Photo courtesy of 1864 The Sea Captain's House, Santorini
A Clifftop Hotel
It may be just a small traditional village, but Oia is where you'll find some of the most glamorous properties on Santorini. The Sea Captain's House, on the other hand, is more like a luxury B&B loaded with antiques, character, and quirky charm. The owner, American Tony Mosiman, ditched his career as an IT consultant for a life on Santorini more than a decade ago. He first opened two restaurants, the upscale Ambrosia and the more casual Ambrosia & Nectar, which are still two of the best restaurants in town, and then in 2004 opened 1864 the Sea Captain's House. Originally the clifftop mansion of a true sea captain, the architecture—high cross-vaulted ceilings, big rooms, and Venetian-style facade—reflects the captain's voyages through Europe. Rooms are decorated in an eclectic mix of antiques and art, with many paintings from local artists. With only three suites, it doesn't get more intimate than this. Tony and his partner, Panayiotis, are almost always on hand to assist, feed, and advise their guests. The Sea Captain's House succeeds in feeling like a home away from home.
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Oia is a picturesque maze of a traditional Greek whitewashed village that happens to be home to some of the island's most exclusive properties. Because of its prime position over the caldera, tour groups can crowd the streets around sunset. But otherwise, it's a charming town loaded with excellent little cafés, restaurants, and independent shops like Atlantis Books and Iama Wine Shop.
Need to Know
Rooms: 3 suites. From $405, including breakfast. Check-in: 2 p.m.; check-out: noon. Dining options: Guests here rave endlessly about the “lazy breakfasts” that can be served anytime. Tony and Panayiotis deliver such a generous spread—including Champagne—that there's no need for lunch. And while there is no official dining room, Tony's two restaurants in town, Ambrosia and Ambrosia & Nectar, deliver to the hotel. Spa and gym details: The property's Caldera Massages Studio offers a variety of excellent rubdowns, including several couples treatments. Make appointments before you arrive, as often massage therapists are booked, especially in the summer. There is no gym here, but the best exercise is an early morning three- to four-hour hike between Oia and Fira that follows the rim of the caldera.
Who's it for: Couples who appreciate cozy and quaint over glamorous; those who want to feel at home and don't mind giving up a bit of privacy in exchange for warm, friendly service. Our favorite rooms: The Sailing Suite is a bit more spacious than the Venetian Suite and has access to a terrace with stunning ocean views. The terrace is the perfect place to have breakfast and start your day. Explore the area: The property can help organize the perfect boat trip to explore the island's more hidden beaches and bays, and also prepare tasty picnic lunches.