Porto Santo Stefano, Italy

Porto Ercole (“Port Hercules”) sits pretty in the municipality of Monte Argentario, in the Province of Grosseto, Tuscany—one of two towns that form the township, along with Porto Santo Stefano located on the opposite side of this unique peninsula. Stroll their picturesque marinas with sidewalk boutiques, cafes, and restaurants. Travel to Montalcino for the tasting of fantastic Brunello in one of the most celebrated Italian wine regions. Hike to the few castellos (castles) located on top of the three hills surrounding the port, or take in a round of golf with one of the most picturesque backdrops in the Mediterranean.