Sanibel Island, @miabellaballerina
Island-Bound
Goodbye mainland, hello wonderland.
There’s a reason people want to be on island time. It’s the kind of laidback feeling that comes with the sun on your face, the wind in your hair, and absolutely nothing you need to do – except, perhaps, to take in the beauty of your surroundings. Discover the islands that define the Fort Myers area: beautiful, breezy and endlessly inviting.
Coasting the day away
just feels right.
Sanibel Island
Embrace serendipity on a boat tour to Cabbage Key or Useppa Island for lunch, or cross a bridge or two to quiet Pine Island, or Sanibel and Captiva Islands, with their laid-back lifestyle and famous seashells. Whatever mode you choose, island hopping around Fort Myers is an experience you’ll never forget.
North Captiva, @marrymeintravel
Sanibel Island
Islands You Can Drive To
Sanibel Island and Captiva Island definitely deserve their “away from it all” vacation vibe, with beautiful beaches, waterfront dining spots and water sports. On Pine Island, the fishing and birdwatching are amazing, while Estero Island (Fort Myers Beach) offers water sports, sandy beaches and casual restaurants. Beautiful Boca Grande on Gasparilla Island offers a historic inn, quaint shops, the lovely beach at Gasparilla Island State Park and extensive bike trails.
Explore the islands and discover your new favorite activities, such as shell collecting, kayaking, or simply relaxing and taking in the views. Don’t miss a variety of fresh seafood on the menu, and find a great spot when it’s time for sunset.
Tip: Get around like a local – rent a bike or golf cart to explore Sanibel and Captiva.
The Outer Islands
The pace of life is slower on our outer islands, which are accessible only by water. Whether you choose your own boat, a rental boat, or one of several charters or water taxis, your time exploring these barrier islands will be a highlight of your visit.
Pine Island Sound is home to Cabbage Key, where you’ll find a historic inn and rustic cottages (several with private boat docks). At the legendary Cabbage Key Inn & Restaurant, you can have a grilled mahi-mahi sandwich and write your name on a dollar bill, taping it to the wall as many previous visitors have.
Useppa Island is where you’ll find the historic Collier Inn; it’s open only to members or guests of members, but you can eat at the restaurant here if you arrive with Captiva Cruises. Learn about the island’s history at the small Barbara Sumwalt Museum. Or take the Pine Island ferry to North Captiva, the most developed of the outer islands, with its beachfront vacation rentals and casual restaurants.
Tip: Book a shelling cruise to explore the island of Cayo Costa, where the beaches are famous for treasures from the sea.
North Captiva, @north_cap_pantai
See the Sights
Your island-hopping adventure is likely to be filled with wonders. See the historic fish houses of Pine Island Sound, watch dolphins jump in the boat’s wake, and catch a glimpse of manatees in quiet backwaters. Climb to the top of the historic Gasparilla Island Lighthouse (October through May) and be rewarded with breathtaking views. Mangrove and rookery islands delight birdwatchers, especially around sunset, when the birds fly home to roost.
Pine Island, @erinloveslondon
Rent a Boat
If you want to head out on your own, look into boat rentals. They’re available at local marinas, where helpful staff will provide an orientation to your watercraft, charts of local waterways and tips for having a great time.
Tip: Anyone born on or after January 1, 1988, will need to take a boating safety course before renting a boat.
TAKE A BOAT TOUR
Island Girl Charters
Departs from Pineland Marina on Pine Island to Cabbage Key and North Captiva.
Adventures in Paradise
Departs from Port Sanibel Marina; shelling tours include lunch at Cabbage Key or North Captiva Island.
Captiva Cruises
Departs from Captiva Island to Cabbage Key, Useppa, Cayo Costa, Boca Grande (seasonal) and Tarpon Lodge on Pine Island (seasonal).
Tip: Book in advance, as tours often sell out.
Blind Pass, Captiva Island, @jonahforystekphotography
Flightseeing Adventures
Get a bird’s-eye view of our shoreline on a helicopter tour with Str8 Up Aviation. Its scenic flightseeing tours soar over the mangrove and beach coastlines of Fort Myers Beach and Bonita Beach, or you can choose a Sanibel, Captiva and Pine Island tour.
Book a Private Charter
Are you looking for a personalized adventure? An experienced captain who knows the local waters can help. Choose from wildlife-spotting, shelling, swimming and sightseeing excursions from an expert like Captain Cathy Eagle, who departs from Pineland – her dolphin and nature tours take in Cayo Costa and stop for lunch on Cabbage Key.
A Waterside Chat with Captain Brian
We recently talked with Captain Brian Holoway while he was anchored just off Cayo Costa State Park.
Captain Brian is a Certified Florida Master Naturalist who has been exploring Fort Myers’ islands and waterways for 30 years. His business was named the “#1 Best Boat Tour” in the United States by Newsweek Magazine for 2026.
Q: You’ve visited other destinations with islands and beaches. What makes island hopping here in the Fort Myers area unique?
A: Two things – the abundance of wildlife and the history. I’m looking at a bunch of royal terns right now, for example. The bird life is amazing! I do a lot of trips to Cabbage Key, which is on the National Register of Historic Places. People always say “Cheeseburger in Paradise” about the restaurant there, but that is like one percent of the story. It goes back to the Native Americans who lived there, the shell mound, the historic cottages and the inn.
Q: Have you ever had an unexpected moment when you’re out island hopping with guests?
A: Oh, yeah! We saw a baby dolphin born once. We saw the fluke of the tail. Both tips were up and I thought it was a ray. Then we saw it shoot out of the birth canal.
Q: Tell us more about the types of wildlife visitors might see on one of your trips.
A: For birds, we might see black skimmers, oyster catchers, reddish egrets, willets, brown pelicans, plus in the wintertime, white pelicans. Today, I’m at Cayo Costa and we saw a manatee and a pod of eight dolphins. I’m with a family from Long Island and the mom couldn’t believe they saw a manatee… it’s the first manatee she’s ever seen in her life.
Q: What do kids like about exploring our islands?
A: They love finding a lot of different things on the beach. I walk with them, and we’ll see pieces of horseshoe crabs, crab claws, many seashells. They’re always really curious. They’re interested in learning about seashells and their names.
Q: You’re a one-person show, right?
A: It’s just me and my boat.
© 2026 Visit Fort Myers