Pine Island, FL: Things to Do and Where to Eat, Drink & Stay

Ready for your next Florida getaway? Start planning your vacation to one of the Sunshine State’s best hidden gems, Pine Island, FL. This Gulf Coast island, located in Southwest Florida, is a traveler’s secret paradise.

Part of Lee County, Pine Island is Florida’s largest island, located only minutes from Cape Coral and Fort Myers. Unlike other popular destinations, Pine Island has made a concerted effort to maintain its rich heritage and preserve its natural beauty. Its charming and funky vibe attracts people from all walks of life. Around here you’ll run into the biker crowd, the artist community—and everything in between. 

Ready for a laid-back atmosphere, a small-town feel, and beautiful beaches? That doesn’t even begin to cover everything Pine Island has to offer! Be sure to check out this bucket list destination!

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Things to do in Pine Island, FL


Before making it to Pine Island, be sure to stop off at Matlacha Island for the perfect day trip. Matlacha offers a vibrant, quaint atmosphere full of artisan galleries, colorful shops, and antique stores. Take a walk down the main street and enjoy the funky decorated storefronts, colorful telephone poles, and lively waterfront restaurants. 

Matlacha, FL

After you’ve enjoyed the animated town center, take a trip under the Matlacha Pass Bridge for some of the best fishing in Florida. Angler fishing is popular with the locals, and this area is famous for its trout, snapper, and cobia.

If fishing isn’t up your alley, spend time kayaking or paddle boarding down the Matlacha Pass’ calm waters instead.

Leoma Lovegrove Gallery & Gardens

As you wrap up your day in Matlacha, be sure to make one last pit stop at Leoma Lovegrove Gallery & Gardens. Located on Pine Island Road, this infamous treasure serves as a haven for artists, tourists, and locals alike. 

Leola Lovegrove Gallery & Gardens

Leoma Lovegrove, the owner of this art gallery, is a world-renowned painter who is prominently known for her impressionism and expressionism style. Some of her works hang in the White House, Rockefeller Center, and other prestigious locations. With so much success, Leoma has chosen to put her efforts into her gallery in Matlacha, attracting both casual onlookers and avid fans. 

Her gallery and gardens are known for their colorful and imaginative artwork, with the gallery itself even being part of Leoma’s artistic expression, including the building, garden, and patio.

Make sure to liven up your time in Matlacha with a visit to this artistic landmark. 

Pine Island Sound Aquatic Preserve

The Pine Island Sound Aquatic Preserve is a perfect mix with the Caloosahatchee River, San Carlos Bay, and Charlotte Harbor coming together to form beautiful, blue waters. This aquatic preserve works to protect the living wildlife and natural ocean habitats in Pine Island Sound’s waters, allowing visitors to admire the mollusk reefs, salt marshes, mangrove swamps, sponge beds, and seagrass beds.

Pine Island Sound Aquatic Reserve

After you’ve had a chance to enjoy the natural sights, you can make plans to fish, kayak, beach comb, or bird watch while visiting.

Be sure to check out one of the many mangrove kayaking tours, whisking you away on a leisurely, peaceful water tour through the dense, coastal, swamp shrubbery and trees.

Calusa Heritage Trail

On Pine Island’s western shore, you’ll find the Calusa Heritage Trail. Once home to the Calusa Native Americans, this one-mile nature trail takes visitors down Florida’s history through canals, mounds, and an archaeological site, all highlighting the rich history of the Calusa Indian heritage. 

With educational signs leading the way, this trail will allow you to submerse yourself in the natural environment while learning about the natives of the past.

Book one of the many guided walking tours available at Calusa Heritage Trail to truly take in the experience and educate yourself. 

Museum of the Islands

After you’ve explored the trails, be sure to visit the Museum of the Islands, located in Pine Island Center. The museum focuses on preserving Pine Island’s past so that future visitors can learn about its rich and storied past. Visitors can get lost for hours in the many unique and educational exhibits found throughout the museum. 

Don’t forget to check out the beautiful Calusa Village mural dedicated to the Calusa Indian’s way of life. You’ll also be able to study preserved authentic pottery, artifacts, and natural relics from Pine Island’s mound excavations.

While you’re there, don’t miss out on the museum’s famous George Washington art piece, a tapestry made up of 300,000 glass beads! 

Randell Research Center

Randell Research Center is the perfect place to learn about the history of the Calusa Indian’s 1,500-year reign as one of the most powerful native Floridian tribes. Located on Pine Island’s western shores, the Randell Research Center is made up of 67 scenic acres of Pineland history. 

Made up of several important and fascinating historical landmarks, the Randell Research Center is where you’ll find the Calusa Heritage Trail and the shell mound sites. Here you’ll be able to see the remnants of a Calusa Indian village along with the ecological and archaeological remains of the area they once harvested. 

Be sure to book a tour and see Randell’s butterfly garden, Ibis Pond, and live excavations for a truly interactive visit!

Bokeelia Fishing Pier

Plan a full day at the Bokeelia Fishing Pier for an activity-filled stay. This is one of the hottest fishing spots in all of Florida and a popular destination for fishers of all skill levels for over a century. 

Bokeelia Fishing Pier

Be sure to take advantage of the fishing seasons with the warmer months attract snapper, redfish, and snook while the cooler months see blackdrum, grouper, and sheepshead biting. 

