Key West’s tropical climate, abundant ocean activities, and lively social scene make it one of the most ideal destinations for adventurous travelers. Among popular activities like diving, snorkeling, sailing, and golfing, you will find plenty to experience year-round on Key West’s welcoming shores.
But what if you’re craving a relaxed day in town? We’ve got you covered with the gayest Key West walking tour imaginable, highlighting just a few of the great shops this island paradise has to offer.
First thing’s first: When looking for a place to stay, we recommend the Guesthouse District, a happening ‘hood with tons of friendly accommodations. While you can’t go wrong with any of these stays, one great choice is Alexander’s Guesthouse. This villa, built in 1902, creates an inviting atmosphere while providing the perfect launchpad for Key West’s party epicenter on Duval Street.
1. Kirby’s Closet
After breakfast, start your walking tour by heading west on Caroline Street in Old Town. This iconic street, one of the oldest on the island, is lined with some of Key West’s most remarkable conch houses and historical points of interest. Turn right at the end of the road, and you’ll come across Kirby’s Closet, a women’s secondhand apparel boutique. The owner, Kirby, was inspired to give the ladies of Key West a fun place to shop in an inclusive atmosphere with affordable prices.
After you found just the right piece for your island wardrobe, head over to Key West’s first legal rum distillery on Simonton Street. They offer free tours of their facility and have mojito-making classes for interested parties. What’s better than learning something new while day drinking?
2. Books and Books
Once you’re nice and toasty, it’s time to find a beach read for afternoons in the sand. Meander down Eaton Street to the Studios of Key West, a locally-owned, nonprofit neighborhood bookstore affiliated with the national independent bookseller, Books and Books. With over 5,000 titles, you’re bound to find a page-turner for your vacation.
After your visit, wander around the corner to Nancy Forrester’s Secret Garden, a quirky sanctuary for rescued parrots and tropical birds. Local artist and teacher Nancy Forrester has been rescuing and caring for these exotic creatures for over 45 years. She loves to tell visitors each parrot’s story while educating them about wildlife preservation.
3. La Rubia Panama Hats
Let’s continue our walking and shopping tour at La Rubia Panama Hats. While traveling through Ecuador, owner Stephanie fell in love with “Panama style” hats and wanted to share them with her community at home in Key West. She imports from skilled artisans in Ecuador, supporting their rich tradition, culture, and history of weaving these hats by hand. Coincidentally, Panama hats are perfect for Florida’s humid, tropical climate.
At this point, you’ve probably worked up an appetite. If it’s Thursday, you’re in luck. Starting around 2 pm, you will find the Truman Waterfront Market, a weekly market with fresh produce, food vendors, and local artisans. As you wander the stalls and gorge yourself on tropical fruit and hawker fare, you may also stumble across a souvenir or two for your friends back home. Any other day of the week, you’ll want to make a quick detour down Duval Street and check out one of the many excellent restaurants along the way.
4. Graffitti Menswear
Now that you’ve recharged with a bite to eat, complete your look at Graffitti on Duval Street. This menswear outpost has an outfit for every island vibe– whether it’s a day at the beach or a bar crawl with the boys at night. You’ll find muscle tees and tight shorts galore, on the rack and on the cute shopkeepers. If you have room in your schedule and want to learn a bit of queer history, check out the Tennesee Williams Museum nearby. This openly-gay playwright called Key West home for over 30 years.
Now that you have a book, sunhat, and new outfit, it’s time to hit the beach. Make your way south to Higgs Beach, Key west’s unofficial gay beach, for some fun in the sun. Just a word of warning, Key West has only a few beaches, and Higgs is by far the busiest. If you want to avoid a crowd, it’s best to go later in the day, as most folks want to catch the sunset on the other side of the island. Higgs’ shallow waters make for good snorkeling and swimming, though umbrella chair rentals are also available if you fancy a nap in the shade.
5. Shade & Shutter
The last stop on our walking tour is a locally-owned and operated art gallery that truly captures the “one human family” spirit of Key West. At Shade & Shutter, not only will you find artfully crafted pottery and gorgeous photography, but also a deep sense of community pride. Owners Mike and Sarah are members of the Key West Business Guild and want to give back to their beloved island home. When they first opened their doors in 2019, they pledged to donate 10 percent of their profits to local charities like Equality Florida and Sister Season. In 2020, they doubled their contributions.
After visiting the last shop on our list, you might need a late afternoon pick-me-up. Turn the corner onto Truman Street and treat yourself to Cupcake Sushi. These adorable, delectable cupcake creations are a worthwhile reason to spoil your appetite for dinner. Though, if you rather skip straight to supper, we recommend taking White Street back towards the Guesthouse District and hanging out with the friendly folks at Off The Hook Grill. Located next to Key West’s Historic Seaport, this snug seafood bistro has something on the menu for everyone, even the dogs!