10 Best Things to Do After Dinner in the Florida Keys

A sunset cruise in the Florida Keys lets you spend a relaxing evening on the waves. There’s no easier way to enjoy a meal and an unforgettable evening. The price of your cruise includes a dinner buffet (featuring local seafood, Caribbean fare, and American favorites) and entertainment like dancing or music. But the best part is witnessing the spectacular sunset from the deck of a luxurious vessel.

Some of the top sunset cruise operators include Cruisin’ Tikis Key Largo, Sunset Sail Key West, and Floridays. There are cruises available at all price points and in many types of boats.

The Sunset Celebration at Mallory Square is a daily gathering of locals and visitors that’s been going for centuries. Mallory Square has been a center of commerce and society for over 200 years, and it happens to be on a port with a spectacular view of the sunset.

Gather at dusk to share a drink and chat with others as you watch the sun go down. It’s a great opportunity for vacation photos and romantic moments. Arrive with plenty of time to spare to shop around or grab a bite at the many shops and restaurants in Mallory Square.

The Waterfront Playhouse opens its door after dark, hosting some of the highest-rated entertainment in Florida. The historic theater has been running for over 80 years. It can accommodate 150 guests looking to enjoy a thrilling and intimate performance in Key West. 

The playhouse hosts daily performances year-round, spanning all genres and including world-premieres. Crowd favorites include The Rocky Horror Show, Spamalot, and Frozen. Make sure to book in advance – it's popular with locals and visitors, so tickets sell fast. The Waterfront Playhouse is located in Mallory Square, which means you can enjoy an iconic sunset and a show on the same evening.

Lorelei Restaurant & Cabana Bar is a classic American roadhouse in Islamorada. It's known for its laidback atmosphere and fresh-caught seafood, as well as its lengthy cocktail menu and live music by local artists. The Lorelei Sunset cocktail is a must-try, featuring tangerine vodka made exclusively for this cabana bar.

Lorelei is a music pub, but it’s not a party bar. This is the place to kick back and relax on the water or enjoy a delicious meal before going out for late-night fun. Happy hour is from 4 pm to 6 pm every day. Come early for drink specials and a nice view of the sunset. 

Caribbean Club is the place to be after dinner in the Florida Keys if your goal is to spend as much time on the beach as possible. This watering hole is famous for being the filming location of the Humphry Bogart movie, Key Largo.

At Caribbean Club, you can spend your evenings on the sand under palm trees. As live music competes with the sound of the lapping waves, you’ll find it hard to imagine a better place to spend a chill evening in the Florida Keys. The beverages here are far from generic. Cocktail lovers will love the Key Lime Pie Rum Punch, while beer lovers can choose from a range of local craft brews.  

The Cabaret at La Te Da is a rollicking drag show that’s guaranteed to put a smile on your face. Consistently rated one of the best shows in the Florida Keys, the lovely “ladies” blend dance, comedy, and erotic fun for the 21+ crowd.

The Broadway-quality shows are hosted by some of America’s most famous performers, who develop and premier unique shows at La Te Da. Not in the mood for a drag show? La Te Da also has a piano bar that requires no ticket. It offers relaxing entertainment from 8.30 pm to 11.30 pm.

Capt Tony’s Sedan is one of the oldest bars in Floria. The stools at this Key West dive have hosted some of the country's most famous figures, including Ernest Hemingway, Truman Capote, President John F. Kennedy, and Jimmy Buffet.

Built in 1852, Capt Tony’s has seen its share of American history over the years. Nowadays, it’s a popular spot for live music and themed parties in Key West. Don’t forget to toss a quarter into the mouth of a fish hanging above the door – it brings good luck!

The Smallest Bar in Key West is about the size of a jail cell. The only difference is that you won’t easily want to leave this tiny space. Being small isn’t this bar’s only claim to fame. It’s also home to some of the Keys’ most affordable (and dangerously drinkable) cocktails. Stop in for a sip if you can find a seat or mingle with the crowd gathering on the sidewalk outside the bar.  

You’ll find all the classic beachy cocktails, from piña coladas to margaritas. The Smallest Bar is also open much later than most other bars in the area – until 3.30 am every night.

Green Parrot Bar is a quintessential American bar in Key West, featuring live tunes, an old-school jukebox, and ice-cold beers. Frequently packed with visitors and locals, it has been a local institution since 1890.

Green Parrot Bar is a no-nonsense nightlife venue. You may have to stand among the locals while enjoying live music. However, the atmosphere is never stuffy thanks to large open windows letting the sea breeze pass through. Come here to make friends or discover your next favorite band. Green Parrot Bar has daily happy hour promos from 4 pm to 7 pm.

Aqua Bar and Nightclub is a prominent dance club that often stays bust until the wee hours in Key West. It features a variety of shows and parties, including one of the best drag shows in Southern Florida. The dance club hosts DJs every night of the week and happy hour until 11 pm.

The dress code is as laidback as Key West, meaning you can walk off the beach and into the club without hassle – even sandals are welcome (though some special parties have a dress code). Feeling hungry? Grab a late-night poké bowl at the bar before enjoying a night of dancing.