Well, it’s happening – we’re watching our Schengen days tick down. For those unfamiliar, travelers from non-EU countries, like us, are limited to 90 days in any 180-day period within the Schengen Zone, which encompasses most of Europe. And as much as we’d love to linger in every coastal village and cliffside harbor, the clock is ticking, and so is the weather forecast. There’s also this little thing called “work” that limits our vacation days, but is necessary to finance our adventures!

With strong Mistral/Maestral winds predicted later this week, our weather window to cross the Adriatic Sea (the body of water between Italy and Montenegro) is rapidly shrinking. That means: time to move. No more lingering. Just a determined push north.
This next leg was different from the rest of our sailings this summer in the Med. It was our first overnight sail of the season, and though we were both still shaking off the fatigue of the past week’s adventures, the calm conditions and vast sky beckoned. We set off along the southern Italian coast, sails trimmed and spirits steady.
Doug took the helm until about 10:30pm before passing it off. Karen, who’d barely slept the night before while we were at anchor – sleeping in the galley with an alarm clock set at regular intervals to check on things given the wind gusts in the area – took the 12-3am shift. Doug returned for the third and final shift of the night, and before long, the first blush of sunrise crept across the water.
Night sailing is a different world. You become hyper-aware of safety: lifejackets always on, tethers clipped to the boat, and strict rules – no one heads forward on deck without announcing it, and only if absolutely necessary. At sea, especially in darkness, the margin for error is slim. Spotting a person overboard can be nearly impossible – within seconds, they can vanish into the blackness without a trace. Red headlamps are used at night because they let you see without ruining your night vision – huge thanks to Evan and Amanda Macaluso for gifting us ours!



But it’s also magical. There’s a stillness that settles over the water. The rhythmic hush of waves, the occasional call over the radio (there’s some funny people out there on Italian waters!), and the canopy of stars overhead – our only audience. It’s the kind of silence that makes you think bigger thoughts. Reflect. Reset.
Karen spent part of her night watch catching up with Kaitlyn and her parents – true MVPs when it comes to keeping her awake on long solo drives and now solo turns at the helm. Though let’s be honest, a good chat only goes so far without lollies/candy, and sadly, the last of Oscar and Chelsea’s strawberry creams has officially sailed. 😢
At 8am, we pulled into the marina at Crotone, bleary-eyed but feeling victorious. The air hit us like a furnace – 105°F (40°C) – but that didn’t stop us from stretching our legs. We headed out early to explore a bit before the heat fully settled in. First stop: the Castle of Charles V, an imposing 16th-century fortress built on the bones of earlier Norman and Byzantine structures. Commissioned during the Spanish rule of southern Italy, the castle was designed to guard the coastline against Ottoman invasion. Its high stone walls now overlook peaceful gardens, but you can still feel the layers of history in the air – sieges, reinforcements, and the evolution of empires all echoing through the stone.






After a walk through the grounds and the nearby gardens (a modest 12,000 steps for the day!), we retreated to the boat, grateful for the return of AC. Karen tackled a deep clean of the starboard hull – our main sleeping quarters – and prepped Kaitlyn’s cabin for her upcoming arrival. Doug caught up on much-needed sleep.
That evening, with the sun low in the sky and the heat finally easing, we got to work in the galley – prepping several meals in anticipation of the coming stretch. Doug popped out during the cooking to grab some bottles of lemonade, claiming refreshments would be needed given rising temps, but suspiciously returned freshly shorn and empty-handed – turns out the real emergency wasn’t thirst, it was that sailor’s shag in the summer heat. Haha! The next few days will be full-on, with long sails (and likely another overnight) as we make our way to Montenegro before the weather – or our dwindling Schengen days – closes the window.
