Boating in Southwest Florida: The Keys, the Bahamas, and the Broker I Trust

I write a lot on this site about living in Naples on land — fees, taxes, insurance, which community fits which buyer. But ask anyone who’s been here a while what they actually love about Southwest Florida, and a surprising number of them will point at the water.

I get it. Not long ago my fiancée and I did a private sunset cruise off Marco Island, and it reset my whole sense of the place. There’s a version of this region you only really understand from a few miles offshore — and once you’ve felt it, the idea of having your own boat stops sounding crazy.

So this one’s about the water: why boating here is as good as it gets, and the one person I send everyone to when they’re ready to actually buy or sell a boat.

Why boating in Southwest Florida is hard to beat

Most places, getting on the water is an event you plan around. Here it’s just Tuesday.

Step out of Naples or Marco and the Gulf of Mexico is right there — flat, warm, and forgiving for most of the year. Point south and you’ve got the Ten Thousand Islands, a maze of mangrove keys and empty sandbars where the dolphins basically escort you out. The Florida Keys and the Dry Tortugas are real, satisfying runs for a long weekend. And the Bahamas — those impossibly blue flats — are a crossing from Florida’s east coast that a lot of local owners make every season.

In between, the everyday stuff is the real luxury:

• Fishing that ranges from backwater snook and redfish to offshore grouper, snapper, and pelagics.
• Diving and snorkeling over reefs, ledges, and wrecks once you’re out past the beach.
• Sandbar afternoons where half of Southwest Florida seems to anchor up, wade in waist-deep water, and let the kids run.
• Sunset cruises and dolphin watching that never, ever get old — I’ve done it a dozen times and still grab my phone every time a pod rolls past the bow.

You don’t need a 70-footer for any of it. But spend enough evenings out there and the math changes — and that’s where most people get a little lost.

Buying a boat is a lot like buying a house

This is the part I understand in my bones, because it’s exactly what I do with real estate.

A boat is a big purchase with a hundred ways to go sideways. There’s the survey (a boat’s version of a home inspection), the sea trial, the documentation and title work, the financing and insurance, and — for the bigger ones — haul-out, transport, and storage. Buy the wrong hull or miss a problem in the survey and it’s an expensive, soggy lesson. Get it right and you’ve bought yourself years of the best days you’ll have down here.

In other words: you want someone in your corner who actually knows boats, knows these waters, and treats the messy details as their job instead of yours.

The guy I trust: Ted Gates at Yachts360

I’ve personally bought and sold a boat with Ted Gates, and he’s the first call I make for anyone getting into — or out of — a boat in our area.

Here’s why. Ted’s a genuinely good, trustworthy guy who knows boats cold, and he attends to every detail beyond what most brokers bother with. The survey hiccup, the transport logistics, the bit of paperwork nobody warned you about — Ted handles it, so problem-solving stays on his desk and you stay focused on where you’re going to anchor first. Both of my deals with him were smooth, and that is not an accident; it’s how he works.

It’s also in his blood. Ted grew up in Lake City, Minnesota, on Lake Pepin — a wide stretch of the Mississippi that calls itself the birthplace of waterskiing — and he’s been around boats since he could walk. He started a yacht management and detailing business in 2000, moved into brokerage in 2006, and went all-in in Fort Myers by 2010, captaining yacht charters across Florida, the Bahamas, and the Caribbean. That’s decades of actually running boats, not just selling them.

Today he’s a broker at Yachts360 out of Fort Myers, working mostly in the 40- to 100-foot range across Southwest and Southeast Florida — including the local boating communities like Gulf Harbour Yacht & Country Club and Town & River. If you’ve got something to sell, he knows what it’s worth and how to move it. If you’re buying, he’ll talk you out of the wrong boat as fast as he’ll find you the right one.

Reach Ted: Ted Gates, Yachts360 — Fort Myers, FL · (239) 849-5357 · Ted@Yachts360.com · yachts360.com/ted-gates. (Full disclosure: Ted’s a friend, and I’ve personally bought and sold a boat through him — that’s exactly why he’s the one I point people to.)

Where the boat people actually live

Here’s where my world and Ted’s overlap. The best boating life starts at home — specifically, a home with Gulf access and a dock of your own, so the boat’s waiting out back instead of an hour away.

Around Fort Myers, that’s communities like Gulf Harbour Yacht & Country Club — a gated waterfront community on the Caloosahatchee with a deep-water marina that handles yachts up to 100 feet — and Town & River, where wide, Gulf-access canals run right behind the houses. Closer to Naples, the Gulf-access pockets (think Royal Harbor, the Isles of Capri, and parts of Marco Island) carry a real premium for exactly this reason: deep water and a private dock are the whole game.

Matching the right waterfront home to the boat you want is genuinely one of my favorite parts of this job. So here’s the dream team: Ted gets you the right boat, and I’ll help you find the home to keep it behind.

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Thinking about a Gulf-access home with a dock — or just trading the snow for evenings on the water? Reach out and I’ll give you honest, local answers, or start with my free Moving to Naples guide. And if you haven’t yet, the Marco Island sunset cruise is the best way to test-drive the whole idea.