Trading the open road for the open ocean is no small feat, but that is exactly what Chesca and Ben—formerly known to their YouTube audience as Overlanding Sophia—have decided to tackle. After five years of navigating the world and the Americas in their van, they recently purchased a yacht to call home. As a lifelong yacht skipper and instructor who has followed their van adventures for years, I reached out to offer my expertise. Fast forward to today, and I found myself stepping aboard their newly renovated floating home in Port Solent, ready to help them master the ropes over a short, hands-on sailing trip.
Our journey began with a round of morning coffees and a briefing on the day’s plan, which importantly included outfitting their dogs in brand-new life jackets. Once everyone was kitted up and the boat was prepped, we slipped our moorings. Navigating out through the busy mouth of Portsmouth Harbor past Portchester Castle required a steady hand, with dozens of small boats sharing the waterway, but we quickly found our rhythm. The dogs, getting their first real taste of freedom on the water, settled in beautifully and barely seemed to notice the shifting deck beneath their paws.
Out on the open water, we hoisted the sails to take advantage of the light winds and easy seas. The conditions were absolutely perfect for learning. Ben even took the opportunity to launch their drone to capture some spectacular aerial footage of the yacht under sail. Flying a drone from a moving vessel is one thing, but catching it by hand as it hovers precariously over the deck is an entirely different level of stress. Thankfully, Ben was brave enough to scoop it safely out of the air, keeping all our fingertips intact and securing some brilliant footage in the process.
By late afternoon, we smoothly navigated into Cowes Yacht Haven for the night. The marina was surprisingly peaceful after a busy weekend, giving us a perfectly relaxed atmosphere to unwind. While Chesca prepared some snacks and Ben took the dogs to explore the pontoons, I spent time reviewing camera footage on the aft deck, watching a stunning tall ship pull into the harbor. Later, we wandered into Cowes for some hearty pub grub at the Anchor, wrapping up a highly successful day on the water.
The next morning greeted us with slightly stronger winds and a deck damp from the overnight dew. After a much-needed decaf coffee thoughtfully prepared by the crew, we shifted our focus to the more technical side of boating. We spent the morning running through essential power maneuvers, practicing confined space turns and perfecting the intricate art of power parking. Chesca and Ben are facing a massive, steep learning curve, but their progress has been genuinely incredible to witness.
With our parking practice complete, we raised the sails one last time and enjoyed a brilliant run back through the lock at Port Solent. Ending the trip with a final cup of coffee and a biscuit back at the marina, it was clear that these two are already much better sailors than they give themselves credit for. Sharing my knowledge with such eager, capable friends was an absolute privilege, and I cannot wait to see where the wind takes them next.
