San Juan, Puerto Rico’s capital, is a city where cobblestone streets lead to centuries-old forts and pastel-colored buildings overlook the Atlantic. The district of Old San Juan is a UNESCO World Heritage Site, known for its Spanish colonial architecture and thick stone walls that once defended the city from pirates and naval attacks. The city hosts regular events such as La Campechada, which celebrates Puerto Rican art and literature with live performances and open-air exhibits.

Alberobello in southern Italy’s Puglia region captures the imagination with its distinctive trulli houses. These structures were built using a dry-stone technique passed down over centuries, without mortar or cement, and their unique form comes from layer upon layer of limestone nestled from nearby fields. Alberobello’s trulli are so remarkable that in 1996 the historic center was inscribed as a UNESCO World Heritage Site, where more than 1,600 of these buildings still stand.

Adara is a small, remote village on Atauro Island in Timor-Leste, known for its quiet charm and deep connection to the sea. Nestled between steep mountain slopes and the turquoise waters of the Wetar Strait, the community lives largely from fishing and small-scale agriculture.

Tortola, the largest island in the British Virgin Islands, beckons travelers with its idyllic beaches and vibrant culture. Known for its stunning natural beauty, Tortola offers crystal-clear waters, lush landscapes, and a range of outdoor activities. Cane Garden Bay, one of the island’s most famous beaches, is renowned for its powdery white sand and turquoise waters.

From grand castles to resplendent cathedrals, Tallinn’s Old Town neighborhood, a UNESCO World Heritage Site, is the perfect place to begin exploring. Enter through Viru Väravad, or Viru Gate, the former fortress whose remaining two towers beckon you into the heart of the city.