
Confessions of a Lifelong Rag Sailor
Two shirts, 20 years and a boatload of memories: How a wardrobe of wreckage became my badge of honor.

Two shirts, 20 years and a boatload of memories: How a wardrobe of wreckage became my badge of honor.

Boaters on Lake Michigan can now book slips at Navy Pier Marina by the hour, thanks to Downtown Docks’ new system.

From Mount Gay in St. Barts to daiquiris in Cuba, a sailor charts his enduring affinity for the Caribbean’s signature spirit.

Every trip yields something to add to my list—sometimes the easy way, sometimes the hard way, and always with a good story.

Owning a crewed yacht in the Caribbean can unlock tax advantages, turnkey bookings, lifestyle upgrades and long-term value.

What began as a pricey truck haul north for my battered Pearson 365 quickly spiraled into a hard lesson in reality.

Cruisers Ingrid and Robert Schnabl share their Iceland sailing adventure, from rugged fjords to puffins and whales.

Hall of Famers Steve and Doris Colgate reflect on 60 years of sailing, teaching, and Offshore Sailing School.

Chartering is more than a vacation—it’s a crash course in cruising that builds skill, confidence, and real-world perspective.

A veteran charter operator shares how one skipper’s shaky story—and a surprise cameo from Gary Jobson—set the record straight.

Cruising the Bass Strait reveals that the most rewarding sailing destinations are often about mindset—not location.

Cap’n Fatty Goodlander shares how a life afloat, three circumnavigations, and countless tales were all done on a cruiser’s budget.

Two shirts, 20 years and a boatload of memories: How a wardrobe of wreckage became my badge of honor.

Boaters on Lake Michigan can now book slips at Navy Pier Marina by the hour, thanks to Downtown Docks’ new system.

From Mount Gay in St. Barts to daiquiris in Cuba, a sailor charts his enduring affinity for the Caribbean’s signature spirit.

Every trip yields something to add to my list—sometimes the easy way, sometimes the hard way, and always with a good story.

Owning a crewed yacht in the Caribbean can unlock tax advantages, turnkey bookings, lifestyle upgrades and long-term value.

What began as a pricey truck haul north for my battered Pearson 365 quickly spiraled into a hard lesson in reality.

Cruisers Ingrid and Robert Schnabl share their Iceland sailing adventure, from rugged fjords to puffins and whales.

Hall of Famers Steve and Doris Colgate reflect on 60 years of sailing, teaching, and Offshore Sailing School.

Chartering is more than a vacation—it’s a crash course in cruising that builds skill, confidence, and real-world perspective.

A veteran charter operator shares how one skipper’s shaky story—and a surprise cameo from Gary Jobson—set the record straight.

Cruising the Bass Strait reveals that the most rewarding sailing destinations are often about mindset—not location.

Cap’n Fatty Goodlander shares how a life afloat, three circumnavigations, and countless tales were all done on a cruiser’s budget.
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