Boating adventures in Southwest Florida

Gordon Pass

Naples Bay to the Gulf

The front door. Markers, a little current, and then the Gulf. If a boat cannot do this run comfortably, Capt. Red will not sell it as a Naples boat.

Keewaydin Island

South of Gordon Pass

A barrier island that still looks like Florida. Anchor off the beach, walk for shells, and leave before the afternoon storm builds over the mainland.

Ten Thousand Islands

South of Naples, into the maze

Mangrove after mangrove, tea-colored creeks, and a chart you should actually look at. This is why bay boats exist in Southwest Florida.

Naples Bay & Port Royal

In town

Waterfront houses, still water, and a cruise that does not require a cooler full of fuel. The listing-photo run — and a good first sea trial.

Doctors Pass

Vanderbilt Beach

North Naples inlet. Shorter, tighter, and a weeknight sunset that does not ask you to run all the way to Gordon. Capt. Red films here often.

Rookery Bay

Estuary south of town

Birds before engines. Glassy water, a mudflat, and a reminder that Naples is still an estuary town if you leave the dock early enough.

Marco Island

South by the Gulf

A crescent beach, a different skyline, and a lunch stop that makes the fuel burn feel planned. Good shake-down run for a new-to-you hull.

Backwater sandbars

Inside the islands

Ankle-deep water, a cooler, and the boat that got the family on the water in the first place. Capt. Red will tell you where — and how not to be that boat.