Breezy Madeira is an eponymous island in the Madeira Islands, a Portuguese archipelago. The capital city of Funchal was settled in the 15th century and is a colorful collection of gardens, religious sites, and quirky tourist attractions like the thatched-roof Madeira Story Centre. Hike to the summit of Pico Ruivo and you’ll feel like you’ve climbed through the clouds. Unwind over a glass of Madeira wine, an historic fortified beverage that’s musky and subtly sweet.

Located in northwest Italy’s Lombardy region, the province of Bergamo offers more than just a day-trip diversion from the big city of Milan. This hilltop town is known for its architectural gems, including medieval and Renaissance structures that continue to amaze tourists and locals alike. Don’t miss the historic Piazza Vecchia with its 12th and 16th century buildings. And Bergamo’s Galleria dell’Accademia Carrara is an art gallery featuring works from Italian legends including Botticelli, Titian, Canaletto and Raphael, to name a few.

The festive city of San Juan is the perfect place to experience true Puerto Rican culture. Get to know its roots by exploring the vibrant neighborhood of El Viejo San Juan (Old San Juan), which consists mostly of Spanish colonial buildings. Flesh out your self-guided history lesson with a visit to El Castillo San Felipe del Morro, a 16th century citadel that’s a UNESCO World Heritage Site. Then reward yourself with a cooling dip at Luquillo or Carolina Beach, then a tasty tour of the Bacardi rum plant.

Puerto Morelos, a peaceful village on the Mayan Riviera, is a place to experience the genuine Yucatan. Puerto Morelos makes an excellent base if you’re looking for someplace quieter than glitzy hotspots like Cancun and Playa del Carmen. Government eco-reserve designations protect the reef and mangroves—and the village itself—from development. Outdoor options range from thrilling jungle and diving adventures to serene bike rides or moped explorations.