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Florida Keys Things To Do
Range From Gastronomic To Zany

Florida Keys things to do cover the gamet from power boat racing to gourmet food fests. Fishing tournaments to marathons and relays.

This monthly breakdown of Florida Keys activities will help ensure you don't miss out on fun things to do when planning your next Florida Keys vacation.


Islanders and vacationers alike find that the near perfect climate is the recipe for a full Florida Keys calendar of events each month.

A variety of Florida Keys events are held each month in Key Largo, Tavernier, Islamorada, Marathon, Lower Keys and Key West.

Some of these Florida activities occur only once, some are sporadic, and some are long lived. Some long standing Florida Keys activities are no longer being offered, while new Florida events are popping up around the islands.

As you spend time in the Florida Keys you'll discover that there are many wonderful local Florida Keys things to do that I've not included. Church bazaars, rummage sales, flea markets, school events, estate sales, pet rescue programs, square dancing, poetry readings, garden club events, and a myriad of other routine local activities are always popping up some place.

On this page, I've also not included some of the other Florida Keys things to do that we cover elsewhere on this website, including fishing tournaments, Fantasy Fest, and Sunset celebration.  Instead I've provided links to them further below.


Numerous Florida Keys Festivals With Different Themes Fill the Year
State Archives of Florida, Florida Memory, Dale M. McDonald Collection


However, if you're in the Florida Keys and you love to fish, don't forget to check out our Florida Keys fishing tournaments page each month to make sure you're on top of the where's and when's of these popular Florida Keys fishing events.

You also don't have to wait for any special day or time of year to enjoy another of the more popular Key West things to do - ghost encounters. Whether you're on your own at a bar, museum, or even in your room, you're likely to have an "extreme other worldly" experience.  

However narrated ghost tours are one of the more popular Key West events, and they're a great way to get acquainted with the many long departed Key West residents.

You can also get books through Amazon that detail the ghostly apparitions inhabiting Bone Island. They discuss the local legends and tales so you'll have an even better idea of who or what you might bump into. It also doesn't have to be dark to have a ghostly encounter in Key West!


Likewise, the Key West Fantasy Fest 10 day adult extravaganza's roster of Key West events is not listed here. The event is mentioned, but the Key West activities are so numerous and detailed that it's better for you to get the information on our Fantasy Fest Schedule of Events page linked to further below.

We also have a page dedicated to Florida Keys marathons and relays. I've briefly identified them here for the month they typically occur in. However if you're an avid runner, you'll want to stay abreast of the races by checking our 
Florida Keys marathon and relay page which includes the more popular races including Seven Mile Bridge Run and Ragnar Relay which has now been cancelled - at least temporarily.

The following calendar of events of Florida Keys things to do purposely does not include specific dates. The reason for this is that dates change for many reasons. 

My intent is to provide you with a comprehensive overview of the top things to do in the Florida Keys, so you can see what will interest you. You can then contact the event direct, for up-to-date information regarding scheduling, costs, planned events, directions and parking questions.

Of course there are other Florida Keys events that are a permanent part of life in the islands. Occurring nightly for decades, unless otherwise dictated by weather, is one of the most popular Key West events, Sunset Celebration at 
Mallory Square.

The following 12 month calendar of events is a summary of some of the best Florida Keys things to do when you're on a vacation in the Florida Keys. 

January Florida Keys Things To Do


Founder's Park New Year's Day Celebration
MM 84, Oceanside, Islamorada

Kicking off the New Year, this Islamorada FL event starts at 8:00 am with the annual 5k run, walk and crawl along the paths of Founder's Park. A boat parade, blessing of the fleet, and other fun activities round out this Florida Keys events family oriented theme. For additional information call 305-853-1685.


Ragnar Relay Florida Keys
Miami - Key West
The wacky and fun non-stop Ragnar Relay from Miami to Key West kicks off the year's Florida Keys marathons and relays.


