A Day in Key West: Itinerary for Cruisers & Drivers

We have visited Key West three times, twice during a Virgin Voyages cruise stop and once when we drove down from Miami and stayed for a couple of days.

Whether you are arriving at the cruise port or driving down the coast, planning a day in Key West is all about knowing how to navigate this colorful, tree-lined island. It is the most popular of the Florida Keys, and we want to share everything we’ve learned to help you build a helpful itinerary.

*This post might include affiliate links, meaning I could earn a commission if you buy through my link, without any additional cost to you. But don’t worry because I only recommend products or services I genuinely believe in and think will add real value to you. Affiliate links help me keep this website up and running. Thanks for your support. Read the Privacy Policy for more information.

Read More: If you like to DIY your walking tours like we do, check out my post on using GPSmyCity App to build your itinerary.

How to Get To Key West?

If you’re not arriving via cruise, driving from Miami takes about 3.5 hours. Another option is flying into Key West International Airport (EYW), which is a quick 15-minute drive from the Old Town area.

Read More: If your Florida trip starts further north, read our Florida Brightline Train: Orlando to Miami Guide.

Where is The Key West Cruise Port?

The cruise port is in the northern part of the island near the Key West Museum of Art & History. We have sailed on two different Virgin Voyages stops, and the cruise ships docked in Pier B.

Because Key West is such a popular cruise stop, there is so much to do in a day that you generally don’t have to book a cruise excursion.

We really recommend that if you want to do a snorkeling experience, you book it directly with your cruise, as it is the only excursion that guarantees you will be back on the ship on time.

If you aren’t visiting on a cruise, then this snorkeling experience will take you to see the beautiful reefs along the coast.

How to Get Around In Key West?

To get around Key West, we honestly don’t recommend renting a car because Old Town is very pedestrian-friendly, and parking is limited and super expensive.

During our first stay, we booked an Airbnb near the EYW airport, so we just kept our car parked there and used Uber to get to the downtown area.

If you prefer not to walk, you have a few convenient options:

• Rent a bike: Exploring by bike is a great option. This Guided Bicycle Tour is conveniently located just a 7-minute walk from the port, so you won’t have to stress about returning it too far from the ship.
• Take the bus or trolley: Another convenient way to explore the downtown area is the bus or trolley routes, which stop at most of the historical highlights you must see in Key West.
  • Old Town Trolley: If you want to learn the history as you go, there is a hop-on, hop-off trolley that stops at 13 historical places. It departs every 30 minutes and includes a narrated tour.
  • Key West Conch Train Tour: This is a fun mini-train that has three stops for you to hop on and off. If you decide to do the entire loop without getting out, you can see the town in 60 minutes with live narration.

Things to Know Before Visiting Key West

• Fantasy Fest: Unless you intentionally want to participate in the festival, we would recommend checking October dates before you book. Fantasy Fest is a 10-day festival located on Duval Street from Front Street to Truman Avenue. You will find a lot of people in costumes, partying, performing, pub crawls, and a parade, making this season super crowded and expensive.

• Hurricane Season: It might be cheaper to visit during this time, but keep in mind that due to its location, it gets hit by these weather conditions like any other town near the Caribbean.
• Winter Season: It tends to be busy because most snowbirds and cruises with Caribbean routes tend to make a stop in this beautiful port.

• The Chicken Law: During your visit, you will encounter one or more free-roaming chickens and roosters. You might be tempted to feed them, but you need to be aware that these animals are protected by the Key West Chicken Law. Avoid feeding them, or you might end up paying penalty fees.
• Beaches vs. Reefs: There aren’t many beautiful white-sand beaches near Old Town. However, if water activities are your thing, it is an absolute paradise for scuba divers, snorkelers, kayakers, and catamaran sailors looking to explore the beautiful reefs. You can book your favorite water activities here.

A Day in Key West Itinerary: Must-See Spots

1. Truman Little White House

• Open: Daily from 9:30 AM–4:30 PM
• General Admission: Starting at $22.75 online

Pro tip: Tickets are cheaper when purchased in advance here.

The Truman Museum is where President Truman used to stay when visiting Key West from 1946 through 1952, which is why the house is known as the Little White House. Several other presidents have also stayed here during their terms in office. Your visit includes an interesting and educational 20-to-30-minute guided tour that departs every half hour.

Just a heads up, photography isn’t allowed inside the house, but you can snap as many pictures as you want on the grounds outside. Inside, you’ll see the original furniture, including the famous poker table tucked in the corner of the living room. Visiting this spot is a must since this very little house was the site where major national official decisions were discussed.

2. Southernmost Point

The Southernmost Point is a famous monument marking the closest spot to Cuba (just 90 miles away). It is easily the most photographed landmark in Key West.

