Lauren Lockett

You're familiar with, and may have already visited, Lisbon, Porto, or even the Algarve—but the Azores are a frequently overlooked destination that deserves its own trip. The largest island in Portugal's Azorean archipelago, São Miguel is small enough to never feel intimidating but full of adventure, from hiking to farm-to-table dining to whale watching and canyoning. Within a single drive, you can experience four seasons, as well as volcanic calderas, blue-green crater lakes, and a landscape that shifts from steaming geothermal fields to pastoral valleys full of cows. In keeping with the spirit of the Azores, I stayed at an eco-beachfront property that felt luxurious without being fussy. Just a nonstop flight away from major Northeast cities like New York and Boston, São Miguel deserves a top spot on your travel list.

Round Hill is the epitome of "old-school Caribbean glamour" seamlessly blended with modern luxury. Set on a lush 100-acre peninsula that was once a pineapple and coconut plantation, the property feels like a private enclave rather than a standard resort. The Ralph Lauren-designed interiors provide a timeless aesthetic that honors the estate’s storied history. The lack of in-room TVs doesn't feel like a missing amenity; instead, it encouraged me to actually unplug and soak in the resort’s quiet, elegant atmosphere.

After spending three weeks in Mexico City this winter, I was completely in awe of everything the city has to offer—from the high-low food scene to the incredible greenery and warmth of the people. With over 22 million people and the most museums per capita in the world, the sheer scale of culture is impossible to fully capture in three weeks, let alone a long weekend. I’ve distilled my favorite highlights into this four-day edit to give you a taste of the magic that already has me planning my next trip back.

Nantucket’s cobblestone streets, historic charm, and natural beauty provide me with an immediate sense of peace. There’s a carefree feeling on the island that makes it easy to unplug, which is why I’ve been going every summer for the past 15 years (with the same group of friends for the most part). The highlights are the diverse beach options and the restaurant scene, which ranges from lively energy downtown to the relaxed atmosphere of Sconset and Wauwinet. It’s the ultimate place to slow down and connect with my favorite people!