A nonstop Azores Airlines flight delivers you from Boston to São Miguel in under five hours. From the airport, it’s a quick cab ride to Ponta Delgada’s city center.
Though all rooms at the Azor Hotel in Ponta Delgada have marina views, the real wow factor comes courtesy of the rooftop Whale Watching Bar (so named for the waters’ many cetaceans). Even splashier, the White Exclusive Suites and Villas boast a seaside infinity pool and whitewashed outdoor spaces—a Santorini vibe 6 miles from downtown.
Stop by the decidedly old-school café/gourmet shop Louvre Michaelanese for a São Miguel–grown Chà Gorreana tea en route to the bustling Mercado da Graça, where seafood of all stripes and locally made sausages tempt passersby. Don’t miss the pungent O Rei dos Queijos (“The King of Cheeses”) stand—locals get sentimental just talking about the Azores’ most famous wheel, the sharp Queijo São Jorge. Once you’ve had your fill, hop in a rental car and head 15 miles west to Sete Cidades: Home to the vibrant twin lakes Lagoa Azul and Lagoa Verde, this 3-mile-wide caldera, or volcanic crater, is ringed by scenic walking trails ideal for a sunny fall day. Another hiking hot spot is Lagoa do Fogo, a dramatic crater lake located in the center of the island.
Nighttime is the right time to stroll Ponta Delgada’s cobblestone streets: That’s when you’ll find the open squares humming and architectural gems such as the Gothic Igreja Matriz de São Sebastião and the three-arch Portas da Cidade (“gates of the city”) bathed in light. Unwind with wine at Reserva Bar, an unassuming tapas spot where you can pair bottles from the Portuguese mainland with plates of tinned fish, roasted chestnuts, and more. The lively A Tasca, meanwhile, is the perfect place to sample an Azorean delicacy: plump grilled limpets (aquatic snails) with garlic and butter. Cap off the evening with live jazz or fado (Portuguese folk music) at Lava Jazz before heading off to dreamland with visions of calderas and codfish dancing in your head.
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