Private Sunset Caldera Cruise, Santorini

Your five-hour adventure on the Aegean starts with a pick-up at your hotel or a local meeting spot. Your driver will take you to the small port of Ammoudi Bay, just below Oia, where your captain and crew will welcome you aboard a private 35-foot (10.6 m) power catamaran. After a quick briefing, sip a cool drink and enjoy a fresh fruit plate as you chart a course southwest, passing the unspoiled coastline of Thirassia. Santorini's smaller, quieter neighbor is often described as "Santorini fifty years ago," and if conditions are right, you'll pause off the quaint village of Manolas for some swimming or standup paddleboarding.

Your next stop is the tiny volcanic islet of Palea Kameni, famous for its hot springs, where you can soak in the healing waters before continuing your loop around the caldera. Keep your camera close as you pass coastal beauty spots and admire the hidden caves, sheltered coves, and volcanic beaches where you can stop to snorkel or swim. As evening approaches, your captain will drop anchor off the Old Port of Fira, nestled at the foot of dramatic cliffs. Here, your crew will prepare a delicious Greek-style barbecue of souvlaki, salads, and sides accompanied by Santorini wines.

After dinner and dessert, sip a glass of wine or ouzo from the open bar and watch the sun start to dip into the Aegean as you cruise back toward Ammoudi Bay. Your captain will time the route perfectly so that you'll pass the cliffs of Oia (known as the island's best sunset-watching spot) just as the horizon is set aglow in shades of orange and red. Then it's time to cruise back into port, where you'll say your goodbyes to your captain and crew, and join your driver for a transfer back to your hotel.