Don't be like me—wear sneakers, or at least sturdier sandals. Due to its altitude and location closer to the coast, Sintra is often chillier than Lisbon, which was definitely the case when we visited. I recommend dressing in layers, and bringing a light jacket or sweater.

When visiting Sintra, Portugal, the most important factor is layering and footwear. Sintra has a unique microclimate that is often 5–10°C cooler and significantly mistier than nearby Lisbon. Even on a sunny summer day, you may encounter damp fog at the Pena Palace. Wear comfortable, sturdy walking shoes or sneakers with good grip, as the terrain is hilly and the centuries-old cobblestones can be incredibly slippery when wet. Avoid high heels or flimsy flip-flops. A breathable base layer, a light sweater or fleece, and a windproof/water-resistant jacket are essential. Because you will be walking up steep inclines to get between sites like the Moorish Castle and Quinta da Regaleira, moisture-wicking fabrics are highly recommended. Don't forget a small daypack to store your layers as the temperature shifts throughout the afternoon and the "Sintra mist" clears.