These Key West Hotspots Find Their Niche Serving Out-of-the-Box Pleasures

When it comes to adult-style fun in the sun, there’s no doubt Key West does it best.

A walk through Mallory Square reveals Key West’s unique ability to attract visitors from all walks of life: Families, sunset seekers, and bachelorette parties alike can find whatever they’re looking for in this low-latitude locale.

Key West has a rich history that blends with contemporary vibes. It showcases offbeat shops, delectable restaurants, and booming nightclubs. The owners of these long-established businesses do things their way, and guests can take it or leave it.

With its own eclectic energy, this vibrant area attracts guests looking to let loose. However, visitors shouldn’t venture down Key West’s infamous Duval Street if they’re looking for run-of-the-mill entertainment.

This lively strip of island nightlife embraces its party reputation, throwing the idea of cookie-cutter service overboard. Live music resonates from inside clubs that are as different as the people inside—from cowboy saloons to drag bars to intimate coffee shops, guests can take their pick depending on their mood.

Key West has boomed back from post-pandemic lulls, proving to be much more than pirate life and margaritas. A recent visit reveals some highlights of what guests can expect in the offbeat, colorful city of Key West.

Did somebody say dessert?

It’s as good as it gets in the Keys, at least according to Len and Dani Johnson, who created their specialty dessert restaurant Better Than Sex to combine their passions for sweets and the Florida Keys.

Meeting as servers at a popular restaurant chain, Len and Dani loved vacationing in Key West. They finally decided to start their own business after Dani’s home-baking experiments became standout dishes. Len exclaimed after eating one of her desserts: “This is better than sex!” Five years of perfecting her dishes led to the inception of Better Than Sex.

The interior resembles a moody speakeasy, with tasteful nude portraits plastered on every wall and inside every dimly-lit booth. Tables are for the most part privately partitioned, so couples can enjoy a truly romantic atmosphere.

Now operating in multiple cities, Better Than Sex’s Key West location only has 18 tables, and in keeping with the speakeasy theme, they do not accommodate large parties and discourage guests from bringing children.

A reservation is a must for guests wanting to make sure they have a chance to enjoy some Peanut Butter Perversion Pie or Key Lime Pearl Necklace.

Loud, proud, and effortlessly fabulous

Since the early 20th century, the queer community has found a safe haven in open-minded Key West. The LGBTQ+ population is largely responsible for developing the area into the booming travel destination it has become.

Queer tourists are attracted to Key West’s arts scene and gay entertainment industry. Some of the best spots guests can experience while they’re in town – regardless of sexual orientation – are the drag shows like those at 801 Bourbon Bar. Their nightly performances, cabarets and singalongs are all-inclusive, ensuring that anyone and everyone can participate in the good times.

801 Bourbon Bar features classic on-stage entertainers bathed in neon lights, but performers also surround the magnificent center bar and are stationed outside to allure patrons to come in for a good time.

Once they enter, guests are signing themselves up for an open-minded adventure. The performers reserve the right to tease and taunt anyone they choose.

Nightly shows cost an entrance fee, but 801 Bourbon Bar strategically offers a free 5pm matinee that blasts loudly for anyone walking by to hear. The sidewalks outside the bar are almost as lively as the magical events happening inside.

As for cost, ticket prices are more than fair considering the singing, dancing, and all-around superb showmanship the ladies have to offer.

Pizza, beer, and fierce competition

After an evening of dessert sex, drag shows, and dancing the night away in various clubs and bars, guests will of course want one thing: really good pizza.

Luckily, there’s Angelina’s. Located next door to Rick’s (an infamous hotspot in its own right boasting a two-story bar/nightclub complex), Angelina’s is a small pizza joint featuring vintage arcade games and a wall full of devoted celebs that double as satisfied customers. Known as “The Best Piece in Town,” Angelina’s fits right in with the feisty energy of Duval.

Kit Carson Smith started Angelina’s back in 1988 after supporting himself through college working as a bartender. His dedication to the hospitality trade led Smith to develop a passion for pizza. Pizza plus a love for island life was the perfect recipe for Angelina’s.

Affectionately called the Earl of Pizza, Smith even has his own podcast: Sit With Kit includes conversations with Key West characters that pop into Smith’s pizza joint.

Some of the most interesting moments at Angelina’s come from regulars who station themselves at the video games lining the wall. Guests can watch as these fierce competitors  get into intense showdowns over that night’s Golden Tee golf game.

One thing’s for sure: Whether guests come to Key West for dessert, entertainment, pizza, or something else entirely, there’s something for everyone.