Keys

Anne’s Beach is barely a beach in the conventional sense and that is exactly why it works with very small children. The water off Lower Matecumbe is so shallow that you can walk out several hundred feet and still be at knee height, warm as a bath in summer, with a soft bottom. A boardwalk runs behind it through the mangroves to a second stretch of sand. Parking is roadside and limited, there are restrooms but no concessions, and kiteboarders use the far end on windy days. It is free, which makes it the cheapest good hour in the Keys.

Most of the Keys have very little actual beach; Bahia Honda is the exception and it is why the park fills early. Sandspur Beach shelves so gently that children can walk out a long way in warm, clear water, and Calusa Beach on the other side is even calmer. The ruined Flagler railroad bridge arcs overhead, half of it removed, which makes the whole place look like a film set. Snorkelling is decent close in around the rocks though not reef-quality. It is a two-hour drive from Key Largo, so this works best as part of a Keys trip rather than a day out from Miami.

Curry Hammock has the calmest paddling water in the Keys - a shallow protected bay where the bottom is visible the whole way and there is nowhere for a novice to get into trouble. Boats are available at the launch, but not from the park - a third-party self-serve kiosk runs on a QR code and a smartphone, so have signal and a card. The beach is small and rarely crowded, which is the trade for it being less spectacular than Bahia Honda. In autumn the park hosts a raptor migration count, and on a good October day thousands of hawks and falcons funnel down the Keys directly overhead. The campground is one of the harder Florida reservations to get.

Getting to the Dry Tortugas is most of the experience - two and a quarter hours by ferry across open water, or a seaplane if the budget allows. What you arrive at is Fort Jefferson, an enormous unfinished nineteenth-century fort covering almost an entire small island, surrounded by water clear enough to see the coral heads from the walls. Snorkelling straight off the beach is the best in the state because there is no run-off and almost no boat traffic. Bring everything you need; there is no shop, and the ferry leaves on schedule with or without you. Rough seas make the crossing genuinely unpleasant, so watch the forecast.

The Overseas Highway is 113 miles of two-lane road hopping 44 islands, and the standard family mistake is treating it as a drive to Key West. It isn’t. Key West is the least kid-friendly thing in the Keys, and the best parts are the stops you pass at 55mph on your way to it. So this runs the other way round: three days, never more than about 40 miles between beds, and Key West as an afternoon rather than a destination. Mile markers count down as you go south, which is how everything here is addressed. ...

Key West is short on good beaches and this is the one locals use. The water drops off quickly compared to Bahia Honda, which makes it less suited to toddlers but much better for snorkelling - the rocky edges hold parrotfish, sergeant majors and the occasional small barracuda within a short swim of the sand. Behind the beach sits the Civil War fort itself, with the largest collection of seacoast cannon in the country and cool brick casemates that make a good hour out of the sun. Water shoes matter here; the entry is rocky.

Pennekamp protects the northern end of the only living barrier reef in the continental United States, and the snorkel trips are the point: a boat runs out to the reef, drops a line, and you swim over coral heads full of parrotfish and barracuda. The reef is two and a half hours round trip and can be choppy, so there is a real minimum age - roughly five for a confident swimmer, and a calm forecast matters more than the season. For younger children the park has two protected beaches, Cannon Beach with a scattered replica shipwreck to snorkel over in chest-deep water, and Far Beach, plus a glass-bottom boat for anyone who would rather stay dry.

Long Key’s canoe trail winds through a shallow tidal lagoon where the mangrove tunnels are close enough to touch on both sides and the water is often under two feet deep. It is a quiet, sheltered paddle with herons and small sharks in the shallows, and the reason to come. Bring your own boat: there are no rentals here and the dockage was removed. Be realistic about the rest of the park before you plan a day around it. Hurricane Irma in 2017 and Ian in 2022 took the oceanfront campground and the beach with it, and there are no plans to rebuild - only a few walk-up primitive sites remain, and as of mid-2026 those and the Golden Orb Trail are closed for construction. What is open is the lagoon, a nature trail and waterfront picnic tables.

Sombrero is the middle Keys’ family beach and it is free, which in this stretch of Florida is worth saying twice. The sand is soft, the water stays shallow a long way out, and unlike most Keys beaches there are mature palms giving genuine shade over the picnic tables. There is a playground, clean restrooms and a volleyball court. Loggerhead turtles nest along here in summer, and marked nests appear on the sand. It is a good midpoint stop breaking up the drive between Key Largo and Key West.

This is an old quarry where Flagler’s crews cut building stone out of an ancient reef, and the saw marks left behind sliced clean through fossil coral. The result is a set of stone corridors where you can walk up and put your hand on a brain coral that was alive when the sea was higher and this was underwater. It takes about an hour, is entirely shaded, and is the best rainy-hour option in the upper Keys. Children who like dinosaurs tend to like this a great deal. Hours are limited and it closes some days of the week, so check before driving out.