Start your trip in Ponta Delgada, the largest city in Azores and capital of Sao Miguel. Visit the Igreja de São José, a beautiful 18th-century church in the city centre, then take a stroll on the Avenida Infante Dom Henrique promenade and enjoy the ocean view. End the day with a dinner at A Tasca Restaurant, serving modern Azorean cuisine with fresh, local ingredients.
Take a morning flight to Pico Island and visit the Museu do Vinho, showcasing the traditional vineyards and wine production of the island. Head to Lajes do Pico, a charming coastal village, and have lunch at DoisCinco Restaurante & Vinhos, offering fresh seafood and local wines. In the afternoon, visit Museu do Cais do Pico, a whaling museum located in an old whaling factory.
Explore the UNESCO World Heritage city of Angra do Heroismo, located on Terceira Island. Visit the impressive Sé Cathedral, dating back to the 16th century, and the Museu de Angra do Heroismo, showcasing the history and culture of the city. Take a break at Café da Praça, a historic coffeehouse in the city centre. In the evening, have dinner at O Pipas Restaurante, a traditional Azorean restaurant serving local specialities.
Discover the cosmopolitan city of Horta, located on Faial Island. Start the day with a visit to Peter Café Sport, a legendary bar and meeting place for sailors from around the world. Take a walk in the scenic Parque da Alagoa, a park with a lagoon and a botanical garden. Have lunch at Convés Restaurante, a seafood restaurant overlooking the marina. In the afternoon, visit the Whaling Museum, located in a former whaling factory, and learn about the history of whaling in the Azores.
Explore the enchanting town of Furnas, located in the eastern part of Sao Miguel Island. Start the day with a visit to the Terra Nostra Park, a botanical garden with a natural hot spring swimming pool. Have lunch at Tony's Restaurant, serving traditional Azorean stew and other local dishes. Take a walk in the Caldeiras das Furnas, where you can see geysers and hot springs in action. End the day with a relaxing bath at Poça da Dona Beija, a natural hot spring complex.
If you have more time, consider adding a day trip to the volcanic island of Graciosa, taking a whale-watching tour from Horta, or hiking in the Sete Cidades crater on Sao Miguel Island. If you have less time, you could skip Pico or Faial Island, or combine Days 1 and 5 to spend more time in Furnas.