Florida Keys Seafood Festival
Bayview Park, Key West
Running from late morning to early evening, this is one of the Key West events that's family oriented. Held at the corner of Truman Avenue & Jose Marti Drive a variety of seafood delicacies along with more traditional non-seafood fare are available. Children's entertainment along with live music round out this full day of Key West food and fun. Call 305-872-9026 for additional information.


Old Island Days House & Garden Tour
Key West
One of the longest standing Key West events, the tour season kicks off in January. Several historic Key West homes and gardens are included. Call 305-294-9501 for information on dates and homes. 


Uncorked Food & Wine Festival
Key Largo
Featuring food and wine from Key Largo & Islamorada restaurants and wineries, the 10 day gourmet extravaganza includes cooking demonstrations, pairing classes, wine dinners, live music and more. For additional information on this Key Largo event call 305-394-3736.


Key West Literary Seminar
Key West
Throughout January, three separate 4 day long seminars are conducted focusing on prominent writers and the mark they've made on society. For information or to register call 1-888-293-9291.


Quantum Key West Race

Key West
One of the more popular Florida Keys things to do is this world class regatta. It  takes place over 5 days, and attracts sailboats from all over the world to compete in one of the more thrilling and rigorous Key West events. For race details call 1-781-639-9545.

Key West Food & Wine Festival
Key West
4 days of gourmet food, wine tasting and educational seminars make this one of the tastier Key West events. Numerous locations participate in this gourmet event featuring local fare and chefs. The event also includes the popular Key West Master Chef where top restaurants compete in different menu categories. For details on participating locations and daily activities call 1-800-474-4319.


Key West Craft Show

Whitehead and Greene Streets, Key West
Near the end of January this annual Key West event features over 100 artisans and is held from 10:00 am - 5:00 pm. Exhibits feature an array of different artists and their unique styles. Paintings, sculptures and photography are presented during this annual Florida Keys event. Call 305-294-1241 for additional information.

February Florida Keys Things To Do


Old Island Days House & Garden Tour
Key West
The second tour in the Key West historic homes and gardens series is held in February. Call 305-294-9501 for times and rates.


Pigeon Key Art Festival
1 Knights Key Blvd, Marathon Florida
Beautiful Pigeon Key, located at the south end of the Seven Mile Bridge is home to this annual art festival. While at Pigeon Key take the time to visit the museum that focuses on Henry Flagler and his massive undertaking, often referred to as Flagler's Folly. For more information on this Marathon Florida festival call 305-743-5999.

Pigeon Key and The Flagler Museum is at south end of Seven Mile Bridge


Pigeon Key And Flagler Museum, South End Of Seven Mile Bridge


March Florida Keys Things To Do


Sombrero Beach Run

Marathon
Good weather permitting, the Key West Southernmost Runners Club sponsor a 10K Run and 5K Walk along Sombrero Beach typically held the first Saturday of March. For more information call 305-289-9868.


Old Island Days House & Garden Tour #3
Key West
The third segment of the long standing Key West heritage home and garden tour series is held in March. For details call 305- 294-9501.


Woofstock Music Fair
Founder's Park, Islamorada, MM 87
Out of all the family events, this is one of the more fun Florida Keys things to do. Typically held the second Saturday in March, this pet themed Islamorada event runs from 11 am - 7 pm. Live music, food, demonstrations, and prizes are awarded.


Marathon Seafood Festival
Marathon Community Park, MM 49 Oceanside
Traditionally held the second weekend of March, this 2 day food extravaganza features fresh seafood, live music and loads of fun. The Marathon Florida event runs from 10 am Saturday through to 5 pm on Sunday. Call 800-262-7284.for additional information. 


Conch Shell Blowing Contest
Key West
One of the wackier Florida Keys things to do, this is an ongoing tradition that's part of the Old Island Days.  This March Key West event draws contestants from all age groups. Musical skill is not the focus however at this conch blowing event. Instead, entrants are graded on unique presentation, loudness and duration of their blowing. Shells are provided or you can bring your own. Additional details are available at 305-294-9501.


