Port Royal, Crayton Cove and Gordon Pass: the back story

About Port Royal, Crayton Cove and Gordon Pass: the back story

By the ULTIMATE Naples Editorial Team

The southern tip of Naples, below Old Naples, is where the city meets the sea on two sides: the old City Dock at Crayton Cove on the bay, and the canals of Port Royal running down to Gordon Pass.

The old waterfront

Crayton Cove, on Naples Bay at the end of 12th Avenue South, is one of the oldest corners of the city. In the early days, when Naples could only be reached by water, the bay side was a working waterfront of boats, fish houses and docks. The City Dock is still here, and so are The Dock at Crayton Cove restaurant and the Cove Inn, with boat tours and the Sweet Liberty catamaran leaving from the waterfront.

The streets between the cove and the Gulf form part of the Naples Historic District, listed on the National Register of Historic Places in 1987, with old frame cottages among the newer houses.

In 1938 a Chicago radio-advertising pioneer chose quiet Naples over Palm Beach and began buying land at the southern end of town.

Port Royal

In 1938 John Glenn Sample, a Chicago pioneer of radio advertising, came to Naples. He had read about the glamour of Palm Beach but preferred the relaxed Gulf coast, and he began buying property at the southern end of town. In the decades after the war that land became Port Royal, a residential district of canals and waterfront estates between Naples Bay and the Gulf, ending at Gordon Pass.

Port Royal is private and residential, with no shops or attractions, and the best way for a visitor to see it is from the water.

Gordon Pass and beyond

Gordon Pass links Naples Bay to the Gulf. Dolphins often feed in the pass, and across it lies Keewaydin Island, the undeveloped barrier island that Naples chose to protect. Hurricane Ian’s storm surge in 2022 flooded many low-lying streets in this part of the city, and rebuilding continues under stricter flood rules.

Our advice: take a sunset cruise or a sail from the bay out towards Gordon Pass, then have dinner at Crayton Cove and walk back through the historic district to the pier.

Opening hours, prices and seasonal openings change, so please check with Port Royal, Crayton Cove and Gordon Pass: the back story before you go.