Annual Events & Festivals - Annual Events
No one knows how to throw a party better than residents of the Florida Keys. Come dress with us in period attire as we relive eras of our past. Or join locals and folks from across the world in a challenging road race on a bridge spanning miles of open sea.
We also have boat parades, bikini contests, battle reenactments, and our own unplugged, underwater concert. Or try your angling skills in one of our many fishing tournaments (see the Fishing chapter for an expanded listing). Immerse yourself in Florida Keys arts and culture at our historical observances, music festivals, or arts and crafts fairs.
And my, how we love to eat. From Key Largo to Key West, food festivals abound. These events provide an inexpensive means of sampling incredibly fresh seafood and menu items from leading local restaurants.
Overview
The following selection of festivals and events is a sampling of what we offer annually in the Florida Keys. Additional events occur sporadically from year to year. Dates and locations often change, and admission prices vary. Call the local chambers of commerce for details: Key Largo, MM 106 Bayside, (305) 451-1414 or (800) 822-1088; Islamorada, MM 82.5 Bayside, (305) 664-4503 or (800) 322-5397; Marathon, MM 53.5 Bayside, (305) 743-5417 or (800) 262-7284; Lower Keys, MM 31 Oceanside, (305) 872-2411 or (800) 872-3722; Key West, 510 Greene St., (305) 294-2587 or (800) 527-8539. You can pick up the annual Attractions & Events brochure at any of these chambers. You also will find annual event information on the official website of the Monroe County Tourist Development Council: fla-keys.com.
1. Art Under The Oaks
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 360-8556
Address: MM 89.5 Bayside, Plantation Key, Islamor
Description: Begun in 1982, Art under the Oaks, held in the gardens on the grounds of San Pedro Church, is always a tremendous community gathering. This 1-day celebration in mid-Jan is held in a natural setting under a lovely canopy of oak trees. It offers homemade crafts, fine art from local artists, specialty food booths, self-guided nature tours of the gardens, children’s arts and crafts, raffle items, and live music. Because of the large turnout, free shuttle bus service runs from the Plantation Key School’s parking lot to the event.
2. Cheeca Lodge & Spa Presidential Sailfish Tournament
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 664-4651 or (800) 327-28
Address: MM 82 Oceanside, Cheeca Lodge, Islamorad
Description: In 1989 when George H. W. Bush was our president, he came to Islamorada on holiday and to fish. This exciting 3-day tourney has been taking place for more than 20 years in mid-Jan and is part of the Florida Keys Gold Cup Sailfish Championship and world Billfish Series. Cash prizes and trophies are awarded in this catch-and-release event.
3. Key West Craft Show
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 294-1241
Insider Pick:
Description: Key West ends the month of Jan with a weekend-long exhibit of original crafts. Among the one-of-a-kind items offered for sale, you’ll find handmade jewelry, leather goods, wood carvings, kitchen accessories, and exquisite hand-thrown pottery from Pottery by Grace, a fifth-generation Conch (potterybygrace.com). Exhibitors come from throughout the Keys and the US. The crafts show takes place in the street—on Whitehead Street between Eaton and Greene. Admission is free.
4. Key West Food And Wine Festival
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (800) 474-4319
Insider Pick:
Description: The Key West Food and Wine Festival is 4 fun-filled days of culinary delights and funky events you would only expect to experience in Key West. The festival’s signature events are the Kick Off Your Flip-Flops Barefoot Beach Party; the Grand Tasting, with a refined selection of wines; and Duval Uncorked, which leads guests along Duval Street for a mile-long food and wine tasting extravaganza. There are also neighborhood strolls, one-of-a-kind fund-raisers like coconut bowling, various informative seminars, and an outdoor wine market.
5. Key West Historic House And Garden Tours
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 294-9501
Insider Pick:
Description: Olde Island Restoration, a nonprofit organization that encourages preservation of Key West’s many historical structures, sponsors this popular tour—spanning Dec, Jan, Feb, and Mar—to show off some of the city’s finest private properties. Typically each event features 5 or 6 privately owned homes. Tours explore shotgun-style cottages, Conch-style mansions, and everything in between. The tours are self-guided, but participants may meet at the Olde Island Restoration offices along Mallory Square and then embark on a Conch Train bound for the tour site. Scheduled dates vary from year to year. There is an admission fee.
City: Florida Keys, FL
Category: Annual Events & Festivals
7. Sculpture Key West
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 295-3800
Description: Sculpture Key West may be viewed by land, seen by boat, or observed by air. Showcased in Jan, this annual event has grown from a handful of Key West locals to a nationally and internationally prominent exhibition showcasing world-renowned contemporary sculptors.
