Here’s what’s coming up in the Keys right now.
For a list of other great events happening this Winter and Spring go to destinationfloridakeys.com
January 25 – 26
35th Annual Key West Craft Show
Key West: This juried, nationally recognized outdoor craft festival attracts over 100 fine and skilled artists who showcase their beautiful pottery, fabric, glass, wood, jewelry and other colorful handmade works. Takes place from 10am – 5pm along Whitehead St from Greene St to Eaton and on Caroline St at Truman Annex in Key West. Info: 305-294-1243.
January 26 – February 2
Key West Food & Wine Festival 2020
Key West: Celebrate the local culinary arts community and enjoy lots of lively events all over the island including a Welcome Beach Party, Wine Dinners, Shrimp Boil, Wine & Food Seminars, Bad Ass Brunches, “Duval Uncorked,” Neighborhood Wine Strolls, Grand Tasting and much more. Info: 305-292-1622; KWFoodWineFest.com.
January 26
Annual Schooner Wharf Wrecker’s Cup Race
Key West: This is the first leg of the spirited 7 mile race to Sand Key where bragging rights is top prize. Race kicks off at 1pm with an Awards Ceremony at 7pm. Takes place at Schooner Wharf Bar in Key West’s Historic Bight. Info: 305-292-3302; schoonerwharf.com.
January 26
26th Annual Master Chefs Classic
Key West: Local chefs go head to head as they compete for best of the best in Appetizer, Entree and Dessert categories as they provide an amazing array of incredible food for those who are lucky enough to snag tickets. This event always sells out early and is a fundraiser for the MARC House. Takes place from 4 – 7pm at Margaritaville Key West Resort & Marina, 245 Front St. Info: 305-294-9526; masterchefsclassic.com. Tickets: keystix.com.
January 28 – February 1
3rd Annual Mile 0 Festival
Key West: This island-wide festival stages an early Kick Off Party on Tuesday, January 28 with a free concert on Duval Street. Subsequent concerts take place on numerous stages throughout Key West. Info: mile0fest.com.
February 4
Joan Osborne
Key West: As one of the great voices of her generation, this multi-platinum selling recording artist and seven-time Grammy nominee is renowned for her gritty blues-based rock. Doors open 7pm; Showtime 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
February 9
Songwriter Speakeasy Series: Gary Hemsey, Dan Holberg, Joel Nelson
Key West: One of Key West’s best kept secrets, this monthly series showcases local songwriters who perform their original works and tell the stories behind the songs. Doors open 6:30pm; Showtime 7pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
February 9
4th Annual Food Truck Festival
Key West: The Key West Art & Historical Society plays host to this family friendly musical feast that showcases the grooving tunes of local and international acts as well as top-notch food trucks. Takes place from noon – 7pm at Fort East Martello parade grounds.
February 9
Annual Bra Walk
Islamorada: Join the Islamorada Moose Lodge’s annual March Against Cancer during this fun “Poker/Pub Run” event where you draw cards at various locations. Registration begins at the Whistle Stop from 10am – 2pm and ends up at the Islamorada Moose Lodge where there will be music, food, libations, auctions, raffles, and more. Info: 305-664-8120.
February 12
Anne McKee Artist’s Fund – 25th Annual Fine Art Auction
Key West: Supported by artists with the sole purpose of benefiting artists, this is one of the most popular, passionate and artsy parties of the year. Proceeds help fund the vital grant program for Keys artists. Takes place at 7pm at The Studios of Key West, 533 Eaton St, Key West. Special Preview from Feb 6 -12. Info: 305-296-0458; tskw.org.
February 13
Johnsmith in Concert
Key West: With faded jeans, blue eyes, and an infectious smile, Johnsmith is a guy who simply loves life, his family and friends, and sharing songs and stories. Showtime 8pm at The Studios of Key West, 533 Eaton St. Info and advance tickets: 305-296-0458; tskw.org.
