✓ Accommodations ✓ Flights ✓ Rental Cars
Did you know Pine Island is Florida’s largest barrier-free island, spanning 17 miles long but featuring zero traffic lights? This hidden gem offers an authentic slice of old Florida that’s increasingly hard to find in the Sunshine State’s more developed areas. Unlike its sandy neighbors, Pine Island is fringed with mangroves instead of beaches, creating a unique ecosystem that supports world-class fishing and abundant wildlife.
Getting to Pine Island
Pine Island is accessible only by car via the “fishingest bridge in the world” from Cape Coral, or by boat for the more adventurous traveler. The island sits about 30 minutes from Fort Myers and 15 minutes from Cape Coral, making it an easy day trip or extended stay destination.
Plan Your Journey to Pine Island
Ready to experience this hidden Florida gem? Start by booking your flights to nearby Southwest Florida International Airport (RSW) in Fort Myers.
Once you arrive at the airport, you’ll want to rent a car as public transportation to Pine Island is limited. The drive from Fort Myers to Pine Island takes you through Cape Coral before crossing the Matlacha Pass Bridge, which serves as the colorful gateway to island life.
Pine Island Communities
Pine Island consists of five distinct communities, each with its own character and charm. Understanding these areas will help you plan your visit more effectively.
Matlacha
Pronounced “MAT-la-shay,” this tiny islet serves as the colorful gateway to Pine Island. Once a fishing village, it’s now a vibrant arts community with brightly painted galleries, seafood restaurants, and shops lining both sides of the main road.
Bokeelia
Located at the northern tip of Pine Island, Bokeelia (pronounced “Bo-KEEL-ya”) offers stunning views of Charlotte Harbor. It’s home to palm nurseries, tropical fruit groves, and the famous Bokeelia Fishing Pier where you can catch snapper, redfish, and more.
St. James City
At the southern end of the island, St. James City features waterfront homes, marinas, and popular restaurants like the Ragged Ass Saloon. It’s a favorite spot for boaters and those looking to access the southern waters of Pine Island Sound.
Pineland
On the western shore, Pineland houses the Randell Research Center, an important archaeological site showcasing Calusa Indian history. It’s also home to Tarpon Lodge, a historic lodge and restaurant offering upscale dining.
Pine Island Center
The island’s commercial hub features the island’s only shopping center, post office, library, and fire department. While not as picturesque as other areas, it provides essential services for visitors and residents.
When to Visit
The best time to visit Pine Island is from October through May when temperatures are pleasant and rainfall is minimal. Summer months (June-September) bring higher humidity, afternoon thunderstorms, and mosquitoes, though prices are lower during this off-season.
Where to Stay on Pine Island
Pine Island offers a variety of accommodations that capture the island’s old Florida charm. From historic lodges to waterfront cottages, you’ll find options that feel worlds away from typical hotel chains.
Tarpon Lodge
This historic lodge in Pineland offers upscale rooms and cottages with Old Florida charm. Its on-site restaurant is considered one of the best dining experiences on the island, featuring fresh seafood and an extensive wine list.
Matlacha Cottages
These colorful, artsy cottages put you in the heart of Matlacha’s vibrant community. Stay within walking distance of galleries, shops, and restaurants while enjoying waterfront views.
Vacation Rentals
For longer stays or family trips, numerous vacation homes and condos are available throughout the island, many with water access, docks, and fishing opportunities right from your backyard.
Find Your Perfect Pine Island Stay
Browse our selection of Pine Island accommodations ranging from historic lodges to waterfront cottages and vacation rentals.
Best Things to Do in Pine Island, Florida
While Pine Island may lack the sandy beaches found elsewhere in Florida, it more than makes up for it with unique activities and natural attractions that showcase the island’s authentic character and rich ecosystem.
Explore Matlacha’s Vibrant Art Scene
The tiny community of Matlacha packs an enormous artistic punch. Once a fishing village, it transformed into an art haven after commercial fishing declined in the 1990s. Today, the colorful buildings house galleries, studios, and shops featuring works from local artists.
Don’t miss these notable galleries:
- Lovegrove Gallery & Gardens – Known for artist Leoma Lovegrove’s colorful, eccentric pieces
- WildChild Art Gallery – Features everything from serious to whimsical art
- Matlacha Menagerie – Showcases unique local artwork and jewelry
- Island Visions – Specializes in colorful Floridian paintings and prints
- Bert’s Pine Bay Gallery – Offers a diverse collection of local art
World-Class Fishing Opportunities
Pine Island is a fisherman’s paradise, surrounded by productive waters teeming with snook, redfish, tarpon, trout, and more. The island’s fishing heritage remains strong, with numerous options for anglers of all skill levels.
Popular fishing spots include:
- Matlacha Pass Bridge – Known locally as the “Fishingest Bridge in the World”
- Bokeelia Fishing Pier – Offers excellent fishing without needing a boat
- Pine Island Sound – Perfect for targeting redfish and snook around mangrove islands
- Charlotte Harbor – Known for seasonal tarpon fishing
Book a Pine Island Fishing Charter
Experience world-class fishing with local guides who know exactly where to find the best catch. Half-day and full-day charters available.
Kayaking Through Mangrove Tunnels
Pine Island is surrounded by three aquatic preserves, creating ideal conditions for kayaking and canoeing. Paddle through serene mangrove tunnels, open bay areas, and narrow canals while spotting wildlife like dolphins, manatees, and numerous bird species.
