Day 1: Miami and the Drive to Key Largo
Start the trip in Miami with a morning on South Beach. The famous Art Deco strip along Ocean Drive is worth seeing in person, and the beach itself is wide, clean, and consistently beautiful. Get there before 10 a.m. if you want to avoid the worst of the crowds and the intense summer heat. Walk north along the beach toward Lummus Park for a quieter stretch of sand, or head south toward the quieter sections past 5th Street. After a few hours on the sand, grab breakfast or brunch at one of the Ocean Drive cafes and then start loading the car for the drive south.
The drive from Miami to Key Largo takes about 90 minutes under normal traffic conditions, but leave extra time because the stretch through Homestead on US-1 can slow down significantly, especially on Friday afternoons when everyone else seems to have the same idea. Once you clear Florida City and pay the toll into the Keys, the road changes character immediately. The land narrows, the sky opens up, and you get your first views of the bay to the north and the Atlantic to the south simultaneously. That first glimpse of the Keys water, that particular shade of aquamarine blue that does not look real, is a moment that sticks with you.
Key Largo is the first and largest island in the Keys, and it has a lot going on despite not having the most beautiful beaches. It is famous as a diving and snorkeling destination, primarily because John Pennekamp Coral Reef State Park sits here, the first undersea park in the United States. If you want to snorkel the reef on your first day, Pennekamp runs morning and afternoon snorkel trips by glass-bottom boat and by boat to the reef itself. The park's own beaches are calm and pretty, shaded by tropical trees. Spend the evening at a waterfront restaurant on Card Sound Road or the main drag through Key Largo, watching the sun go down over Florida Bay.
Day 2: Key Largo to Islamorada
Islamorada (pronounced eye-lah-muh-RAH-dah) is not one island but six, spread across a 20-mile stretch of the Upper Keys. It bills itself as the Sport Fishing Capital of the World, and the claim is legitimate. The backcountry flats north of Islamorada are among the finest shallow-water flats fishing grounds anywhere, with tarpon, bonefish, and permit all available to fly fishers who hire one of the exceptional guides based here. Even if fishing is not your thing, the area has some genuinely lovely spots and a more sophisticated dining scene than Key Largo.
Anne's Beach, located at the southern end of Lower Matecumbe Key, is one of the nicest natural beaches in the Upper Keys. It is shallow, calm, and backed by a mangrove boardwalk that you can walk to stretch your legs. The water here is a little greenish and murky compared to the lower Keys, but the setting is peaceful and the beach is rarely jammed. Robbie's Marina, a few miles north of Anne's Beach, is an essential Islamorada stop. You can hand-feed enormous schools of tarpon from the dock, rent a kayak, or book a fishing charter. It is touristy but genuinely fun. The waterfront restaurant there, Hungry Tarpon, is excellent for lunch.
Plan to stay overnight in Islamorada, where accommodation ranges from funky old-Florida fishing camps to boutique resorts. Cheeca Lodge is the historic grande dame of Islamorada hotels and has one of the best small beaches in the Upper Keys right on its property. The town has good restaurants, and the sunsets over Florida Bay are spectacular from any of the west-facing waterfront spots. Morada Bay Beach Cafe does a monthly full moon party right on the water that is worth timing your trip around if you can.
Day 3: Bahia Honda State Park and Long Key
Bahia Honda State Park is the destination that most people think of when they imagine a beach in the Florida Keys. The park sits on a small island in the Middle Keys and has three separate beach areas, each with different character. Sandspur Beach on the Atlantic side has the clearest water and the finest sand. Calusa Beach on the Gulf side is calmer and more sheltered. The old Bahia Honda Rail Bridge, a remnant of Henry Flagler's Overseas Railroad, looms over the park and is climbable for a dramatic view of the surrounding waters. Come early. The park fills to capacity on summer and holiday weekends, sometimes turning away cars by 8 a.m.
The snorkeling at Bahia Honda is some of the best in the Keys that you can access without taking a long boat ride. The reef immediately offshore on the Atlantic side has good coral coverage and diverse fish life. The park rents snorkel gear and runs guided snorkel tours from the marina. Kayak rentals are also available, and paddling around the mangrove-lined shorelines of the park is a great way to see herons, ospreys, and the occasional manatee. Plan to spend the majority of the day here.
Long Key State Park, about 30 miles north of Bahia Honda on US-1, is worth a stop if you have time in the afternoon or if you are working your way down from Islamorada. The park has a beautiful beach on the Atlantic side and a coastal hammock trail through a dense thicket of tropical hardwoods. The camping here is some of the most sought-after in the Keys, with sites right on the water that book up months in advance. Even if you are not camping, the day-use beach and the hiking trails are worthwhile. This is a quieter, less visited park than Bahia Honda, and the crowd reflects it.
Day 4: Marathon and Sombrero Beach
Marathon is the largest city in the Middle Keys and has a working-class, local feel that contrasts with the tourist-oriented Upper Keys and the bohemian Key West vibe to the south. It is a real town where people live and work, with grocery stores, a hospital, and neighborhoods that have nothing to do with tourism. That grounded quality makes it a refreshing stop after days of resort towns and vacation rentals. The historic Pigeon Key, accessible by ferry from Knight's Key, sits beneath the old Seven Mile Bridge and has an excellent museum about the construction of the Overseas Railroad. The new Seven Mile Bridge, one of the longest segmental bridges in the world, runs right alongside the old one and offers views that are genuinely awe-inspiring when you are driving across it.
