What to Do During Your Port of Call Cruise to Key West

By Janet K. Keeler

There’s a lot of action and history packed into the roughly seven square miles of Key West. Key West is a city in Florida that’s just 165 miles from Miami but it feels like a million miles away.

Tropical breezes, the bluest water that America has to offer and a laid-back vibe that whispers “vacation” are just some of the hallmarks.

When your cruise ship docks at the Port of Key West, you’ve officially arrived in America’s tropics. And actually, there are three piers that handle cruise ships—Mallory Square, Pier B and Outer Mole. Mallory and Pier B are an easy walk to town; in fact, there are sites to see as soon as you disembark. Outer Mole is a bit farther away but there are shuttles and other ways to get cruisers closer to the action on Key West’s Duval Street.

Unlike the six other cruise ports in Florida, Key West is not a point of origination but rather a port of call for Western Caribbean and Mexico cruise itineraries. That means your stop in the Conch Republic will likely be during the day so you’ll miss the legendary Key West nightlife. Not to worry, live music and refreshing cocktails flow long before the sun goes down.

Because Key West is a small place, you’ll want to get up and be ready to get off of the ship as soon as you can to beat the crowd. This is the day you should be the early bird and save the sleeping in for your day at sea. Same with the sunbathing. For all of its attributes, Key West isn’t much of a beach town.

The Old Town Trolley tour (13 stops) and the Conch Train excursion (three stops) which take you past all the major sites. These tours are especially good for cruisers who want a less-strenuous activity. These can be booked through the cruise line or independently.

The Hemingway House, where writer Ernest Hemingway lived from 1931-1939 and where he wrote “For Whom the Bell Tolls” and the short story “The Snows of Kilimanjaro,” among other works. The beautifully restored and maintained 1850s French Colonial home is one of the island’s most popular attractions. The many cats, some with six toes, that roam the grounds are a big draw, too, though their lineage to a Hemingway pet is disputed.

It’s not just the house that celebrates Hemingway’s legacy. Sloppy Joe’s on Duval Street is said to be a favorite watering hole. Best news for cruisers is that the live music starts at 10 a.m. Papa’s Pilar rum distillery is named after Hemingway’s boat and aims to capture his sense of adventure (and possibly love of spirits?). Papa’s Pilar offers distillery tours and tastings.

Key West’s other famous some-time resident was President Harry S. Truman who wintered in the warm tropical paradise. The Truman Little White House is open for guided tours only. In December they decorate the Christmas tree in vintage ‘40s and ‘50s style. More than one visitor has said, “I could live here,” during the tour of the home that started in 1890 as a duplex for Navy officers and their families.

A 90-minute Jet Ski tour provides a different view of Key West, a glass-bottom boat eco tour reveals what’s under the water and a morning reef snorkeling trip keeps the daytripping tourists in mind. It wraps up by about noon, leaving time for lunch at Pepe’s Cafe, the oldest restaurant (1909) in town. Get the Key West Pink shrimp and an order of fish dip made from local catch.

Here are four other ideas for whiling away your day in Key West.

Key West’s Lit History

And by lit, we don’t mean literature or overindulgence, but lit as in the tip of a cigar. Keep in mind that Havana is just 90 miles across the Strait of Florida and that Key West’s connection with Cuba is deep. Nearly 200 years ago, Cubans began migrating to Key West in search of freedom. Among those who arrived were cigar rollers who opened shops. In the late part of the 1800s, there were 150 factories turning out millions of hand-rolled cigars every year. Catch the history at the Rodriguez Cigar Factory on Fitzpatrick Street, also known as Cigar Alley. They give tours and you can watch the cigar rollers in action.

Key West on Two Wheels

Even though Key West’s narrow streets can get crowded during the temperate winter months and with the influx of people from cruise ships, it still maintains its reputation as a biking town. There are many bicycle rental shops in the old town, like Fury and We Cycle, where you can rent one for the day and strike out on your own. Or, you can book a tour for a two-hour guided excursion with Lloyd’s Bike Tour and get narration about the town’s interesting architecture plus samples of tropical fruit including mango and fresh coconut in season.

Key West for Nature Lovers

It occasionally rains in this tropical paradise but you are still going to want to venture out to explore. The Key West Butterfly and Nature Conservancy is a good place to hang out if it’s drizzling. Or even when it’s not. The facility is glass-enclosed and while keeping everyone dry in a controlled 85 degrees, it also provides a home for more than 50 butterfly species plus a couple of flashy flamingoes. There’s a Learning Center that can be visited before viewing the butterflies and the scientists in the group will appreciate knowing more about the life-cycle of the butterflies before seeing them flutter and float. The Conservancy is open every day of the year. You aren’t far from the Southernmost Point marker so this might be the best time to get that required snapshot. La Te Da restaurant is just across the street from the butterfly garden and closer to the Southernmost Point is the Southernmost Point Cafe with a view that might make you book a return trip. Both take reservations.

Key West is the Final Stop

About 100,000 people are buried in the still-active and historic Key West City Cemetery. Established in 1847, it is the final resting place for the diverse populations that lived—and died—in Key West. Cemetery rambles aren’t for everyone but many history buffs find old tombstones intriguing. If you’ve got any cemetery enthusiasts in your group (or you are one yourself), they will find markers for Cuban cigar rollers, Bahamian mariners, Spanish-American War veterans and people of diverse religions and ethnicities. Some worthy marker-spotting:  “Sloppy” Joe Russell, Hemingway’s fishing guide and barkeep at Sloppy Joe’s; Ellen Mallory, one of Key West’s first female settlers, and P.L.F. de Ayala whose grandfather wrote the Cuban national anthem. Extra points for finding the tombstones with the inscriptions “I told you I was sick” and “I am just resting my eyes.” You might get lucky and be in Key West on one of the two days a week that guided tours are given.