Last updated on April 7th, 2020 at 03:00 pm
To get to Pine Island, you drive through Cape Coral and the colorful shops and crowded galleries of Matlacha, but once you cross the bridge into Pine Island, everything changes. You can turn right or left, but no matter which way, you’ve turned back time–you’re in another decade, maybe even another century.
This is a guest post from Erika J. Waters, author of “Discovering Old Florida, A Guide to Vintage South and Central Florida.” To research her book, she explored Florida’s back roads. Pine Island surprised and delighted her.
Pine Island, the largest island in the entire state, is 17 miles long and two miles wide. Mostly arable land bordered by mangrove trees, it wasn’t even on the radar during the Florida Land Boom years, and the railroad that brought pioneers to the west coast was miles away.
Developers never coveted its sandy beaches—because there aren’t any. As a result, the tourist economy never flourished here—there are no traffic lights, no chain hotels or restaurants, only about 8,000 residents, and hardly any tourists.
The first village you encounter is Pine Island Center, the commercial center of the island, but that’s relatively speaking. It boasts the island’s only large supermarket, public swimming pool, and museum. The Museum of the Islands, housed in the first library, is definitely worth a stop for an introduction to the island: you’ll see an extensive shell collection, artifacts from Calusa Indians, a great number of dolls, and even an old buggy.
After that, you have two choices: A left turn takes you to St. James City, the most populated village on Pine Island (again, relatively speaking) and the center of fishing and watersports activities. Here, you’ll find professional fishing guides, charter boats, kayaks and fishing boat rentals–the waters around Pine Island are renowned for fishing–plus a few restaurants and small B and B’s.
But if you haven’t come for fishing, then hang a right. As you drive along the island’s main street, Stringfellow Road, you’ll soon see what Pine Island is really all about: fields and fields of tropical fruit groves and commercial nurseries.
Pine Island has long been appreciated for its fertile land, and has long been supplying the entire state with palm trees, landscape plants, vegetables, and fruits. A two-day summer festival, “MangoMania” is held every year and there’s even a MangoMania queen.
Turn left at mile marker 12 onto Pineland Road. Soon, you’ll see Promised Land Mangoes, the old Pineland Mango Grove first planted in the 1950s. You can buy pesticide-free mangos, preserves, chutneys and honey from the dedicated family who operate this stand.
The village of Pineland on Pine Island
You’re close now to the village of Pineland, population 400, with its charming post office. As you continue on, you’ll pass Old Florida homes, and “cracker houses” in varying states of repair. Named for the whips of early Florida cowboys, these are small wooden houses with distinctive front porches. Then, as you come around a curve, you’ll see Tarpon Lodge.
Tarpon Lodge was built in 1926 as a private home and has been an inn for decades–President Jimmy Carter and 23 family members once vacationed here. Renovated rooms are available not only in the lodge, but also in an adjacent boat house and cottage; breakfast is included. Everything about Tarpon Lodge shows attention to detail: the lobby is beautifully restored, and the restaurant offers award-winning cuisine. Sit in the bar with a tarpon over the stone fireplace (Rumrunners especially recommended), or outside overlooking the water.
Next door is Pineland Marina which offers boat trips and water taxis to nearby islands. Here you can take the short hop to Cabbage Key, another historic inn and restaurant (owned by the Wells, who also own Tarpon Lodge), Cayo Costa State Park, and Boca Grande.
Located conveniently across the street from Tarpon Lodge is the Randell Research Center (part of the Florida Museum of Natural History), with its Calusa Heritage Trail. Walking the trail transports you even further back in time, 2000 years ago when the Calusa Indians made this their home. The Trail is less than a mile, and you can view the scenery from the top of a 300-foot Calusa shell mound.
Back on Stringfellow Road, you’ll see Fruitscapes, a Fruit Tree Nursery and Market on the right. The friendly owners sell a variety of tropical fruits, including some rarely available in the US, such as jack fruit, sour sops, and sugar apples. They also sell homemade bread and will open up a coconut and stick in a straw for you, too.
Driving further north, you’ll come upon The Mango Factory. This grove was started by the Mango Man in 1964, and now his son and grandson are in charge. You’ll find nine varieties of mangoes here, and they’ll even arrange for a U-Pick if you call in advance.
The village of Bokeelia on Pine Island
Soon you’ll reach the northern end of the island, the tiny village of Bokeelia which looks out towards Boca Grande on Gasparilla Island (on a good day) and to Little Bokeelia Island, a private island which recently sold for $14 million. This village is about as Old Florida as it gets and feels truly remote with only a few small condo complexes, commercial fishing enterprises, tour boats, and a picturesque 100-year old fishing pier. It costs $8 to fish and no strolling allowed.
But stop at Capt’n Con’s Fish House, located in what was once a private home and then the first post office. It’s the only restaurant in town but offers good food with a lovely sea view—and a few ghosts as well. Doors open and close at random, and the men’s bathroom reportedly locks itself from the inside. Such spooky activity doesn’t bother the waitstaff in the least; they just laugh and shake their heads.
The ghosts in Bokeelia, they’ve decided, are friendly.
Resources for visiting Pine Island
(These are physical addresses, not mailing addresses.)
Museum of the Islands
5728 Sesame Drive
Pine Island Center
Randell Research Center, Florida Museum of Natural History
13810 Waterfront Drive
Promised Land Mangoes
7127 Pineland Road
13771 Waterfront Drive
12870 Stringfellow Road
7180 Tropical Lane
Cap’n Con’s Fish House
8421 Maine St. (Charlotte Harbor Drive)
Bokeelia, FL 33922
Other things to do near Pine Island
Matlacha: Sometimes considered part of Pine Island, this is a narrow island filled with galleries, shops, and many fine waterfront restaurants. See a Florida Rambler guide to Matlacha.
Tour boats to other islands: If you’re staying at Pine Island for more than a day, consider taking a charter boat for lunch to Cabbage Key or a full day trip to Cayo Costa State Park or the Useppa Island, a private island.
Places to explore near Pine Island
- Cayo Costa State Park: Dreams of a private island (just west of Bokeelia by ferry or for advanced kayakers)
- Manatee Park and the Orange River for winter manatee viewing
- Telegraph Creek: Unspoiled kayak trail worth discovering and not just for llamas, about a half hour east.
- Six Miles Cypress Slough Preserve
- Fort Myers Beach: Charming seaside getaway
- Lovers Key State Park for manatees, kayaking and beaches
- Mound Key State Archaeology Site
- What makes Sanibel special and nine ways to experience it.
Erika J. Waters, Ph.D, who now lives part of the year in Naples, Florida, was formerly an English professor at the University of the Virgin Islands, St Croix, where she edited The Caribbean Writer and collections of fiction, poetry, literary criticism, and drama. She then taught English part-time at the University of Southern Maine, wrote books on Maine and the Virgin Islands, and was a Fulbright Scholar to Finland.
Since moving to Florida, she’s taught writing and literature at the Renaissance Academy of Florida Gulf Coast University and written for the Marco Island Historical Society. She enjoys kayaking and sailing.