What's Up

What’s Up

So you’ve reached your final Florida destination, now what? Well, hold tight because this is one Florida destination where the fun never stops! In fact, there are probably more events and festivals going on in the Florida Keys & Key West than in any other Florida destination. Here’s a quick list of fun Keys’ happenings that you won’t want to miss!


Jazz at Tavern N’ Town

Key West: Some of Key West’s top talent including “Island Chanteuse” Carmen Rodriquez and Michael Thomas perform nightly from 5-7pm during Key West’s best Happy Hour. Takes place at Marriott Beachside Resort, 3841 N. Roosevelt Blvd. Info: 305-296-8100; tavernntown.com.

Key West Sunset Celebration

Key West: Each evening, about two hours before sunset, flocks of people gather at Key West’s Mallory Square and on the pier behind the Margaritaville Resort & Marina to watch the sun slowly sink into the Gulf of Mexico and to revel in the colorful street performers, local artists, psychics and food vendors who have made Key West’s Sunset Celebration a world-famous, multicultural happening. Experience it nightly at the end of upper Duval Street.

Every Tuesday
Mario Sanchez Original Works & Lecture

Key West: Owner of Key West’s renowned Gallery on Greene, Nance Frank has curated multiple exhibits of famed Cuban artist, Mario Sanchez with catalogues for his exhibit presented by The American Folk-Art Museum, The Museum of the City of New York as well as Cuba’s National Museum. Her weekly presentation about Sanchez’s life and work is absolutely fascinating. Takes place at 2pm every Tues at the Gallery on Greene, 606 Greene St, Key West. 305-304-2323; galleryongreene.com.

Every Wednesday
Aqua Idol

Key West: Now through March 25, “Aqua Idol” is raising money for Key West’s beloved Waterfront Playhouse, one of the crown jewels of the island’s cultural scene. Needless to say, this special fundraiser draws some of the area’s top talent who sing their hearts out for a great cause. Get there early if you want a good seat. Info: 305-294-0555; aquakeywest.com

Wednesday – Saturday
Cabaret in The Gardens

Key West: Key West’s Gardens Hotel is one of the most beautiful boutique hotels on the island and every Weds through Sat from 5 – 7pm, you can enjoy wonderful, live piano music in the Hotel’s intimate Cabaret. Full bar and stellar wines are the coup de gras. Find at 525 Angela St, Key West. Info: 305-294-2661; gardenshotel.com.

Every Saturday & Sunday
Big Pine Flea Market

Big Pine Key: Discover all kinds of great finds at unbeatable prices at this long-time Lower Keys Flea Market that showcases an eclectic mix of both used and new merchandise, as well as locally made soaps, tools and tarps, fishing supplies, watches and jewelry, fresh seafood and produce, homemade ice cream, weekend Fish Fry and inflatable bounce houses and rides. Open from 8am – 2pm every Sat and Sun through July. Free admission and parking. Find it at 30250 Overseas Hwy, Oceanside on Big Pine Key. Info: 305-872-4103; bigpinefleamarket.com.

Every Sunday
Jazz in The Gardens

Key West: Enjoy some terrific jazz amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne and fabulous wines. Takes place from 5:30 – 8pm at the Gardens Hotel, 526 Angel St, Key West. Info: 305-294-2661; gardenshotel.com.

First Thursday Art & Shopping Walk

Key West: Each month, The Studios of Key West (TSKW), along with many other neighboring galleries in the 500 Block of Fleming St, host special exhibitions from 6 – 9pm. More info: : 305-296-0458; tskw.org.

Third Thursday Morada Way Art Walk

Islamorada: Fine arts, live music, and “culinary art” are the hallmarks of this festive monthly event that showcases both national and local artisans in galleries along the Morada Way Arts & Cultural District. Takes place from 6 – 9pm on Old Hwy, MM 81.5, Oceanside, Islamorada. Info: 305-393-6012; moradaway.org.

Every Third Saturday Native Plant Sale

Key West: Peruse over 2,000 native, rare and endangered plants from the Keys, Cuba, and the Western Caribbean at this terrific monthly plant sale. It takes place from 9am-Noon at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.

