KEY WEST: THE SOUTHERNMOST US CITY
Story and photos by Kathleen Walls
Key West is a popular destination for spring break and winter vacations. Parking in Old Town is limited and expensive, unless you have a handicapped tag, which allows free parking for up to four hours.
Tours
The best way to tour Old Town is on either the Old Town Trolley or Conch Train Tour. The Conch Train offers a nonstop tour, while the Old Town Trolley lets you hop on and off close to most attractions. I took both, plus the Ghost and Graveyards Tour, which is a fantastic nighttime adventure that not only drives by but makes a couple of stops and takes you off the trolley for a more dramatic experience.
Mallory Square
While in Mallory Square, visit the Key West Historic Memorial Sculpture Garden with busts of notable figures in Key West history. Don’t miss Sunset at Mallory Square for entertainment, food, and beautiful sunsets.
I visited during the Conch Republic Festival, celebrating the Keys’ secession from the union for a few minutes in 1982 due to a US Border Patrol blockade at the entrance to Key Largo that was destroying the Keys’ commerce. Each year, they celebrate with a 10-day festival. The highlight of the festival is a mock battle where the Conch Republic flagship, the schooner Western Union, and other boats engage the USCG Cutter Diligence using water hoses and tossing stale bread.
On land, Commander Scarlett Jay Somers, this year’s Supreme Commander and General of the Conch Republic, struck a US naval officer across the head with a load of stale Cuban bread. Land-based cannons were mounted in Mallory Square, pointing at the harbor, and fired multiple times.
Ultimately, the Coast Guard surrendered, and participants proceeded to Schooner Wharf Bar for the surrender ceremony. Prime Minister emeritus, Dennis Wardlow, who was mayor of Key West then, mentioned aid typically provided to a country upon surrender but noted that while they are still waiting for the U.S. aid package, the barricade in Florida City was removed the next day. Hence their motto, “We seceded where others failed.”
Museums
There are several museums in or near Mallory Square. I began my tour at the Key West Shipwreck Treasure Museum, which provides information about the wreckers who made Key West the wealthiest city in the US in the 1830s by salvaging ships that wrecked on the nearby reef.
Key West Aquarium, opened in 1935, features sea life found in the waters surrounding the Keys.
Custom House Museum presents the city’s history through art.
Located just outside Mallory Square, the Mel Fisher Museum displays the treasure discovered by the well-known treasure hunter Mel Fisher.
At the Ernest Hemingway Home and Museum, I met many of the descendants of Hemingway’s six-toed white cat, Snow White. She was a present to Hemingway from Captain Dexter.
Visiting Harry S. Truman’s Little White House offers an insightful journey through one of America’s most significant historical periods. Our guide, Steve, was terrific.
I enjoyed Sails to Rails, a small museum that tells the history of the ships and Flagler’s railroad.
There are two nature-related museums. Key West Botanical Garden displays unique plants. Key West Butterfly and Nature Conservancy features some of the most beautiful butterflies I’ve ever seen.
The Fort East Martello Museum, a historic Civil War fort, features exhibits that narrate the history of Key West. Among its collections is Robert the Doll, an artifact renowned for being the most haunted object in Key West. For a comprehensive account of Robert the Doll’s story, take the Ghosts and Gravestones Tour.
There are some fascinating, lesser-known museums that are worth a visit. Key West Firehouse Museum, housed in a 1907 fire station, has antique fire trucks and other historic artifacts.
U.S. Coast Guard Cutter Ingham Maritime Museum, docked at Truman Waterfront Park, served in World War II, Korea, and Vietnam. It’s a real ship, so beware that the stairs are steep and best descended like a ladder. If you are there on Thursday, the park hosts the Truman Park Farmer’s Market.
Southernmost Point Buoy
If you want a selfie at the Southernmost Point Buoy, expect a long wait. It looked like the rest of the world was in line the three times I passed by it.
Key West Cemetery
You may not think of a cemetery as a tourist attraction, but Key West Commentary is. One of the most unusual tombstones is a conch shell, marking the grave of Sir Peter Anderson, who was the Secretary-General of the Conch Republic.
Many of the tombs are engraved with humorous sayings like the two sisters. One was the town hypochondriac. Her tombstone says, “I told you I was sick.” Her sister reads, “I’m just resting my eyes.”
Not only humans, but sometimes pets are buried here. Elfina the deer’s grave is in the Otto family burial ground along with three dogs and Robert Eugene Otto, the owner of Robert the Doll.
Sunset Cruise
I took a sunset cruise on the Hindu, a 50’ wooden schooner built in 1925, which only accommodates about 35 people, but our group comprised about a dozen people. It was interesting watching Captain Erin and mates, Emma and Jen, raise and lower the sails. We sailed into a terrific sunset while enjoying snacks and wine.
Perry Hotel
There’s a great place to stay with easy access to Old Town while avoiding the hustle and bustle of traffic. Perry Hotel is the perfect home-away-from-home. They are one of only three Florida Keys hotels to receive a prestigious MICHELIN Key in 2024 and are nominated for Best Hotel in the 2025 Condé Nast Traveler Readers’ Choice Award 2025. They have unique art by local artists in the lobby and rooms, and parking is free. I was glad to see some guests checking in with their cute pooch. I love pet-friendly hotels.
There is a concierge at the front desk to help if you have any questions, and you can book tickets for the town trolleys here. The hotel is named after Commodore Oliver Perry, whose brother, Matthew C. Perry, planted the US flag at Key West in 1822. You’re about 15 minutes away from Old Town Key West, but if you don’t want to fight the traffic, the Perry offers a shuttle to and from Old Town or you can rent scooters, golf carts, or bikes to make parking easier. My room overlooked the waterfront pool and the marina, the largest deep-water marina in the Keys.
The Perry has two great dining options. Matt’s Stock Island Kitchen & Bar serves breakfast and dinner. For breakfast, I had buttermilk biscuits with pork sausage gravy with two eggs, and for dinner, the Key West Shrimp Linguine with Blue Crab and Citrus Cream, Roasted Tomato, Basil, and Asiago.
Salty Oyster Bar and Grill sits next to the pool if you want a quick snack while swimming. There is music some nights, and several times a month, they have Yappy Hour when dogs get to enjoy the patio with their owners.
Dining
Key West has dozens of dining options in Old Town.
Schooner Wharf Bar is on the dock where you board the Hindu or other cruises. The food is great bar food, and there is usually entertainment.
Half Shell Raw Bar was a shrimp warehouse turned into a restaurant in 1972. The seafood is so fresh, you will probably see it being offloaded from a shrimp boat.
Of course, there’s Sloppy Joe’s made famous by Hemingway.
As one of my tour guides noted, “Key West is closer to Cuba than the nearest Wal-Mart.” It should be on everyone’s bucket list.
Kathleen Walls is publisher/writer for American Roads and Global Highways at https://www.americanroads.net/. A member of the International Food Wine & Travel Writers Association, her articles and photographs have appeared in numerous magazines and online publications. She is also an author of numerous travel books, online travel guides, and fiction novels. Learn more about her books at https://katywalls.com/.
