While Milan is an ok city to visit (cute cathedral in the central square, high-end shopping, good espresso), I personally don’t need a whole weekend there. A short (1.5hrs) drive outside the city towards the pre-alps lies Menaggio on Lake Como. Although the village itself isn’t the most beautiful in the region, it is the starting point for a number of gorgeous hikes up in the mountains and there are plenty of hotels or hostels to choose from.
The hike up Monte Grona is absolutely beautiful, winding at the bottom through wooded areas and small clusters of farm houses, leading upwards with increasingly gorgeous views over the lake. A short scramble close to the top leads to a stunning peak with 360deg views – most notable of the pre-alps. There’s a refugio/cafe halfway up that serves cold beer, wine, coffee and a selection of cakes. The trail is easy to find and depending on fitness can take anywhere from 4-6hours. Climbing is also really popular in the area.