First Fridays on Fleming

Key West: “The Fabulous 500 Block of Fleming Street” showcases boutiques, galleries, and eateries with all kinds of cool events including jewelry trunk shows, art openings, book signings, tastings, and libations. Takes place on Feb 7, March 6 and April 3 from 6 – 9pm.
Info: 305-304-9001; shoplocalkeywest.com.

First Friday MM 104 Block Party

Key Largo: Stroll among artists, shop for gifts, enjoy street bites from local eateries, and more during this fun monthly Block Party. Takes place on the First Friday of every month from 6 – 10pm, rain or shine along the Overseas Highway at mile marker 104 in Key Largo. Info: keylargofirstfriday.com.

Second Saturday Art Stroll

Stock Island: The Stock Island Arts District throws open its doors on the second Saturday of each month, where you can leisurely stroll about the many art galleries, working studios, and eclectic shops. Look for the festive pink “Art District” banners flying at each participating location. Takes place from 11am – 4pm on Feb 8, March 14 and April 11. Info: 305-731-5780; ILoveStockIsland.org.

Snook’s Luau & Pig Roast

Key Largo: Swivel your hips and feast like a king during this monthly tropical extravaganza that boasts fire dancers, hula dancers, great live music, and continuous live entertainment that will keep you jumpin’ all night long. The party kicks off at 6:30 pm on Sat, Feb. 15 and Sat, March 21. Reservations a must! Takes place on the waterfront at Snook’s Bayside & Grand Tiki, MM 99.9, Bayside, Key Largo. Info: 305-453-5004; snooks.com.

February 23 & March 29
35th Annual Wrecker’s Cup Race

Key West: This is the second and third legs of the spirited 7-mile race to Sand Key, where bragging rights is the top prize. The race kicks off at 1pm with an Awards Party at Schooner Wharf Bar in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.

March 22
5th Annual Islamorada Seafood Festival & Art Show

Islamorada: This lively, hometown festival is a local favorite and always draws a fun crowd who take to the street for a day of yummy fresh seafood, culinary delights, fine art, crafts, and jammin’ entertainment. It takes place from 11am – 5pm in the Morada Way Arts & Cultural District at MM 81 on Old Hwy in Islamorada. Info: 305-664-8120.

March 28
Pops in The Park

Islamorada: Enjoy “Swaying Sounds of Paradise” by the Keys Community Concert Band at this free bayside outdoor concert. Bring your chairs and blankets. Free admission. It starts at 4pm at the Peace Park, Murray Nelson Center, Bayside, MM 102, Bayside in Key Largo. Info: 305-853-7294; keyscommunityconcertband.com.

March 28
Mote Marine’s Annual Ocean Fest

Key West: Celebrate all things ocean during a lively day of great live music, over 80 artists, vendors, conservation exhibitors, and crafts-people, along with lots of kids’ activities, a huge silent auction and more. It takes place from 10am – 6pm at NOAA’s Florida Keys Eco-Discovery Center and the Truman Waterfront. Info 305-393-6022; keysoceanfest.org.

March 28 – 29
29th Annual Florida Keys Island Fest

Islamorada: Two full days of music, food, and fun including one of the largest crafts shows in the Keys, live entertainment, sandcastle-building, kids’ activities, and the annual “Taste Of Islamorada” — a local chefs’ competition which happens on Sunday. Free admission. Takes place from 10am – 5pm at Founder’s Park, MM 87, Bayside, Islamorada. Info: 305-664-4503; islamoradachamber.com.

April 1 – 3
Dignity, Always Dignity: A Post-Apocalyptic Cabaret

Key West: Following an apocalyptic event in 2022, Tony-nominated Broadway star Bryce Pinkham finds himself stranded, coming to terms with his fate and the fate of humanity. Bryce passes the time attempting to perform the entirety of Singin’ in the Rain, determined to ‘make em laugh’ all the way to the end. Showtime 8pm at The Studios of Key West, 533 Eaton St. Info and advance tickets: 305-296-0458; tskw.org

April 3 – 5
5th Annual Papio Kinetic Sculpture Parade & Celebration

Key West: Inspired by, and named for, the late Keys artist Stanley Papio, a humorous rebel metal-artist who explored the value of recycled materials long before it was hip to be rusty. The fantastical, family-friendly cavalcade of totally human-powered art sculptures begins at noon on April 4 at the Custom House (281 Front St) and proceeds down Duval St. Info: 305-295-6616; papioskineticparade.com.

