Skip to content
Nanci Gilbert, PA logo

Blog · Outdoor Life

A Family Day Trip to the Florida Keys From Homestead

The Keys are closer than many South Florida families realize. Here is a relaxed day-trip plan from Homestead to Key Largo and Islamorada.

By Nanci Gilbert, PA September 28, 2026
Header image for "A Family Day Trip to the Florida Keys From Homestead"

From Homestead, the Overseas Highway puts the Florida Keys within a morning drive. Key Largo is about thirty miles and roughly forty minutes away, and Islamorada is about an hour. A day trip is not only possible. It is one of the best-value family outings in South Florida.

Stop for fruit on the way

Robert Is Here, the fruit stand at 19200 SW 344th Street in Homestead, is a tradition at the start of the drive. Milkshakes, fresh fruit, and a small menagerie of animals make it a natural first stop before the highway narrows over the water.

John Pennekamp Coral Reef State Park

At mile marker 102.5 in Key Largo, Pennekamp is the first undersea park in the United States. Families can take a glass-bottom boat tour over the reef, paddle a kayak, or swim off the beach. The visitor center and gift shop keep the pace easy, and you never need your own boat.

Theater of the Sea

Farther south at mile marker 84.5 in Islamorada, Theater of the Sea is a family-owned marine park that has operated since 1946. Dolphin, sea lion, and parrot shows run through the day on seventeen acres of lagoons and gardens, and animal encounters are available by reservation.

Feed the tarpon at Robbie's

At mile marker 77.5, Robbie's Marina is famous for one reason: enormous wild tarpon that rise to the dock for a bucket of bait. Kids hand-feed them over the rail while parents watch, and the waterfront restaurant and gift shop make it a comfortable rest stop before the drive home.

Make it a loop that works

The round trip from Homestead to Robbie's and back is roughly a hundred miles, about two and a half hours of driving with plenty of time at the stops. Bring sunscreen, water, and towels, leave early, and let the day unfold at the pace of the road. Nanci has made this drive with families more times than she can count, and it never gets old.

Nanci Gilbert, PA is a South Florida realtor who guides growing families, sellers, and buyers across Miami-Dade and Broward. Questions about this topic? She answers every message within one business day.