To truly appreciate the "dragon-shaped" island of São Jorge in the Azores, you should ideally budget 3 to 4 full days. This island is famous for its unique fajãs—small coastal plains at the base of steep cliffs created by lava flows or landslides. A 4-day itinerary allows you to hike the iconic trail from Serra do Topo down to Fajã da Caldeira de Santo Cristo (where you can taste the island's unique clams) and continue to Fajã dos Cubres. You will also have time to visit the western tip at Ponta dos Rosais and explore the town of Velas, known for its natural swimming pools. If you are a fan of slow travel or "cheese tourism," adding a 5th day is recommended to visit the Union of Dairy Cooperatives and sample the famous aged São Jorge cheese (DOP). Because the island’s weather can be unpredictable and the roads are winding and steep, having a flexible 4-day window ensures you won't miss the dramatic "sleeping dragon" views due to fog or rain.