A Weekend in the Florida Keys: What to Book First

September 28, 2026 · 4 min read · My FL Guide

The Keys are an island chain strung along a single highway, which makes them perfect for a weekend and terrible for indecision. The trick is one water activity a day, with the driving in between. Here is a three-day shape built only from places with real, verified listings.

Day one: Key Largo, get straight in the water

Start at John Pennekamp Coral Reef State Park (102601 Overseas Hwy), a park built around living coral reef. Entry is $8 per vehicle for 2-8 people, $4 for a single occupant and $2 for pedestrians. Snorkel tours start at $30 per adult and the glass-bottom boat is $32 per adult. If you would rather swim from shore, Pennekamp Beach - the Cannon and Far Beach area - is inside the same park, with snorkel gear rental at the concession.

Finish the day at Alabama Jack's on Card Sound Road (58000 Card Sound Rd), an open-air original with a football-sized conch fritter and live bands on weekends. Boaters, bikers and day-trippers all pull in for the same cold beer.

Day two: Marathon and the Seven Mile Bridge

• Curry Hammock State Park (56200 Overseas Hwy) - $15 per vehicle for up to 8 people, with paddleboarding, stargazing and camping on a quiet stretch of the Middle Keys.
• Bahia Honda State Park (36850 Overseas Hwy, Big Pine Key) - the Keys' best natural beach, with snorkeling off the old bridge pilings and white-sand swimming. $8 per vehicle; camping is $36 a night if you want to sleep on it.
• Sunset at Sunset Grille & Raw Bar (7 Knights Key Blvd, Marathon) - shoes off on the sand, a dozen oysters, and the sun dropping behind the Seven Mile Bridge.
• Late dinner at Burdines Waterfront (1200 Ocean View Ave, Marathon) - upstairs above the bait shop, with boat-watching tables and the fried key lime pie.

Day three: Key West

• Fort Zachary Taylor Historic State Park (601 Howard England Way) - a Civil War fort with a swimming beach, clear calm water and snorkeling along the jetty. $6 per vehicle for 2-8 people, $4 single occupant, $2 pedestrians; beach chair rental is $12.
• Dry Tortugas National Park - the Yankee Freedom III ferry leaves from 100 Grinnell St at $200 per adult and $135 per child with park entry included. Seaplane runs $400 to $700 per person, and camping on the island is $15 a night. Book this before anything else; it sells out.
• Schooner Wharf Bar (202 William St) - Key West's open-air living room, with live music over the sound of rigging and fishing boats gliding past.
• A&B Lobster House (700 Front St) - the old-school white-tablecloth room on Key West Bight, overlooking the marina, for the one dinner you dress up for.

Where to sleep and what to know

• Camping is the cheapest bed in the Keys and it books out early. Bahia Honda is $36 a night, and both the John Pennekamp State Park Campground in Key Largo and Curry Hammock State Park offer sites.
• Keys addresses are mile markers as often as street addresses. Windley Key Fossil Reef Geological State Park, for example, sits at Mile Marker 84.9 on Overseas Highway - navigate by the marker when a street address looks odd.
• State park entry is charged per vehicle and it adds up over three days, so pick the parks you actually want and group them by day.
• Reserve the two big-ticket boats - the Dry Tortugas ferry and any snorkel tour - before you book anything else.
• Coolers and water beat concession prices. Several of the stops on this route are in parks that close at sunset, so plan dinner near where you sleep.

Every park, restaurant and campground in this itinerary has a full card in My FL Guide with its address, real prices, parking and directions, so you can build the three days in the app and take it with you.