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Day Trip or Cruise Port Stop in Key West: 2024 Guide

Are you going on a cruise with a Port Day stop at Key West? Have you never been to Key West and want to fly in and check it out for a day? Are you planning a trip to the Keys and only have a day to spend in Key West? Well, this blog is just for you! This blog will touch base on various places you can visit in Key West.

Day Trip to Key West

Seven Mile Bridge

There are various ways to get to Key West for a day trip! Here are some of the most popular options:

- Drive in using the Overseas Highway, the southernmost 113 miles of U.S. Highway 1 (This option is feasible for a day trip if you are already staying in another Florida Key)
- Fly into the Key West International Airport (Flying in is probably your best bet if you can book an early flight in and a late flight out - maximizing your time on land)
- The Key West Express Ferry from Fort Myers Beach or Marco Island (Another great option if you live near or are visiting this Southwest Florida area.)
- Bus Shuttle Services from the Miami and Fort Lauderdale Airports (This will probably be the least feasible for a day trip, but a great option if you are staying for a longer period.)

Key West Cruise Port

Virgin Voyages Scarlet Lady at the Key West port

The Key West Cruise Port is a vibrant hub for cruise ships, welcoming passengers from major cruise lines like Royal Caribbean, Holland America Line, and Virgin Voyages. The Port of Key West accommodates these vessels at Pier B or the Navy’s Outer Mole Pier.

Pier B is a bustling terminal that offers cruise ship passengers their first taste of the city of Key West, with walking access to art galleries, Mallory Square, and various shore excursion starting points. Meanwhile, larger ships often dock at the deeper Navy’s Outer Mole Pier, ensuring smooth arrivals and departures for cruise ship passengers.

Visit the Southernmost Point Buoy

DLT! at the Southernmost Point Buoy in Key West, Florida

When you think of Key West, you probably envision the Southernmost Point Buoy, an iconic landmark many people take pictures of daily.

Not only is it a great picture spot to commemorate your time in the southernmost city of the continental U.S., but it is neat to say that you have been to the southernmost point of the continental United States. We recommended starting your day visiting this, as the line to get a picture typically grows the later in the day it gets.

Eat at Ana's Cuban Café

A breakfast Cuban Platter that consisted of rice and beans, two eggs, and Cuban toast we ordered a side of breakfast potatoes and a Coca Cola

A couple blocks away from the Southernmost Point Buoy, you will find Ana's Cuban Cafe and Southernmost Grocery. They sell traditional Cuban cuisine, including Cuban roast pork, Picadillo, and Cuban sandwiches.

We shared a breakfast Cuban Platter that consisted of rice and beans, two eggs, and Cuban toast we ordered a side of breakfast potatoes as well - it was delicious!

Get a Drink and/or Catch a Tour at Papa’s Pilar Rum Distillery, Hemingway Rum Company

The bar entrance is on Simonton Street - here you can enjoy various drink concoctions made from their rum. Once you enter, you will see a life-size statue of Ernest Hemingway standing at the bar.

This bar is a great hang-out spot for enjoying a drink alone or with others. Moreover, on Greene Street, they have another entrance where you can partake in rum tastings, shop for souvenirs, and purchase tickets for a guided tour of the distillery.

Moreover, if you are a fan of Ernest Hemingway, visiting the Hemingway House offers fans a glimpse into his life during his time in the city.

The historic landmark, where Hemingway resided from 1931 to 1939, offers guided tours providing insights into the author's life and Key West's rich history. On your tour, keep an eye out for the famous six-toed cats, descendants of Hemingway's cat, Snowball.

Check out The Koffie House

Next door to the above location, you will find The Koffie House. It was the cutest coffee shop I have been to in a while. The atmosphere is so cozy and inviting - I was drawn into the shop immediately when I saw it! This location sells high-quality coffee and freshly baked pastries.

So, whether you are a coffee lover or a pastry enthusiast (like me), you will want to take the time to relax and enjoy the delicious treats here. P.S. They have various Instagram-worthy spots for a little photoshoot!

Enjoy a Slice of Key Lime Pie from Kermit's Key West Lime Shoppe

Down the road from the above two locations, you will find one of the two Kermit's Key West Lime Shoppes in Key West. A cute little shop filled with Key Lime-flavored treats - they sell pies, candies, sauces, and salsa.

We purchased a Key Lime Pie slice, and it was delicious! I am not a fan of lemon or lime-flavored desserts, but I enjoyed their Key Lime Pie. This location also has a nice seating area in the back amidst a garden and fountain - it was quite relaxing and a great little retreat away from the sun.

Grab a Bite to Eat and Hit the Arcade at The Waterfront Brewery

You can find The Waterfront Brewery in the Historic Key West Bight. They offer a diverse selection of food and craft beers. It features a large open-air seating area with stunning waterfront views, making it the perfect place to relax and enjoy a drink or meal with friends and family. They also have an arcade area that can be used even if you do not drink or dine with them.

Be an Aquaholic at Dante's Key West Pool Bar & Restaurant

Dante's is also found in the Historic Key West Bight. It has a large pool with a waterfall rock formation in the back, two bars, plenty of seating, and a restaurant. They also have a stage where live performers come to entertain during certain times of the week.

The atmosphere here is exciting, the drinks are incredible, and the food looks good! If you want to grab a drink or a bite to eat while relaxing by the pool, then this is your place.

Hang Out at Sloppy Joe's

Drink menu and bar at Sloppy Joe's

Sloppy Joe's is a popular bar and restaurant on Duval Street, in the heart of Key West. They have been open since 1933 and offer live music and a separate area for watching sports.

A distinct feature of Sloppy Joe's is that they have two Duval Street live cams where you can send the link to your friends and family back home and wave to them from the camera. They also have a few cameras within the bar capturing what's going on there, including their live performers (without audio).

