How to author a weekend getaway to Key West
Breeze Airways is now flying to Key West several times a week, so TPA’s Joshua Gillin and his wife visited the island for a quick summer getaway.
Editor’s note: Tampa International Airport Senior Manager of Communications Joshua Gillin and his wife, Stephanie, took a quick weekend trip this summer to Key West with TPA’s nonstop flight on Breeze Airways, which started flying to Key West International Airport in June.
The Sunshine State is full of tourist hot spots, but few evoke such a sense of place with out-of-state visitors and Florida residents as Key West.
Laid-back vibes and local lore abound in the Conch Republic, so-named for a minute-long, mock secession from the United States in 1982. It’s a place where people go to get away from it all – including Floridians looking for a quick change of pace.
Getting there was simple enough: When Breeze Airways began its nonstop route from TPA to Key West International Airport in June, my wife Stephanie and I scooped up tickets for a long summer weekend without our child, who was away on an overseas trip. We were looking to take it as easy as we could for three nights of grownup fun, packing a single bag each and not making any plans beyond our hotel reservation.
The flight was easy, lasting less than an hour in the air before rolling up to the airport’s newly renovated passenger terminal. We skipped renting a car and took a quick ride from the airport to our hotel, the excellent La Concha Key West on Duval Street, in the heart of all the touristy fun. The six-story building opened in 1926 and hosted guests like Ernest Hemingway (more on him in a moment), President Harry S Truman and Tennessee Williams, whom the hotel says completed A Streetcar Named Desire while staying here.
Literary legends have some storied history on the island, with countless writers living on or being inspired by Key West, making for some great bookish tourism. Robert Frost wintered on the island for many years. Current resident Judy Blume owns a small bookstore, Books and Books @ The Studios of Key West, just down the road from La Concha. Shel Silverstein died in his longtime home on William Street.
And Hemingway … well, let’s just say you can’t go anywhere without seeing some reference to Hemingway, whose larger-than-life personality dominated the island for years. He fished off his famous boat Pilar (a nickname for his second wife, Pauline) in the waters nearby, and many of the people he knew on Key West made their way into his novel To Have and Have Not.
The Hemingway Home and Museum is a must-see, even if only to check out the famous six-toed cats that to this day lounge about the grounds on Whitehead Street. Hemingway lived here in the 1930s with Pauline until they eventually divorced in 1940. Tour guides dish on this tumultuous tale with plenty of juicy details, including the story of how an angry Pauline built the only in-ground swimming pool within 100 miles with her husband’s last penny, which is still pressed into the concrete pool deck.
And since we’re talking about Hemingway, we simply must discuss bars. The famous Sloppy Joe’s Bar, the hangout where Ernest met his third wife Martha, gets plenty of visitors even among Duval’s numerous watering holes, thanks to its rich history. The Green Parrot Bar has been a local landmark since originally opening as a grocery store in 1890. And on the basis of strong drinks per square foot, no other establishment can top the tiny Rum Bar at the Speakeasy Inn, where you can hammer a mean daiquiri or sip a rum flight before heading to one of this LGBTQ+-friendly town’s raucous and fun-loving drag shows at the 801 Bourbon Bar or Aqua Bar’s Birdcage Cabaret.
At some point you’re going to want to get some food, which on Key West is much more than conch fritters and the catch of the day. Fighting the throngs at the Southernmost Point marker on South and Whitehead streets or wandering through the Key West Butterfly and Nature Conservatory can really activate your appetite.
The Hemingway Home tour guide noted that Ernest allegedly frequented a brothel a couple of blocks away that now houses the tasty alfresco eatery Blue Heaven, which is now filled with live music and Key West’s ubiquitous free-range chickens, as well as a stellar Key Lime pie. First Flight Island Restaurant and Brewery makes its own beer and has good bar food, leaning into the building’s history as the first ticket office for Pan American World Airways in 1927. Perhaps the most affordable late-night option is ordering a custom slice at Angelina’s Pizzeria near the Rick’s Bar megaplex.
While packing up to leave, my wife and I discussed the things we simply hadn’t had time to do: No snorkeling, no glass-bottomed boats, no treks to see the splendor of local wildlife. We had barely scratched the surface of Key West.
It’s a good thing it’s so easy for us to come back.
Want to follow in their footsteps and book a flight on Breeze Airways? Click here.