- Distance from Miami: 161 miles
- Best time: December to April; July
- Best for: Girl's GetawayFood and WineShopping
The food scene in Key West is so much more than conch fritters and key lime pie. Dip down to the southernmost point in the continental United States to sample inventive spins on fresh seafood and the growing number of restaurants that understand it takes more than a rum runner to please discerning palettes. Bahama Village, just off the main Duval Street thoroughfare, has been a significant contributor, with a mini boom of quality restaurants in recent years. The compact nature of Key West's historic Old Town makes it easy to navigate among our recommended weekend escape spots on foot or by bicycle, so leave the car at your hotel or at home. – By LoAnn Halden
Key West Cheat Sheet
View a printable list of all sights, restaurants, entertainment, and hotels from this itinerary. View
1Get acclimatized to the island's eclectic rhythms with a stroll on Duval Street, the main drag of Old Town's shopping and nightlife. "Colorful" aptly describes the people watching and the retail mix that combines wacky T-shirt shops with high-end Towels of Key West.
2For dinner, head east to always-bustling Nine One Five, a Victorian-home-turned-wine-bistro with front porch seating overlooking Duval. An extensive wine list accompanies plates sized for all appetites, from foie gras with fig jam to Key West black grouper and steak frites.
1Ensconced in a charming clapboard cottage, Sarabeth's caters to early birds and late risers with a breakfast menu that spills well into the afternoon. As the southern outpost of NYC jam maker and pastry chef Sarabeth Levine, count on baked goods to die for.
2Burn off a few breakfast calories with a 10-minute walk west to Pier House for a treatment at the resort's Caribbean Spa. The Milk and Honey Rehydrating Treatment is a long-running favorite for nourishing sun-baked skin.
3Head to Santiago's Bodega, tucked about five blocks off Duval in Bahama Village, for a tapas lunch and homemade sangria. Dishes like goat cheese stuffed dates wrapped in proscuitto, pork skewers with apple-mango chutney, and spicy shrimp bisque have made this tiny spot a dining destination.
4Walk back to the west end of Old Town for some tasty island gifts to bring home. Peppers of Key West encourages visitors to belly up to their tasting bar to sample a flight of sauces, escalating from mild to fiery. The Peppers-branded Asian marinade gets our vote.
5The shopping continues at Kino Sandals, which has turned out handcrafted, affordable footwear in Key West since the mid-'60s. Then pass through the Sponge Market in Mallory Square to pick up any size or shape of natural sponge imaginable.
6Rowdy booze cruises abound, but only Danger Charters' Wind & Wine Sunset Sail accompanies its two-hour sunset viewing excursion with a top-notch tasting of eight wines from around the world. The ship docks at the Westin Resort & Marina.
7Fresh seafood is the hallmark of Key West dining, and off-the-beaten-path favorite Seven Fish makes the most of the local waters, updating its menu daily around the latest catch. Make a reservation because tables vanish quickly at this small, chic bistro nestled among Old Town residences.
1Start off with a French treat at La Creperie Key West, where offerings range from sweet fruit-filled crepes to their savory counterparts made from organic buckwheat and stuffed with brie, ratatouille, or smoked salmon. The restaurant has enjoyed a renaissance since relocating to this more spacious indoor-outdoor location in Bahama Village.
2Key West isn't renowned for its beaches, but Fort Zachary Taylor Historic State Park, about a mile from Bahama Village, is worth a post-breakfast visit. Tour its National Historic Landmark fortress, snorkel, and soak up sun on the sands at the southern end of the park.
3Wind down the weekend with a stop at the Keys' classic B.O.'s Fish Wagon, a license-plate-laden, open-air shack that serves tasty grouper sandwiches, shrimp, cracked conch, and burgers on the west side of Old Town.
Where to Stay
Conveniently positioned where U.S. 1 meets Duval Street, Orchid Key Inn (rooms from $199/night) upgrades motel-style lodging with boutique flair. Each room is a hip oasis with mosaic glass-tiled bathrooms and custom furniture. The onsite Orchid Bar, where talented mixologists create seasonal cocktails, adds an urban edge.
Historic Casa Marina (rooms from $249/night + $25/day resort fee) sits on a private beachfront near the Southernmost Point. In a town overflowing with small guesthouses, it's a welcome opportunity for resort-size anonymity–complete with two oceanfront pools, hammocks, and watersports rentals.
When to Go
Key West receives less rainfall than other parts of Florida, with December to April boasting the most sunny days. Visit in July, the driest of the summer months, to savor a quieter Key West. Hotel rates are reduced, and there's a greater likelihood of booking a weekend stay without a three-night minimum requirement.
Key West throws a great party, most notably Fantasy Fest in October for Halloween and its New Year's Eve celebration. During major events, many hotels raise their minimum weekend stay requirements to five nights. To keep track of Key West festivities year round, check out the Florida Keys online events calendar.
How to Get There
By car: Key West is a little more than three hours from Miami. Take the Florida Turnpike South. The Turnpike ends in Florida City at U.S. 1, which runs all the way south to Key West.
By Shuttle: Keys Shuttle makes six daily trips each way via Miami International Airport to/from Key West. The trip takes about four hours both ways. Key West is easy to navigate without a car; most visitors either walk, bike, or rent mopeds. The island's signature pink taxis are also readily available.
Car Rental Deals
- Up to 20% Off -- Discounted Car Rentals Across the U.S. Sixt rent a car
- $33 -- Compact Crossover SUV Rentals through Fall Sixt rent a car
- Up to 15% Off -- Discounted Car Rentals Across the U.S. Sixt rent a car
- $39 & up -- Luxury Car Rentals this Fall, incl. Mercedes Sixt rent a car