Key West Tropical Forest & Botanical Garden 
Hot Havana Nights

5210 College Road, Key West
Near the end of March the action heats up for this popular Cuban themed event. Guests enjoy live music, drinks, authentic Cuba food, and a beautiful setting. Call 305-296-1504 for details.

Rare Endangered Cuba Palm At Key West Tropical Forest And Botanical Garden


Endangered Cuba Palm At Key West Tropical Forest And Botanical Garden

April Florida Keys Things To Do

Florida Keys Island Fest
Founder's Park, MM 87 Bayside, Islamorada
This fun, family 2 day Islamorada event features sand castle building, classic car shows, arts and crafts, musicians, and the delicious "Taste of Islamorada".  One of the longer standing Florida Keys events, Island Fest has been scheduled as early as late March or as late as early May. It's best to check with the Chamber of Commerce at 305-664-4503 for current dates and times.


Robert Frost Poetry Festival

Key West
Robert Frost Cottage, Key West's Heritage House Museum, Key West
This annual event features a poetry writing contest and workshop that typically occurs in April, or late March. For dates and details call 305-296-3573.


Seven Mile Bridge Run
Marathon Florida
Highly anticipated Seven Mile Bridge Run takes place with entrants from all over competing in this fast paced race from Knight's Key to Pigeon Key. 


Conch Republic Independence Celebration
Key West
Wild and wacky fun headlines one of the zanier Florida Keys things to do. This Key West event commemorates the bold declaration of the Conch Republic's secession on April 23, 1982. 10 days of frivolity include parades, bed races, food, drink, music and a host of parties to round out the merriment. For additional information call 305-296-0213.


Key Largo Conch Republic Days
Key Largo
Traditionally running for 8 days from the last 2 Sundays of April, this is one of the Key Largo events you hate to miss. Celebrating the Conch way of life and it's brief declaration of independence, food, fun, hilarious re-enactments and entertainment make this a lively Florida Keys event. For more information call 305-394-3736.

May Florida Keys Things To Do


Humphrey Bogart Film Festival
Key Largo
May, 2013 showcases the first Humphrey Bogart film festival. Chosen as the perfect fit, Key Largo will host a rotation of selected films starring this icon. One of the more highly anticipated Key Largo events, several different locations will serve as viewing locations. To vote for your favorite Bogie film's inclusion or for additional information, visit bogartfilmfestival.com.


Key West Songwriters Festival
Key West
One of the more highly anticipated Florida Keys things to do is this Key West music festival. Attracting top songwriters from all over, music is performed at various Key West bars. This 5 day, 5 night Florida Keys event headlines 20 free shows. To view the Key West calendar of events for this festival go to keywestsongwritersfestival.com.

Battle in the Bay Dragon Boat Festival
Set for the second Saturday in May, this sanctioned race is off Key West at the Truman Waterfront. For registration information and other details call 305-766-1053 or download your registration form from BattleInTheBay.org.


Keys100 Marathon
Key Largo - Marathon - Key West
Typically held mid-May, this Florida Keys race is broken into 2 legs giving entrants the option to choose how far to run. The full leg goes from Key Largo to Key West. The 50 mile leg goes from Marathon to Key West. For more information go to keys100.com.


Marathon Super Boat Grand Prix
Marathon
Typically scheduled for mid-May, this high-octane power boat race is a thrill to watch as boats fly through the water and race beneath the 7 Mile Bridge. Call 305-296-6166 for more information. 

June Florida Keys Things To Do


PrideFest Key West
Key West
Held in early June, this week long event celebrates Key West's diverse nature and generosity in allowing gays, lesbians, bisexuals, transvestites and transgenders to openly celebrate their lives. Call 305-292-3223 for current information. 


Cuban American Heritage Festival
5570 3rd Avenue, Key West
Held mid-month, this annual festival honors Jose Marti, and promotes the Cuban culture and lifestyle. For details call 305-295-9665. 