Sombrero Beach is Marathon's public beach and one of the best free beaches in the Keys. It sits off Sombrero Beach Road, away from the main highway, on the Atlantic side of the island. The beach is well-maintained, family-friendly, and has clean restrooms, picnic pavilions, and a boat ramp. The water is calm and clear, protected by an offshore reef. Sea turtles nest here in summer, and the park is active in turtle conservation with nighttime patrols during nesting season. It is a genuinely lovely beach that feels more real than some of the more manicured spots in the upper Keys.
Also worth a stop in Marathon: Coco Plum Beach, a small and peaceful beach on the Gulf side that has a very different character from Sombrero Beach. The water is shallower and calmer, the scenery is dominated by mangroves and sea grapes, and the crowd is almost entirely local. It is the kind of place where you can spend an hour without seeing another tourist, which is not something you can say about many Keys beaches in peak season. Stay in Marathon for the night to position yourself for an easy drive down the Seven Mile Bridge in the morning.
Day 5: Key West Beaches
The drive south from Marathon through the Lower Keys on US-1 is one of the most beautiful road trips in America. You cross over a succession of small bridges connecting tiny islands, with open water visible in every direction and osprey nests perched on the old bridge pilings. Big Pine Key, about 30 miles south of Marathon, is home to the National Key Deer Refuge, where a subspecies of white-tailed deer roughly the size of a large dog lives in the pinelands and roams freely across the roads. Drive slowly through Big Pine Key in the early morning or evening for your best chance of seeing them.
Key West is the final island on the chain and Florida's southernmost city, a place that has always operated by its own rules. The beaches here are not as naturally beautiful as Bahia Honda or the best Middle Keys spots, because Key West sits on the Gulf side of the reef system and the nearby water is shallower and less clear than the open Atlantic beaches to the north. But the beaches are still lovely, and the surrounding town makes the experience unique. Smathers Beach is the biggest and most popular, a long crescent of imported sand along South Roosevelt Boulevard on the Atlantic side. Water sports vendors line the beach, and the vibe is festive and social. Fort Zachary Taylor State Park has the clearest water in Key West and a more relaxed, shaded setting. The Civil War-era fort there is one of the best-preserved in the country and worth the extra hour to tour.
Higgs Beach and Rest Beach sit side by side on the Gulf side of White Street, close to downtown. Higgs Beach has a popular restaurant right on the water, a volleyball court, a playground, and one of the most diverse crowds of any beach in Florida. Rest Beach is smaller and quieter, separated from Higgs by the White Street Pier. Both face west, making them excellent spots for the famous Key West sunset. Mallory Square gets all the publicity for sunsets, and the nightly Sunset Celebration there is a genuine event worth attending once, but the beaches are often better for an unobstructed view of the sun dropping into the Gulf.
Planning Tips
The Overseas Highway (US-1) is the only road in and out of the Keys, and it has no passing lanes for much of its length. Traffic backups on Sunday evenings heading north out of Key West can stretch for hours. If you are flying in or out of Miami, try to schedule your arrival or departure on a weekday. The drive from Miami to Key West is 160 miles and takes about 3.5 hours without stops, which means budget at least 5 hours if you plan to make any stops along the way (and you should).
Fuel up whenever you see a gas station, because stations in the Keys are sparse and prices run significantly higher than the mainland. Groceries are also more expensive, so stock up in Florida City before you cross into the Keys if you are planning to cook at a vacation rental. Bring cash, because some of the best local spots (small restaurants, bait shops, waterfront stands) do not take cards. Phone coverage is good along the main highway but can be spotty in some of the more remote state parks and off the main drag.
Where to Stay
Key Largo has the most lodging options in the Upper Keys, ranging from chain hotels near the highway to fish camp-style waterfront resorts. Islamorada has more character and some of the best small hotels and boutique resorts in the Keys. Bahia Honda State Park has an excellent campground that books up months in advance, but it is one of the best camping experiences in Florida if you can get a site. Marathon has good mid-range hotel options and is a central base for exploring both the Upper and Lower Keys. Key West has the widest range of accommodation from hostels to luxury resorts, and the Duval Street area puts you within walking distance of most of the action, though it is loud. Guest houses on the quieter streets of Old Town offer more character at similar prices.
Best Time to Go
The Florida Keys are one of the few places in Florida that have excellent beach weather year-round. December through April is peak season, with dry weather, lower humidity, and water temperatures in the mid-70s that are comfortable for snorkeling. The Keys are also significantly less crowded than South Florida's beaches during this period, making it a good winter escape. March and April can be busy around spring break, especially in Key West. May and June are an excellent shoulder season choice, with warm water, lower prices than peak season, and manageable crowds before the summer rush. July and August are hot and humid with frequent afternoon storms, but the water temperature peaks above 85 degrees and the reef snorkeling is spectacular. Hurricane season runs June through November, but the Keys historically have good advance warning of approaching storms and the state park infrastructure is set up for rapid closures when needed.