Structure Your Charter Crew for Maximum Sanity

Five people sitting around a wooden table in a casual restaurant with bamboo screens and plants in the background, smiling as they enjoy drinks and conversation. Glasses, a bottle, a red condiment bottle, a stainless-steel tumbler, a menu, and eyeglasses are on the table.

Once onboard the Spindrift, a massive 50-foot catamaran that felt like driving a luxury SUV, rituals emerged to soften the inevitable friction of life in tight quarters. These weren’t enforced chores or rigid schedules. Instead, our crew naturally synchronized into a rhythm of coordination, achieving what Kent described as perfect geometric stability.

A Grenada Sailing Adventure – Part 2: Island Rhythms & Safety Drills

Bright blue ocean in the foreground with a lush green island and a line of sailboats along the shore beneath a mostly clear sky with scattered clouds.

This trip was born from a sudden change in plans three weeks before departure: our original 41-foot monohull was replaced by a massive Moorings 5000 catamaran. A whirlwind scramble to find crew commenced, and within a week, against the odds, we assembled a five-person team ready to embrace the unknown. What follows is Part 2 …

A Grenada Sailing Adventure – Part 1: Finding Our Sea Legs

Boat bow in the foreground facing a golden sunset over calm ocean water, with a sailboat anchored mid‑distance and hilly coastline on both sides beneath dramatic, glowing clouds.

This trip was born from a sudden change in plans three weeks before departure: our original 41-foot monohull was replaced by a massive Moorings 5000 catamaran. A whirlwind scramble to find crew commenced. Within a week, against the odds, we assembled a five-person team ready to embrace the unknown. My sister Maria and her friends, …

Crossings: Lakes and Thresholds

Red Sky on the dock in New Buffalo, sun setting in the background.

Winds up to 22 knots, a reef that wasn’t there, and the quiet thrill of doing something you once thought was too much — our second crossing of Lake Michigan was equal parts challenge and growth. This is the story of how our comfort zone expanded, one gust at a time.

Embarking on Season Three with SailTime Chicago

The mainsail hoisted high on the mast of a sailboat

Kent and I are excited to return for our third sailing season with SailTime Chicago aboard Red Sky, our Jeanneau Sun Odyssey 349. We've enjoyed memorable moments, from hosting family during events like the Chicago Air and Water Show to crossing Lake Michigan. We're eager for more adventures and updates in 2025!