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Wandering Sommelier: Jean K. Reilly in Greece

Adventure travel in Greece means an abundance of choices. Dive into the turquoise waters of Corfu. Kayak around the white rocks of Milos. Climb to the top of Mount Zeus, the highest peak in the Greek Cyclades, on Naxos island, and peek inside the god’s hidden cave. Travel to Santorini, and hike from Fira to Oia at sunset to see a dramatic view of the sun sinking behind the caldera. In Greece, adventure is a given.

You can’t beat this - a delicious, freshly caught seafood dinner on the edge of the Aegean Sea. Sunset Taverna is located in Ammoudi, at the base of the cliffs in Oia, Santorini - dramatic scenery for simple, rustic, delicious food. From the castle in Oia, enjoy a leisurely, winding walk down to the marina (or take a car down the coastal road). Feast on lobster spaghetti, fresh grilled seafood, baked feta, stuffed eggplant, Fisherman’s Salad. Hike back up to Oia under the clear, starry night.

Imagine sitting in your own private jacuzzi sipping Greek wine, while the shops, restaurants, and homes in the village of Oia are bustling with people and lit with their warm glows. It is from the balcony of the Endless Blue Suite at Aspaki Hotel that you can experience this magic. While there are an abundance of accommodations at your fingertips in the stunningly beautiful, white-washed village, the traditional Aspaki Hotel is unique and truly luxury with a personal and friendly touch. Set on one of the most-photographed private pathways in Oia, the Endless Blue Suite is gorgeous with its peach and light blue colored exterior, and can be seen throughout the town and spotted from the water below. The suite has a loft-style bedroom, spacious living area and kitchen with windows throughout, but it’s the outdoor balcony with jacuzzi that sets it apart from the rest. With an uninterrupted panoramic view of the Caldera and village, it feels as if you’re hanging on the cliff’s edge overlooking the Aegean Sea. It doesn’t seem quite real and is like your own Greek island home that you don’t want to leave. I highly recommend the Endless Blue Suite for a couple on their honeymoon or celebrating a special occasion, and Aspaki Hotel also offers other suites perfect for any stay.

It’s hard to believe that this iconic property once consisted of just two 17th-century “caves” that had been used to store wine when it launched in 1985. Today, the family-owned hotel has 17 rooms spread out over five floors, all of them with terraces or balconies and jaw-dropping views of the caldera and brilliant blue Aegean. The rooms were completely refurbished in 2015—followed by the public areas and infinity pool in 2017—favoring clean, contemporary lines, white-washed walls, and luxury that envelops you without distracting from the stunning scenery; several rooms feature heated plunge pools, while one has a free-form “river pool” that runs through it. A poolside bar serves lunch and snacks, but you shouldn’t miss dinner at sister property Canavas Oia Suites, just a short walk away. For a truly unforgettable experience, you can even charter the hotel’s yacht for a sunset tour.

Santorini, Greece is an unquestionably beautiful island, but you can take the island experience up a notch, from beautiful to breathtaking, by hiking the ancient footpath from Thira to Oia. Start just before sunrise and meander the ancient dirt and cobblestone path, which is perfectly nestled at the cliffs edge, providing breathtaking views of the caldera. I set out on this path alone for a 4 hour hike, not too sure of what I would find along the way. Way up high, above the sea, away from the island crowds, as if walking through the clouds, I experienced the true beauty of the island- obvious natural beauty that surrounds you in every direction, but an ancient, deeply rooted beauty that can only be found in the silence, in the white washed churches scattered along the path, in the sun-smoothed cobblestone of the path ... in the clouds. Don’t forget layered clothes as once the sun rises the temperature does as well, comfortable walking shoes, bottled water & a camera!

Nothing says Santorini like an aqua-blue infinity pool, and Katikies has three of them—all the better to take in westward-facing sunset views. Carved out of the cliff side 300 feet above the Aegean, the hotel’s public spaces are connected by a series of bridges and Escher-esque stairways as they descend from the town of Oia above it. Cube-shaped rooms and suites are minimalist but inviting, nearly every surface painted or clothed in calming white; all have verandas, while a few large suites have outdoor plunge pools or Jacuzzi tubs and alfresco seating areas. Upon check-in, guests are given cell phones to summon 24/7 service from anywhere on the property. They use them to order light snacks at the poolside bar and restaurant or make reservations for some of the best sushi on the island at the champagne bar, but the candlelit rooftop restaurant—serving Greek and Anatolian cuisine—is about as romantic as it gets.

For one of the best views and best meals in Santorini, try Red Bicycle. Located at the tip of Oia on the northern part of the island, the restaurant is housed in a 19th-century Santorini mansion with a 180-degree view of the famed sunset and the volcano caldera. It was heavenly. Soft island breezes on the open-air terrace. The best food I had in Greece (fresh, local Mediterranean dishes with Greek/Santorini influences). A warm hostess who was incredibly kind to our two children. We ate here twice during our weeklong stay - I definitely hope to go back.

It’s little wonder why the cerulean infinity pool at Perivolas has graced more than its fair share of magazine covers. Overlooking shimmering Aegean waters to the Santorini caldera beyond, it feels like heaven on earth. But in fact, the luxury hotel had humble beginnings: Onetime fishermens’ residences in the typical yposkafa style—with cave-like rooms excavated from native volcanic stone nearly three centuries ago—the property has been a family-run boutique lodging since 1983. All 20 rooms have a sea view with terraces to take in the Greek sunsets; some suites feature private infinity pools and Jacuzzis, while the Perivolas Suite is the ultimate indulgence, claiming not only a huge indoor hot tub, but also a steam room and swim-out pool that stretches from inside the cave to the terrace. Furnishings are minimal but sumptuous, with occasional pops of fuschia and purple to add contemporary flair and skylights that flood the whitewashed walls with light. If you can peel yourself away, Perivolas is an easy 15-minute walk from Oia. But with its own highly regarded Greek restaurant, that gorgeous pool, and a cliffside spa with sauna, steam room, and outdoor hot tub, is there really any reason to leave?

Everyone goes to Santorini for the famous sunset in Oia. However, the moonlight at the black sand beach in Kamari is worth going as well. Plus, along the beach are shops, bars and restaurants one after another. Most of them are outdoor, so you can enjoy your favorite drink while enjoy the ocean under the moonlight.

Tour the Greek Isles on Windstar’s seven-day cruise through the Aegean, which includes ancient sites, beautiful beaches, and one-of-a-kind experiences.