February 14
Valentine’s Day Champagne & Aphrodisiacs Sunset Sail
Key West: Celebrate Valentine’s Day aboard the romantic Schooner America 2.0. with an oh-so special Champagne and Aphrodisiacs Pairing Sunset Sail. You and your true love can sail along Key West’s beautiful turquoise green waters sipping luscious champagnes and sparkling wines from around the world paired with a titillating selection of gourmet hors d’oeuvres. Ooh-la-la! Find it on the docks behind Schooner Wharf Bar in Key West’s Historic Seaport. Info and reservations: 305-293-7245;
sail-keywest.com.
February 14
Annual Wesley House Valentine’s Day Gala
Key West: This heartfelt block party doubles as a fundraiser for Wesley House Family Services and includes top entertainers, the island’s largest silent auction, open bar, dancing and a lavish buffet dinner. Takes place from 6:30-9:30pm at Key West’s historic Curry Inn, 511 Caroline St., Key West. Reservations and info: 305-809-5000. keystix.com.
February 14 – 15
60th Annual Key West Home Tours
Key West: Local residents open their doors for a good cause during this popular event where you can tour private homes ranging from colorfully, quirky preserved relics to avant-garde designers’ visions. Take place from 10am – 4pm. Tickets and tour schedule at oirf.org.
February 15
4th Annual ALR Coral Head Music Festival
Marathon: This two-day, jam-packed charity event showcases several nationally recognized bands as well as many local favorites and over 80 vendors. Proceeds benefit various local charities. Takes place from Noon – 10pm at Marathon Community Park. Info: songkick.com.
February 15
Upper Keys Garden Walk
Key Largo: Tour several private out–of-sight gardens, then enjoy a complimentary Tea Party, spectacular Garden Market and groovy art show. Takes place from 10am – 4pm and kicks off from the Francis Tracy Garden Center, MM 94, Bayside in Key Largo. Info: gardenclubupperkeys.org.
February 19 – 22
Anna in the Tropics
Key West: Nilo Cruz’s Pulitzer Prize winning script celebrates the cultural history of Cuban immigrants during an era of sultry tropical nights shrouded in cigar smoke. Showtime 8pm at The Studios of Key West, 533 Eaton St. Info and advance tickets: 305-296-0458; tskw.org.
February 22 – March 30
Tennessee Williams Birthday Celebration
Key West: This series of island-wide arts and cultural events includes a big bash at the Tennessee Williams Museum celebrating Tennessee Williams’ birthday on March 26. There will also be ongoing curator tours of the award-winning museum at 513 Truman Ave. Info: kwahs.org.
February 26 – 29
Anna in the Tropics
Key West: Nilo Cruz’s Pulitzer Prize winning script, celebrates the cultural history of Cuban immigrants, during an era of sultry tropical nights shrouded in cigar smoke. Showtime 8pm at The Studios of Key West, 533 Eaton St. Info and advance tickets: 305-296-0458; tskw.org.
February 22 – 23
Annual Gigantic Nautical Flea Market
Islamorada: Get great deals on new and used boats, marine equipment, electronics, fishing tackle, dive gear, nautical arts & crafts and more from over 200 vendors. Takes place from 8am – 3pm at Founders Park, MM 87, Bayside. Info: 305-712-1818.
February 22 – 23
55th Annual Old Island Days Art Festival
Key West: This nationally recognized juried fine art show attracts fine artists from across the country and includes painters, sculptors, photographers, collage artists and other non-functional fine arts. Takes place from 10am – 5pm on lower Whitehead and Caroline Streets. Info: 305-294-1243; keywestartcenter.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 top prize. 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.
February 29
Pops in The Park
Islamorada: Enjoy this free bayside outdoor concert by the Keys Community Concert Band. Bring your chairs and blankets. The fun begins at 4pm at Founders Park, MM 87, Bayside in Islamorada. Info: 305-853-7294; keyscommunityconcertband.com.
See more at DestinationFloridaKeys.com.
