Florida Keys Road Trip: Miami to Key West in 3 Days (+ Dry Tortugas)

Leave Miami early and head south on US-1. Just before the Keys, in Homestead, Robert Is Here is the classic first stop: a fruit stand that started in 1959 with a 6-year-old’s hand-painted sign, famous for its fresh-fruit milkshakes (open daily 9 a.m. to 6 p.m.).

In Key Largo, Pennekamp (around MM 102.5) was the first undersea park in the United States, and the reef is the reason to stop.

• Glass-bottom boat to Molasses Reef, about 6.5 miles offshore, if you’d rather stay dry.
• Snorkel tour, with 1 to 1½ hours on the reef. Some snorkel trips go to the Christ of the Deep statue at Key Largo Dry Rocks. Book tours online ahead of time (information: 305-451-6300).
• Entry is $8 per car plus $0.50 per person, open 8 a.m. to sunset every day.
• The Christ of the Deep is a 9-ft bronze statue placed in 1965, under about 25 ft of water. Only snorkel and dive boats can take you there.
• The African Queen (MM 100, at the Holiday Inn marina): the actual 1912 steamboat from the 1951 Bogart and Hepburn film, still running 1½-hour canal cruises ($59).

Islamorada starts at MM 91, a string of islands known for fishing and shallow sandbars. Spend the afternoon here and sleep here.

• Robbie’s (MM 77.5, bayside): buy a bucket of fish ($5, plus $2.50 dock admission) and feed the giant tarpon off the dock.
• History of Diving Museum (MM 83): helmets from around the world and a diving-bell replica.
• Theater of the Sea (MM 84.5): a marine park open since 1946 ($49.95 for ages 11 and up).
• Keys History & Discovery Center (MM 82, at the Islander Resort): the story of the Keys, including Flagler’s railroad to Key West.
• Hurricane Monument (MM 81.5): built in 1937 for the victims of the 1935 Labor Day hurricane, among the strongest and deadliest ever to hit the United States.
• Anne’s Beach (MM 73.5): a mangrove boardwalk and knee-deep water. It’s free, but parking is limited.
• Sunset at the Lorelei (MM 82, bayside): the bar with the giant mermaid sign is the local spot to watch the sun go down.

The new Seven Mile Bridge (MM 47 to MM 40) is the most famous drive in the Keys. Before you cross it, walk or bike the old one beside it: after a restoration of about $44 million, 2.2 miles of the 1912 railroad bridge reopened in January 2022, for walkers and cyclists only.

• Park at the lot near MM 47, by the visitors center.
• The path ends at Pigeon Key, a tiny island with the historic camp of the railroad workers. Entry is $15 for adults if you walk or bike in, or $30 on the train from the visitors center (tours at 10:00, 11:30, 1:00 and 2:30).

Also in Marathon:

• The Turtle Hospital (MM 48.5): a rescue hospital for injured sea turtles, visited on a 90-minute guided program ($38 for adults, every half hour from 9 a.m. to 4 p.m.). Booking ahead is highly recommended.
• Crane Point (MM 50.5): a 63-acre nature preserve with trails, a natural history museum and a house built in the early 1900s by a Bahamian settler, George Adderley.
• Sombrero Beach: Marathon’s palm-lined city beach, at the end of Sombrero Beach Road.

Bahia Honda State Park (MM 36.8) has some of the best beaches in the Keys, with real sand and clear water.

• Calusa Beach on the bay side and Sandspur Beach on the Atlantic side.
• The short trail from Calusa Beach climbs onto the Old Bahia Honda Bridge for the classic view down the Keys (check at the entrance that the overlook is open).
• Entry is $8 per car plus $0.50 per person. The park can close to new cars when it’s full, so come early on weekends.

Just after, Big Pine Key is home to the tiny Key deer, found nowhere else. The National Key Deer Refuge forbids feeding or touching them, and the speed limits on US-1 through the island are enforced: slow down, especially at dusk. The Blue Hole, a freshwater-filled old quarry on Key Deer Blvd about 3 miles off US-1, has a short trail to a viewing platform where you may see turtles, wading birds and sometimes an alligator.

For dinner or a beer, the No Name Pub on Big Pine Key has been around since 1931, with thousands of dollar bills stapled to the walls and pizza that people drive out for.

Then drive the last 35 miles or so to Key West.

Park the car for the day: Old Town is small, flat and easier on foot or by bike.

• Ernest Hemingway Home & Museum: $19 for adults, with a guided tour included, open 9 a.m. to 5 p.m. Tickets are sold at the gate only. Say hi to the nearly 60 cats: about half have six toes, and some descend from Hemingway’s own six-toed cat, Snow White.
• Fort Zachary Taylor Historic State Park: a Civil War-era fort and the best beach in Key West ($6 per car plus $0.50 per person).
• The Southernmost Point buoy, at South and Whitehead Streets, “90 miles to Cuba”. Expect a line for the photo.
• Mallory Square Sunset Celebration: every evening, starting about two hours before sunset, with street performers and the whole town watching the sun go down. It’s free.

The rest of the Key West classics are below the itinerary.

Seventy miles west of Key West, Fort Jefferson sits on a tiny island in turquoise water. You can only get there by boat or seaplane.

• The Yankee Freedom ferry leaves from 100 Grinnell St at 8 a.m. (check-in at 7) and gets back around 5:15 p.m. Day trips start at $260 per adult, including the park fee, a breakfast snack, a box lunch, snorkel gear and a 45-minute fort tour. It sells out weeks in advance: book as soon as your dates are set.
• A seaplane is faster (about 40 minutes each way) but costs from about $527 per adult for a half day, plus the $15 park fee.
• The park entrance fee is $15 per person aged 16 and up. The new 2026 surcharge for non-U.S. residents does not apply at Dry Tortugas.