The southernmost point in the continental United States, Key West is less than a three-hour nonstop flight from Northern Virginia, making it perfect for a long weekend getaway. Located on the tip of the Florida Keys, the small island is encircled by the Atlantic Ocean on one side and the Gulf of Mexico on the other — and the weather stays warm year-round.
Some travelers fly into Miami and drive the overseas highway, stopping to check out the chain of islands that make up the Florida Keys.
Accommodation Options
Key West has an array of accommodations, from beachfront resorts to cozy inns to rental cottages. The Marker Key West Harbor Resort will put you in the heart of Old Town, where the freewheeling party vibe mixes with historic attractions. Or stay at the luxurious Casa Marina Key West for beachfront access and resort amenities. Away from the hectic downtown, Oceans Edge Key West Resort & Marina offers complimentary shuttles to Old Town, along with the use of kayaks and paddleboards.
Vibrant History
“I recommend first-time visitors take the Conch Tour Train,” says Florida Keys historian and author Brad Bertelli. “It gives you a background on the island and the neighborhoods.” The open-air train completes a 75-minute loop through Old Town with a guide who shares stories about Key West. Old Town Trolley Tours is another choice that allows riders to hop on and off throughout the day.
Indigenous peoples were the first inhabitants of South Florida, but Spanish conquistador Juan Ponce de León documented his explorations of the region in 1513. What he saw through his spyglass inspired him to name the Florida Keys “Los Martires,” or martyrs. “Because of the fossilized coral reef and gnarled roots of the red mangroves, Ponce de León thought the islands looked tortured,” says Bertelli.
Had Ponce de León walked down festive Duval Street, beside bachelorette parties and flip-flop wearing tourists, the explorer might have changed his mind. “Key West is laid-back,” Bertelli says. “Things have changed since the 1970s when it was an artists’ town, but it’s still very open and welcoming to everyone.”
Few know that Key West was once America’s wealthiest city. “Before there was a Coast Guard, wreckers sailed along the coast to rescue ships that crashed on the coral reef,” Bertelli says. “Wreckers were the first responders of their day, and sailors were happy to see them. They paid a percentage of the cargo’s value, and that industry made Key West rich.” You can learn maritime history at the Key West Shipwreck Treasure Museum, and if you’re up for it, climb the 88 steps of the Key West Lighthouse to view the coastline from the island’s highest viewpoint.
Island Flavors
“Key West casual” is how the locals describe dining attire; you can walk into almost any restaurant after a beach day and feel comfortable. Louie’s Backyard is a Caribbean-American eatery with tables overlooking the water and delicious Bahamian dishes like conch chowder. Bertelli explains the island cuisine: “There’s a lot of Bahamian influence in the Keys. Paired with the Cuban and New England migration, Key West becomes this gumbo of Bahamian, Cuban, New England, Caribbean, and Spanish.”
Key West is 90 miles north of Havana, and you’ll find a crowd at Cuban Coffee Queen ordering the Cuban breakfast burrito. People line up to pose by the colorful Key West vintage postcards mural and watch the chickens that freely wander the streets.
Fans of Cuban cuisine will love El Meson de Pepe, an Old Town hot spot known for its vaca frita and ropa vieja. Cubans began migrating to South Florida in the 1860s to roll cigars. Now, the flavors of Cuba are an essential part of Key West culture.
El Meson de Pepe is located at Mallory Square, the spot to watch a Key West sunset. Crowds gather there nightly for the “Sunset Celebration,” a festival with jugglers, musicians, and craft vendors that begins two hours before sundown. When the skies transform from amber to mauve, and the gold orb drops beneath the horizon, cheers erupt.
Away from the hustle and bustle is Blue Heaven, an acclaimed restaurant worth the wait. Tables are nestled among tropical foliage as the resident chickens and cats meander in the yard. While the Jamaican jerk chicken and Caribbean shrimp are legendary, save room for Blue Heaven’s famous key lime pie with its sweet-tart filling, topped with meringue.
Best Beaches
Of Key West’s five public beaches, the locals favor the one at Fort Zachary Taylor Historic State Park. After walking through the Civil War–era fort, you can swim and snorkel in shallow waters, and the white sandy beach is an uncrowded place to watch the sunset.
The best day trip from the island city is the Yankee Freedom ferry to Dry Tortugas National Park, an all-day expedition to a remote island 70 miles off the coast of Key West. The ferry includes a tour of the fort, snorkeling gear, and lunch. As the ship speeds through the surf, you’ll see bottlenose dolphins leaping across the waves, graceful as synchronized swimmers.
At Dry Tortugas (named for the sea turtles that inhabit the island), snorkeling beside a healthy reef and touring the Civil War–era Fort Jefferson feels like a once-in-a-lifetime experience. The massive brick fortress was designed to deter attacks on the harbor and held conspirators charged in President Abraham Lincoln’s assassination.
Cool Cats
Have a frozen rum runner and some conch fritters at Sloppy Joe’s, a well-known Key West bar that opened in 1937. Its long-standing tradition of “Caturday” honors Ernest Hemingway’s beloved pets. The author was a regular patron, and mementos of his friendship with bar owner Joe are on display. To learn more about these colorful characters, visit the Hemingway Home & Museum, where descendants of Hemingway’s six-toed felines still roam the house and garden.