8. Civil War Heritage Days
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 292-6850
Description: History comes alive at Fort Zachary Taylor (see the Recreation and Attractions chapters) during the first 2 weeks in Feb, when the fort is the setting for a Civil War battle reenactment. During the event the fort is filled with activity, with many enthusiasts wearing the uniforms of Union and Confederate soldiers. Other participants in period attire portray merchants and citizens. Events include the capture of a blockade runner, with the captain of the vessel standing trial. Key West was the only Southern city that stayed in the Union throughout the Civil War, and the fort was a key point in guarding the shipping lanes to Union ports.
9. Old Island Days Art Festival
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 294-1241
Description: If you appreciate art, your heart is bound to beat faster at the sight of several blocks of exhibits by talented local artists. Inspired by this southernmost city, they take this opportunity to showcase their vivid creations. Virtually all artistic media are represented in this juried weekend-long show, usually held at the end of Feb, including oil, watercolor, and acrylic paintings; graphics; wood, metal, and stone sculptures; glasswork; and photography. Judges provide merit awards within each category. Old Island Days Art Festival exhibits line Whitehead Street from Greene Street to Caroline and into Truman Annex. No charge for browsing.
10. Conch Shell Blowing Contest
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 294-9501
Description: Come to this fun “Conch Honk.” The Conch Shell Blowing Contest offers adults and children the opportunity to sound off. Prizes are awarded to the loudest, the funniest, and the most entertaining conch-shell blowers in several divisions. This 1-day, springtime event takes place on the waterfront and on various dates each year, but usually in Mar or Apr. Participation is free.
11. Key West Garden Club Flower Show At West Martello Tower
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 294-3210
Description: Established in 1949 by former Key West politician Joe Allen, the Garden Club organizes monthly educational seminars for the public. Plant-swapping sessions also are popular. The group holds a prejuried show every other year. Held at the Joe Allen West Martello Tower, home of the Key West Garden Club, the show features some 800 entries of floral arrangements, potted plants, palms, rare tropical flowers, and hybrids. Judges from garden clubs throughout the state of Florida award ribbons and prizes in several categories. The flower show is typically held during the spring, not necessarily always in Mar. There are admission costs.
12. Conch Republic Independence Celebration
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 296-0213
Insider Pick:
Description: This 10-day festival officially commemorates Key West’s attempt to secede from the US on April 23, 1982, after the US Border Patrol established roadblocks at the end of the mainland to screen for drugs and illegal aliens. Independent Key Westers rebelled, creating their own flag and attempting to secede. The secession fizzled, of course, but locals here find the brief attempt at independence a reason to party nevertheless. Around this same time every year, officials of the fictitious Conch Republic—secretary general, prime ministers, navy, air force, and all—host events like picnics, balls, Conch cruiser car shows, the Red Ribbon Bed Race down Duval Street, and what has been dubbed “the world’s longest parade.”
13. Seven Mile Bridge Run
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 395-7040
Insider Pick:
Description: For more than 30 years, men and women from around the world have flocked to this 7-mile roadway, which spans the open water between Marathon and Bahia Honda. In the wee morning hours, these spirited individuals participate in the most scenic competition of its kind: a run across one of the world’s longest bridges. Designed to raise money for local schools and youth groups, the run is said to be the only one in the world held completely over and surrounded by water. Prizes are awarded in various categories. Usually the run begins on the Marathon end of the Seven Mile Bridge. Expect to pay an entry fee. Spaces are limited, so if you plan to run, reserve your spot early.
14. World Sailfish Championship
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (866) 550-5580
Description: Presented in mid-Apr, this 3-day sailfish challenge is one of South Florida’s most illustrious tourneys. Winners of previous sailfish tournaments, elite anglers, and celebrity participants are challenged in this event. VIP registration is available for teams wanting to rub elbows with the likes of baseball greats Johnny Bench and Wade Boggs, and sometimes even fish with a celebrity teammate. Cash prize money, reaching six figures, is awarded to the team for the largest confirmed number of sailfish caught and released during this hard-fought championship.
15. Cinco De Mayo Celebration
City: Florida Keys, FL
Category: Annual Events & Festivals
Telephone: (305) 292-3302
Description: In 1994 the first Cinco de Mayo Celebration kicked off with all the sizzle and salsa anyone could handle. Still going strong, this zany festival is usually held the first week of May. In honor of the victory of the Mexican army over the French at the Battle of Pueblo in 1862, current revelers pay homage with everything from a taco-eating contest to taking shots of tequila, eating hot jalapeño peppers, and drinking beer in record time.