Jason lives in the Leonida Keys, and the second trailer spends a lot of its time there: a canal-side house, a tiki bar at sunset, a boat running flat out through mangroves, and a long bridge over water that does not look real. The real Keys are a chain of islands hanging off the bottom of Florida, strung together by one road for roughly 110 miles. This trip is for anyone who wants to drive that road properly, over three days instead of a frantic day out from Miami, and see the Florida the game’s quieter half is built on.
Go from December to April for the dry season and the calmest water; it is also the busiest and priciest stretch. May and early June are a sweet spot, hot but quieter and cheaper. Hurricane season runs June through November, and while a direct hit is rare, September and October are the months to watch the forecast.
Day 1: Miami to Islamorada
Morning. Leave Miami early and skip the main highway. Take Card Sound Road, the back road into the Keys, a two-lane causeway through mangroves and saltwater flats with a small toll and almost no traffic. Alabama Jack’s, the open-air bar on the water at the Card Sound end, opens late morning; stop for conch fritters if the timing works (check the hours). The road rejoins US-1 at the top of Key Largo, and from there you are on the Keys highway, the Overseas Highway, for the rest of the trip. Watch the green mile-marker posts: everything in the Keys is given by mile marker, counting down to zero in Key West.
Afternoon. Key Largo’s residential side streets, between the highway and the water, are the canal neighborhoods that Jason’s canal-side home is drawn from: single-story houses on stilts, a boat lift at the bottom of every garden. Do not cruise people’s streets gawking; rent a kayak from a bayside outfitter and see them from the water, which is how the game shows them. Then drive south to Islamorada and stop at Rain Barrel Village, mile marker 86.7, for the giant roadside whale, which in real life is Betsy, a 30-foot lobster. Five minutes, free, and pure Keys. Robbie’s, at mile marker 77.5, is the other roadside classic: pay a few dollars to hand-feed tarpon off the dock.
Evening. Islamorada calls itself the sportfishing capital of the world, but at sunset it is the tiki bar capital. The waterfront tiki bar covers the bayside spots where you watch the sun drop into Florida Bay from a stool. Lorelei, at mile marker 82, is the famous one, with live music most nights. Stay in Islamorada tonight.
Day 2: Islamorada to Key West
Morning. Book a backcountry trip for first thing. Running boats through the mangroves is the trailer’s most repeated Keys shot, and Florida Bay behind Islamorada is exactly that: shallow, glassy water threaded with mangrove channels. Guides run flats fishing, eco tours and kayak trips; two to three hours is plenty, and the water is calmest early.
Afternoon. Drive south through Marathon to the long bridge over turquoise water. The modern Seven Mile Bridge carries the highway; the old one beside it, reopened in 2022, is for walkers and cyclists only, as far as Pigeon Key, about two miles out. Park at the Marathon end and walk out; that is the view. Twenty minutes further on is the beach under the old bridge, Bahia Honda State Park, with the best sand in the Keys and the broken span of the old railroad bridge above it. Per-vehicle entry is under $10. Swim, then keep going; Key West is another 45 minutes.
Evening. Check in, then walk to Mallory Square for the sunset celebration, the nightly street-performer show that has run for decades.
Day 3: Key West
Morning. The end of the road is Duval Street and the blocks of wooden conch houses around it. Walk it early: the Southernmost Point buoy at the bottom of Whitehead Street (the line gets long later), the Hemingway Home and its six-toed cats, the old harbor. Cuban coffee and a Cuban sandwich from a window counter is the breakfast.
Afternoon. Pick one: a snorkel trip to the reef, a sail, or the drive back. Key West to Miami is around 160 miles and three and a half to four hours without stops, more on a Sunday afternoon when everyone leaves at once. If you would rather not drive back, Key West’s airport has direct flights to several US cities, and one-way rentals are possible for a fee.
Evening. Sloppy Joe’s on Duval for the Hemingway story, or a quieter bar on a side street. Either way you are at mile marker zero.
Practical notes
Where to base yourself. Islamorada, bayside, on night one; Key West’s Old Town on night two, and night three if you can stretch it. Key Largo works for night one if you want to dive; Marathon if you want to split the drive.
Getting around. You need a car. There is a public bus along the Keys, but it is slow, infrequent and useless for the side stops. In Key West, park the car and walk or rent a bike; Old Town is small and parking is scarce and expensive.
What it costs. Lodging is the big number: $200-300 a night in Islamorada in season, $300-500 in Key West. Boat trips and guides run $50-150 per person for a group trip and $400-700 for a private half-day charter. State park entry is under $10 a car. Meals $20-40 a head; fresh fish is the value.
The thing people get wrong. Trying to do the Keys as a day trip from Miami. The road is one lane each way for most of its length, the speed limits are low and enforced, and every stop is a “just five minutes” that becomes an hour. Give it three days, drive slowly, and stop when something looks good.