18 Things To Do In Key West At Night

If you want to continue your Key West adventures into the night, the fun doesn’t stop. Even though Key West is known for its sunny days, the nighttime can be just as charming. The vibrant streets lit up with lights and the stars shining in the sky both make the perfect backdrop for your evening activities. Whether you want to walk Duval Street or spend a more romantic evening on the water, there are a few things to choose from.

One of the most beautiful parts of this time of day is watching the sunset go down and light up the sky with stunning colors. It’s one of our favorite experiences in Key West and we even put together a guide on the best sunset cruises in Key West.

Looking for more things to do in Key West? Here is our guide on all the best things to do in Key West.

Sunset Cruise With Dinner

Dreamy sunset views with a delicious dinner is one of the best ways to spend an evening in Key West. Start out the evening with a drink in hand as the custom-built yacht glides across the water. Then head over to the buffet style dinner where you will be served by the crew your choice of food. The buffet is tropical-themed and includes dishes like Caribbean pulled pork or marinated chicken, beans and rice or potatoes, plantains, and various veggies and salads with bread.

After dinner, it’s time to see the sunset which you can view from the upper deck. As you watch the sky turn beautiful colors, there is also live music to enjoy. Once the sun sets, the boat returns back to the seaport where you can continue your night in Key West.

Another option is to take a private sunset cruise around the island for a more intimate experience.

Night Kayaking

Explore the water around Key West in a different way by going on a night kayaking adventure. The kayaks are clear with LED lights that illuminate the surrounding water so you can see everything underneath you. It’s such a cool way to see the marine life by maybe even seeing species you wouldn’t have during the day.

The guide takes you to all of the best spots to make sure you spot marine life and have a memorable adventure. Some things you might spot are lobsters, jellyfish, sharks, crabs, and various types of fish. Just make sure to bring your mosquito spray!

Stargazing Sail

Take off into the night on an astronomer guided stargazing cruise aboard a schooner to see an amazing display of the night sky. As you leave the island and get out on the water, the light pollution fades away and you can see the dark skies revealing a canvas of stars.

The knowledgeable astronomer, who is also a NASA Solar System Ambassador, offers a live narration all about the constellations, planets, galaxies and shooting stars. It’s one of the most unique night experiences in Key West that is perfect for anyone who is an astronomy enthusiast. The tour lasts about 1.75 hours and includes one drink but more are available for purchase.

Stroll On The Pier

Strolling on the pier is a simple but good way to spend an evening. The warm sea breeze and soft sound of the ocean is very calming and you’ll see quite a few people enjoying the same thing. The Edward B. Knight Pier near Higgs Beach is the favorite for locals and visitors alike. It’s even a good place to go fishing if you choose to do so right on the island.

Private Tiki Boat

A tiki boat is another fun way to experience the island by water with a private sunset trip. Enjoy drinks, conversation and television while sitting on the padded stools. You will pass many of the famous attractions on the trip like the Sunset Pier, Mallory Square and Trumbo Point.

Not only do you get the best views of the sunset on the tiki boat with your group, you can be on the lookout for dolphins and other sea creatures. You can choose to listen to music, a narration by the captain about Key West facts, or just have conversation with your friends while enjoying the sound of the water.

Night Fishing

If you love fishing but have never tried night fishing, this is one experience you shouldn’t miss. As the sun sets, the guide takes you out to the best fishing spots around the island. This gives you a chance to catch some of the fish species that are more active in the cooler night hours. These can include snapper and tarpon, which on the right day, you could catch a ton of.

The lights surrounding the boat attract the fish to the boat as the light dances in the water. Nighttime fishing is also easier since it’s not as hot as in the heat of the day in Key West. Afterwards, you get to keep your fish and get a taste your incredible and fresh catch of the day.

Have Dinner At Louie’s Backyard

If you want to spend your evening having a nice dinner with a view, book a reservation at Louie’s Backyard in Key West. There, you will get to have a delicious meal on the terrace with a beautiful view of the ocean that you can’t beat.

They serve classic island food like the famous Key West conch made into a chowder, cracked conch with hot pepper jelly and wasabi cream, or seared bacon-wrapped scallops with creamy ravigote. For the main entrees you have your choice of fresh fish, lamp chops, or a steak. The restaurant blends traditional flavors with special twists that elevate their dishes.

The restaurant is located in a building that was built by Captain James Randall Adams who made his fortune in the wrecking and sponging industries of the time. The home stayed in the Adams family for many years until Frances and Louie Signorelli bought and turned it into the restaurant, Louie’s Backyard. In 1984, it earned a place in the National Register of Historic Places.

Nighttime Full Moon Sail

This Nighttime Full Moon Sail is one of the more romantic things to do in Key West at night. You will embark on a 1.5 hour sail under the moonlight where you can relax and enjoy the cooler night. There’s nothing like seeing the moon rise over the horizon while sailing on the calm sea.

This peaceful escape is great to get away from the crowds and enjoy a magical experience under the glow of the moon. Whether you’re celebrating a special occasion or simply want a memorable nighttime outing, this sail is a good opportunity.

Sunset At Mallory

One of the classic things to do in Key West is to catch the setting sun in Mallory Square. The sunset is accompanied by the sunset celebration where street performers, arts and crafts exhibitors, and food vendors put on a show for thousands of visitors from around the world. You’ll find jugglers, magicians, local artists and so many more cool things to see there.