Barley Bay Festival
Plantation Yacht Harbor, MM 87 Bayside, Islamorada
Promoting a healthier, cleaner Florida Keys, this worthwhile 2 day event held at the end of June celebrates the life and death of George Barley, champion of Everglades National Park. Free snorkeling and diving excursions are offered as part of the reef cleanup event. Great music by top rock bands follow later in the afternoon. For additional information call 305-451-4040.

Rare Endangered Cuba Palm At Key West Tropical Forest And Botanical Garden


Cuban Heritage Awareness Is Promoted At San Carlos Institute

July Florida Keys Things To Do


4th of July Fireworks and Celebration
. Key Largo 4th of July celebration
Annual parade starts at 10 a.m. from MM 98 to MM 100. Evening fireworks display over Key Largo's Blackwater Sound starting at 9:00 pm at MM 101, Bayside.

. Islamorada 4th of July celebration

Founders Park at MM 87, 6 - 9:30 pm - entertainment and fireworks

. Marathon Florida 4th of July celebration
Parade starts at 10:30 am and goes from MM 50 Oceanside to Sombrero Beach. Full day of events include food, drinks, crafts, entertainment and large fireworks display at night.

. Sugarloaf Key 4th of July celebration
Fireworks at 9:00 pm at MM 17, Bayside, at Sugarloaf airport.

. Key West 4th of July celebration
Harbor Walk Bar Stroll at 2:00 continuing along to popular stopovers on the planned route. Annual hospice picnic at Casa Marina with fireworks at 9:00 pm

Underwater Music Festival
Looe Key
Typically held mid-July, this is perhaps one of the more amusing Florida Keys events held underwater at beautiful Looe Key Reef. Musicians, dressed the part, serenade underwater theme appropriate music while snorkelers, divers and perhaps even the fish enjoy the musical entertainment. For additional information contact 305-872-2411.

Hemingway Days Festival
Key West

July 21 is the date of Hemingway's birthday and this 6 day event revolves around his life and many accomplishments. One of the highlights of this highly anticipated Key West event is the Papa look alike contest. Another is Key West's unique twist on the famous 'running of the bulls', an event Ernest Hemingway was particularly fond of. Call 305-296-2388 for event details.

August Florida Keys Things To Do


Lobsterfest
Duval Street, Key West
Heralding the start of lobster season, this tasty 3 day Key West event occurs the first part of August. Activities include a street fair, live music, and the sampling of local lobster prepared a variety of ways.

September Florida Keys Things To Do


Key West Poker Run
Miami to Key West
Mid-September brings hundreds of bikers from all over the United States to ride from Miami to Key West to help raise money for local charities. Call Peterson's Harley Davidson south location in Miami at 305-235-4023 ir north location at 305-651-4811 for more information. 


WomenFest
Key West
Another one of the more popular themed Key West events, this lesbian-oriented festival focuses on making new friends and connecting with old. Parties, golf, excursions and other Key West activities round out the 6 day event which draws women from around the world. Call Key West Business Guild at 305-294-4603 for more information. 


Florida Keys Birding & Wildlife Festival
Marathon, Curry Hammock State Park, MM 56.2
In late September, or early October each year, this Florida Keys festival sponsors a number of different field trips. They extend as far south as Dry Tortugas National Park and north to Dagny Johnson State Park outside of Key Largo. Call 305-872-0774 for more information. 

Crowds Gather at Peterson's Key West Poker Run


Crowds Admiring Bikes At Peterson's Key West Poker Run
Photo Courtesy of Bob Hansen

October Florida Keys Things To Do


Goombay Festival
Bahama Village, Key West
Occurring the first 2 days of Fantasy Fest, this street fair ushers in the beginning of the ribald Key West Fantasy Fest. 


Fantasy Fest
Key West
Organized to coincide on or near Halloween, this 10 day adult extravaganza is filled with masquerade balls and parties designed to titillate, tempt and tease. The hectic Fantasy Fest Schedule of Events keeps this hottest of Key West events rocking day and night.


