Encircling a sea-filled caldera, spectacular Santorini scores top points for dramatic beauty. Bleached white villas tumble down volcanic cliffs. Blue-domed churches rise against the sparkling sea, and bright sprays of bougainvillea add to the eye-popping canvas of color. Perched atop the black lava cliffs, the settlements of Firá and Oia are the island’s most picturesque, and pricey, destinations, and Oia ranks among the most photographed locations in the world. Other highlights of the island include Akrotíri Archaeological Site, Ancient Thira, the black sand beach of Perissa, and of course, the sublime sunsets. Sailing into this stunning caldera surrounded by soaring sea cliffs makes an unforgettable first impression.