On the Gulf Coast, sleek yachts stretch the length of 100-plus-slip marinas; fly ties whistle through the air deep in the backcountry; and glowing sunsets kiss the water each night. Locals know to pull out our compasses and point them toward the blue because, regardless of how you experience the waterways, the region’s treasures lie just beyond the shoreline.
Capt. Daniel Andrews, co-founder of one of our strongest local conservation defenders, Captains for Clean Water, offers his guidance. The Fort Myers native grew up charting the rivers, channels and sections of the Gulf and spent nearly a decade as a fishing guide. Though he spends more of his days educating others about the water than on boating it now, his daily conversations with fellow captains and avid anglers keep him informed on the ins and outs of the region’s bounty. Here, he charts a course through the region’s boating culture.
Photography by Brian Tietz
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A Fort Myers native and former fishing guide, Daniel Andrews shows how the boating experience shifts along the coast—from backcountry fishing in the Ten Thousand Islands to pleasure cruising in Naples and island hopping around Boca Grande.
The Backwater Beckons in the South
You won’t find yachts and pleasure cruises navigating the waters around Everglades City, Chokoloskee and the Ten Thousand Islands, Daniel says. No—this is the fisherman’s domain, where it’s just you and the surrounding nature. “A lot of our donors in Naples—CEOs and chairmen of boards—[Chokoloskee] is their escape. They go out with the same guide to fly-fish once a week,” Daniel says.
You can fly-fish and cast for light tackle near the docks at the 1950s Parkway Motel & Marina in Chokoloskee, where freshwater flows in from nearby creeks and rivers for a variable bounty. During the winter, head deeper into the backcountry, where fish swim upstream as to find warmer water. In the summer, Daniel recommends heading out through the channel into the Ten Thousand Islands, where permit, redfish, snook and tarpon are likely abundant.
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Photography by Anna Nguyen
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The dock at Boca Grande Marina.
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Avid anglers come for the chase. With fewer boats crisscrossing the backcountry, fish move naturally through the mangroves. You don’t return to a reliable spot—you read the tides, wind and water temperature to track your catch. “I could end up covering a 30-mile stretch in a single day,” Daniel says. Even longtime anglers use a guide in these wild waters, where the conditions are always changing across a maze of mangroves, oyster bars and mudflats. Though notoriously hard to book, Capt. Jeff Legutki is a backcountry legend, famed for tracking giant snook into the tightest, un-navigable mangrove channels and tarpon in the backbay. For the open flats, Daniel points to Capt. Kevin Grainger, who pairs sharp game knowledge with a cool-headed patience and uncanny ability to coach novice to seasoned anglers.
Leisure Cruising in Naples
Social cruising and boat-up dining draw day boaters to Naples. Start your journey with a short cruise that loops through Naples Bay and down to the Gordon River Pass, where scoping the Port Royal mansions from the water is practically a rite. Though it seems cliché, a dinner cruise aboard the Naples Princess opens the door for those who want to appreciate the city’s lifestyle. “A lot of people are like, ‘I can’t afford a $400,000 boat or a $1 million boat, but maybe for me, it’s going out on that boat for dinner one night,’” Daniel says. A plus: The more people experience the pristine waters, the more they care about protecting them.
When evening comes, tie up at one of the city’s many waterfront restaurants. Daniel’s favorite, The Syren Oyster & Cocktail Bar, from longtime local restaurateur Peter Tierney, emphasizes a rotating menu of fresh seafood, including underrated Gulf catch like triggerfish and East and West Coast oysters. “It’s like an upscale version of an oyster house,” Daniel says. He admires that they prioritize sourcing from local supplies and fishermen.
Photography by Nathan Lopez
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Seafood at The Syren Oyster & Cocktail Bar.
For those seeking long-term docking for their vessel and a community of fellow yachters, the Hamilton Harbor Yacht Club, Naples Sailing & Yacht Club and Naples Yacht Club offer concierge services, maintenance and captains on standby. (Prospective members: Anticipate a waitlist.)
