Inside Key West Music Festivals

Key West boasts a live music scene that is sometimes said to rival those of Nashville and New Orleans. The island is home to many talented musicians, and many more visit each year. Local artists and world class acts alike can be found on stage any day of the year in a multitude of venues. From the blues to calypso, country-western, hip hop, jazz, reggae, retro, or the Keys’ own trop rock, something is always happening around town.

For the lucky folks who will be in Key West the week of May 3-11, and those who love outdoor music in tropical settings enough to make sure they will be there, the best musical happening in the Keys is set to go off. The week will kick off at 5 pm on Saturday, May 3rd, with the second annual Keystock Festival bringing rock legends The Doobie Brothers and local favorite Howard Livingston to the Truman Waterfront on the end of Southard Street in Key West.  Maybe we are showing our age here, but for those who may actually not know the Doobies, they are old school rockers with 40 years, 4 Grammys, and international hits including “China Grove,” “Black Water”, “Listen to the Music”, “Long Train Runnin”, and “What a Fool Believes” under their belts. To open the show, Howard Livingston and the Mile Marker 24 Band will break out their outboard motor-powered margarita blender and apropos tunes like “Blame It On the Margaritas” and “Livin’ On Key West Time”.

Keystock is the latest addition to an already great Key West music scene, and it is the creation of a collaborative effort by Alabama native Joe Cleghorn, owner of the Lazy Lakes RV Resort on Sugarloaf Key, musician Howard Livingston, Cleghorn’s business partner Dave McGlathery, and the staff of Lazy Lakes. For several years, Cleghorn and crew had been putting on concerts at the RV park, bringing in artists such as Jerry Jeff Walker, Mac McAnally, and Blood Sweat & Tears, along with hundreds of music lovers to enjoy sunshine, good tunes, and good times in the quaint setting of Lazy Lakes.

As the crowds grew, ideas about bigger venues and larger objectives began bubbling, including forming the non-profit Homes For Veterans, Inc., and using a music festival to raise the funds to award a paid-in-full home to a selected military veteran. With some inspiration from country music star Cowboy Troy of Big and Rich, and some Nashville connections, Keystock was born in 2013 when Livingston and the Mile Marker 24 Band opened for Three Dog Night and thousands of fans at the Truman Waterfront.  Now, what is already being called the greatest concert series in the Keys is set to bring it again, and do it for a good cause, with The Doobie Brothers in town with the kind of showmanship that has sold over 40 million albums.

The bands play on from May 7-11 when fans and performers from across the country hit town for the Key West Songwriter’s Festival. The Festival is by far the largest musical event held in Key West, with 5 days of performances and special events on tap. The biggest songwriter festival in the US, organized by BMI Nashville, America’s largest music rights organization and a major incubator of new talent and new music, the Key West festival pulls in many of America’s finest songwriters from Nashville and elsewhere. Over 150 artists will entertain fans from afternoon to evening. The event features many special shows including studio performances, sunset cruises, shows at the historic San Carlos Institute and Tropic Cinema, pool parties, a champagne brunch performance, a dinner show, and free street concerts. There is something here for every live music fan, and it is a chance to meet the artists behind some of your favorite songs.

If you love live music, and want to see some great bands in a tropical outdoor festival setting, the first week in May is the time to come down to Key West. Make plans now and don’t miss two great Key West Music Festivals.

Inside Five Brothers: The Old Key West Corner Store

No visit to Key West is complete without a stop at the Five Brothers corner store for a Cuban café con leche and maybe a mixto sandwich as well. This classic little neighborhood grocery occupies a vintage building at Southard and Grinnell (930 Southard St.) in the heart of town, and locals and tourists alike have been dropping in for 23 years to grab coffees, sandwiches or lunch plates, groceries and sundries, and hand-rolled Cuban seed cigars. People drop by Five Brothers to catch up on town gossip and soak up the atmosphere as their Key West neighbors chat in Spanish and grab cups of the strong, sweet coffee brewed fresh from the 24 pounds of beans the store goes through every day.

A true family operation, Five Brothers is now run by the son of one of the original namesake 5 whose pictures make up the logo for the store. Be prepared to find a line of local working people and visitors when you drop in to sample the creations of owner Heriberto Paez Jr. and his family members. These hometown folks work six days a week to turn out the delicious coffees and authentic Cuban bread sandwiches like egg and cheese, fried grouper, mixed meat, palomilla steak, and roast pork. Besides sandwiches that have earned a solid reputation with everyone from Key West police and firemen, construction and utility crews, to retired millionaires and visiting celebrities, Five Brothers puts on daily lunch plate specials with treats like beef stew, chicken fricassee, picadillo, ropa vieja, and empanadas.

Prices are reasonable and with no tables, everything is grab and go, so this is the perfect place to pick up a picnic snack and head over to Mallory Square, down to the waterfront, or into the nearby historic cemetery. I find that the Cuban mix sandwiches do live up to their reputation as some of the best around, and the Fried Grouper and BBQ Pork sandwiches are also local favorites. And because this store caters to everyone, there’s even a veggie burger that is pretty good. The food and coffee are well worth the wait if you happen to catch the line during the morning or lunch rush.

After placing your order, take a minute to browse the eclectic selection of groceries and dry goods that capture the Cuban flavor of Key West with items like votive candles, chorizo, domino sets, spices, guava paste, beans and rice, violet cologne, and wines from the screw-top to the fine. Or just stand in line and eavesdrop on the local gossip because this place is a real crossroads of island society. Like many others, you will probably find yourself returning multiple times because each visit is an interesting treat that goes beyond the great-tasting coffee and lunch. However, if you want to catch lunch by the pool or in your room, Five Brothers delivers from 7:00 am to 2:30 pm.

Enjoy the Cuban/Key West cross-cultural mix in the neighborhoods of Old Town with a stop at Five Brothers. Chances are you will put this little corner store on your must-visit list for every trip you make to the island.