How to Spend Less than One Day in Key West

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In this article, we’ll share how we made the most of our brief visit to Key West on a cruise, offering our itinerary and additional suggestions for alternative activities. We’ll also highlight some favorite foodie spots we’ve tried when we’ve visited.

Cruising to Key West Cruise Port

Key West continues to debate the extent to which cruise ships should be allowed to dock. The island remains a vibrant and enticing destination for those cruises that do make the stop. The picturesque approach to Key West, whether you’re arriving from the sea or driving down the iconic 7-mile bridge from Miami.

One of the best parts of taking a cruise that stops in Key West is that the ships mostly dock at Mallory Pier or Pier B. Walking off the cruise ship, you’re close to Duval Street. So you are right in town and within walking distance of the most popular things to do in Key West. It’s rare, but it can happen that your cruise ship will dock at Outer Mole Pier right outside of town. Best to verify with your cruise for planning purposes.

One Day in Key West, Florida

When we visited Key West on a cruise, this is how we spent our day. Our goal is to inspire you and give you ideas on what to do while in Key West.

Old Town Trolley Tours

Every seasoned cruiser we chatted with recommended the Old Town Trolley Tours. Unlike typical hop-on, hop-off tours that we usually avoid due to poor past experiences with long delays and incomprehensible audio guides, this tour was a pleasant surprise. You get not only transportation for the day but also valuable insight.

Here’s why Old Town Trolley Tours stood out:

• Vintage Charm: The trolleys boast a classic feel with wooden two-seater benches and open-air viewing.
• Local Insights: The drivers are locals—friendly, knowledgeable, and ready to share personal anecdotes and tips instead of recorded audio.
• Efficiency: The service was quick with minimal wait times, avoiding the usual traffic snarls, making it an excellent choice for short visits.
• Comprehensive Touring: Lasting about 90 minutes, the tour covers all the essential spots in both old and new Key West, offering historical insights, must-visit stops, and even the drivers’ favorite local eateries.

Given the limited time available in Key West, taking this tour early in your visit is a great way to scope out the places you’d like to explore more thoroughly later. Look at their map to see what stops are near the attractions you’d like to see.

Where to buy tickets for Old Town Trolley in Key West: Tickets are available online at the Old Town Trolley Tours official website or at various ticket booths around Key West. For added convenience, you can also purchase them directly from a shop in Mallory Square when you disembark your cruise ship.

Visiting Ernest Hemingway’s home in Key West quickly became a highlight as we planned our trip. We stumbled upon this historic site while looking for unique activities on the island, which certainly sparked our interest. Conveniently near a trolley stop, the estate offers a deep dive into Hemingway’s adventurous life, featuring memorabilia and tales of his times in Cuba, excessive drinking, and turbulent marriages.

Walking through the lush, well-maintained grounds was a serene experience. The courtyard offers cozy corners where visitors can relax and soak in the atmosphere that inspired one of America’s greatest writers.

After exploring the museum, you might want to follow in Hemingway’s footsteps to Sloppy Joe’s, his favorite local bar, for a drink to cap off your visit.

Old Town Key West

After visiting the Ernest Hemingway Home and Museum, consider strolling through the historic Old Town Key West. The area boasts over 3,000 historical buildings, offering a picturesque backdrop that echoes the island’s rich past.

Key Points of Interest in Old Town Key West

• Key West Lighthouse
• Southernmost Point
• The Key West Butterfly and Nature Conservatory
• Truman Little White House
• Mallory Square
• Duval Street

Southernmost Point

When visiting Key West, the Southernmost Point is a landmark you shouldn’t miss. This iconic buoy marks the southern tip of the continental U.S. and is one of the most photographed spots in the area.

Heads Up: Expect a long line for photos. While we chose to skip the wait, remember this is your vacation. Feel free to stop and snap a picture if that’s what you’d like to do. It’s all about making the most of your experience in a way that feels right for you.

Stop by Cuban Coffee Queen

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There is never a time that we turn down a cup of Cuban cafe con leche. We knew what we were having after our trolley tour when we spotted Cuban Coffee Queen. We made a beeline to the closest one near Hemingway’s and ordered two cafe con leches; mine was iced (it was hot out) and fresh warm Cuban bread with guava and cream cheese.

We were in heaven. This brought me back to my childhood when I had guava con queso with my kiddie version of Cafe con leche while vacationing in Puerto Rico. Don’t you love the rush of memories food brings?

On a more recent visit, we decided to try their Cuban sandwich and were not disappointed—it ranked as one of the best we’ve ever had.

Before leaving, we purchased a few pounds of their roasted coffee to take home, a tangible reminder of our trip. For those who can’t make the trip, Cuban Coffee Queen also offers their roasted coffee beans online, perfect for bringing a taste of Key West into your home.

Where to Eat in Key West

The number one food in Key West to have is Key Lime Pie. Everywhere you go, you’ll see signs for Key Lime Pie. Everyone sells “the best” on the island. Besides the pie, there are plenty of places to eat in Key West. eyond this beloved dessert, Key West offers a variety of dining options that capture the local flavor. Here are some of the spots we’ve tried and loved:

Cuban Coffee Queen: As we discovered during our trip, Cuban Coffee Queen is a must-visit spot in Key West. With three locations across the island, it’s conveniently accessible whether you’re starting your morning or looking for a mid-day boost. Their coffee, especially paired with a Cuban pastry, some buttered Cuban bread, or one of their delicious sandwiches, offers the perfect combination for a satisfying breakfast or lunch.

Salute on the Beach: For a full beachside dining experience, you can head over to Salute on the Beach. This casual spot, recommended by one of our trolley drivers, offers indoor and outdoor seating with an ocean view. This is one of those stops you came with the hop-on-and-off trolley. It’s a sister restaurant to Blue Heaven, renowned for some of the best Key Lime Pie in Key West. Surprisingly, it wasn’t crowded when we visited, which was a definite plus.

Sunset Pier: For drinks with a view, head over to Sunset Pier at the Ocean Key Resort at the end of Duval Street near Mallory Square. This spot offers a perfect backdrop for oceanview dining and is ideal for enjoying the sunset. We spent a relaxing afternoon here, sipping on a coconut mojito alongside delicious pork belly tacos. The Key Lime Pie was surprisingly delicious as well. Sunset Pier features an array of seafood dishes, and though it is a bit pricey, the scenic location justifies the expense. It’s a great place to linger until the sunset paints the sky.

Other Key West Foodie Spots to Try

• Blue Heaven: Their Key Lime Pie is well-known and delicious, but breakfast here also seems to be a hit.
• Better than Sex: Reportedly the best dessert restaurant in town.
• Pepe’s Cafe: A local and presidential favorite; Truman himself dined here.
• DJ’s Clam Shack: A Guy Fieri favorite known for the best lobster roll on the island.

Is it Worth Going to Key West for a Day?

If you’re visiting Key West as part of a cruise or already in the Florida Keys, spending a day in Key West is worthwhile. However, if you’re considering driving from Miami, remember that the journey takes about four hours each way. This means you would drive roughly eight hours in a single day, not including any potential traffic delays. Given the travel time, you might consider staying at least overnight to make the most of your visit without feeling rushed. There are so many stops along the Florida Keys you can make along the way.