Under & Over

The original commercial airboat operation on the Tamiami Trail, opened by John Cooper in 1945 when the road was still a rough two-lane through nowhere. Three Cooper brothers — John, Jay, and Marion — came down from Melbourne looking for better frog hunting; John was the one motorists spotted running the sawgrass in his flat-bottom, and the ride business grew out of that. Family-run ever since. The sign at the drive lists "Coopertown, Population 8" — a nod to the family, not a legal count (Coopertown is unincorporated Miami-Dade, not an actual municipality). Small gift shop, a diner serving gator tail and frog legs, and a rack of airboats out back.

Key Largo paddle base for kayaks, paddleboards, canoes, and guided backcountry tours into the bayside mangroves.

ATV, UTV, jet ski, and horseback outfitter on the SW 177 Ave spine — last civilization before the Everglades. Guided tours (no license needed, full safety training first), self-guided runs, and private group trips. Open late — Mon–Thu til 10:30p, Fri–Sun til 11:30p — night rides are a thing. Right in the middle of the 27 Run's Homestead-to-Krome stretch; next stop north before you commit to the Everglades run.

Airboat operator on the east edge of the Glades, four miles west of Coopertown on the Trail. Larger and glossier than the family shops — a 25-acre park with a raised boardwalk over a gator pond, a jungle-trail wildlife enclosure holding rescued cats and reptiles, and an alligator handling show slotted between airboat departures. Boats push out every 25 minutes until 4:30p. Not the oldest name on this stretch — built newer and packaged for the tour-bus crowd coming out of South Beach, so expect coach traffic and a queue at midday. Efficient, cleanly run, easier for a first-timer than the backcountry shops.

The country's first undersea park, with glass-bottom boats, snorkeling, scuba, and reef access right at the top of the Keys.

A Tamiami Trail airboat stop for seeing sawgrass, wildlife, and the western edge of Miami-Dade before Florida turns fully wild.

Long-running Key Largo dive and snorkel operator with two-location reef trips and a preservation-minded dive culture.

PADI 5-Star dive center at Three Waters Marina, with wreck charters and shallow reef trips for snorkelers.

The elder statesman of Everglades airboat outfits on the Tamiami Trail. Raymond Wooten started giving rides in 1953 after tourists driving US-41 stopped, watched him run his own airboat, and asked to pay for a turn — the first commercial airboat operation in Southwest Florida. The company passed to his son Gene in the 1990s and is now run by the Patel family, who kept the name and the sprawl: airboats across the sawgrass, swamp buggies through the cypress hammock, and an on-site alligator and wildlife sanctuary with a live gator show. Not the quiet Everglades — the working, roadside, mid-century American one.

One of the last free-flowing tributaries into Lake Okeechobee — a cypress-swamp creek that runs wild through Fisheating Creek Wildlife Management Area. The Outpost on US-27 is a real base camp: 48 RV sites, 68 tent sites (many right on the water), a cabin, a store, and a fleet of 80 canoes, kayaks, and SUPs. Paddles range from a one-hour out-and-back to a 16-mile wilderness run. This is the Florida that was.

Marathon dive shop with snorkel and dive trips, boat rentals, bait, tackle, and paddle-trip connections.

Family-owned live bait and tackle shop right on US-27 in Lake Placid — the actual road the 27 Run is named for. Live bait, tackle, gear, and the local read on what's biting where. Open every day 6a–6p — early enough to grab shiners before the water gets hot, late enough for after-work rod runs. Small-town shop; counter conversation is half the value.

Clear-kayak eco-tour operator for shallow Lower Keys water, where stingrays, sea turtles, and starfish can pass beneath the boat.