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Pine Island: Step back in time, without a tourist in sight

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.

A post office on Pine Island (Courtesy of Chief Dennis, Tarpon Lodge)
A post office on Pine Island. (Courtesy of Chief Dennis, Tarpon Lodge)

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.

Pine Island was hit hard by Hurricane Ian in September 2022. Much, but not everything, has been rebuilt and re-opened. This story predates the storm but has been updated.

In contrast, Pine Island is surrounded by the islands where that sand did wash up. Sanibel and Captiva are south and west of Pine Island; also west is the island of Cayo Costa, where a state park protects miles of pristine sandy beaches, and northwest is Boca Grande, where millionaires have homes on shell-laden sandy beaches.

Where the sand builds pretty beaches, people follow. And that means people left Pine Island sort of as they found it.

The Tarpon Lodge on Pine Island in the community of Pineland has a magnificent location on the water.
The Tarpon Lodge on Pine Island in the community of Pineland has a magnificent location on the water. (Photo: Bonnie Gross)

Exploring Pine Island

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. It is open; check the hours here.

The dining area of the Tarpon Lodge overlooking the water on Pine Island.
The dining area of the Tarpon Lodge overlooking the water on Pine Island. (Photo: Bonnie Gross)

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. You’ll also find 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.

Most mango trees were damaged in Hurricane Ian and the summer 2023 crop was minimal. Growers are optimistic that 2024 and subsequent years because mangoes are tropical trees that thrive in hurricane-prone climates.

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. Cabbage Key reopened, but Cayo Costa State Park is still closed due to hurricane damage, as of summer 2023.

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. About 1,000 feet of the trail, which was less than a mile, has reopened.

Sunset at the pier in Bokeelia, on Pine Island.
Sunset at the pier in Bokeelia on Pine Island. (Photo: Bonnie Gross)

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.

An osprey on its next at sunset at the pier in Bokeelia on Pine Island.
An osprey on its next at sunset at the pier in Bokeelia on Pine Island. (Photo: Bonnie Gross)

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 and tour boats.

The picturesque 100-year old fishing pier was slammed by Hurricane Ian but reopened in August 2023, almost a year after the storm. It costs $15 to fish and no strolling is allowed.

Cross the street Capt’n Con’s Fish House, is located in what was once a private home and then the first post office. It’s the only restaurant in town but offers 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
(239) 369-3896

Tarpon Lodge
13771 Waterfront Drive
(239) 283-3999

12870 Stringfellow Road
(239) 462-2341 

Mango Factory
7180 Tropical Lane
(239) 283-0830

Capt’n Con’s Fish House Here’s TripAdvisor page, as there is no web site.
8421 Maine St. (Charlotte Harbor Drive)
Bokeelia, FL 33922
(239) 283-4300

 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. It was nearly destroyed by Hurricane Ian and is still rebuilding a year later. Florida Rambler on 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

Discovering Old Florida book by Erika J. Waters
Erika Waters
Erika J. Waters

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. 

You can order her book, “Discovering Old Florida” here. 

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Monday 17th of May 2021

Cool places. Impetuous Thoreau's will research and anticipate sun and biting-insect protection. No-see-ums will conquer the most inveterate explorer.


Sunday 26th of July 2020

1 chain restraunt in Bokeelia, Pink Flamingo

Bob Rountree

Tuesday 28th of July 2020

I think you mean the Lazy Flamingo, which has four locations in the area: Bokeelia, two on Sanibel Island and one in Fort Myers.

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