KICKING BACK IN KEY WEST and the Florida Keys defines time off for busy travelers and a relaxed way of life for residents. Arrive by air at Key West International Airport and you’ll immediately notice the island’s easygoing vibe. Drive the roughly 160 miles from Miami along the Overseas Highway and the scenery begins the moment you leave the mainland. Ferry service from Miami offers another scenic arrival option across the Straits of Florida.
The Florida Keys are an archipelago of about 800 islands; U.S. 1 reaches only a fraction of them, so plan to explore a few keys along the way. Key Largo, one of the first islands you’ll encounter, is home to the historic Caribbean Club, made famous by the 1951 film Key Largo. That venue still captures the laid-back atmosphere, food and cocktails that characterize the drive south toward Key West.
If you enjoy marine life, John Pennekamp Coral Reef State Park is an ideal stop for snorkeling over one of the few living coral reefs in the United States. Families can take part in dolphin encounters or visit the park’s wild bird sanctuary, where volunteers rehabilitate native birds. For a taste of local flavors, the Conch House in Key Largo serves classic conch fritters, a nod to the area’s “Conch Republic” identity.
Further south, Islamorada markets itself as a sportfishing capital and offers full-service marinas, charter options, and a variety of water-based activities. Robbie’s of Islamorada is a convenient one-stop for boat and charter rentals, dive trips, and an open-air market. From here you can also catch excursions to Indian Key Historic State Park and Lignumvitae Key Botanical State Park to see how the islands looked before modern development. Upper Matecumbe Key nearby features shops, bars, seafood restaurants and accommodations to suit many budgets.
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Drive past Layton into the Middle Keys and you’ll reach Marathon, where Sombrero Beach is a local favorite. Marathon also hosts Island Hoppers Aerial Adventures for aerial views of beaches and reefs, an unforgettable experience for many visitors. Families often visit the turtle hospital on Vaca Key to learn about sea turtle rescue and rehabilitation. For a relaxed lunch in pleasant grounds, Hawks Cay Resort on Duck Key provides dining options and waterfront views.
Crossing the iconic Seven Mile Bridge brings you into the Lower Keys and eventually Key West. On Big Pine Key, the National Key Deer Refuge offers a chance to see the diminutive Key deer and other wildlife. The Blue Hole and nearby reefs provide additional diving and snorkeling opportunities. For a secluded luxury escape, Little Palm Island Resort & Spa on Little Torch Key offers a private-island experience accessible only by boat or seaplane. There are also many family-friendly lodgings scattered throughout the islands.
Key West itself is the highlight for many visitors. Begin with the Conch Tour Train to get an overview of popular sites and local history. Old Town and Duval Street invite self-guided exploring of restaurants, bars, galleries and small attractions like the butterfly conservatory. Many visitors stay in charming guesthouses and boutique hotels in Old Town, while waterfront resorts and marinas offer another lodging style.
Renting a bike is an affordable, convenient way to tour Key West and reach attractions such as the Ernest Hemingway Home and Museum (known for its six-toed cats), the Audubon House & Tropical Gardens, the Key West Lighthouse, and the lively Schooner Wharf Bar at the Historic Seaport. The Mel Fisher Maritime Museum displays nautical artifacts and treasures, while those seeking outdoor adventure can choose diving, snorkeling, kayaking, hiking on nearby islands, or sportfishing. A boat trip to Dry Tortugas National Park—68 miles west—lets visitors explore historic Fort Jefferson and distant coral reefs.
Sunset is a daily celebration in Key West, with Mallory Square hosting a nightly gathering of street performers, food vendors and live music. Many visitors opt for a sunset cruise aboard sailboats or catamarans that include food, drinks and dancing, or simply take in the view from shore.
Dining choices on Duval Street and throughout Key West range from casual bars and seafood shacks to fine dining. For a special evening, restaurants such as Café Solé and Michael’s draw favorable attention for elevated menus and creative island cuisine. Nightlife continues long into the evening, with many dining and entertainment options concentrated in Key West compared with the quieter keys along the Overseas Highway back toward Key Largo and the mainland.
Key West is also a welcoming and prominent LGBTQ+ destination. Annual events like Fantasy Fest and PrideFest attract visitors worldwide, and the island’s nightlife includes venues known for drag shows, themed events and lively entertainment. The community atmosphere is open and inclusive, with many establishments catering to diverse visitors.
INFO TO GO
There are four main ways to reach Key West and the islands that span between the Gulf of Mexico and the Atlantic Ocean. Most business travelers fly into Key West International Airport or Miami International Airport and then drive the scenic Overseas Highway. Miami International offers the most flights and international connections, while Key West receives direct service from major U.S. carriers and regional airlines. Ground transportation in Key West includes taxis, shuttles and rental cars; the airport is a short drive from downtown and Duval Street.
Greyhound provides bus service from Miami, and seasonal ferry routes run from Miami and Florida’s west coast. If you drive, be mindful that parking can be limited during peak festival seasons—check your hotel’s parking policies before you arrive.
LODGING
CASA MARINA KEY WEST, A WALDORF ASTORIA RESORT
This historic resort offers the only private beach in Key West, along with pools, gardens, spacious suites, business services and ocean views. Guests also have access to The Reach Resort and its spa.
1500 Reynolds St., Key West
$$$$–$$$$$
HAWKS CAY RESORT
A family-oriented resort near beaches with multiple pools, restaurants, a marina for water activities and conference facilities. The property includes accommodations for larger groups and on-site attractions such as resident dolphins.
61 Hawks Cay Blvd., Marathon, Duck Key
$$$–$$$$
LITTLE PALM ISLAND RESORT & SPA
A private-island retreat with oceanfront suites, secluded beaches, pools, spa services and gourmet dining. The resort emphasizes privacy and relaxation; guests arrive by boat or seaplane.
28500 Overseas Highway, Little Torch Key
$$$$–$$$$$
DINING
CAFÉ SOLÉ
A French-Caribbean dining experience offering dishes such as duck à l’orange and fresh mutton snapper, plus classic key lime pie.
1029 Southard St., Key West
$$$
SIXTY-ONE PRIME
An upscale steakhouse at Hawks Cay Resort serving prime beef and classic sides in a polished setting.
Hawks Cay Resort, 61 Hawks Cay Blvd., Marathon, Duck Key
$$$$
SLOPPY JOE’S BAR
A historic Key West saloon dating back to the 1930s, offering live music, dancing, a casual menu and a lively atmosphere on Duval Street.
201 Duval St., Key West
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