By Kris Hundley

To make the roughly 90-mile boat trip from Naples to Key West, you head south in the Gulf of Mexico and sail all night.

If you stay the course – and you’re not buffeted by storms or plagued with mechanical problems – you’re there by morning.

Our boat trip from Naples to Key West begin at about 2 p.m., past the mansions on the Gordon River. By dusk, we were somewhere far off Everglades City in about 30 feet of water. Not another vessel in sight. And no moon, only a cast net of stars to lead our way.

In the inky blackness, we were sailing blind, dependent on our GPS and the route traced in magenta to the Key West bell.  We suited up with lifejackets and harnesses and set up three-hour watches. Two on deck, one down below. The wind was on our nose, the weather clear, the engine strong.

With no point of reference – no shoreline or markers or anything but darkness – it was easy to wander off course, meandering through the night. So we let the auto-pilot take over while sailing from Naples to Key West and concentrated on watching for hazards ahead. The boat’s running lights helped pick out a line of fish pots in our path. Tangle the lines from one of those in your prop and someone has to go over the side with a knife.  Each time one of the white bobbers marking a pot washed by in our wake it was like a little blessing.

Sometime after midnight, faint white lights from a fishing boat appeared in the distance off our starboard bow. They remained there for hours, neither fading nor coming closer, just trolling.

By 4 a.m., we could see a pale glow on the southern horizon: the lights of Key West.

As the sky was turning from black to gray to pink, mangrove islands materialized out of the dark. We could make out the flashing light on green bell #1, marking the entrance to the Key West approach.  Keeping Tank Island to port, we sailed past Mallory Square, past the Coast Guard station and into Key West’s harbor.

Dodging wide-beamed catamarans filled with tourists and big-dollar, high-powered sport fishing boats, we headed to a marina in the heart of town.

Docked by 10, we had eaten by 11, showered by 1 and seen enough of Key West to put us to sleep by 3.

Part 7
Sails Full of Florida: Moored in Marathon
Naples to Key West

Colors of the sun light the horizon.

- Kris Hundley for VISIT FLORIDA

boat trip from naples to key west

Stopping near A&B Marina.

- Kris Hundley for VISIT FLORIDA