Sailing to the Keys: Part 1 — Pensacola to Port St. Joe

Distance: 113.5 NM

Time: 25 Hours

Departure: April 9, 2025

Arrival: April 10, 2025

Hours Under Power: 7

Fish Caught: 5 Bonita

Anchorage: 29°52.149'N 85°23.460W

On April 9th, just before noon, both Quark and Footloose slipped away from the docks in Pensacola, setting sail on what promises to be a legendary trip to the Florida Keys. We motored through the familiar waters of Pensacola Bay, then out through the pass into the open Gulf, where the breeze was waiting.

Winds out of the west-southwest held steady at 15 knots through most of the first day and deep into the night, pushing us along nicely. Around midnight, the wind dropped off, and we were left floating under a blanket of stars. By 2 a.m., the wind returned—this time from the northwest—and eventually shifted to the north by late morning.

We ran the engine for about seven hours total: out of the marina, again from 22:30 to 01:30 when the wind died, and finally for the last ten miles into Port St. Joe. After 25 hours and 113.5 nautical miles, we dropped anchor in a calm, protected spot just inside the bay. Quark had earned a rest, and so had we.

Belle was more than ready to stretch her legs. I loaded her into the dinghy and headed for shore. She tore across the beach, kicking up white sand and wagging her tail like we’d never left land. After some time exploring, we started the ride back toward Quark, with a quick stop at Footloose to say hello.

While I was aboard Footloose, I noticed movement out of the corner of my eye—my dinghy had come untied and was making a slow getaway. Without hesitation, I jumped in and swam the 50 yards or so to retrieve it. First dinghy rescue of the trip: mission accomplished. No harm done, just a good reminder to double-check the knots.

The following day, we explored more of the beach and tried our luck fishing from the boats—though the fish weren’t biting like the day before. While casting lines and enjoying the calm, we suddenly realized Footloose was on the move. Her anchor had come unset, and she was drifting at nearly two knots. We sprang into action for the first boat rescue of the journey and got her safely re-anchored before any trouble could start.

The bay was alive with dolphins, wind shifts, and that buzzing energy that always seems to come just before a front moves through. We’re now anchored and watching the weather as a cold front approaches. Once it passes, we’ll make our next move: a long, open-water leg straight across the Gulf toward the Tampa area—roughly 180 nautical miles.

The journey’s just beginning, but already the Gulf is reminding us why we love this life. Stay tuned—next up: deep water and open horizons.