The Florida Keys: The End of the Road
The Florida Keys are a chain of over 1,700 islands stretching 120 miles from the southern tip of mainland Florida to Key West — the southernmost point of the continental United States. Connected by the Overseas Highway (US Route 1), driving the Keys is one of the world's great road trips: bridges spanning turquoise water, tiny island communities, roadside fish shops, and a gradual descent into Caribbean-flavoured relaxation.
Key West, the final stop, is a world unto itself — quirky, colourful, rum-soaked, and gloriously unconcerned with convention.
The Drive: Overseas Highway
The drive from Miami to Key West takes approximately 3.5-4 hours without stops (but stopping is the entire point). The journey follows US-1 south over 42 bridges, including the famous Seven Mile Bridge — a seemingly endless span of road over open ocean.
Key Largo (Mile Marker 106-91)
The first and largest Key. Known for:
- John Pennekamp Coral Reef State Park — The first undersea park in the US. Glass-bottom boat tours, snorkelling, and diving over the only living coral barrier reef in the continental US
- Diving and snorkelling — The reef system here is outstanding. Operators offer trips for all ability levels
- Key Largo Undersea Park — An underwater hotel (yes, really)
Islamorada (Mile Marker 90-73)
The "Sport Fishing Capital of the World." A quieter, more upscale Key:
- Deep-sea fishing — Charter boats for tarpon, bonefish, sailfish, and more
- Robbie's Marina — Feed enormous tarpon by hand from the dock. A must-do, especially with children
- Theater of the Sea — Small marine park with dolphin and sea lion encounters
- Anne's Beach — A quiet, shallow beach good for families
Marathon (Mile Marker 65-47)
The commercial hub of the middle Keys:
- The Turtle Hospital — A rehabilitation centre for injured sea turtles. Guided tours are excellent and educational
- Bahia Honda State Park — Often rated the best beach in the Keys. Crystal-clear water, white sand, and the old railroad bridge as a backdrop
- Seven Mile Bridge — The drive from Marathon south crosses this iconic bridge. Stop at the old bridge viewpoint for photos
Big Pine Key & Lower Keys (Mile Marker 46-9)
Quiet, natural, and home to the endangered Key deer (miniature white-tailed deer unique to these islands):
- National Key Deer Refuge — Watch for these tiny deer along the road (especially at dusk). Do not feed them
- Looe Key — Outstanding snorkelling and diving on a spur-and-groove reef
Key West
The southernmost point. The last island. A town of maybe 25,000 people that has hosted wreckers, cigar makers, shrimpers, writers, artists, and rebels for 200 years.
What to Do
Duval Street — The main drag. Bars, restaurants, shops, and galleries from one end of town to the other. It's touristy and occasionally excessive, but it's the beating heart of Key West nightlife and culture.
Mallory Square Sunset Celebration — Every evening, the waterfront fills with street performers, food vendors, and hundreds of people gathering to watch the sunset over the Gulf of Mexico. It's beautiful, communal, and free.
The Ernest Hemingway Home and Museum — Hemingway wrote some of his greatest works here. The house is beautifully preserved, and dozens of six-toed cats (descendants of Hemingway's own) roam the grounds.
Fort Zachary Taylor State Park — The best beach in Key West. Clear water, a historic fort to explore, and a nature trail. The snorkelling off the shore is excellent for beginners.
The Southernmost Point Buoy — The famous striped buoy marking the southernmost point of the continental USA. It's a photo opportunity, not an experience, but everyone does it. Go early morning to avoid queues.
The Key West Butterfly and Nature Conservatory — A glass-enclosed tropical habitat filled with butterflies and birds. Peaceful and lovely.
Where to Eat in Key West
- Blue Heaven — Open-air dining in a ramshackle tropical garden. Famous for Key lime pie and brunch. Chickens wander freely through the restaurant (this is normal in Key West)
- Santiago's Bodega — Tapas and cocktails on Bahama Village. Outstanding small plates
- Latitudes on Sunset Key — Accessible by boat from Mallory Square. Sunset waterfront dining. Special occasion territory
- BO's Fish Wagon — Fried fish sandwiches and cold beer in a gloriously ramshackle roadside setup
- Kermit's Key West Key Lime Shoppe — Key lime pie, key lime cookies, key lime everything. The key lime pie on a stick (dipped in chocolate) is ridiculous and essential
Key West Culture
Key West has a unique culture shaped by its isolation and its history as a haven for artists, writers, and nonconformists:
- Hemingway Days — Annual festival in July celebrating the author with look-alike contests, writing competitions, and a lot of rum
- Fantasy Fest — Late October. A 10-day festival that's part Mardi Gras, part Halloween, part Key West. Outrageous, colourful, and adults-only
- Drag culture — Key West has a long tradition of drag performances and LGBTQ+ culture. Shows at various bars along Duval Street
- Live music — Everywhere. Every bar has live music, much of it surprisingly good
Getting Around Key West
The island is tiny — roughly 2 miles by 4 miles. Walking and cycling are the best ways to get around. Bike rentals are available everywhere. Cars are a hindrance — parking is expensive and limited. The free Duval Loop bus connects the main areas.
Practical Keys Tips
- Driving from Miami: About 3.5-4 hours to Key West. Leave early — the single road gets congested, especially on weekends and holidays
- Fuel: Fill up before entering the Keys. Petrol stations exist but prices increase as you go south
- Accommodation: Key West hotels are expensive, especially in peak season (December-April). Book well in advance. Mid-Keys (Marathon, Islamorada) offers better value
- Mosquitoes: The Keys have mosquitoes. Bring repellent, especially if you're outdoors at dusk
- No-see-ums: Tiny biting insects, especially at dawn and dusk near mangroves. Long sleeves help
- Speed limits: Strictly enforced throughout the Keys. 35-45 mph on most of US-1. There is no overtaking — the road is mostly two lanes
- Day trip vs. overnight: A day trip from Miami is possible but rushed. Staying one or two nights in Key West is strongly recommended to experience the sunset, the nightlife, and the morning calm before the day-trippers arrive
- Water activities: The reef is the main attraction. Book snorkelling or diving trips in advance during peak season. Many operators pick up from multiple locations
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