Where to Book Your Stay in Santorini for a Local Experience

The Andronikos Santorini boutique hotel sits on the highest point of Imerovigli, a dizzyingly appointed village overlooking Santorini’s volcanic caldera. Rooms and suites are curved, keeping with Cycladic design, and come with wraparound views. Start and end your day at the rooftop Skybar, where a fresh Greek breakfast of fruits and yoghurt is served every morning and where cocktails enhance the legendary sunset. The half-hour walk to Thira, the capital, is along a cliffside path with unforgettable views.

Also in Imerovigli is the five-star Princess Luxury Spa Hotel, which has one of the few heated outdoor pools on the island. Book a caldera-view room or suite, and split your stay between stints on the poolside terrace, which overlooks the Aegean, and pampering sessions in the spa, where the wellness menu offers everything from manicures and pedicures to couples’ massages. If you’re feeling energetic, hike to the tip of the Skaros Rock, one of Santorini’s most distinctive volcanic formations (allow 90 minutes for the return).

The smart Ambassador Aegean offers 40 rooms, suites and villas, all of which come with private pools and verandas overlooking the village-topped cliffs to the north. Its decor is impeccably contemporary, with whitewashed walls interrupted by flashes of black from the furnishings and blue from the Aegean. Dress up for dinner at Cabo Rosso, a high-end restaurant in love with local ingredients, or for sunset cocktails at the attached bar. Don’t miss the remains of Akrotiri’s hilltop castle, most of which was destroyed by the earthquake of 1956.

Tranquility is guaranteed at Oia’s four-star Rimida Villas, as its flowing, whitewashed accommodations are located in an area specially reserved for guests (no noise allowed, in other words). Rooms and villas are in the traditional Cycladic style – lots of curves, no sharp edges – and all come with private hot tubs overlooking the volcanic caldera landscape. When you’re not soaking up the bubbles and the view, rent two or four wheels from reception to explore the island, or wander down the road to the boutiques and tavernas of Oia.

Guests at Thira’s boutique Thireas Hotel have two high-up hangouts from which to survey the caldera and the town itself, creeping down the cliffside like overgrown ivy: the Lounge Terrace, where breakfast is served, and even higher up, the infinity pool, which seems to hover in mid-air. Accommodations display a contemporary, minimalist take on the Cycladic style, and range in size from double rooms to family and honeymoon suites. Thireas also runs the luxury 1809 and Windmill villas – in Thira and Imerovigli, respectively – and several plush cave houses in Vourvoulos.

Grand View delivers on its promise, offering clifftop accommodations in the village of Megalochori that require no stairs to reach, unlike most other similarly appointed hotels on Santorini. Stay in the airy pool villa (two ensuite doubles), which has its own rooftop veranda and infinity pool facing the Aegean and the volcanic caldera. Social life centres on the pool bar, where a Greek breakfast of yoghurt, feta and frappé is served every morning, and where you can watch the sunset explode with a ginger mojito. Blue Dolphins, the sister hotel, is in Firostefani.

There’s nothing deceptive about this three-star hotel’s name: set high above the water on the cliffs of Imerovigli, Sunny Villas’ curvy Cycladic accommodations are flooded with Aegean light. Private balconies with limitless sea and caldera views come as standard, whether you’re reserving a two-person studio or the six-person Deluxe Suite. The intimate pool terrace and bar overlook the Skaros outcrop, first used as a defensive fortification by the Byzantines in the early 1200s – a well-worn path takes you 650m (2,100ft) from reception to its pinnacle.

Located just off Thira’s main street, Asteras Villas provides one of the most romantic stays on Santorini. Couples can request a candlelit dinner on their private terraces (a standard feature of all five suites) or book a romance package including satin sheets and rose petals on the bed and Moët Champagne upon arrival. The suites wear sophisticated blacks, whites and golds, and all have heated outdoor jacuzzis overlooking the caldera and the neighbouring island of Thirasia. Unwind with an ancient Indian or Reiki massage in the treatment rooms.

You’ll have to negotiate some steep stairs to reach the four-star Ducato di Oia, but its clifftop location rewards the effort. Accommodations range from cosy doubles to two-bedroom suites, and almost all have uniquely shaped terraces with plunge pools, from which you can survey the volcanic bay and glowing sunset. The shops, bars and restaurants of Oia are just a few minutes’ walk away, and there’s a comprehensive on-site offering, including massages and beauty treatments, a library stocked with holiday reads and speedboat rentals.

Just down the road from the Ducato, virtually hanging off the cliffs, is the Sophia Oia View, a collection of luxury caves with their own plunge pools and terraces overlooking the caldera and Aegean. If, for some mad reason, you want to leave this private haven, check out the nearby Maritime Museum, or the crumbling remains of Oia’s 15th-century castle: once a lookout from which Santorini’s Venetian rulers scoured the seas for pirates, it’s now one of the best places in Greece, and arguably in the world, to watch the sunset.