1. Key West
Best for: nightlife, history, and reef trips | Mile marker: 0 | Drive from Miami: 3.5-4 hours | Airport: EYW | Base: Old Town
Key West is the end of the Overseas Highway and the southernmost city in the continental US, with the Mallory Square sunset celebration, Duval Street bars, the Hemingway Home and its six-toed cats, and Fort Zachary Taylor for the best local swimming. It is the natural base for reef and Dry Tortugas trips.
Parking is tight, so most visitors go on foot, by bike, or by trolley. Stay at Opal Key Resort & Marina near the harbor, and book Sunset Watersports or Fury for sandbar and reef trips. It anchors the bottom of the Florida Keys.
2. Key Largo
Best for: diving and snorkeling | Mile marker: ~100 | Drive from Miami: about 1 hour | Draw: John Pennekamp reef
Key Largo is the first island south of the mainland and the self-billed diving capital of the world, thanks to John Pennekamp Coral Reef State Park and the reef just offshore. Glass-bottom boat, snorkel, and scuba trips run all day, out to the Christ of the Abyss statue.
It is the easiest Keys day trip from Miami, about an hour down US-1. Gilbert's Resort & Marina at the top of the island is a longtime waterfront stop for a drink and a boat launch.
3. Islamorada
Best for: sportfishing and waterfront dining | Mile marker: ~80 | Drive from Miami: about 2 hours | Draw: Robbie's tarpon feeding
Islamorada is a string of middle-Keys islands known as the sportfishing capital of the world, with backcountry and offshore charters, the sandbar scene, and some of the best waterfront dining in the chain. It is calmer and more upscale than Key West.
Stop at Robbie's of Islamorada to hand-feed the giant tarpon off the dock, a classic Keys photo. Book a half-day charter and stay for a sunset dinner on the water.
4. Marathon
Best for: families and the Seven Mile Bridge | Mile marker: ~50 | Drive from Miami: about 2.5 hours | Draw: Turtle Hospital, Sombrero Beach
Marathon anchors the middle Keys and works well for families, with the Turtle Hospital, Sombrero Beach for real sand, and the Dolphin Research Center just up the road. It sits at the north end of the Seven Mile Bridge, the drive's headline crossing.
It is a good halfway base if 3.5 hours to Key West feels too far in one go. Quieter and more affordable than the ends of the chain, in the heart of the Keys.
5. Bahia Honda Key
Best for: the best beach in the Keys | Mile marker: ~37 | Fee: about $8 per vehicle | Draw: state-park sand, old rail bridge
Bahia Honda State Park has the best beach in a chain where sand is rare: soft sand, clear shallow water for swimming and snorkeling, and the old Flagler railroad bridge as a backdrop. It is a required stop on the drive south.
Come early, because the lot fills, and rent snorkel gear on site. For more sand-first islands, see the best islands in Florida.
6. Big Pine Key
Best for: wildlife and quiet | Mile marker: ~30 | Draw: tiny Key deer, National Key Deer Refuge
Big Pine Key in the lower Keys is home to the National Key Deer Refuge and its miniature Key deer, a subspecies found nowhere else. It is a slow, residential stretch that trades bars and shops for nature and calm.
Drive the refuge roads at dawn or dusk to spot the deer, and use it as a peaceful base near Bahia Honda. A change of pace before the Key West finale.
7. Dry Tortugas (Garden Key)
Best for: snorkeling and a sea fort | Access: Yankee Freedom ferry from Key West | Fee: $15 per person park fee | Ferry: about $220 adults, book weeks ahead
Technically beyond the road, Dry Tortugas National Park is seven islands about 70 miles west of Key West, reached by the Yankee Freedom ferry, a seaplane, or private boat. Fort Jefferson on Garden Key sits above some of the clearest snorkeling water in the state.
Book the ferry weeks ahead in peak season, and plan a full day, about 4.5 hours on the island. It is the wildest stop in the whole chain.
8. Duck Key and Grassy Key
Best for: resort stays and dolphins | Mile marker: ~61 and ~53 | Draw: Hawks Cay resort, Dolphin Research Center
Duck Key is home to the Hawks Cay resort, a self-contained family base with a marina and pools, while neighboring Grassy Key holds the Dolphin Research Center. Together they make an easy, low-key middle-Keys stop for families who want a resort rather than a town.
They sit near Marathon, a bit over two hours from Miami. For a hotel base anywhere in the chain, see the hotels and resorts directory, and note the Keys are a world away from the Panhandle at the other end of Florida. Round out a trip with the best small towns in Florida.
Where to base and how long to stay
Top base: Key West | Easiest day trip: Key Largo | Family base: Marathon | Fishing base: Islamorada
Pick your base by what you came for. Key Largo works as a day trip from Miami for diving, with Gilbert's Resort & Marina at the top of the island for a waterfront launch. Anglers stay in Islamorada and book charters near Robbie's, while families settle in Marathon for the midway location and real sand at Sombrero Beach.
For the full end-of-the-road experience, base in Key West and run reef and sandbar trips with Fury, Sunset Watersports, or Sebago from the harbor. Give the drive down a full day so you can stop at Bahia Honda and the roadside stands along the way. Most first trips do two or three nights, enough to dive Key Largo, fish or eat in Islamorada, and still reach Key West for a couple of sunsets without rushing the single road in both directions.
| Island | Drive from Miami | Best for |
|---|---|---|
| Key Largo | ~1 hour | Diving, day trips |
| Islamorada | ~2 hours | Sportfishing, dining |
| Marathon | ~2.5 hours | Families, halfway base |
| Key West | 3.5-4 hours | Nightlife, reef, history |
Frequently asked questions
How long does it take to drive the Florida Keys?
Miami to Key West runs about 3.5 to 4 hours on the two-lane Overseas Highway when traffic is light, covering roughly 160 miles down US-1. Give yourself a full day with stops at Key Largo, Islamorada, and Bahia Honda, and expect delays on holiday weekends when the single road backs up.
Which Florida Key is best for a first visit?
Key West is the classic first-timer's choice for its nightlife, history, and reef access, while Key Largo is the easiest day trip from Miami for diving and snorkeling. Islamorada suits anglers, and Marathon works well as a quieter family base halfway down the chain.
Do the Florida Keys have good beaches?
Natural sand beaches are limited because the islands sit behind a coral reef, but Bahia Honda State Park has the best one, and Fort Zachary Taylor in Key West and Sombrero Beach in Marathon are solid. Most Keys water time is spent snorkeling, boating, or fishing rather than on wide sand.
When is the best time to visit the Florida Keys?
November through April is peak: warm, dry, and calmest for boating and diving, though winter cold fronts can occasionally cancel trips. Summer is hot and humid with afternoon storms but the clearest reef water. Hurricane season runs June through November, so watch the forecast in late summer.