At just over 430 metres high, Pico do Castelo feels a little different from the island’s other viewpoints. It’s greener, quieter, and layered with history. The summit is dotted with conifers, a rare sight on an otherwise dry island. A cannon and the remains of a 16th-century fortress, built to protect the population from pirate attacks, mark its past as a defensive lookout. You can reach the top either as part of the PR2 hiking trail or by tackling the short, steep climb from Vereda do Pico do Facho, which takes about 15–20 minutes on foot. The payoff is a wide view over much of Porto Santo, and on clear days, even Madeira on the horizon.

Be amazed by the collection of gold, gems, silver and so on. The Grünes Gewölbe even has the biggest green diamond in the entire world on display. The Historic Green Vault showcases authentically restored rooms filled with treasures and the New Green Vault displays special exhibits.

From this spot, with a little stretching and bending, you can see the tops of all five of Old Town's spires. Today, the square remains the social heart of the city, a venue for open-air concerts, handicraft fairs and Medieval markets. Each winter, it's home to the town's Christmas tree — a tradition that stretches back to 1441 — and a buzzing Christmas Market. In spring it hosts the Old Town Days festival, a modern version of a medieval carnival, where traditions from the Middle Ages are kept alive.

Rethymno is a picturesque town half-way between Chania and Heraklion. If you want to go on a day trip, this one is a perfect destination. Here you can enjoy the beach, get lost in the Old Town or have a glass of wine in the scenic harbour.