Key West, Florida is the southernmost city of continental USA and gives you a chance of enjoying the much sought-after Caribbean vibe without ever leaving the states.

The island is popular for it’s eccentric, wild and laid-back vibe that is highly inviting to most cruise passengers. So popular is the island that it has provided seasonal homes to notable figures such as the 33rd president and one of the world’s most prolific writers.

The island is rich in History, combining 19th-century history with its vast tropical charms to create a haven for adventurers and historians alike. This town mashes together brightly colored picturesque colonial houses with lush tropical gardens.

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Its narrow streets are lined with vintage shops, eateries, and watering holes. The coastline as well is breathtaking and is graced by the azure waters of the Atlantic and Gulf stream that boards the island on either side.

With all this, it’s easy to see why Key West is an essential port of call for cruise ships and we’ve decided to come up with all the fun things to do in Key West, Florida while on a cruise.

1. It all Starts at Duval Street

One of the most popular streets in Key West is Duval Street. This is the main street in the island stretching from Mallory Square to the Southernmost point. This street contains most of the towns bustle with vintage eateries, watering holes, and artsy shops.

Duval Street, Key West
Photo By: Emrys Thakkar

Through the high seasons, the streets are crowded with people looking for fun. Expect to have fun and meet new people as you explore the art galleries, unique boutiques, food joints and much more.

2. Sunken Treasure Hunt

One of the most popular activities in Key West is the treasure hunt. Shipwrecks and their loot once made this town one of the richest in the USA. There is a well-known treasure hunter called Mel Fisher who made the discovery of “Attocha” the sunken vessels.

These Spanish vessels offer tourists a chance at exploring sunken treasures. Visit the Mel Fisher Maritime Museum to explore the treasures found in the discovered Spanish vessels and go for a dive for further explorations.

3. Sun, Sand, and Sea

While not known for unique beach experiences, Key West still features great accessible beaches for a day of sun, sand, and fun. There are a number of beaches in this region, but the most popular one is Smathers Beach. This two-mile stretch of white sandy beach is beautiful with its jewel-blue waters and serene atmosphere. It’s a nice place to relax and unwind.

Get all your beach accessories for your port of call right here.

The water itself is not always conducive for swimming but activities such as boating; snorkeling can be fun to explore. Unlike Smathers beach, Higgs beach has shallow waters which can be fun if a nice dip is what you are looking for.

However, these beaches being public and near touristy regions makes them susceptible to overcrowding. If you fancy a secluded beach then a trip to Zachary Taylor Fort ‘s beach will do you right.

Also Read: 10 Reasons Why You Should Cruise From Florida

4. Enjoy Biking

At 4 miles long and 1 mile wide, the island of Key West is very walkable. If you want to see all the island’s vast number of attractions and landmarks, a bicycle might come in handy. Rent a bike and enjoy a tour of the island’s highlights.

Ride through the most natural terrain with the challenge only picking towards the cemetery, which is 20 feet above sea level. The rest of the area is friendly for bike adventures. Both short and long-distance biking is recommended. There are several places you can rent the bikes at. Check online for reviews and price comparisons.

5. The Southernmost Point

How else do you let the rest of the world know you have been to Key West? Simple, by taking a selfie or photo of yourself at the Southernmost Point Monument. This monument is a giant buoy built in the 80’s to represent the southernmost tip of the US.

Key West, Florida

However, it’s only actually the second southernmost point but this detail rarely matters due to the inaccessibility of the true southernmost tip. It is brightly marked by red and yellow colors and is only 90 miles away from Cuba.

You can actually buy Southernmost Point souvenirs including magnets and shot glasses by clicking here.

Many tourists tour this iconic site. So, expect to queue, if you want to snap a photo, or go very early in the morning for a picture-perfect piece.

6. Conch Train Ride

For a cheap feel of the town without overindulging, take the touristy Conch Train Ride. This tour takes you through the old town of Key West.

Key West Tour

The ride is about 90 minute’s tops and has three main stops, the station depot, where you can shop till you drop. The Truval Village stop where you can taste the exquisite cuisine of key west and the Ernest Hemming ways home as well as a stop at the museum.

7. Key West Cemetery

If mystery, is your thrill, visit Key West cemetery to learn the interesting part of the town’s former times. The gravestones of fallen soldiers and town’s folks go into depth about the life and death of the individual. Epitaphs like “I told you I was sick” among others can be traced in this location, making it a twisted but interesting fun thing to explore.

Key West Cemetery

For more thrill, take up the haunted tours walk, where you will get to learn about the most outrageous stories of Key West.

8. Take a Rum Tour

The special rum runner drink is a treat that’s found in several bars in Key West like Hogs breathe saloon among others. The Tiki bar (located at the Postcard Inn Beach Resort) is where the first rum challenge originated from.

Here’s the popular Tortuga Caribbean Rum Cake which you can buy from Amazon.

The challenge was to make a cocktail out of overstocked liquor in the bar. Since then, a majority of bars in Key West have added the concoction to their menu. The drink consists of a mix of banana liquor, brandy, grenadine, and Meyers rum. Have a drink, a laugh and enjoy the towns originals.

9. Beautiful Birds View

If fitness and breath-taking vistas are your things, then climb up the 88 steps of Key West’s Lighthouse for a beautiful bird’s view of the entire island and great waters. Learn the island’s history on your way to the top and enjoy the stunning views.

