Florida Bars
Wekiva Island
Want to “experience the real Florida”? Spend a day at Wekiva Island! Our ideal excursion to Wekiva Island involves getting there early in the morning before the crowds, renting kayaks or canoes, and paddling down the Wekiva River. Once we reach Wekiwa Springs State Park (a small admission fee is charged), we take a dip in the crystal-clear springs. Then we leisurely paddle back to Wekiva Island for juicy burgers and ice-cold beers. Wekiva Island features a scenic boardwalk, sand volleyball court, Without a Paddle Cafe, General Store and The Tooting Otter craft beer and wine bar. It’s a great place to take visitors when they need a welcome break from all the stresses associated with theme park exploration! Wekiva Island is located at 1014 Miami Springs Drive in Longwood. Hours are 8 AM to 7 PM Sunday through Thursday and 8 AM to 11 PM Friday and Saturday.
AJ’s on the River
Enjoy a juicy burger and ice-cold beer on an outdoor deck overlooking the Alafia River in the heart of Gibsonton (AKA “Gibtown). What more could you ask for? I recommend the Goat Cheese Burger drizzled with balsamic — absolutely delicious! In addition, AJ’s hosts live music several days a week. AJ’s on the River is located at 9808 Vaughn Street (take Exit 250 off I-75). It is open daily for lunch and dinner.
Showtown Bar & Grill, “Gibtown”
“There’s a place that I remember
Down along a twisted river
It’s a circus come the winter time
It’s just off the road to nowhere
And the carnies always go there
It’s like having family for a while …”
—Al Scortino, “Gibtown“
Green Parrot Bar
Billed as “A Sunny Place for Shady People,” the Green Parrot Bar is one of my favorite Key West dive bars.
Shady Oak Restaurant & Tavern
As a student at Stetson University during the mid-1980s, I would often join a ritual mass exodus off campus each Friday afternoon after classes to a somewhat rundown but lively fish camp overlooking the St. John’s River just off State Road 44 that we called Otis’s and the locals referred to as Sloan’s (both names derived from then-owner Otis Sloan). There we would spend hours hanging out on the dock drinking cheap beer and watching the boats slowly drift by – great memories! According to a September 2, 1998, Orlando Sentinel article, Sloan and his wife Myrtle opened the Shady Oak Fish Camp in 1957. I passed through DeLand in 2015 and took the above photos of Otis’s and it looked pretty much the same as I had remembered it. The Shady Oak Restaurant, which is located at 2984 West New York Avenue just west of downtown DeLand, reportedly suffered a fire in 2017 but has fortunately reopened.
Caribbean Club, Key Largo

According to its official website, the Caribbean Club was opened in 1938 by legendary automotive and real estate promoter Carl Fisher “as a poor-man’s fishing retreat.” It later became a gambling den. The bar served as a filming location for exterior shots from the classic 1948 film Key Largo, which was directed by John Huston and starred Humphrey Bogart, Lauren Bacall and Edward G. Robinson. The photo above was taken by legendary commercial photographer Joseph Janney Steinmetz (1905-1985). The Caribbean Club is the oldest bar in the Upper Keys. Today, the bar offers “live music, daily happy hours, waterfront sunset views and a dog-friendly atmosphere.” Ideally located at Mile Marker 104 bayside, it is open 7 AM to 4 AM “every damn day.” Note: The Caribbean Club is a cash-only bar with an onsite ATM. The bar served as a filming location for the Netflix original series, Bloodline. According to Jimmy Buffett, “It was a bar like many others and then it wasn’t.”