April 5
Bay Jam 26

Islamorada: This open-air music and art festival features local and guest artists performing on the shores of Florida Bay. Bring chairs and blankets. It takes place from 11am – 7pm at Founders Park, MM 87, Bayside in Islamorada. Info: 305-394-2765; keysice.com.

April 9
Cary Morin in Concert

Key West: Described as “one of the best acoustic pickers on the scene today,” Morin plays with a deft fingerstyle and melodic vocals that veer from elation to gritty world-weariness. Showtime 8pm at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org

April 13
25th Annual Taste of Key West

Key West: Over 50 top area restaurants and 100+ vineyards present mouthwatering samples of their cuisine to benefit AIDS Help, Inc. Food and wine tickets cost $1 with “tastes” ranging from $3 – $8. The culinary celebration takes place from 6 – 9pm at the Truman Waterfront Pier. Free admission. Info: 305-296-6196.

April 17 – 26
38th Annual Conch Republic Independence Celebration

Key West: Headquartered at Key West’s legendary Schooner Wharf Bar, this raucous event commemorates the founding of the Conch Republic. The celebration begins at 7pm on Fri, April 17, with the official “Kick-Off Party” and Conch Shell Blowing Contest at Schooner Wharf Bar, followed by all kinds of crazy events throughout the week. Info: 305-296-0213; conchrepublic.com.

April 25
Pops in The Park

Islamorada: This annual bayside concert series wraps up the season with a very special “Young Musicians Concert.” Bring your chairs and blankets. Free admission. The concert begins at 4pm at Founders Park, MM 87, Bayside in Islamorada. Info: 305-853-7294; keyscommunityconcertband.com.

April 26
Wrecker’s Cup Race

Key West: This is the third leg of the popular 7-mile sailing race to Sand Key. Visiting vessels and local captains and crew are all invited to this “all-in-fun” event. The race kicks off at 1pm with an Awards Party at 7pm at the Schooner Wharf Bar in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.

May 5
Cinco de Mayo Celebration

Key West: Grab your salt shaker and party with Margarita during this fun, annual celebration that includes live Salsa music, a Taco Eating & Hot Pepper Eating Contest and prizes for Best Mexican Hat. The action starts at 7pm at the Schooner Wharf Bar in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.

May 6 – 10
Key West Songwriter’s Festival

Key West: The 25th annual showcase of musical magic features America’s foremost performing songwriters with concerts staged in various venues throughout Key West. Info: 305-304-0814; keywestsongwritersfestival.com.

May 14 – 17
Key Largo Original Music Fest
Key Largo: Four days of multiple musical happenings set the stage during this eclectic music festival which showcases hit songwriters from Nashville and beyond, as well as an elite group of local and national singers and bands who perform everything from Rock to Country to Blues and more. The festival kicks off on Thurs, May14 at Sundowners Waterfront Restaurant, MM 104, Bayside and continues all weekend long with multiple stages at neighboring Cactus Jacks and Señor Frijoles. Info: 305-394-3736; keylargooriginalmusicfest.com.


Third Thursday Wine Walk

Punta Gorda: Sample a variety of delicious wines on the third Thursday evening of the month at participating merchants throughout Punta Gorda’s historic downtown district. You can purchase your all inclusive $10 wristband at Hipnotique on the day of the event or at the Punta Gorda Chamber office in advance. Info: PuntaGordaChamber.com.

April 25
Hogtown Craft Beer Festival

Gainesville: Enjoy some amazing local, and regional small-batch brews, food and craft beer pairings, educational seminars, home brewing demos and more during this annual event that celebrates a passion for brewing, beer science, and all things craft beer. Takes place from 11:30am – 5pm at Alachua County Fairgrounds, 3100 NE 39th Ave. in Gainesville. Info:352-331-4000; hogtownbeerfest.com.