16 Best Things to Do in Big Pine Key

Key deer are a subspecies of white-tailed deer the size of a large dog, found nowhere but these islands; about 1,000 remain. The National Key Deer Refuge covers most of Big Pine and No Name Key. You will see them at dawn and dusk on Key Deer Boulevard and the side streets, and almost always on No Name Key. Do not feed them, it is a federal offense and the reason they get hit by cars. The speed limit drops to 35 at night for this reason.

An old quarry on Key Deer Boulevard, now a freshwater pond with an observation platform, alligators, turtles and the deer that come to drink. Free, five minutes from the highway, a 10-minute stop. The Watson and Mannillo nature trails start nearby for a short walk through pine rockland.

At the end of Watson Boulevard on the way to No Name Key, a 1936 bar with roughly $100,000 in signed dollar bills stapled to every surface. Pizza and a beer; cash still matters here. Combine it with the drive to No Name Key for deer at dusk.

Looe Key is a spur-and-groove reef 5 miles south of Big Pine in 5–35 ft of water inside a sanctuary preservation area: no fishing, no lobstering, which is why the fish are big and tame. Shared half-day boats from Ramrod Key run about $60 per snorkeler with gear, three sites, four hours. It is the best shallow reef between Key West and Marathon.

A private charter for up to six that snorkels Looe Key and then anchors at Picnic Island, the Lower Keys sandbar, runs about $500 for the boat from Little Torch Key. Sunset-only charters are $350. Good value split four or six ways.

Two-hour guided tours on clear-bottom kayaks through the Sugarloaf mangrove channels, $69 per adult, no experience needed. The water is a foot or two deep and the kayaks are transparent, so stingrays, baby sharks and conch pass under your seat.

The same idea after dark: clear kayaks lit from below with LEDs on a two-hour night tour from Big Pine, $75 per person. The light pulls in fish and squid and the water is dead calm. Book the morning eco-tour if you would rather see it in daylight.

A two-hour guided run through the backcountry islands off Cudjoe Key for up to four people, about $400 for the boat: sponge flats, mangrove keys, dolphins and the birds. The captain also runs fishing and paddleboard trips from the same dock.

Lower Keys guides work the Gulf-side flats for tarpon, permit and bonefish and the reef for snapper and grouper. Two-hour charters start around $400 for the boat, half-days $650–$800, lobster trips in season from $650. The Content Keys and the Marquesas are full-day runs.

Mile Marker 37, 8 miles north of Big Pine. Calusa Beach on the bay side and Sandspur on the ocean side are the best natural beaches in the Keys, with a kayak concession, a campground that books 11 months out, and the ruined 1912 railroad bridge you can walk up for the view. Entry about $8 per vehicle; the gate closes when the lots fill, usually by 10–11am in winter.

At the Marathon end of the Seven Mile Bridge, a free county beach with picnic tables, shade and calm water. Smaller and quieter than Bahia Honda and never closes for capacity.

A rough, natural shoreline at the south end of Long Beach Drive: seaweed, shallow flats and almost nobody. Not a swimming beach, but the best place on the island to watch the sun go down over the water for free.

A restored 1950s fruit grove on Big Pine with mango, sapodilla, jackfruit, breadfruit and 90 other tropical species, run as a nonprofit. The 90-minute guided tasting tour is $38 and changes with what is ripe. Saturdays are market days.

Weekends at Mile Marker 30, oceanside: fishing tackle, produce, t-shirts and whatever fell off a boat. Open from 8am, done by early afternoon, cash.

The private-island resort off Little Torch Key opens its restaurant to non-guests for lunch and dinner by reservation. The launch leaves from the Little Torch dock; expect $100 or more per person before drinks, and Key deer on the island grounds.

The Overseas Heritage Trail runs through Big Pine along US-1, and the back roads to No Name Key are flat, empty and lined with deer. Rentals in Big Pine and Key West; bring water, there is little shade.