Discover amazing Pineland activities and premium in-home experiences.
Pineland is a serene escape where old-world charm meets lush landscapes and vibrant ecosystems. A gateway to the Calusa heritage, this quaint community invites visitors to explore its historic sites, nature trails, and verdant gardens that celebrate Florida's rich natural beauty. Whether you're wandering through ancient mounds or enjoying tranquil views of Pine Island Sound, Pineland promises an experience steeped in history and tranquility.
Experience a scenic cruise at sunset and spot playful dolphins in Southwest Florida waters.
Cruise San Carlos Bay to spot playful dolphins and learn about local marine wildlife.
Spot dolphins and explore a mangrove island on a relaxed 3-hour eco cruise
Paddle calm Caloosahatchee waters at dusk, spotting dolphins, manatees, and seabirds with a certified naturalist guide
Rent a kayak or paddle board to explore mangrove islands and spot local wildlife.
Paddle through mangrove mazes with expert guides and discover local wildlife and history.
Enjoy days of paddling with included gear and free delivery to your vacation home.
Enjoy multi-day fishing kayak rentals with free delivery and all essential gear included.
Enjoy convenient paddle board rentals delivered to your vacation home for multiple days.
Navigate mangrove waterways on a 2-hour self-guided kayak or paddle board adventure.
Enjoy flexible multiday kayak rentals delivered to your vacation home.
Effortlessly explore Cape Coral at your own pace with easy-to-use electric bikes.
Paddle through winding mangrove tunnels with certified naturalists and spot local wildlife up close
Ideal for fishing with up to 7 people and flexible rental durations.
Cruise and fish local waters with up to 7 people on a comfortable, powerful boat.
Ideal for fly fishing with up to 3 people and flexible rental durations.
Cruise and fish local waters with up to 6 people on a versatile 20′ Tidewater boat.
Cruise local waterways with friends or family on a spacious deck boat.
Spot playful dolphins and other wildlife on a relaxing 1.5-hour morning cruise.
Ride top-tier WaveRunners on Fort Myers waters with flexible 1–8 hour rental options
Cruise Estero Island and nearby waters with up to 14 passengers on a spacious boat.
Cruise with up to 14 passengers on a spacious trimaran for a memorable day on the water.
Cruise with up to 10 passengers on a 20' trimaran for a half or full day adventure.
Cruise with up to 14 passengers on a spacious pontoon for a relaxing day on the water.
Enjoy a lively 90-minute pirate-themed cruise with interactive games and family fun.
Enjoy a 90-minute adults-only pirate cruise with comedy, music, and themed fun on the water.
Experience a relaxing wildlife cruise and explore coastal ecosystems with a naturalist guide.
Watch dolphins and birds on a relaxed 90-minute evening cruise with space for just 28 guests
Spot playful dolphins and diverse birds on a relaxed 90-minute cruise led by certified naturalists
Spot playful dolphins and collect shells on a small-group 3-hour cruise led by certified naturalists
Reel in snook, redfish and more aboard a stable 31' cat with gear, bait and expert captain included
Discover mangroves and wildlife on a beginner-friendly paddleboard eco tour in Bonita Springs.
Experience marine life up close in a clear tandem kayak and enjoy a unique paddling adventure.
Paddle at your own pace and explore secluded beaches with included gear and guidance.
Glide in a transparent tandem kayak among dolphins, manatees and mangroves on a flexible two-hour self-guided adventure.
Discover barrier island seashells and marine life on a beginner-friendly paddle in Bonita Springs.
Paddle to a secluded beach at sunset and return under colorful LED lights for a unique experience
Enjoy paddleboarding with included lessons and gear at scenic Big Hickory Island.
Paddle through mangroves and spot wildlife on a beginner-friendly guided kayak tour.
Ride through diverse Florida ecosystems and encounter wildlife on a guided 90-minute buggy tour
Pineland is a tranquil gem where history and nature intertwine seamlessly, offering visitors an authentic taste of Florida's past and present. Known for its rich archaeological sites, this small community invites you to step back in time at the Randell Research Center. Here, ancient Calusa Indian mounds tell stories of early inhabitants while guided tours provide fascinating insights into their way of life.
A visit to Pineland wouldn't be complete without exploring its lush landscapes. The nearby Pine Island Sound Aquatic Preserve offers kayaking adventures through mangrove tunnels teeming with wildlife—perfect for birdwatchers and nature enthusiasts alike. For those who prefer land-based exploration, take a leisurely bike ride along quiet roads lined with towering palms or enjoy a peaceful afternoon fishing from one of the many piers dotting the coastline.
What sets Pineland apart is its serene atmosphere combined with unique local experiences like dining on fresh seafood at waterfront eateries or visiting charming art galleries showcasing regional talent. Whether you're savoring sunset views over Matlacha Pass or discovering hidden trails within tropical hammocks, every moment spent here promises relaxation and discovery away from bustling tourist spots.