Things To Do in Florida

Top Things to Do in Pine Island, Florida

If you're heading to southwest Florida for a day on the water with Dooley Charters, make sure to explore the area before or after your fishing trip. There’s more to Pine Island than its beautiful backwaters and calm fishing grounds. From art-filled villages to peaceful preserves, this hidden gem offers plenty of family activities, cultural experiences, and laid-back attractions that make it well worth a longer stay. Here are some of the top things to do in Pine Island, Florida once your rod and reel are put away.

Stroll Through Matlacha’s Art Galleries

Just minutes from the docks, the colorful village of Matlacha is a must-see. This funky, coastal town is known for its eclectic art galleries, gift shops, and island charm. Take a slow stroll down Pine Island Road and explore vibrant studios like Leoma Lovegrove Gallery, where you’ll find bold Florida-inspired artwork, tropical gardens, and maybe even the artist herself painting live.

Families and couples alike enjoy browsing local handmade crafts, island décor, and unique souvenirs. Matlacha blends small-town Florida with a bohemian spirit, making it one of the most memorable Pine Island attractions to explore between boat rides and beach stops.

Visit the Randell Research Center

For a dose of local history and nature, head to the Randell Research Center in Pineland. This archaeological site and environmental preserve showcases the legacy of the Calusa people, one of Florida’s earliest coastal civilizations. Walk the Calusa Heritage Trail to see ancient shell mounds, native plants, and scenic views of the sound.

It’s an educational yet peaceful experience—great for families, nature lovers, and anyone curious about Pine Island’s deeper past. Bring a water bottle and camera, and take your time soaking in this lesser-known but fascinating part of Pine Island culture.

Explore Pine Island Flatwoods Preserve

If you’re in the mood to stretch your legs, the Pine Island Flatwoods Preserve is a perfect nature walk. This 900-acre conservation area is home to native slash pines, wildflowers, and quiet trails where you can spot gopher tortoises, butterflies, and even the occasional bobcat. It’s a great way to see another side of Pine Island—peaceful, wild, and untouched.

Whether you're birdwatching or just taking a quiet morning walk, the preserve is a wonderful reminder of what makes Pine Island family activities so special: no crowds, just Florida the way it used to be.

Grab Fresh Seafood at Blue Dog Bar & Grill

After a full day outdoors, head to Blue Dog Bar & Grill in Matlacha for a relaxing meal. Known for its local seafood, laid-back vibe, and waterfront views, this is a favorite spot for locals and returning visitors. Try the grouper sandwich, crab cakes, or just sip a cold drink while watching the boats pass by.

It’s a great stop for couples or families looking for dining in Pine Island that feels casual but still full of flavor. The service is friendly, the portions are hearty, and it’s close to most of the day’s other attractions.

Tour the Museum of the Islands

Want to understand the charm and history of this region? Make a quick visit to the Museum of the Islands in nearby Bokeelia. This small but rich museum highlights the natural, cultural, and fishing history of Pine Island and its neighboring isles. Kids love the vintage shell collections, old fishing gear, and antique local photographs.

It’s a great rainy-day option or a perfect morning activity before heading out with Dooley Charters. Entry is donation-based, and the friendly staff are happy to answer questions about the island’s past.

Whether you're fishing with Dooley Charters, exploring Matlacha's galleries, or soaking in natural beauty at local preserves, Pine Island is packed with activities beyond the boat. With its relaxed pace and old-Florida feel, it’s the kind of place where families can unwind, learn, and connect. Looking for the full experience? Book your Pine Island Sound fishing trip with Dooley Charters, then stick around to discover everything else this unique part of Florida has to offer.