Santorini on $60, $160 or $500 a day

Arrive by ferry or plane. Check in at a Fira or Perissa budget accommodation. Museum of Prehistoric Thera (€6 - essential for understanding the island). Fira caldera walk south to Firostefani (30 min, free views).

Walk the caldera path north: Fira to Imerovigli (1h, free - the finest walk on the island; the Skaros Rock promontory at the end). Lunch at a Fira backstreet restaurant (€12-15 for a Greek salad, tzatziki, and grilled fish).

Oia sunset: take the bus to Oia (€2) and arrive at the Kastro viewpoint 90 minutes before sunset for a position. The sunset is genuinely extraordinary - the sun dropping behind the Thirasia island with the caldera and the flotilla of tourist boats below. Walk back to the bus stop (20 min) for the return bus to Fira.

Bus to Akrotiri (€2). The archaeological site (€12 - 2 hours minimum). The excavation is covered by a modern roof and fully walkable: the three-storey houses, the clay pipes, the door frames. Then walk to the Red Beach (10 min, free - the red volcanic cliffs and the dark beach, extraordinary).

Bus to Perissa (€2). The black sand beach for the afternoon. The tavernas on the beach serve fresh fish at the most reasonable prices on the island (grilled sea bream and a salad, €20-25pp). The water is clear and the volcanic mountain backdrop is dramatic.

Return to Fira by bus (€2). Dinner at a Fira backstreet restaurant (the caldera-view places charge a view premium of 50-100%; one street back the same food costs half as much). Wine: a glass of Assyrtiko (the indigenous Santorini white, volcanic and mineral, €6-8/glass).

Early morning in Oia before the tourists arrive (take the 8am bus from Fira): the blue-domed churches, the caldera path, and the village streets before the crowds. Breakfast at a Oia bakery (€5 for coffee and tiropita). The Kastro in morning light is the finest version of Oia.

Return to Pyrgos village for the afternoon (free walk through the medieval streets). Venetsanos or Santo Wines tasting (€15-25 for 3 wines). The caldera view from the winery terrace is unobstructed.

Farewell dinner in Megalochori: a traditional taverna for moussaka, dakos (Cretan barley rusk with tomatoes), and a carafe of local wine (€18-25pp). The most affordable genuine Greek meal on the island.

Rent an ATV or car (€40-60/day) for the day. Museum of Prehistoric Thera (€6) in the morning. Imerovigli: the Skaros Rock walk (free, the finest caldera viewpoint). Breakfast at the Imerovigli cafe with the caldera below.

Drive to Akrotiri (€12) and the Red Beach. Then the south coast drive: the White Beach water taxi (€8 each way from Red Beach), the lighthouse at Akrotiri (free, dramatic cliff edge), and a swim at a quiet southern cove.

Oia dinner: a caldera-view restaurant for fresh lobster pasta or grilled octopus (€50-70pp for a full meal with wine - expensive but the setting is extraordinary). The sunset from the restaurant terrace.

Half-day catamaran sail around the caldera (€100-120pp including lunch, wine, snorkeling stops, and a swim at the hot springs): the caldera from the water reveals its full volcanic scale - the 300m cliffs, the twin volcanic islands of Nea Kameni and Palea Kameni. Swim at the hot springs on Nea Kameni (the water is warm and mineral-rich).

Return by noon. Afternoon wine tour: Venetsanos (caldera-view), Santo Wines (the most accessible tasting), and Domaine Sigalas in Oia (the finest Assyrtiko producer, €25 for the tasting). Three wineries in an afternoon with the rental car.

Dinner at Pyrgos: Kasteli Restaurant (€45-60pp for the finest traditional Greek cuisine in the village, on the battlements of the Pyrgos fortress with the island spread below). Cheaper and better than the caldera-view restaurants.

Ferry to Thirassia (€10-15 return, 30 min - the second island of the caldera, with 250 inhabitants and almost no tourist infrastructure). Manolas village (the main settlement, 250 steps up from the tiny port) has a single taverna that serves the catch of the day. Completely unhurried.

Swim in the caldera from the Thirassia rocks. Return to Santorini by afternoon. The afternoon in Oia: the caldera-edge walk north of the main village where the crowds thin.

Farewell dinner at Koukoumavlos in Fira (1 Michelin star, €90-120pp for the tasting menu - the finest contemporary Greek cuisine on the island; the caldera-edge terrace; reserve 2 weeks ahead).

Stay in an Oia infinity-pool villa (the Katikies, Mystique, or Grace Santorini - the archetypal caldera-view luxury, from €800/night; the private pool above the caldera is the defining Santorini luxury experience). Private guided tour of the Museum of Prehistoric Thera with an archaeologist.

Lunch at Fanari (the finest caldera-view restaurant in Fira, €80-100pp). Private wine tasting at Domaine Sigalas with the winemaker (the finest Assyrtiko producer on the island - a vertical tasting of 5 vintages, arranged through the hotel, €150pp).

Sunset dinner at Amoudi Bay (the caldera-floor fishing village below Oia, accessible by path or water taxi): Dimitris Ammoudi (€60-80pp for the freshest seafood in Santorini, lobster from the tank, the sunset over the volcanic islands). The path down from Oia takes 10 minutes; the sunset from the water is different from and arguably better than from the village above.

Private early-access tour of the Akrotiri excavation before public opening: an archaeologist guide who has worked on the site explains what each room was used for, why the city was abandoned before the eruption, and why no bodies have been found (unlike Pompeii - the Minoans evacuated). The site in silence before 8am is extraordinary.

Private yacht charter (from €600 for 4 hours): the caldera, the volcanic islands, a swim at the hot springs, and lunch on deck. Alternatively: a helicopter transfer to Mykonos for lunch and back (€400pp return, 15 min each way).

Dinner at Selene restaurant (the finest contemporary Greek cuisine in Santorini, €130-160pp for the full tasting menu; the garden setting in Pyrgos away from the caldera crowds; the wine list is the finest on the island). Book 3 weeks ahead.

Morning at the villa pool. Spa at the Grace Santorini (the finest spa on the island: the volcanic stone massage uses Santorini pumice, €180-250 for 90 min). A private yoga session on the caldera-edge terrace at dawn.

Final Oia walk without the crowds (the village at noon in shoulder season is manageable). Shopping: the Oia galleries have genuine Santorini contemporary art, handmade ceramics, and jewelry. The Atlantis Books (the tiny independent bookshop famous among literary tourists) on the main lane.

Farewell dinner at the hotel restaurant with a private terrace reservation: a Greek meze dinner as the sun goes down over the caldera - tarama, dolmades, fresh grilled octopus, lamb chops, and the island's Assyrtiko. One final bottle of Domaine Sigalas.