The Great Calusa Blueway Paddling Trail offers marked routes around Pine Island, making it easy for even novice paddlers to explore safely. Gulf Coast Kayak in Matlacha provides rentals and guided tours for those without their own equipment.
Explore Pine Island by Kayak
Book a guided kayak tour through mangrove tunnels and aquatic preserves to experience Pine Island’s natural beauty up close.
Discover Calusa Indian History
Pine Island was once home to the powerful Calusa Indians, who built shell mounds and engineered canals throughout the region. The Randell Research Center in Pineland offers a fascinating glimpse into this ancient civilization.
Walk the 0.7-mile Calusa Heritage Trail to see shell mounds created by the Calusa over 2,000 years ago. Interpretive signs along the trail explain the history and significance of these archaeological features. The on-site museum provides additional context about this fascinating lost civilization.
Boat Tours and Water Excursions
Exploring the waters surrounding Pine Island is essential to fully appreciate this unique destination. Several operators offer boat tours ranging from sunset cruises to wildlife excursions.
Popular boat tour options include:
- Captain Jack’s Pontoon Tiki Boat Tours – Offers happy hour, sunset, and fishing tours
- Tropic Star Cruises – Provides ferry service to nearby islands like Cabbage Key and Cayo Costa
- Island Girl Charters – Specializes in dolphin watching, shelling, and birding trips
Explore Pine Island by Water
Book a boat tour to experience Pine Island’s stunning waterways, spot dolphins, and visit nearby islands only accessible by boat.
Where to Eat on Pine Island
Pine Island’s dining scene focuses on fresh seafood, casual atmospheres, and waterfront views. Many restaurants feature the day’s catch brought in by local fishermen, offering a true taste of Florida.
Tarpon Lodge Restaurant
This upscale dining experience in Pineland offers fresh seafood, an extensive wine list, and some of the best Key Lime Pie on the island. The historic setting and water views make it perfect for a special dinner.
Bert’s Bar & Grill
A Matlacha institution dating back to the 1930s, Bert’s offers casual dining with dockside seating. Enjoy burgers, sandwiches, and seafood while watching boats pass by and occasionally spotting dolphins.
Miceli’s Restaurant
This Italian restaurant in Matlacha serves authentic Sicilian recipes alongside fresh seafood dishes. Live music and waterfront dining make it a popular spot for dinner and entertainment.
Ragged Ass Saloon
This laid-back spot in St. James City is popular with boaters and bikers. Enjoy fresh seafood, burgers, and cold drinks while listening to live music on their outdoor patio.
Cabbage Key Restaurant
Accessible only by boat, this restaurant on nearby Cabbage Key is famous for its cheeseburger that allegedly inspired Jimmy Buffett’s “Cheeseburger in Paradise.” The walls are covered with thousands of dollar bills signed by visitors.
The Yucatan Waterfront Bar
Offering waterfront dining in Matlacha, The Yucatan serves up fresh seafood, great burgers, and tropical drinks. Their outdoor seating area provides excellent views of Matlacha Pass.
Practical Information for Visiting Pine Island
Getting Around
A rental car is essential for exploring Pine Island as public transportation is limited. The island is 17 miles long with a single main road (Stringfellow Road) running from north to south, making navigation simple.
Rent a Car for Your Pine Island Adventure
Having your own vehicle is the best way to explore all five communities of Pine Island at your own pace.
Bicycling is another popular option, with the 14-mile Pine Island Bike Path (Stringfellow Trail) running alongside the main road. Bike rentals are available at several locations on the island.
Weather and What to Pack
Pine Island has a subtropical climate with mild winters (January-March) and hot, humid summers (June-September). The rainy season runs from June through September, with afternoon thunderstorms common.
Winter Visitors (October-May)
- Light layers for cool mornings and evenings
- Sun protection (hat, sunglasses, sunscreen)
- Insect repellent for dawn/dusk activities
- Comfortable walking shoes
- Light rain jacket for occasional showers
Summer Visitors (June-September)
- Lightweight, breathable clothing
- Strong sun protection (hat, sunglasses, SPF 50+)
- Insect repellent (mosquitoes are prevalent)
- Rain gear for afternoon thunderstorms
- Swimwear for water activities
Important Tips
- There are no beaches on Pine Island itself. For beach days, visit nearby Sanibel Island or Fort Myers Beach.
- The island operates on “Island Time” – expect a relaxed pace and friendly, unhurried service.
- Bring cash for small businesses and artists’ galleries, as not all accept credit cards.
- If fishing, check Florida fishing license requirements before your trip.
- For boat or kayak rentals, make reservations in advance, especially during peak season (January-March).
- Cell service can be spotty in some areas of the island.
Experience the Authentic Florida
Pine Island offers a rare glimpse into old Florida charm that’s increasingly difficult to find in the state’s more developed areas. Without high-rises, traffic lights, or crowded beaches, the island preserves a way of life centered around fishing, art, and natural beauty.
Whether you’re casting a line from the “fishingest bridge in the world,” paddling through serene mangrove tunnels, exploring vibrant art galleries, or savoring fresh seafood with water views, Pine Island delivers authentic experiences that create lasting memories.
Ready to Discover Pine Island?
Plan your escape to this hidden gem where you can experience Florida as it used to be – natural, unhurried, and full of character.
—
The above is subject to change.
Check back often to TRAVEL.COM for the latest travel tips and deals.
