Destination 01
Miami
South Beach
Start with sand before the Overseas Highway
beach
Wynwood Walls
Street art fuel stop
culture
Florida Keys Adventure
Island-hop the Overseas Highway
Route preview
4 days through Miami, Key Largo, Key West.
Florida Keys Adventure is a 4-day curated route with 3 destinations and 8 suggested stops. Preview stops and timing, then find it in TripsCircle Explore.
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12 stops
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23 stops
Destination 02
Key Largo
John Pennekamp
Snorkel clear reefs and mangroves
adventure
African Queen
Historic boat and waterfront vibes
sight
Florida Keys Wild Bird Center
A worthwhile wildlife stop on the drive south
nature
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33 stops
Destination 03
Key West
Mallory Square Sunset
Street performers as the sun drops
sight
Seven Mile Bridge views
Open water on the drive in
sight
Hemingway Home
Historic rooms and gardens in the heart of Old Town
culture
Route highlights
The moments that shape this trip.
- 01Seven Mile Bridge
- 02Snorkeling
- 03Mallory Square Sunset
- 04Dry Tortugas
Trip guide
Planning Florida Keys Adventure.
A short, sunny trip that follows one long road into the sea. Start in Miami for a night of beaches and food, then drive south to Key Largo, where snorkeling, diving and glass-bottom boat tours show off the coral reefs. Continue along the chain of islands and bridges to Key West, a lively town at the end of the road with sunset gatherings, historic houses and relaxed dining. It is easy to fit into a long weekend.
Good for Groups who want a quick, sun-soaked island drive
When to go
December through May is the drier season with warm, comfortable temperatures and good water conditions for boat trips. It is also busy, especially around holidays and weekends. Summer is hot and humid, with afternoon storms and an active hurricane season in the early fall.
Getting around
Most travelers rent a car in Miami and take the Overseas Highway all the way to Key West, enjoying the views as they go. Traffic can be slow at times, so leave extra time. Some people fly into Key West or take a shuttle for part of the trip.
Tips for your crew
- Break the drive with a stop in Key Largo. Book a snorkel or dive trip ahead, and pick morning departures when the water tends to be calmer.
- Reserve Key West lodging early. Its rooms are limited, and weekends and holidays fill quickly, so a midweek visit can feel more relaxed.
- Start the drive early in the day. You will beat some of the traffic and give the group time for scenic stops and a long lunch.