The writer’s legacy is intertwined with the island, as is Harry S. Truman’s. The 33rd president of the United States spent his winters in Key West, naming his home the Little White House. Visitors can take a guided tour of the property to learn how six American presidents used it as a summit or retreat. For a journey into Truman’s life, reserve the VIP White Glove Tour to ride in one of his personal limos.
Outdoor Adventure
Key West is pedestrian-friendly and a fun place to bike. Cycle to the Southernmost Point marker, then visit Key West Butterfly & Nature Conservatory. This miniature garden paradise is the home of resident flamingos Rhett and Scarlett. No matter your age, there’s something magical about butterflies landing on your shoulder.
Key West is a haven for writers, artists, and musicians. You’ll find music everywhere and local makers selling their wares in shops and at street fairs. A cool place to wander is Bahama Village, a collection of clapboard buildings painted in pastels of pink, blue, yellow, and white. While hip restaurants and eclectic boutiques have moved in, the community strives to retain its Caribbean heritage.
No trip is complete without a boat cruise, and there are dozens of choices, including catamarans with dinner and cocktails; a dolphin-watch cruise with tapas; a private sandbar cruise in a tiki boat; or a wooden schooner where guest sailors can help raise the sails. Key West is also popular for parasailing, and from Smathers Beach, you’ll see daredevils fly high above the waves.
End your vacation with a memorable meal at Latitudes at Sunset Key. A 7-minute boat ride whisks you to a private island, where you’ll sit beachside under gently blowing palm trees. From there, watch the technicolor sunset while listening to Jimmy Buffett tunes, the perfect soundtrack to a relaxed Key West vacation.
How to Get There
United Airlines offers nonstop flights from Dulles International Airport.
American Airlines has nonstop flights from Reagan National Airport.
Look for connecting flights on Delta Airlines and JetBlue.
Where to Stay
The Marker Key West Harbor Resort
Centrally located in Old Town, this four-star resort hotel has three courtyard pools, a restaurant, and bike rentals. It’s walkable to all attractions.
Oceans Edge Resort & Marina
Located on Stock Island, this family-friendly resort offers free shuttle service to Old Town. Every room has marina views, with six pools, complimentary kayaks, bikes, and paddleboards for wildlife viewing.
Casa Marina Key West
Built in 1920 and renovated in 2023, Casa Marina is a landmark where celebrities have stayed. It has a private beach, oceanfront pools, and a spa. The beachfront suites have ample space for families.
Transport and Tour Options
Conch Tour Train
One-day narrative tour of Key West with three stops and open-air sightseeing, $42 to $54
Old Town Trolley Tour
All day unlimited hop-on, hop-off tour of Key West with narrated stories, children $19, adults $77
Boat Rides
Find a full list of boat trips, from eco-tours to snorkeling, sailing, and sunset cruises, at fla-keys.com.
Key West Hydrobikes
The new craze is water bikes, and tours depart from LagerHeads Watersports. Rentals $45.95 to $175.95
What to See
Dry Tortugas National Park
Historic 19th-century fort on an island off the coast of Key West where you can swim and snorkel. Requires transportation via ferry or sea plane. Camp sites available.
Yankee Freedom Dry Tortugas Ferry $200 per person
Ernest Hemingway Home & Museum
Key West’s most famous resident lived and wrote books at this home, alongside his six-toed cats.
Tours $7 to $18
Key West Butterfly & Nature Conservatory
The glass-domed tropical habitat is home to free-flying butterflies, exotic birds, and flamingos.
Admission $12.50 to $17.50
Key West Lighthouse
Tours of lighthouse, with stair climb, and Keeper’s Quarters Museum
Admission $7.50 to $17
Key West Shipwreck Treasure Museum
Learn the history of the wrecked salvage industry in Key West during the 19th century.
Admission $17
Truman Little White House
Only presidential home in Florida with museum tours and other experiences
Admission $22.95; VIP White Glove Tour $645
Fort Zachary Taylor State Park and Beach
Civil War–era fort and beaches for swimming, snorkeling, paddling, picnicking, and fishing
Admission $6 per vehicle
Where to Eat
Blue Heaven Restaurant & Bar
Serves breakfast, lunch, and dinner in a quaint building near the Southernmost Point. The restaurant sources ingredients from farms in Florida and Tennessee. Accepts limited dinner reservations.
El Meson de Pepe
Family-owned, 30-year-old restaurant in Mallory Square serves authentic Cuban cuisine, local seafood, and celebrated cocktails.
Latitudes at Sunset Key Cottages
Waterfront fine-dining restaurant on a private island. Open breakfast, lunch, and dinner but requires a short boat ride from downtown Key West.
Louie’s Backyard
This romantic restaurant offers stunning views of the Atlantic Ocean and serves locally sourced ingredients and imaginative cuisine prepared by Chef Doug Shook.
Sloppy Joe’s Bar & Restaurant
This historic bar has Hemingway artifacts and live music.
Feature image, stock.adobe.com
This story originally ran in our February issue. For more stories like this, subscribe to Northern Virginia Magazine.
