A Return To Old Florida: 6 Fantastic Experiences On Pine Island (2022)

We all have those favorite vacation spots that keep bringing us back. It’s that feeling of peace and comfort that draws us again and again. That’s the way it is for me and Pine Island. I’ve been there four times and still want more.

There are any number of reasons to visit laid-back Pine Island off Florida’s Gulf Coast near Fort Myers. There is solitude and relaxation. Art galleries, fresh seafood, peace, and quiet are in abundance. There are no beaches, no hi-rise condos, not much traffic. But the biggest reason people come here is to fish!

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1. Fish On!

There are lots of fish. Snook, redfish, sea trout, tarpon, and more. People fish with guides, from kayaks, and from the two-lane drawbridge that marks the entry to the island. As locals say, “Fish on!”

Fishing is an industry here, really big business. There are no fewer than a dozen fishing guides ready to put you on that lunker you’ve been dreaming about.

As veteran guide Bill Russell told me, “There is a lot of diversity on Pine Island — a lot of different species you can target. If you don’t find them in one location, you just move on to another.”

If you aren’t up for hiring a guide, there are lots of other options for finding fish. Kayak fishing is popular, and there are any number of places on the island to rent a kayak, or you can bring your own. More on kayaks later in this article.

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The island boasts of having the “World’s Fishingest Bridge” — the drawbridge on Route 78 into the island’s first town, Matlacha. Anglers line the bridge day and night, hoping to snag fish as they move in and out of Matlacha Pass with the tide.

Pine Island has a permanent population of about 2,000 residents. That number grows considerably when winter snowbirds arrive. The fishing season is active all year round, but especially from October to May. In June, the world’s richest tarpon fishing tournament takes place in the nearby Boca Grande channel, drawing large numbers of game fish entrants. The “catch and release” of the giant tarpon has a prize pool that exceeds over $100,000.

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2. Dining

The gateway to Pine Island is the town of Matlacha, which lines both sides of the two-lane road leading onto the island. Traffic in town can be congested, especially on the weekends. The street is lined with galleries, gift shops, restaurants, and of course, fishing stores.

Many of the island’s food joints line the street in Matlacha. There is the Yucatan waterfront restaurant for seafood and great burgers. Miceli’s has Italian. Bert’s Bar and Grill offers a little of everything. For breakfast, there is the huge Big Breakfast at the Perfect Cup restaurant and coffee shop.

The biker crowd roars onto the island on Sundays for a gathering at the popular Ragged Ass Saloon and restaurant in St. James City. Sunday usually features live music outdoors.

For the freshest catch of the day, try Capt’n Con’s at the north end of the island in Bokeelia. They’ll even prepare your own catch from the fishing pier right across the street. You bring in your catch still flopping, and they will clean it and prepare it to order. It doesn’t get any fresher than that.

Offshore is Cabbage Key, a small island with a popular restaurant and a few lodge rooms. It’s only accessible by boat, and tour boats and ferries bring the crowds. Wait times for lunch can often be over an hour. Take the time to tour the island. There is a gopher tortoise colony right by the restaurant and a short hiking path in the wilderness area of the island. Cabbage Key was said to be the inspiration for Jimmy Buffett’s “Cheeseburger In Paradise.” The popular Cabbage Key bar is noted for its walls lined with dollar bills that have been pasted up over the years by patrons.

If your taste and budget run to fine dining, the four-star restaurant at the Tarpon Lodge back on Pine Island in the village of Pineland is the place to go. Fresh fish, seafood, and scallops are mainstays of the menu. The wine list is extensive. The staff’s attentiveness is equal in quality to the food. By the way, for dessert, try the Key Lime Pie. It’s scrumptious.

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3. Lodging

Pine Island lodging runs a wide gamut. Airbnb and Vrbo list lots of homes and condos on the island for seasonal rentals. There are small mom-and-pop hotels in Matlacha including the Angler’s Inn and Matlacha Cottages for short-term stays.

A stay at the Beachouse Inn in Bokeelia is all about fishing. The lodge is right across the street from fishing piers jutting out into Charlotte Harbor.

For higher-end accommodations, the charming Tarpon Lodge has upscale rooms and cottages, and a lot of history. It started out a century ago as a fish camp. Along the way it has been a religious retreat and drug rehab center. About 20 years ago, the Wells family bought the property and renovated it into a well-appointed lodge. The Wells family also owns Cabbage Key.

For RVers, there is the Pine Island Resort KOA in St. James City. A complete list of lodging options on the island is found at the Pine Island Chamber of Commerce website.

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4. On The Water

There are numerous places on the island to rent kayaks to explore local waters. I recommend Gulf Coast Kayak in Matlacha. They offer guided kayak fishing trips, mangrove tours, and sunset paddles. They are located on the north side of Pine Island Road (Route 78), just before you cross the drawbridge into town.

For the real adventure kayakers, the six-mile paddle from Pineland Marina to the barrier island at Cayo Costa State Park takes you across the open waters of Pine Island Sound. The water is protected but choppy and with currents. This is not a day trip for novice paddlers. It is usually a trip for camping at the park for a night or two and requires a decent level of experience with open-water paddling.

If you don’t want to paddle, you can ride in style on Captain Jack’s pontoon tiki boat tours. They offer happy hour tours, plus sunset, fishing, and burial trips for families who want ashes scattered in the Pine Island waters.

To venture farther out into the water there is Tropic Star Cruises. They provide ferry service to Cabbage Key, the State Park at Cayo Costa Island, and Boca Grande at the entrance to Charlotte Harbor. Cruises operate out of Pineland Marina. Reservations are required.

Editor’s Note: Cayo Costa State Park definitely deserves your attention. It made our lists of the best Florida beaches that typically aren’t ridiculously crowded and nine quaint beach towns in Florida.

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5. Nature And Recreation

There are nine nature trails scattered around the island. They are on land owned by the State of Florida, Lee County, The Calusa Land Trust, and University of Florida. Most trails are short and often soggy during the rainy season. They wind through palmetto bush and scrub pines and palm trees. Many of the trails are part of the Great Florida Birding Trail, so bring those cameras and binoculars.

The Calusa Heritage Trail (right across the road from Tarpon Lodge) offers visitors a tour of the 2,000-year history of the Calusa Indians, the original occupants of the island. The site has a museum and covers 67 acres. The trail runs just under a mile and features historical markers that tell of the life and demise of the Calusa. The site is operated and preserved by the Randell Research Center of the University of Florida. There is no entry fee, but donations are accepted.

Biking is another popular activity on the island. A bike trail runs the entire 17-mile length of the island from Bokeelia on the north end to St. James City on the southern tip. The trail is also popular with early morning walkers.

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6. The Arts

Pine Island has a large and active arts community. Art galleries are found around the island, with several along the main street in Matlacha. They range from the quirky Matlacha Menagerie on Pine Island Road to the fine art found at Bokeelia Art Gallery on Stringfellow Road on the north end of the island. If you want to try your hand at painting, the Pine Island Art Association offers classes five days a week during the winter season and two days a week the rest of the year.

Pine Island is off the beaten path, tucked away on Florida’s southwest Gulf coast. You drive Interstate 75 and exit at Cape Coral onto State Route 78 east. Follow that through sometimes congested traffic to the island. The closest airport is in Fort Myers, 30 to 40 minutes away.

Pine Island has that old Florida feel to it: unpretentious, laid back, life moving at a slower pace. It makes for a great couple’s getaway or a family fishing trip.

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