Santorini is one of the world’s most popular islands, known best for its dramatic scenery, whitewashed villages and fiery volcanic activity. Here adventure bubbles above the Aegean Sea in the most bold and breathtaking ways. A cable car takes you to the capital of Fira, a bustling cliff-top town awash with old cathedrals, enthralling museum collections and cozy tavernas. Venture to the coast for a swim in the deep blue waters that lap red and black pebbled beaches. And peel back layers of lava and history among excavated Akrotiri. Whether it’s by bicycle, ATV or on your own two feet, exploring this Cyclades isle never fails to impress.

One of Italy’s oldest port cities, Livorno is a small but historically rich city. Check out the red-hued Fortezza Nuova, a 16th-century fortress, and the surrounding area known as Nuova Venezia (“New Venice”), and take a mini-sailboat ride through its charming canals. Cruise to Livorno and use the city as your jumping-off point to the beauty of Tuscany: Take the 30-minute drive to Pisa and snap a quintessential picture with the city’s famous leaning tower. Or head to Florence — about an hour from Livorno by car or train — where you can see the unmistakable Duomo (“dome”) and the Byzantine-style frescoes of Saint John’s Baptistery.