Lee County’s Ecotour Environs
With over 70% of Sanibel Island functioning as conservation land, wildlife spotting and ecotours through the surrounding waters make for the best nautical excursions. Daniel recommends idling through J.N. “Ding” Darling National Wildlife Refuge, home to nearly 250 bird species. Flatboats and bay boats are welcome in adjacent Tarpon Bay, so sidle up through part of the largest undeveloped mangrove ecosystem in the country. If you want to skip the 30 minutes it takes to navigate the slow speed zones in the sanctuary, Daniel recommends sticking to the outer edge of the refuge, especially during low tide, when roseate spoonbills and other wading birds hop around on the mud flats. Low tide during the dry season gives birders good viewing opportunities—in the summer months, stick to the evening.
Courtesy Visit Florida
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J.N. “Ding” Darling National Wildlife Refuge.
For a day on the water, venture with some of the local guides on Sanibel and Captiva. Tarpon Bay Explorers and Adventures in Paradise are easy go-tos for classic eco and shelling tours. Daniel’s kids love the 40-year-old, family-owned Captiva Cruises out of McCarthy’s Marina.
On the Gulf Coast, where marinas and mangroves share the same shores, you don’t have to escape to the islands for memorable wildlife encounters. In Fort Myers, stop for lunch at the recently opened The Marina at Bonita Fish Company and cruise the Intracoastal Waterway toward San Carlos Bay. Daniel suggests heading toward the inlets, where the moving tides bring through large schools of baitfish, drawing dolphins. “If you come through the Sanibel bridge, you’re almost guaranteed to see dolphins,” Daniel says.
Island Hopping in the North
When locals want to feel like they’re worlds away, they point the bow north. Pine Island Sound, Boca Grande, Useppa and the surrounding islands create a natural island-hopping circuit, perfect for day trips and staycations. Captiva native Capt. Nick Fischer and Pine Island’s Capt. Cory McGuire navigate the waters often, and Daniel swears by the fishermen for customized routes.
If you’ve got your own vessel, make a day of it. Depart from Pine Island in the morning, where an approximately 30-minute boat ride north takes you to Boca Grande. When you dock next to the ships at Boca Grande Marina, the 100-foot yachts tied to the structure make it feel like you’ve just landed at a private oasis. In season, walk about half a mile over to the historic Gasparilla Inn to spend time on the property’s expansive golf course, on-site restaurant, and nearly 200 rooms and suites.
Photography by Anna Nguyen
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Once you’ve had your fill of the land, head south in the water. Back when Daniel was running charters, nearly every trip included a stop at Cabbage Key Inn & Restaurant. Owned by the second-generation Wells family—who also own Tarpon Lodge & Restaurant on Pine Island—the chefs skip the french fries for beans and rice to pair with local catch for a truly Southwest Florida experience. If tripletail is on the menu, that’s what Daniel is ordering.
In the late afternoon, head out to Cayo Costa for some sandbar action. Drop anchor in the shallow waters, dive overboard and lounge for a while. (A warning: Strong fronts can come through and move sand significantly, so check the latest satellite charts to avoid running aground.) If you have extra time, skip the barrier island and head a bit farther down to Picnic Island, just south of Pine Island Sound. The 7.4-acre islet is little more than a ring of sandy beach surrounding a dense stand of mangroves, offering ample shelling.
Photography by Brian Tietz
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For Lee County boaters, the recently opened Marina at Bonita Fish Company offers a convenient launch point for exploring San Carlos Bay. Cruise toward the bay’s inlets, and you’re practically guaranteed to see dolphins, Daniel says.
When it’s time to return to the mainland, idle in Boca Grande Pass (if you’re near Cayo Costa) or Redfish Pass (if coming from Picnic Island) for a wide-open view as the sun dips into the Gulf. “It’s often calm enough somewhere that you can take the boat on the bay side or get on the leeward side of the sea breeze and watch the full cloud formations out in the Gulf,” Daniel says. “Essentially everything west of you, as far as the eye can see, is sunset.”