Key Largo PiratesFest
Key Largo
Beginning the 3rd Thursday of October and ending 4 days later on Sunday, this pirate themed event celebrates the pirate way of life and local legend Black Caesar. An escaped slave turned buccaneer, he was known for his towering form, powerful strength, love of women. During his ill-gotten career he also served as one of Blackbeard's chief lieutenants. His lair, just north of Key Largo is now referred to as Caesar's Rock. Music, festivities, costumes and pirate wares round out this popular Key Largo event. Call 305-394-3736 for more information.

November Florida Keys Things To Do

Florida Keys Bubbafest
Key Largo to Key West to Key Largo
This 8 day event is broken into manageable rides punctuated with plenty of fun Florida Keys things to do along the way. Space is limited so for more information about this action packed, break out of the mold Florida Keys event call 321-759-3433.


Parrot Heads in Paradise Convention
Key West
Members of Parrot Head clubs from around the world gather for this Key West event. Held around the first of November, participants make new friends and celebrate the music of Jimmy Buffett.


Island Jubilee
Harry Harris Park, MM 93 Oceanside, Tavernier
Arts and crafts, food, BBQ cookoffs, music, kids play area, exhibits and various shows make this 2 day Florida Keys event a fun, old fashioned family style festival. For more information call 305-451-4747.


Key Largo Bridge Run
Key Largo
In November entrants can choose from a 5K Walk/Run, a 10K Run or the Half Marathon. Call 305-451-1642 for registration and race details.


Key West Offshore Power Boat World Championships
Key West
Highly anticipated and one of the more dangerous Key West events, this 8 day annual power boat race typically runs in mid-November. Power boats fly through Key West Harbor and around the reefs in their race to gain lead position. For race details call 305-296-6166.


Harbor Walk of Lights
Key West Historic Seaport at Key West Bight
The lighting of the Harbor Walk at the Key West Historic Seaport typically takes place as the sun sets on Thanksgiving Eve and sets the stage for 6 weeks of holiday cheer. 


Big Pine & Lower Keys Island Art Festival
MM 31 Oceanside
This annual Florida Keys event occurs either the end of November or early December. The Florida Keys festival features live music, food and beverages along with special handcrafted creations. For further information call the Chamber at 1-800-872-3722.

December Florida Keys Things To Do


Lower Keys Chamber of Commerce Golf Tournament
Key West Golf Club
In early December, this million dollar prize awarding event is held at the Key West Golf Club. 


Key Largo Christmas Boat Parade
Key Largo
In the evening, lighted and decorated boats of all types, sizes, and shapes travel in a parade along Blackwater Sound's beautiful shoreline. For more information call 305-451-4502.


Key West Holiday Parade
Duval Street, Key West
Held in early December, this is a true old fashioned family style parade on Duval Street. Bands, official dignitaries in decorated cars, Christmas lights and loads of holiday cheer make this the perfect beginning to the holiday season. Call the City of Key West for more information at 305-809-3700. 


Schooner Wharf Bar Lighted Boat Parade
Schooner Wharf at Key West Historic Seaport
Held at night in early to mid December, all manner of boats festivally adorned and lit, ply the waters of Key West Bight. Bands supply the music and crowds cheer on the parade from the observation area at Schooner Wharf.


New Year's Eve
Key West
Forget Time Square, Key West rings in the New Year in total Conch Republic flair. You can celebrate the dropping of the 'pirate wench' from the top of a mast at Schooner Wharf at Key West's Historic Seaport. You can join the huge crowds cheering at Sloppy Joes Key West bar as the massive conch shell drops onto the bar's flat roof. You can even watch the glamorous drag queen slowly descend in the accommodating man sized red high heel shoe at Bourbon Street pub.


New Year's Eve
Key Largo
Traditional fireworks display over Blackwater Sound ring in the New Year in Key Largo.


› Florida Keys Things To Do





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Fantasy Fest Pirate Costumes