Caitlin Stepan

My mother had wanted to return to Alaska for seventy years. Her parents were stationed there in the 1950s, and the airstream they pulled up the Alcan Highway became family lore she never quite figured out how to act on. She’d never been on a cruise. I never thought she would. What finally brought her back was a kind of cruise she didn’t know existed—54 passengers on an 84-guest ship, no port stops once we left Juneau, and a small vessel built for wilderness rather than entertainment. Eight days later, we disembarked as converts. The closest thing I can compare it to wasn’t a cruise at all. It was summer camp with glaciers.

Porto surprised me in every way—the light, the food, the fado, the way the city stacks itself up from the Douro like a painting you keep finding new details in. Torel Avantgarde matched that energy perfectly. A boutique hotel where every room is named after a different artist or visionary, it’s perched above the river with views that stopped me mid-sentence more than once. As someone with an art history background, walking through this property felt less like a hotel tour and more like a private collection.

I came to Madeira for my 41st birthday expecting a quiet island getaway. What I found was one of the most unexpectedly wild landscapes I’ve set foot on—volcanic cliffs that drop straight into the Atlantic, hiking trails that climb above the clouds, ancient laurel forests wrapped in fog, and black stone beaches where the sound of the waves could put you to sleep for days. The pace here rewards slowing down. Hike in the morning, spa in the afternoon, rooftop wine at sunset. The beauty here isn’t just in the landscape—it’s in the rhythm of the day.