Getting Comfortable Being Uncomfortable | EP130 HD 1080p

After island hopping our way down the Bahamian chain, we’ve reached the edge of the islands… and the beginning of something bigger. In this episode, our family of seven rounds the southern tip of Cuba and enters the powerful waters of the Windward Passage, the stretch of ocean between Cuba and Haiti. Here, currents clash. Swell wraps around the land. Winds oppose the sea. It’s a place where different bodies of water collide and become one — confused, choppy, and unpredictable. We face rough seas, shifting currents, and the kind of conditions that demand teamwork from every single one of us. Offshore sailing with five kids means everyone steps up. Watches are stood. Sails are adjusted. Meals are made underway. And together, we push south. This marks a major turning point in our journey — leaving the Bahamas behind and committing to the open Caribbean as we work our way toward Panama. Passagemaking isn’t always calm turquoise anchorages. Sometimes it’s gray skies, stacked waves, and trusting your boat — and each other. ⚓ Next stop: continuing south toward Panama. Subscribe and follow along as we sail one of the Caribbean’s most dynamic stretches of water as a full-time liveaboard family.