Key West Weekend Itinerary
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Use our three-day Key West Itinerary to explore Key West for a weekend getaway.
Key West Weekend Itinerary: (Jump To)
We booked three days at the southern tip of Florida on the island of Key West. It’s been on our hit list for a while so we decided to visit while the world was still slowly reopening for foreign travel. There is a small airport on the island with plenty of routes and carriers from major cities. We had a connection in Dallas.
The island is quite small but the airport is on the opposite side from where you’ll be spending most of your time. We booked three nights at the Casa Marina Key West on the southern shore of the island. We attempted to take the bus from the airport to the hotel, but after about thirty minutes of waiting, the bus never came. The bus had some rates for one-day and multi-day passes that would have been a great way to save some money. Sadly the bus turned out to be very unreliable so we depended on rideshares and good old-fashioned walking for the rest of the trip.
Key West Itinerary Day 1
The main tourist strip is Duval Street. The street is lined with shops, bars, and restaurants. It’s just over a one-mile walk from the north shore to the south shore via Duval. Mallory Square at the northernmost point of the street has a few great shops, a shipwreck museum, and a small aquarium.
After settling into our hotel and taking the obligatory tour of the pool and beach we headed out for dinner. On a recommendation, we picked a Cuban restaurant called El Siboney. The menu is vast, the portions are enormous, and the prices are reasonable. We ordered the roast pork with a side of sweet plantains. It was absolutely marvelous.
After dinner we had a few drinks at the Bourbon Street Pub, spending most of the time at the outside bar near the pool out the back door. The crowd was light, but the people were friendly!
Key West Itinerary Day 2
While Elliott worked, I started the next morning with a walk through the Key West Garden Club at West Martello Tower. The tower is all that’s left of a 19th-century fort. Inside is a small but beautiful garden kept up by volunteers. Admission was free.
Later in the day, we visited the island’s other fortress, Fort Zachary Taylor. For $2.50 each, we took a self-guided tour. During the Civil War, the Union-controlled fort played an important role in stopping Confederate supply ships from leaving the Gulf of Mexico. The fort is home to the largest arsenal of Civil War cannons in the United States.
After leaving the fort we walked by the “Little White House.” This was the winter residence of President Harry Truman. The tree-lined street and colonial architecture are part of the most beautiful residential neighborhood on the island. Tours of the Little White House are available. Our interest was not peaked, so we opted to observe from outside.
Similarly, Ernest Hemingway’s 1930s residence on the island is open for tours. Apparently, there is a colony of six-toed cats living there who are direct descendants of Hemingway’s cats. As amazing as that sounds, we also opted out of the rather expensive tour.
A block off Duval Street is Onlywood Pizza, which we visited for dinner. They’re known for their Napoli-style pizza cooked in an oven built with bricks imported from the Italian region. They also have a selection of pasta dishes. One pizza is plenty for two, making it a great place for an inexpensive yet nice dinner. We dined on their gorgeous patio.
Key West Itinerary Day 3
Our final full day on the island was spent with a drink in our hands and sun on our faces at the hotel pool. The collection of wild chickens and friendly iguanas were our only distraction as we soaked up some Florida sunshine.
We kept it casual for dinner opting for some upscale bar food at the Old Town Bar and Grill before finishing the night with another visit to the Bourbon Street Pub.
One of the biggest photo ops in Key West is the Southernmost Point in the Continental United States. We kept walking past to find a block-long line of people waiting to take a family photo in front of the landmark. It is strange to me for a few reasons, but mostly because it is obvious that the true southernmost spot is next door over the fence in the restricted military space. Nevertheless, I woke up before the sun the next morning to catch a “tourist-free” shot of the landmark before flying back home.
I think three days was a perfect amount of time to explore the small island community. With another day or two, we probably would have booked some fun in the water on a jet ski or a tour slower around-the-island boat tour. It was a perfect three days of relaxation and exploration.
If an all-inclusive experience is more your style, check out our visit to Atlantis Paradise Island.
