At the southern tip of the coral cay archipelago known as the Florida Keys lies Key West, a beach town known for its colorful conch-style architecture, vibrant nightlife, and storied past. Just 90 miles from Cuba, Key West is the crown jewel of the Keys.
Once a haven for pirates and buccaneering, it has also served as the winter home to a U.S. president and several icons of American literature. Anything goes in Key West, where the attitude is more relaxed than refined — just how the locals like it. With so much to see and do, including several new attractions, there’s always a reason to plan a weekend in Key West to escape to the Conch Republic.
FRIDAY
If you’re driving in from Miami, the scenic road trip will take you past a slew of unique natural and manmade wonders, from Everglades National Park, which recently celebrated its 75th anniversary, to the Old Seven Mile Bridge, which just reopened as a fresh air “linear park” after a longtime closure for restoration.
Old Seven is perfect for biking, strolling, and wildlife watching, from the sea turtles, manta rays, and nurse sharks below the surface of the turquoise water to the ospreys and seagulls soaring above. On one end of the bridge sits Pigeon Key, a 5-acre island and landmark with a museum that tells the history of the bridge, once referred to as the eighth wonder of the world.
Once you’re on the island of Key West, kick off your visit at Mallory Square. Known worldwide for its nightly sunset celebrations, it recently unveiled a massive restoration and expansion with enhanced landscaping, seating, new sunshades, and outdoor performance space at the Waterfront Playhouse.
For dinner, fresh catch awaits at Louie’s Backyard, originally a charming Victorian-style home that’s now one of Key West’s longest-standing waterfront restaurants. Sip a frozen concoction at the massive surfside dock and dip your toes in the water between sips. Whether you dine indoors or out, the sound of the waves will lull you into relaxation mode as you prepare for the fun that lies ahead.
SATURDAY
Wake up to roosters crowing on your weekend in Key West at local-favorite Blue Heaven Café, where blueberry pancakes are served at al fresco tables under a canopy of trees. Walk off your meal with a stroll through the Key West Historic District, a maze of streets lined with conch-style cottages that make the perfect backdrops for snapping selfies. There are many things to do in Key West!
Right smack in the center, near the shops and cafés of bustling Duval Street, is the Tennessee Williams Museum. Housed in a historic home, it details the life of the famous playwright who wrote “Cat on a Hot Tin Roof,” “The Glass Menagerie,” and “A Streetcar Named Desire.” Detailing his life in Key West for over 30 years, the exhibit includes first-edition plays and iconic photographs.
Just a five-minute walk away you can pay tribute to another iconic American writer at the Hemingway Home and Museum, where the author of “For Whom The Bell Tolls” and other iconic works lived in the 1930s. The estate is largely untouched, complete with six-toed cats roaming about that are rumored to be descendants of one gifted to him by a ship’s captain. It’s one of the top things to do in Key West.
While these literary icons helped Key West gain cultural recognition, President Harry Truman added another layer of distinction when he made Key West the site of the winter White House. Today the Little White House is just as he left it, with memorabilia lining the walls and furniture arranged almost exactly as it was in Truman’s time. Just down the street in Truman Waterfront Park, the Florida Keys Eco-Discovery Center recently unveiled a major renovation that includes interactive exhibits about the Florida Keys National Marine Sanctuary.
When all these history lessons leave you famished, tapas and sangria at Santiago’s Bodega are the perfect antidote. Off the beaten path in the neighborhood known as Bahama Village because of its colorful Bahamian architecture, it’s near the Southernmost Point of the Continental U.S., where an oversized buoy makes the perfect picture spot.
SUNDAY
Key West is a dream for shoppers who love handmade goods. The Shops at Mallory Square is a haven for artisans and craftspeople who use the space as both store and studio. From pottery and paintings to woodwork and jewelry, it’s all packed into a historic brick building constructed in the 1850s, lending your visit an added layer of charm.
Spend your final hours strolling the mile-long harbor walk at the Key West Historic Seaport. Check out the schooners that bob in the water and keep your eyes peeled for manatees and hungry tarpon looking for handouts. Take in the views from the outdoor deck at Alonzo’s Oyster House, a local favorite since 1947, and start planning your next Key West adventure. As it comes to a close, hopefully you enjoyed your weekend in Key West.
