Santorini

Arrive at Santorini's small airport (or Athinios ferry port if coming from Athens) and transfer directly to Oia at the island's northern tip — the most iconic village on the most photographed island in the world. Your cave hotel is hewn directly into the caldera cliff face, and when your host opens the door to your suite and you step onto the private terrace above the caldera for the first time, all 900 feet of volcanic cliff dropping to cobalt blue water below you, the gasping is entirely involuntary. Tonight, walk Oia's narrow marble lanes for a casual dinner at one of the village's cliffside restaurants, and then walk to the ruined windmill at the village's eastern end to catch your first Santorinian sunset — a nightly ritual that draws visitors from all over the island.

Wake before sunrise and take the path from Fira south-to-north along the caldera rim — the 10km trail is one of the world's great walks, traversing the villages of Firostefani and Imerovigli with the entire caldera below you and the submerged volcano island visible in the center of the water. Hike back to Oia as the morning light turns from gold to white, arriving at your hotel's terrace for a late breakfast with the caldera below. Afternoon is for the cave hotel pool — most caldera properties have infinity pools that appear to merge with the water 900 feet below, an illusion that you never fully adjust to. In the evening, take a table at Ambrosia or Lauda for dinner — restaurants carved into the caldera cliff where the view competes seriously with the food.

A private or semi-private catamaran departs from Ammoudi Bay below Oia in the morning — you'll sail the full caldera circuit, stopping first at the crescent island of Nea Kameni (the still-active volcano) where you can hike to the sulfurous crater rim with views of the entire caldera surrounding you. Then swim in the natural hot springs at Palea Kameni, where geothermal vents warm the sea to bathwater temperature in rusty red mineral water. Continue south to the dramatic red and white cliffs of Therasia and anchor for afternoon swimming in utterly clear Aegean water. As the sun descends, the catamaran returns across the caldera with dinner served on deck — octopus, tzatziki, grilled seafood — and the Santorini skyline above you lit orange.

Santorini's beaches are unlike any in Greece — black volcanic sand at Perissa and Perivolos, dramatic red and ochre cliffs at Red Beach near Akrotiri, and the grey pebbled shore of Monolithos near the airport. Rent a quad or ATV from your hotel to explore independently — Santorini is small enough to circumnavigate in an afternoon. Red Beach is best visited early before the crowd arrives; its sheer red volcanic cliffs rising 40 meters from the water's edge are best photographed in the morning light. Have lunch at a beachside taverna in Perissa with fresh grilled octopus and a carafe of local wine, then spend the afternoon on the black sand before heading north for the evening. Tonight: stay in your hotel terrace with wine, cheese, and the caldera entirely to yourselves.

Santorini's volcanic soil produces some of the most unusual and distinctive wines in the world — the island's ancient assyrtiko grape grows in low basket-shaped vines (kouloura) trained close to the ground to survive the fierce Aegean winds, yielding a mineral, bone-dry white wine unlike anything produced anywhere else on earth. A private wine tour visits three of Santorini's top estates: Santo Wines above the caldera with its famous terrace tasting bar, Domaine Sigalas in the north for biodynamic whites, and Venetsanos Winery perched on the caldera rim at Megalochori. Between stops, the tour includes the ancient site of Akrotiri — a Minoan Bronze Age city preserved in volcanic ash for 3,500 years, Santorini's own Pompeii.

Keep today unstructured — this is Santorini's greatest gift. Sleep in, eat a long breakfast on your terrace, swim the hotel pool until noon, take a spa treatment, and read on the daybed watching the volcanic islands float in the center of the caldera. In the afternoon, take the ancient stone path down to Ammoudi Bay — Oia's tiny fishing harbor at the base of the cliff — for fresh red-grilled octopus and cold ouzo at the water's edge, then climb back up as the light begins to warm. Tonight is Oia's famous sunset: position yourselves at the ruined castle viewpoint a full hour before the sun falls, champagne and cheese ready, and prepare to share one of the world's most celebrated moments with your person.

Your last Santorinian morning: coffee and honey cake on the caldera terrace as the morning light turns the white buildings gold and the volcanic islands below slowly emerge from the morning haze. No plans, no agenda — just the particular suspended quality that Santorini induces, where time moves in a different rhythm against the backdrop of one of earth's most dramatic landscapes. Your private transfer departs for the airport at your arranged time, and as the plane banks left over the caldera on takeoff you'll see for the first time from above the full extraordinary geometry of this drowned volcano — and understand why, of all the places in the world, couples choose this one to begin a marriage.