Ilioperato Hotel

Ilioperato Traditional Apartments was a private mansion when it was originally built over 200-years-ago. The white and blue Cycladic structure was fully renovated into an upscale boutique hotel in 2007, and is still one of the best maintained and most elegant hotels in Imerovigli. Views of the caldera and Skaros Rock are prevalent from the pool area and terraces, including a gorgeous terrace that's often used for wedding ceremonies. When not in use, the space is set with white furniture enveloped by white curtains to block the sun. Kids are allowed in some of the rooms with advance notice, but most of the visitors here are couples and honeymooners. The hotel is family owned and staff are incredibly helpful. Note that the hotel closes from November through mid-March. 

Imerovigli village offers the same stunning (especially at sunset) caldera and Aegean Sea views that make Oia and Fira famous, but the crowds here are smaller and the pedestrian path along the caldera is easier to traverse. There are several good restaurants in Imerovigli (Le Moustache and Avocado) and a smattering of souvenir shops and boutiques. For a larger selection of dining and shopping outlets, a walk to Fira will take about 20 minutes along the caldera. This is also where the larger bus station and cable cars to the ferry port are located. Oia can be reached in about a two-hour walk, a popular activity, though the path is steep and unpaved in some sections. Taking the bus or a car along the highway is faster, at about 20 minutes. Santorini Airport is a 15-minute drive from the hotel. It's about a 30-minute drive to Red Beach. 

There are just 12 rooms here, and some are stacked on top of each other on the cliff -- which means furnished balconies aren't quite as private as some couples might like. For those searching for total privacy, the Honeymoon Suite has a secluded balcony. Still, all of the cave-style rooms are nicely decorated in tones of gray and white, and they include high-end touches like espresso makers and Coco Mat mattresses. Other features include free Wi-Fi, flat-screen TVs, mini-fridges with cold drinks, wet bars, and air-conditioning. Closets hold robes, slippers, and hairdryers. Renovated and modern bathrooms include wonderful cave-style showers with rainfall showerheads. Some rooms have jetted tubs. Toiletries are provided. 

Features are as lovely as the rooms and public spaces. Guests select from a menu of pastries, eggs, fruits, and Greek yogurt to be delivered to their balconies at a pre-determined time. The meal is included in room rates. For lunch, dinner, and drinks, there's a quaint restaurant with large windows overlooking the caldera. The menu offers everything from pizza to gyros and salads. There is a pool here, and though it's small, it's a beautiful space with gorgeous views and some padded sun loungers. An adjacent terrace provides more space to sunbathe and is often used for wedding ceremonies. Wi-Fi is free throughout the property. The reception desk is available 24 hours and there's a porter service for luggage assistance. The nearest parking lot is just up the cliff, off of the village square.