Key West from the Lighthouse

10. Sloppy Joe’s Bar

Key West has a wild nightlife. One of its most iconic bars includes the Sloppy Joes. Sloppy Joe is an old vintage bar that brags of Ernest Hemmingway as a longtime patron.

Sloppy Joe's Bar, Key West
Photo By: Emrys Thakkar

While it might be thrilling to enjoy the same drink as the famous writer did, keep in mind that the place gets overcrowded and is quite pricey. You might want to visit during off-peak hours.

11. The Bahama Village

Take a walking tour of the Bahama Village. Here you get to experience different cultural histories. The village used to be a landing area for Bahamian workers and has a higher concentration of 19th-century structures.

Explore the narrow streets and the history found at every turning point. Enjoying the local cuisine and shopping available along the streets.

12. The Hemmingway Home

Visit the Hemmingway Home, an 1851 Spanish colonial building that hosted one of the world’s greatest writers of all time. The most intriguing thing about this home is that the famous writer lived here for almost a decade.

It’s worth reading books by Ernest Hemingway, view collection here.

The house is located in a picturesque, lush peaceful environment and is easy to see why Ernest Hemmingway was inspired to write some of his masterpieces here.

Hemingway House, Key West

Other than touring the well-preserved decor and furnishings of the house that make up the museum’s exhibit. You will also get to meet cats from snow white’s lineage (Hemmingway’s beloved six-toed cat) who was owned by the family. This home is now considered the heart of Key West town and is now a museum.

13. Truman’s Little White House

Another home that requires some attention would be the Little White House. This home was originally a naval station’s command headquarters during World War 1 and World War 2. Harry Truman the 33rd US president called this house, home for several winters.

Truman visited Florida 11 times and used to reside in this little white house. The home is currently owned by the state of Florida but managed by non-profit institutions as a museum with rich historical artifacts.

14. Dry Tortugas National Park

Lack of fresh water in this park led to it being named “dry”. This is a small island located a few miles offshore and only accessible by boat or airplane. It hosted a very strategic military fort in the 19th century.

This piece of land which was once the functional Fort Jefferson is now turned into a park with rich beauty and teeming with marine life.

The park consists of submerged coral reefs that are home to plenty of aquatic life. You can swim, dive and snorkel offshore of this park’s beaches. Make sure to explore Fort Jefferson while you are at it.

15. Key West Lime Pie

Being a signature dessert for Key West, this is a taste you don’t want to miss. Your sweet tooth is in for a treat with this pie that contains limes, a graham cracker crust, and other secret ingredients. Best of all the pie is available in restaurants across all the Keys.

16. Dolphins Research Centre

For an encounter with dolphins visit the Dolphin Research Centre or go on a Dolphin Safari. It’s a good place to learn the upkeep of dolphins and sea lions as you interact with them. However, if you fancy more play time with these cheerful mammals then a boat tour offshore will take you to their natural habitat for a more up-close interaction.

17. Watersports

Key West has plenty of healthy coral reefs to explore. Apart from exploring the island, water sports are the most popular activities on the island.

Key West Water Sports

You can charter boat rides to explore the coastline or go snorkeling, scuba diving, kayaking, paddle boarding or even parasailing. You are definitely guaranteed ridiculous fun.

Water Shoes are a must for these type activities, get yours here.

18. Shop Art and Souvenirs

There are many art galleries at your disposal, whether you intend to buy or just be inspired. Streets like Duval showcase plenty of mind-bogglingly beautiful art.  Every month there are art events that showcase new artists. So be on the lookout for something new and otherworldly beautiful.

Get all your Key West souvenirs online so you don’t have to worry when in port.

19. Theatre

Be entertained all round, by making a stopover at one of the many theatres in Key West. Most familiar spots include Key West Theatre, Waterfront Play House, Tennessee Williams theatre, or Red Barn Theatre.

20. Mallory Square

Lastly but not least, you cannot say you have been to Key West if you didn’t join in on the island’s sunset watching celebration at Mallory Square.

Key West Cruise Port

Grab a drink of your choice, get your camera ready and enjoy an unforgettable sunset as well as upbeat music and energetic performances at the square. The performances include jugglers, tight-rope walkers, musicians and magicians who display their talent for your entertainment.

Also Read: Top 5 Things to See When Cruising South Florida

Expect to laugh, cry, get shocked, and glare in amazement as the trained experts do their thing, for the better part of the night. It’s also a great place to take some pictures and buy unique local crafts as you enjoy the sunset.

Key West Weather

The Florida Key regions normally have a tropical climate with the dry season running in late fall. Some months like August and September occasionally experience Hurricane disruptions. Best time to cruise through would be in winter or early spring when the tropical weather is calm.

Being in such a hot climate you’ll need sunscreen and bug spray, they can be expensive on the ship.

We’ll See You There!

While on tour, make sure not to miss the conch delicacies of Key West. Definitely try the lobster fest, you will thank us later. Another tasty dessert to try is the chocolate covered coconut candy that’s found in all the major shops.

You might also want to explore the world’s largest artificial reef, sample spiny lobsters, shop authentic island souvenirs. Visit the key toy factory, the sandal factory that manufactures handcrafted footwear, get cultured. Or learn about sea turtles among others.

There you have it, all you need to know about Key West, Florida. Enjoy your visit there. Happy Cruising!!

Check all these fun things to do in Key West, Florida while on a cruise vacation. We've got cruise tips to make sure you have the best time at this Florida destination.