert the Doll can be found.
 Take interesting pictures with metal sculptures to make fun memories with your friends and family. Just 3.6 miles from our inn.

Tennessee Williams Museum

 With his works such as The Glass Menagerie, A Streetcar Named Desire and Cat on a Hot Tin Roof and many other classics of the American stage, Tennessee Williams earned two Pulitzer Prizes, Tony Awards, the Presidential Medal of Freedom. In the 1950's Tennessee Williams' plays were adapted into films that reached audiences worldwide. 
Learn about the life of this famous playwright, who lived in Key West from 1941 to his death in 1983,  by visiting  the exhibits of photographs, newspapers, and videos on display and scattered throughout this house. A 10-minute walk from Caribbean House.     

Home Tours

Get a taste of the architecture and culture of Key West by touring the historic houses scattered throughout the city. Each tour is different from the last, so you can learn something new each time you go.

Home Tours

Get a taste of the architecture and culture of Key West by touring the historic houses scattered throughout the city. Each tour is different from the last, so you can learn something new each time you go.
The local art in Key West is also something you won't want to miss. You can find information about what local art galleries are open here.
Rams Head is your entertainment center for purchasing tickets to upcoming concerts. A family-owned business, this company helps manage well-organized and -produced events. Have fun at a thrilling, local concert! The most popular time of year to attend a concert is during the early summer months.

The venues Rams Head works with includes Key West Amphitheater, Sunset Green Event Lawn and Key West Theater. Additionally, you'll find tickets for events at the Coffee Butler Amphitheater and other nearby venues in Key West. The events at The Key West Coffee Butler Amphitheater and the  are within walking distance to Caribbean House!

Stay with Us

By staying at the Caribbean House, you can have easy access to these events and the rest of Key West, Florida's attractions. Book your stay now!
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