Take it Easy at Sunset Pier

Located at the end of Duval Street, you will find Sunset Pier. This location offers stunning sunset views over the Gulf of Mexico - during the day, the views are just as breathtaking! You can enjoy drinks and seafood at the dockside eatery while enjoying the water views and live music.

Shop at the Mallory Square Market

There are plenty of handmade crafts, souvenirs, and local products available at the Mallory Square Market. You can find jewelry, clothing, art, and home décor, all perfect for taking a little bit of Key West back home with you. Located in the heart of Mallory Square, it is the ideal spot to explore other attractions nearby.

Check out the Key West Shipwreck Treasures Museum

Entrance of Key West Shipwreck Treasures Museum in Key West, Florida

The Key West Shipwreck Museum in Mallory Square depicts the story of Key West's maritime heritage through interactive exhibits and artifacts. They also have a 65-foot lookout tower where you can enjoy the panoramic views of Key West and a replica of a 19th-century wrecker's warehouse.

Hop on the Conch Tour Train and/or the Old Town Trolley

The World-Famous Conch Tour Train takes visitors on a 90-minute narrated tour, highlighting Key West's history, culture, and architecture - it is a round-trip attraction without getting off.

The Old Town Trolley Tours are a hop-on-hop-off tour that offers a similar experience, with stops at over 13 locations throughout Key West - you can get on and off this all day. Both tours are great options for sightseeing and learning about Key West's fascinating history and culture.

Visit the Key West Aquarium

Entrance of Key West Aquarium in Key West, Florida with a mermaid fountain in front

If you are interested in the fascinating underwater world of the Florida Keys, this one is for you! The aquarium features a variety of exhibits and interactive experiences that allow visitors to get up close and personal with sharks, sea turtles, and other marine animals.

Catch a Movie at Tropic Cinema

Tropic Cinema in Key West, Florida it is decorated with Art Deco Miami neon and has Marilyn Monroe in the front holding her dress over the air vent

Tropic Cinema is a non-profit housed in a beautifully restored Art Deco building. They offer independent, foreign, and documentary films that, typically, are not shown in mainstream theaters.

Have a Drink at the "Oldest Bar in Florida," Capt. Tony's Saloon

Capt. Tony's Saloon signage at Capt. Tony's Saloon with a fish on top in Key West, Florida

Capt. Tony's Saloon is a legendary bar in Key West frequented by many famous people back in the day and has been a fixture of the island's entertainment scene for over 150 years. 

According to its sign, it is the oldest bar in Florida, but that is not true. The building is from 1851, but it started as an icehouse that doubled as the city's morgue and did not turn into a bar until 1933 when it became the first Sloppy Joe's.

Fort Zachary Taylor State Park

Fort Zachary Taylor State Park, situated around a historic Civil War-era fort, offers various activities for visitors, from bicycling and birding to fishing and picnicking.

The nearby breakwaters harbor a colorful array of tropical fish, adding to the allure of snorkeling and scuba diving adventures. Affectionately known as "rocky beach" by locals, it boasts the finest swimming opportunities on the island.

For refreshments, the Cayo Hueso Café conveniently serves drinks and light meals right by the beach. Additionally, visitors can rent chairs, umbrellas, and snorkel gear from a nearby hut, ensuring a comfortable and enjoyable day by the shore.

Truman Little White House

The Truman Little White House, originally built in 1890 as the naval station's command headquarters, has a rich history as a presidential retreat. Used by former President Truman as his winter haven, it later welcomed other US Presidents like Eisenhower, Kennedy, and Clinton.

Today, visitors can embark on guided tours through Truman's former residence, gaining insight into the unique role this historic site played in American presidential history.

Key West Lighthouse

Key West Lighthouse

Located on Whitehead Street and formerly owned by the U.S. Navy, the Key West Lighthouse offers visitors the opportunity to ascend its 88-step staircase for breathtaking views of the Atlantic Ocean, Gulf of Mexico, and downtown Key West.

Explore the restored Keeper's Quarters and peruse displays of nautical artifacts, antique furnishings, maps, and vintage photos to delve into the lighthouse's rich history.

Audubon House & Tropical Gardens

The Audubon House & Tropical Gardens, built in the 1840s, is a testament to Key West's rich history and architectural preservation efforts. Saved from demolition in 1958 its restoration marked the beginning of Key West's restoration movement.

Visitors are treated to a glimpse of 19th-century Key West life as they tour the elegantly furnished home and explore the lush one-acre tropical gardens, complete with a replica 1850s-era cookhouse. The gardens, adorned with orchids, bromeliads, and rare tropical palms, offer a serene escape into the island's past.

Key West is Calling!

Marina in the Historic Key West Bight in Key West, Florida

Explore the best of Key West on your day trip with this guide. From historic landmarks to delicious eats, there is something for everyone to enjoy. Whether you are cruising, flying, or driving in, make the most of your time in this tropical paradise!

Have you gone to any of these places in Key West? Let me know in the comments below! Share this article with the person or people you want to go on your next adventure with! Also, be sure to SUBSCRIBE below to learn about other places you should add to your "To Visit" List! Ready? Okay, vamos. Time to have fun!

Vehicle used for Key West Rides the app that treats it like an Uber Bus in Key West, Florida

Bonus Tip

You can walk a majority of the tourist areas, but they also have public transportation to save you some time. The coolest part is that they have this app called Key West Rides - think of it as an "Uber Bus."

It is their public transportation in Uber format where you put "I am here" and "I want to go there," and they will find you the nearest driver to get you where you need to be. Understand it is a shared bus, and you may have some stops in between. We paid $4 per person for the entire day - it was so worth it!

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