Sailing in the Mediterranean Episode 294 ICW 2026 PT 1

Every sailor has a vision for how a voyage is supposed to begin. Mine involved launching in Indiantown, pointing the bow toward the Bahamas, and slipping into warm trade winds and turquoise water.

Instead, 2026 had other ideas.

In this episode of Sailing in the Mediterranean and Beyond, I tell the story of the first leg of this year’s sailing adventure — a trip defined less by tropical anchorages and more by stubborn weather forecasts, cold nights, and constant recalculating.

After launching the boat in Indiantown, I waited for a weather window that never really arrived. Rather than bash east into uncomfortable conditions, I made the difficult decision to abandon the Bahamas plan entirely and head north up the Intracoastal Waterway instead.

What followed was a voyage full of the kinds of moments every cruiser knows well:

Grumpy lock keepers who seemed personally offended that we existed

Barnacles multiplying underneath the boat and slowing us down

Long cold passages where “Florida” felt a lot more like winter than paradise

The challenge of adapting plans when nature simply refuses to cooperate

Eventually, I brought the boat to Cape Marina at Cape Canaveral, where I tucked her away for two months before returning later with my family to continue the trip north toward St. Augustine.

This episode is about flexibility, frustration, and the reality that cruising rarely looks like the glossy version we imagine beforehand. Sometimes the adventure is not the one you planned — but the one you end up with anyway.

If you’ve ever had to scrap the “perfect plan” and make the best of changing conditions, this story will probably feel very familiar.