There is a lot to explore and enjoy across this little area of Florida. With wildlife, Calusa archeological sites, quirky island towns, fishing, hidden beaches, and Gulf sunsets, Pine Island and the surrounding area feel like stepping into a slower, old-Florida way of life.
Whether you want to spend the day kayaking through mangroves, island hopping by boat, or eating seafood and key lime pie by the water, here are some of our favorite spots and local recommendations.
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One of our favorite ways to experience the area is by kayak or paddleboard. Matlacha Outfitters is a great option to tour through winding mangrove tunnels and quiet inlets while bird watching, and if you’re lucky, you may even spot dolphins or manatees.
We recommend going early in the morning when the wildlife is the most active and before the Florida heat sets in.
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This list doesn’t feature everything on the island, but here are a few options! The island is mostly known for its laid-back seafood restaurants and dive bars, but there’s a lot to explore.
In Matlacha:
Local coffee roaster with excellent breakfast and chocolate chip pancakes.
A laid-back waterfront spot for seafood, drinks, and live music.
Grocery Stops Before Heading to the Island
Located when you enter Pine Island
Good option if you’re staying on the south end of the island
On Pine Island
Bokeelia (North Pine Island)
Probably the most “upscale” dining on the island, featuring local produce and fresh seafood. Reservations highly recommended.
A Pine Island staple with fresh seafood, marina water views, and laid-back atmosphere.
A quirky outdoor spot also featuring waterviews and seafood. They also have live music on occasion!
St. James (South Pine Island)
The Waterfront Restaurant & Marina
More laid-back vibes, seafood, and outdoor seating.
A cute coffee truck. Closed on Thursday and Sunday.
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Fishing is the foundation of the civilization of Pine Island, beginning with Calusa people who inhabited the island for more than 1, 500 years and then the emergence of commercial and sport fishing in the late 19th century.
The waters surrounding Pine Island are known for their incredible diversity of fishing environments — from shallow grass flats and winding mangrove creeks to deeper channels and open water.
Fishing charters are also a great way to spot wildlife, like dolphins, sharks, osprey, pelicans, and stingrays.
Tarpon Lodge provides several great recommendations for guides. We recommend early morning trips as the wildlife and fish are more active, and the temperature is more comfortable.
You can also fish by kayak, but there isn’t a great place to rent gear. You also need a fishing license, and there are regulations for specific species.
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Explore Pine Island Sound
If you have extra time, we highly recommend getting out on the water. Pine Island Sound is dotted with tiny islands, mangroves, shell-covered beaches, and hidden old Florida spots that are best accessed by boat.
Located right next to Tarpon Lodge, Island Girl Charters is a great option for island hopping, sightseeing, wildlife spotting, and lunch on the water. They have regularly scheduled trips throughout the day that go to Cabbage Key and North Captiva. Typically, you need to reserve your tickets 24 hours in advance, but you can call to check on last-minute spots.
The first stop on the boat is Cabbage Key Restaurant. Known for its “Cheeseburger in Paradise,” dollar-bill-covered walls, and resident giant tortoises, Cabbage Key has been a family tradition for us for decades after long days exploring the surrounding islands by boat.
The water taxi also visits North Captiva, an island only accessible by boat. You can visit the beach here for the day or check out the local bar and grill, Mainstay.
If you charter your own boat, we highly recommend visiting the following islands:
Cayo Costa
One of our favorite places in Florida.
Only accessible by boat, the island features untouched beaches, nature trails, and some of the best shelling in the world.
Captiva Island
If you’re looking for beach access with plenty of food and shopping nearby, Captiva is hard to beat.
You can rent beach gear from:
…and spend the day relaxing by the Gulf.
Captiva is especially famous for its sunsets — although honestly, it’s hard to find a bad one anywhere around here.
Where to Eat on Captiva
A kitschy 1940s-inspired restaurant known for over-the-top desserts and some of the best cake in Florida.
Great lunch and dinner spot with outdoor seating, live music, and excellent key lime pie.
Recently completely rebuilt after the 2022 hurricane, the Mucky Duck is a great place to grab a cocktail, play the ring game, and walk out onto the beach for sunset.