Pine Island & Matlacha Guide | Sarah’s Small Town Escapes
Just 30 minutes from Fort Myers, Pine Island is the largest island on Florida’s Gulf Coast, yet it still feels like a hidden gem. Unlike nearby Sanibel and Captiva, you won’t find sandy beaches here. Instead, you’ll discover mangrove shorelines, tropical fruit farms, and a resilient community dedicated to preserving Pine Island’s Old Florida charm.
1. Explore Matlacha’s Colorful Art Shops
On your way to Pine Island, you’ll pass through Matlacha (pronounced Mat-luh-SHAY), a small island village known for its vibrant art scene. Matlacha was hit hard by Hurricane Ian and Milton, but some shops and galleries have reopened. Don’t miss:
Matlacha Menagerie for local art and pottery
Mariann’s Boutique for Italian-made clothes and accessories
Island Flair for unique gifts and island-inspired treasures
2. Eat Local at Blue Dog Bar & Grill
With its bright yellow exterior, Blue Dog Bar & Grill is hard to miss in Matlacha. In just over a decade, it’s become a favorite for locals and visitors alike. The restaurant prides itself on sourcing from local fishermen, farmers, and breweries. Menu favorites include the Mullet Sampler, Cracked Conch, and Blue Crab Cakes. And, save room for homemade dessert, like the lemon blueberry cheesecake.
3. Paddle the Mangroves with Matlacha Outfitters
Water is a way of life on Pine Island and Matlacha, and exploring by kayak or paddleboard is one of the best ways to experience the area’s natural beauty. The new Matlacha Outfitters makes it easy to get out on the water. On my paddle, I spotted osprey, ibis, stingrays, and even an anhinga drying its wings. Rentals are available daily for two hours, three hours, or all day (until 5 p.m.). Local fishing charters, like those with Captain Miles Meredith, are also popular for anglers.
4. Take a Scenic Drive from Bokeelia to St. James City
To really grasp the size and character of Pine Island, start with a drive along Stringfellow Road, which nearly stretches the island’s full 17-mile length. Along the way, you’ll pass through four distinct communities:
Bokeelia (the northern tip)
St. James City (the southern end)
Each town has its own personality, so allow time for detours and spontaneous stops.
5. Taste Tropical Fruit Grown on Pine Island
Thanks to its fertile soil, Pine Island is known for tropical fruit like mangoes and lychee. Many stands and farms sell fresh, seasonal fruit year-round. One favorite stop is Hot Tropic Fruit Farm near St. James City, a family-run spot where you can sample what’s in season, take a farm tour, or even enjoy a u-pick experience depending on the time of year.
6. Step Back in Time at the Museum of the Islands
For a deeper look into Pine Island’s history, stop at the Museum of the Islands. This small but fascinating museum covers everything from the Calusa to the area’s early pioneers. A short audio guide gives a great overview before you explore the exhibits in detail.
History lovers should also check out the Calusa Heritage Trail at the Randell Research Center in Pineland (currently closed during my visit in August, but highly recommended).
7. Stay and Dine at the Historic Tarpon Lodge
For an authentic Old Florida experience, book a night at the Tarpon Lodge, built in 1926. This historic fishing lodge sits right on Pine Island Sound and is Pine Island’s most iconic place to stay.
Guests can choose from charming lodge rooms with original hardwood floors, the elevated Island House, or more private stays in the Boathouse or Cottage.
The on-site Tarpon Lodge Restaurant is a four-star gem with sweeping views of Pine Island Sound—perfect for sunset dining.
And while you’re here, be sure to check out Tarpon Lodge’s sister property, Cabbage Key, just a short boat ride away.