The square is one of the best places to see the sunset while being on the island. Join hundreds of people enjoying the celebration and the views for one of the memorable ways to spend an evening in Key West.

Evening Stroll On Duval

Duval is lively no matter what time of day so taking a stroll down this street is another thing you can do in the evening. Peer into shops and galleries and find a bite to eat while walking around. It’s the perfect way to soak in Key West’s vibrant energy. You will probably hear music pouring out of places as you walk by and people’ chatter.

A casual evening stroll is the way to explore Duval if you want to see it without the heat of the sun. Some places might be closed but it is still enjoyable to see what Duval looks like in the evenings.

Hemingway Nighttime Tour

Learn more about the life of Ernest Hemingway on this nighttime tour. You will explore places where he lived, worked, and played. He was a renowned author and journalist whose work still remains significant today.

On the tour you will enjoy listening to music at different venue, have a guide that will show you all of the cool local spots, and be able to get a drink anywhere you choose while on the tour. The tour is about 65 minutes long and begins at 7:00pm. After you the tour you will have learned incredible stories about Key West’s past and the significant role Ernest Hemingway played in it.

Watch Show At Key West Theater

The Key West Theater is a special place featuring different kinds of events. There are music events, comedians, and games that you can book tickets to. The events usually begin at 7pm or 8pm and doors open an hour before the starting time.

Bingo is one of the popular games to play at the theater. The bingo card can be purchased at the door for $5 and the grand prize winner takes the pot at the end of the night. All of the other event tickets can also be purchased on their site online.

Indulge In Desserts

What better way to end the day than to indulge in lots of dessert? Good thing there is no shortage of delicious desserts around Key West. One of the best dessert places to visit is Better Than Sex dessert restaurant on Simonton Street. You don’t have to have a special occasion or even a romantic date to go and enjoy delicious desserts here. Some of their desserts include a peanut butter silk pie on a chocolate chip cookie dough crust, double stuffed Oreo bread pudding, classic carrot cake and cheesecake. The restaurant is open Wednesday-Friday from 6pm-11pm, Saturday until 12am, and Sunday until 11pm.

Another option for dessert in Key West is the classic Key Lime Pie. You can visit Kermit’s Key Lime Pie shop for sweet and tart Key Lime Pie desserts. Their shop is open until 9:30pm in the evenings.

Tropic Cinema

Watch a movie at the Tropic Cinema for an evening activity. This movie theater features different kinds of movies from new releases to good oldies. The time varies for the movies but many start from 6,7, and 8pm in the evening. You can go on their website to see what movies are playing and coming up in the theater to determine if there are any you want to see while in Key West.

Relax At The Beach

Relaxing on the beach in the evening is one of the most peaceful and grounding experiences you can have in Key West. You can unwind from the day and enjoy the soft waves rolling onto the beach. The Fort Zachary State Park is one of our favorite beaches in Key West to hang out at. The beach is one of the best on the island whether you want to go swimming or just relax on the beach but it does close at sunset.

Another beach that you can hang out in without hour limits is Smathers Beach which is one of the largest beaches in Key West. The palm tree lined shoreline is perfect for a walk on the beach or relaxing as the sun sets.

Comedy Key West

For the best live stand up comedy head over to Comedy Key West. It’s the only comedy club in Key West and a good late night activity that will give you a good laugh. There are different headlines every week that feature a lot of local comedic talent. Visit the site calendar to see the upcoming shows during your trip there. There is a drink menu available and a two-item minimum during the shows.

Go On A Bike Ride

There’s no better way to explore Key West than on a bike. With Key West Bike Rentals you can rent a bike to use on the island. The rates start at $14 per day depending on the kind of bike you want to rent. They have options of cruisers, E-bikes, comfort fitness, road and kids bikes. With these options you can enjoy biking all over the island with the whole family.

The rentals are by calendar day so that means you have to have your bike back by 9am the next day. This means you have the whole evening to enjoy biking and exploring the island. They offer delivery and pick up and have a driver from 9am-5pm every day with roadside assistance if needed.

Late Night Snacks

If you’re staying up late and realize you’d like to get some more food, there are a few options to choose from with late hours. The first is a Key West favorite, Blue Heaven where you can eat in the courtyard surrounded by roosters. One of their must-try things on the menu is their sky-high key lime pie topped with a tower of meringue so with closing time at 10pm you have plenty of time to try this delicious dessert.

Another local favorite for late night munchies is Mr. Z’s that serves up delicious pizza and Philly cheesesteaks. They have much later closing times at 1am and even 4am on Friday and Saturday.

Escape Room

For a fun adventure in Key West try out their escape room experience. It’s a classic thing to do if you don’t have anything else to do and a great indoor activity for those days with bad weather. Get your group together and try to beat the clock solving the puzzles and uncovering clues to solve the mystery. Most games last about an hour and are suitable for both beginners and experienced players.

Photo Shoot

Taking a photo shoot is one of the unique things to do in Key West that you might have not thought of. But it’s the perfect opportunity to capture the sunset colors and this moment forever by taking some pictures. Whether you want to have a family photoshoot, with your spouse, or even take some portraits, there is no better place to do it.

This private professional photo shoot gives you 45 fully edited, high-resolution photos within 5 business days. You have your choice of photogenic sites to choose from or go with the classic a sunset on the beach.