Interestingly enough, this concrete buoy was actually built to replace an old wooden sign that visitors kept stealing. We highly recommend making this your very first stop in the morning to grab your perfect Instagram-worthy photo, because the line of tourists builds up incredibly fast.

3. Hemingway House Museum

• Open: 9:00 AM–5:00 PM daily.
• General Admission: Starting at $19, and tickets are only available at the main gate.

Pro Tip: We recommend bringing cash because a 3% fee is added to all card and mobile transactions.

If you are a literature fan, this is an absolute must-see. Your admission includes a 20-to-30-minute guided tour that runs every 15 minutes. Ernest Hemingway did the majority of his writing in this beautiful French Colonial-style home, which also boasts an awesome view of the nearby lighthouse.

Out back, you’ll find the second-story carriage house that he converted into his personal writing studio. The house is still filled with some of his original furniture, and the in-ground pool outside was actually the largest residential pool on the island back in the day.

As you walk around, you’ll notice several cats roaming the property. Most of these cats are direct descendants of Hemingway’s original cat, and many have six toes, a trait sailors believed brought good luck.

Fun fact: This house was also used as a filming location for the James Bond film Licence to Kill, specifically the scene where he jumps off the veranda.

4. Key West Lighthouse

• Open: 10:00 AM–5:00 PM daily.
• General Admission: Starting at $17 at the museum.

Pro tip: Online tickets here start at $15.50.

The lighthouse was originally built to prevent shipwrecks. The museum park includes the keeper’s quarters, which is set up like a museum where you can see the lighthouse keeper’s clothing and the original lighthouse lenses.

To get to the top, you need to climb a spiral staircase with 88 steps. Once you are up there, you get an amazing 360-degree view of Key West. The view is incredible, and you can even see the Hemingway House right from the top.

5. Mel Fisher Maritime Museum

• Open: 10:00 AM–4:00 PM daily
• General Admission: Starting at $17.50

Pro tip: Tickets for the Mel Fisher Maritime Museum can be purchased in advance here.

During our visit, we were amazed to see the actual artifacts collected from shipwrecks. One of the most significant things we saw was the recovered treasure of The Atocha, a wreck that included tons of gold and silver. The museum also has an impactful collection from other shipwrecks like the Henrietta Marie, an illegal slave ship.

6. Mallory Square For Sunsets

The sunsets in Key West are legendary, and Mallory Square is a perfect place to watch them. When we cruised here, our ship departed early, so we couldn’t see the sunset, but on our visit, when we drove and stayed on the island, we visited a few times just to enjoy it.

Besides the lively atmosphere and street performers, boats and catamarans were sailing by, and the view was simply breathtaking.

7. Bar Crawling in Key West

Key West is packed with great bars, and doing a bar crawl is a very popular activity in Key West. Here are a few of the most popular options:

• The Bull & Whistle Bar features live music on the first floor and a fantastic second-floor balcony where you can sip drinks while people-watching over the street below. If you’re feeling adventurous, the building is also home to the “Garden of Eden,” an adults-only, clothing-optional rooftop deck.

• First Flight is another historic spot serving house beer. The building is where Pan American World Airways sold its very first international ticket in 1927.

• Sloppy Joe’s is a famous staple you have to check out. It was the favorite local bar that Ernest Hemingway used to visit when he lived on the island.

Vegan Food in Key West & The Famous Key Lime Pie

Key Lime Pie is a massive deal here because it was actually invented in Key West. Unfortunately, the original recipe is not plant-based, but you absolutely cannot leave without trying the local specialty. Head to Moondog Cafe for their Mini Vegan Key Lime Pie Tart (made with key lime coconut curd, toasted meringue, and an almond flour tart shell).

While we couldn’t find a massive amount of purely vegan spots, Cuban food heavily influences Key West, meaning you can often find great plant-based rice, beans, and yuca dishes. We recommend visiting Kaya Island Eats right on Duval Street, which offers some vegan options in a really fun island atmosphere.

Heading to Miami next? Check out our top spots with vegan option in Miami South Beach and our El Cielo Restaurant Miami Michelin Star: Vegan Menu Review.

What to Wear In Key West?

The temperature in Key West is relatively warm year-round, with the summer season being super hot. Since you will be doing a lot of walking in the heat, we highly recommend packing comfortable walking shoes and breathable, lightweight clothing. During the summer, a hat is also an absolute must.

Where to Stay in Key West?

As I mentioned, we stayed in an Airbnb near the airport once, but we needed to use Uber to move to the downtown area, which is why we really recommend staying downtown instead. If you want to stay in the heart of the action, one of our favorite hotels is the Ocean Key Resort.

It is incredibly close to the action but also offers some rooms with balconies overlooking the ocean, giving you some of the best sunset views on the West Coast.

We hope you enjoy your visit to Key West! It is one of our favorite cruise stops due to its safety and the proximity of all the different activities.