Naples has a reputation for its dining, its shopping, and its Gulf-side sunsets. What a lot of visitors do not realize is how much water surrounds the city and how many places it can take you. Naples Bay opens to the south through Gordon Pass, connecting to the Intracoastal Waterway, the Gulf of Mexico, and a network of barrier islands, mangrove channels, and protected estuaries that stretch all the way to the edge of the Everglades.
A single day on the water from Naples can include a barrier island beach, a sandbar stop, a cruise through a national estuary, a wildlife encounter, and a waterfront lunch. The variety of destinations within reach is one of the things that makes chartering out of Naples so appealing, especially for groups that want to do more than sit on one beach all day.
Here is where your captain can take you.
Keewaydin Island
Keewaydin is the most popular boat-day destination from Naples and the one most people hear about first. This eight-mile barrier island sits between Naples and Marco Island, accessible only by water. About 85 percent of its 1,300 acres is public land, with miles of soft white sand beach on the Gulf side and calm, protected water on the bay side.
The southern tip of the island is the social hub. On weekends and holidays, boats anchor along the shore and food concession boats sell burgers, hot dogs, ice cream, and cold drinks. The northern stretches are quieter and offer some of the best shelling in Southwest Florida. Sand dollars, conchs, whelks, and fighting conchs wash up in good condition because the beach sees far less foot traffic than mainland shores.
Keewaydin is also the only beach in the Naples and Marco Island area where dogs are allowed, though they must be leashed at all times. The island is an important nesting ground for loggerhead sea turtles, with nesting season running May through October.
The ride from most Naples marinas to the southern tip of Keewaydin takes about 20 to 30 minutes.
Rookery Bay
Rookery Bay National Estuarine Research Reserve covers over 110,000 acres of mangrove forest, tidal creeks, and protected estuary between Naples and Marco Island. The Intracoastal Waterway runs through the heart of it, and cruising this stretch of water feels surprisingly remote given how close you are to two developed cities.
The birding here is excellent, particularly during the cooler months when migratory species pass through. Herons, egrets, roseate spoonbills, ospreys, and pelicans are common along the mangrove edges. Dolphins are frequent in the channels, and manatees are regularly spotted in the slow-speed zones that are posted throughout the reserve.
Most charters pass through Rookery Bay on the route between Naples and Marco Island, but the area is worth slowing down for on its own. Your captain can cruise the quieter tidal creeks for a closer look at the wildlife and the landscape.
Marco Island
Marco Island sits about 90 minutes south of Naples by boat following the Intracoastal Waterway. The route passes through Rookery Bay and along the backside of Keewaydin Island, making it easy to combine stops along the way.
Once you reach Marco, there are a few good options. The Snook Inn on the Marco River is one of the area's best-known waterfront restaurants with dock space for boaters. Capri Fish House and Pelican Bend on the nearby Isles of Capri offer quieter alternatives with easy docking. Tigertail Beach on the northwest side of Marco is one of the area's top beaches, with soft sand, calm water, and a lagoon popular with wading birds and families.
A full-day or six-hour charter from Naples is the most comfortable way to make the Marco Island run, with time for a Keewaydin stop and a waterfront lunch.
The Ten Thousand Islands
The Ten Thousand Islands begin just south of Marco Island and extend into the Everglades. This is one of the most remote and pristine coastal ecosystems in Florida. Thousands of small mangrove islands stretch in every direction, connected by shallow channels and tidal creeks. There are no roads, no buildings, and very few other boats once you get past the first few miles.
Even a short cruise into the northern edge of the Ten Thousand Islands gives you a sense of the scale and the wildness of the place. The fishing here is exceptional, with snook, redfish, and tarpon holding in the backwater channels. Dolphins are common, and the birding rivals Rookery Bay.
Reaching the Ten Thousand Islands requires more travel time, so a six-hour or full-day charter is recommended. Your captain can plan a route that combines the islands with other stops along the way.
Cape Romano
Cape Romano sits just south of Marco Island and is a destination with a unique story. The site was once home to the Cape Romano Dome House, a futuristic structure of six concrete domes built on stilts in 1981 by retired oil producer Bob Lee. Over the decades, storms and erosion gradually reclaimed the island beneath the house. Hurricane Irma damaged the structure in 2017, and Hurricane Ian submerged the remaining domes in September 2022.
Today the site is completely underwater, but it remains a popular stop for boaters and snorkelers. The submerged concrete has become an artificial reef, attracting marine life to the area. The beach nearby at Cape Romano is a good spot for shelling and swimming, and the surrounding water is clear and calm on most days. It is a unique stop that pairs well with a Marco Island or Ten Thousand Islands itinerary.
Wiggins Pass Sandbar
North of downtown Naples, near Delnor-Wiggins Pass State Park, a sandbar forms at the mouth of Wiggins Pass where the backwaters meet the Gulf. This is a popular anchoring spot for boaters who want a shallow-water stop without heading south to Keewaydin. The water is clear, the sand is firm, and the surrounding area is lined with mangrove islands that attract ospreys, kingfishers, herons, and egrets. It is a calmer, more low-key alternative to the busier scene at Keewaydin's southern tip.
Wildlife You May See
The waters around Naples support a diverse range of marine and coastal wildlife. What you encounter depends on the season, the route, and the conditions, but common sightings include:
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Bottlenose dolphins — Year-round residents in the channels and passes. Frequently seen riding bow wakes, feeding in the shallows, and cruising alongside boats.
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Manatees — Most visible during the cooler months (November through March) when they seek warm, shallow water. Common in Naples Bay, the Intracoastal Waterway, and the slow-speed zones through Rookery Bay.
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Sea turtles — Loggerhead, green, and Kemp's ridley turtles are present in the waters around Naples. Loggerheads nest on Keewaydin Island from May through October.
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Ospreys — Nest on channel markers, power poles, and treetops throughout the area. One of the most frequently spotted raptors on any charter.
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Wading birds — Great blue herons, snowy egrets, roseate spoonbills, and white ibis are common along mangrove shorelines and tidal flats, especially in Rookery Bay and the Ten Thousand Islands.
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Pelicans — Brown pelicans are everywhere along the coast, diving for fish and resting on pilings.
Chartering Out of Naples with Us
We operate private charters out of Naples, and our captains know these waters well enough to build an itinerary around any combination of these destinations. A half-day charter covers Keewaydin and the nearby sandbars comfortably. A six-hour trip opens up Marco Island, Cape Romano, and the edges of the Ten Thousand Islands. A full day gives you the flexibility to hit multiple stops, fish, snorkel, and still have time for a waterfront lunch along the way.
Our boat, the Axopar 37 XC Cross Cabin, is built for this kind of day. The shallow draft gets you into the tight spots along Keewaydin and the mangrove creeks. The enclosed cabin keeps your group cool between stops. And the sunbeds, bathroom, and Bluetooth sound system mean everyone stays comfortable for the full trip.
You can check availability and book at sea-eo.com.