Castiglione della Pescaia is the chicest and most sort-after seaside destination in the Maremma. Located just outside of Grosseto, this seaside town is home to the very luxurious holiday houses of more than one Italian celebrity – Sofia Loren spotting anyone. But Castiglione della Pescaia is better known for securing the coveted title of Italy’s most beautiful beach for both 2014 and 2015. If you want to check out this award winning swimming hole, head over to Le Rocchette, which is located just outside the main town. The beach offers both a selection of paid areas with sundecks and umbrellas and a small slice of free beach where you can sunbake without parting with any euros. Back in Castiglione della Pescaia, the atmosphere is relaxed and pleasant. Stroll down the main strip for plenty of resort-wear shops and restaurants or head up to the Old Town to get some spectacular views of the surrounding coastline. Castiglione della Pescaia is naturally best visited during the summer season when all the shops are open and vibrant. Things get a little quite in winter, so don’t expect to find everything open.