Kasimatis by La Perla, Santorini

Pros

• You'll find yourself in a dramatic cliffside setting in the small but upscale village of Imerovigli. 
• The chic, cave-like rooms and suites include private terraces, some with panoramic caldera views and outdoor Jacuzzis.
• There's an adjoining restaurant (just a few levels up the cliff) that serves all-day Greek classics from a clifftop terrace.
• A central courtyard features a petite pool, a bar for drinks and light snacks, and plenty of sun loungers.
• The hotel's location is ideal for walkers and hikers—it sits midway along the scenic Oia to Fira path.

Cons

• This is an adults-only property; ages 13 and over are welcome, but its quiet, romantic feel is more popular with couples. 
• Upper floors are accessed by stairs only, and the village's steep setting means this isn't a good fit for guests with limited mobility.
• The private Jacuzzis are meant to be refreshing in summer, so expect warm water, not hot.
• This is a seasonal property, and it closes off-season (November through March).

Authenticity

One of three La Perla properties on Santorini, Kasimatis by La Perla opened in 2017, converting a historic canava (cliffside wine storage caves) into an intimate boutique hotel. It's a romantic spot, with rooms and suites carved into steep terraces overlooking the island's volcanic caldera; the overall aesthetic is classic Cycladic chic, melding invisibly into the surrounding village. The boutique feel extends to the service, which is warm and personalized. Porters whisk your luggage up the winding terraces, and a discrete knock each morning announces a colorful breakfast tray, served al fresco on your private terrace. 

Location

You'll be located in the tiny village of Imerovigli, just a 10-minute drive north of the capital of Fira. Full of traditional cave houses and upscale hotels carved into the cliffside, this is a quiet and spectacularly scenic spot, home to some of the best restaurants on the island. You can walk down to Fira in 30 minutes along a caldera-rim path, and the dramatic Skaros Rock is a 15-minute stroll away. Farther north, the "sunset village" of Oia is a 25-minute drive. The ferry port is reachable in 25 minutes, and the island's airport in 15. There's parking available on-site, and the hotel can arrange shuttles and transfers for an added fee. 

Rooms & Bathrooms

The hotel's 14+ air-conditioned, cave-style rooms and suites are all unique, arranged across four levels of cliffside terraces. Interiors highlight classic Cycladic minimalism, with thick whitewashed walls, curved lines, and organic textures. All open onto private terraces, some with spectacular caldera views and outdoor Jacuzzis carved into the white stone. Double rooms are ideal for couples, while larger suites can sleep 3-4 comfortably with additional seating areas and sofa beds. Bathrooms are compact but beautifully appointed, with rain-style showers in carved recesses. 

Amenities

You won't find the amenities of a large hotel at this boutique-style property, but there's an inviting (if petite) pool on the central terrace, complete with sun loungers and a bar that serves drinks and light snacks. There's no on-site spa, but you can arrange for in-room treatments. A complimentary continental breakfast is served on your private terrace (many guests note this as a real highlight), and a 2-minute climb up the cliffside takes you to the hotel's neighboring restaurant, Ammilos. Featuring some of the best views in town from its caldera-facing patio, it offers an all-day menu of refined Greek classics. 

Family-Friendliness

This is an adult-only property. Teens 13 and above are welcome at the hotel, but younger kids and infants are not permitted.