Sailing Good, Bad, and Uglyvideo

Lived on a Boat for 4yrs BUT can SHE SAIL IT Sailing GBU

October 10, 2021 · 29 min · 158K views · Puerto Rico

What this video covers

Kristen performs a solo sail of the couple's engine-less, 30-foot-class sailboat, Good, Bad, and Ugly, in the light winds off Vieques.3:44 Without an engine, windlass, or autopilot, she manages the entire process: checking weather via the Windy app, scouting for hazards on Navionics, setting the staysail and mainsail, and anchoring in Sun Bay.6:07 During the transit, she encounters minor technical challenges, including a tangled line on a winch and a near-miss with the shoreline while managing sail handling.17:47 She notes that the physical labor of hoisting sails and operating the manual windlass—which the crew calls Helga—is the most demanding aspect of the operation.27:48 The exercise serves as a test of her ability to handle the vessel independently in case of an emergency.27:25 The experience confirms that while manual sailing is manageable in light conditions, the lack of mechanical assistance requires constant attention to line management and physical stamina.

Watch on YouTube

More from Sailing Good, Bad, and Ugly

SOMETHING BIG IS COMING TOGETHER!Oct 2026Everything Just Got a Lot HarderOct 2026BIG SPLURGE IS IT WORTH IT?!Sep 2026Infested, Moldy Disaster to Dream Transformation Start to FinishSep 2026

From Sailing Good, Bad, and Ugly — see the channel’s boat, crew, and every analyzed video.

The Sailing Directory Newsletter

One email with the fleet's best finds — the moments, boats, and stories worth your watch time. Enter your own address to get your own copy.

Report an issue