The pier has fishing tackle and bait available for purchase and requires no fishing license. You can even rent a boat and ride out past Boca Grande Pass from the pier’s convenient boat ramp for incredible offshore fishing. 

Bokeelia Art Gallery

After you’ve finished fishing at the pier, be sure to stop by the Bookelia Art Gallery. This artisan gallery is not only beautiful but exceptional in the experience it provides its visitors. The well-crafted setup for each piece along with intentional lighting gives you a unique appreciation for the gallery’s art. 

Housing art from over 50 different artists, both locally and nationally recognized, Bookelia showcases captivating paintings, pottery, jewelry, beaded tapestries, pottery, and more. 

Be sure to plan carefully since Bookelia Art Gallery is closed on Sundays and Mondays. ​

Gulf Coast Kayak

Located in Matlacha, Gulf Coast Kayak is the perfect destination for outdoor enthusiasts. With a wide variety of kayaks available, you can find the most comfortable way to explore Matlacha’s Pass Aquatic Preserve’s beautiful, serene waters for you. Choose from single and tandem kayaks, sit-in and sit-on kayaks, fishing kayaks, and even paddleboards. 

Operating for three decades, Gulf Coast Kayak prides itself on the reputation it’s built over the years. Known for its exceptional service, this family-owned company focuses on providing meaningful experiences to its customers.

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Enjoy relaxing sunset paddles, kayak fishing trips, or recreational kayaking down the peaceful waterways. 

Galt Preserve

When you’re back on Pine Island, just take a quick drive to visit the quiet and beautiful Galt Preserve. The preserve is perfect for a family outing with hiking trails that stretch for 2.5 miles, a fishing pier, a boardwalk, and picnic areas. 

Enjoy the water activities or natural park area where you can hike with your leashed dog, or enjoy the tranquility of the preserve from the various viewing areas. From here, you might catch a glimpse of a bobcat, the swamp’s alligators, or if you’re really lucky, one of the park’s majestic bald eagles! 

With restrooms, spacious parking, and outdoor eating pavilions, Galt Preserve is the perfect place for a family day of fun. 

Cayo Costa State Park

Cayo Costa State Park is an island only accessible by kayak or boat, offering nine miles of glorious beaches. Its waters are perfect for boating, fishing, paddling, scuba diving, shelling, and snorkeling. Anyone looking for fun in the beautiful, blue waters and on the perfect sandy shores is sure to fall in love with Cayo Costa. 

Cayo Costa

Once you’re back on land, the island is made up of dunes, exotic trees, and countless acres of greenery. Once a fishing ground for the Calusa Indians, the island is great for walking, hiking, or biking on the numerous trails. If you don’t want to leave straight away, the park is even available for overnight camping on its grounds.

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Birdwatching has also become an especially popular activity in Cayo Costa State Park. From the shoreline, you might even see rare wild marine life like porpoises, sea turtles, or manatees! 

Where to eat & drink

With so much to do on Pine Island, you’re sure to work up an appetite along the way. The island offers some tasty options for eating and drinking.  

Phuzzy’s Boat Shack is a popular restaurant in the St. James City neighborhood of Pine Island. With a lively atmosphere overlooking the water, this is the perfect restaurant to unwind.

Take advantage of the great happy hour specials which include both drink and food options. Definitely try the coconut shrimp or the blackened Mahi, two dishes sure to leave you satisfied! Phuzzy’s also offers nightly entertainment with live musical acts.

For some fine dining with a fresh take on seafood, head over to The Waterfront Restaurant & Marina. Located in the Henley Canal, the restaurant offers fantastic outdoor dining seating.

If you’re traveling by boat, you can slip into one of the 16 easily accessible boat docks only available to customers. After a hearty plate of delicious seafood, be sure to finish off your meal with the coconut-crusted fried cheesecake with raspberry and chocolate sauce! 

As one of the best-reviewed restaurants in Pineland, the Tarpon Lodge & Restaurant is an experience you shouldn’t pass up. While Tarpon Lodge is also a luxury hotel, it serves some of the tastiest food, including include blackened fish bites and smoked fish dip, in its fine dining restaurant with fantastic sunset views. 

Ragged Ass Saloon

Since 1954, Ragged Ass Saloon has been serving up tasty bar food and even better drinks. With its own dock for boats and spacious parking, be sure to visit for an evening for fun. The bar has live music with a dance area for those looking to let loose and dance the night away! 

Located only a block away from Ragged Ass Saloon, Froggy’s is another bar with a laid-back and fun atmosphere. Great music, a good selection of beer, and tasty bites make this place a good time all around. Be sure to try the prawns and, if you’re up for it, their specialty frog legs! 

Another great option right on the water that is known for not being overly crowded is Low Key Tiki. With great views of the canal waters and boat parking, the bar looks like a tiki hut on the outside and offers great outdoor dining.

If you’re there with the whole gang, Low Key Tiki is family-friendly and plays live music. Make sure you try the fish tacos – they’re a local favorite!

Where to stay

Casa Pineland

Casa Pineland

Located in Bokeelia, this beautiful holiday home is the perfect retreat for a Pine Island getaway. The home offers a full range of amenities, including 3 bedrooms, 2 bathrooms, kitchen, private pool, and patio.


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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