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This monastery, located on the Akritori peninsula of Crete, is run by monks who make wine and well-priced, quality olive oil. The building is surrounded by peaceful groves and orchards.

Named for the Japanese word for enlightenment, this boutique property marries classic Cycladic architecture (cube-shaped structures, whitewashed stone walls, arched entryways) with the clean lines of locally made furnishings in naked wood. None of the 25 rooms and 10 suites are the same, but most have private outdoor whirlpools or plunge pools, plus plush beds that make it impossible to leave. Nearly all of the public spaces, however, offer stunning views over Mykonos (about 1.5 miles away) and the bay, and make striking use of night-lighting, especially at the pool, which is built into the natural rock face. A grottolike spa features two treatment rooms, a futuristic-looking whirlpool area, and a hammam for stylish pampering sessions. The hotel offers complimentary transportation to Mykonos, but with its inviting Bar & Sunset Lounge and a restaurant that is garnering awards and accolades, you may decide to stay put for the duration of your vacation.

A classic Plaka hotel close to Syntagma Square, the Electra Palace checks all the boxes for convenient location, rooftop restaurant overlooking the Acropolis, comfortable rooms, plus niceties like a gym, spa, and pool. Spacious suites feature views of the Parthenon, marble bathrooms with Jacuzzi tubs, and handwoven carpets. A Greek breakfast buffet is served in the downstairs garden, and drinks and food are served all day on the fifth-floor rooftop. Hydrating facials, body wraps, and Cretan olive oil massages are given at the spa, which also has a heated indoor pool and jacuzzi. For spring and summer visitors, an afternoon at the outdoor pool overlooking the city’s monuments and neoclassical archicture is practically a requirement.

On a typical day during Mykonos’s high season, you can see why Santa Marina has cemented its status as the ultimate jet-set destination. Megayachts bob in the bright blue waters of Ornos Bay, and a long pier lined with stylish couples curled up in cocoon-shaped sun chairs gives way to a stretch of sandy beach sprinkled with privileged bathers. In fact, the Santa Marina is the only hotel on the island with its own exclusive shoreline. Just steps away, the whitewashed property’s rooms climb a granite hill that looks out over the Aegean; expect a private balcony and marble bathroom in every space. Two restaurants, a bar, three pools, and a first-class spa and gym add to the country-club atmosphere, especially for those who might have their mini-me’s (wearing baby designer duds) in tow: The underage crowd has a dedicated pool, playground, and supervised kids’ club.

The 2nd-century Roman emperor Hadrian spent much of his 20-year reign traveling through his empire, absorbing architectural inspiration from Greece to Egypt. His vision for a luxury villa was realized in Tivoli, a Roman suburb, where he constructed a sprawling palatial complex decked out with the finest statuary of the age. Hadrian’s Villa is a UNESCO World Heritage site, and it contains the ruins of over 30 epic structures. Be sure to check out the Maritime Theater, which Italian authorities managed to partially restore.

Most people come to the tiny town of Ioannina to cruise Lake Pamvotida -- the town’s most popular landmark. You’ll find yourself on a small island in the middle of a beautiful fjord, where the water is smooth as glass and your surroundings are spectacular. Ioannina itself is an intellectual city, known particularly for its university. Several famous poets and novelists call this place home, and the city often runs several arts-related events year round.

Psarou Beach is posh rather than party, ringed by upscale hotels and beach clubs and punctuated with a scuba center. The sand is white and the water is turquoise. Restaurants and bars are expensive here, as are the waterside amenities like chairs and umbrellas, but the ambiance is clean and very stylish. Beach dwellers tend to be fit and fabulous so bring your A-game beach attire.

The queue is long and you’ll have to eat standing up, but this spotless hole-in-the-wall does some of the best souvlaki in town. If you get antsy while you wait, be mindful of the multiple signs behind the counter saying: OXI AGXOS (NO STRESS). You won’t find frozen fries or garlicky tzatziki here. Just perfectly grilled pork skewers wrapped in a grease-free pita and garnished with sliced tomatoes, onions, parsley, a dollop of yogurt, and plenty of paprika. Don’t worry if you confuse it with the other Kostas souvlaki joint just off Agia Irini Square on Vassiliki Street, where the thing to order is pita bread stuffed with meatballs and spicy tomato sauce. Pull up a plastic chair and watch hipsters drink craft beer while you dribble tzatziki down your chin.

Super Paradise Beach is a gigantic stretch of sand tucked away next to Paradise Beach. It’s only reachable by taxi-ferry or by public bus, but the trek is worth it. It’s also a notorious party destination, with a friendly gay community. Super Paradise Night Club is the most popular club in the area, and caters to a ritzy crowd. When the sun goes down, this beach really comes to life. If you’re seeking a quieter atmosphere, show up early.

The unique quality of soil on Santorini is all due to the island’s history of volcanic activity. The soil is known as “aspa,” and is rich in essential minerals. Santorini is home to some excellent wineries, including Santos Wines Winery, Gavalos Winery, and Estate Argyros. A wine tour will get you out and experiencing the best of the best, all while being introduced to the local culinary scene. You’ll see Santorini’s unique vineyards, with its vines coiled in the island’s rich volcanic soil.

The historic King George Hotel has the kind of glamorous gravitas found only in a royal residence. Open since 1930, the King George has hosted celebrities and dignitaries to Athens in grand style ever since, and became a member of Starwood’s Luxury Collection in 2013. Refined guest rooms and suites have herringbone wood floors and marble bathrooms, and might include a window seat or a private balcony. While the dazzling rooftop pool is private only for guests of the two-bedroom Presidential Suite, mere mortals can enjoy a similarly spectacular setting next door at sister property Grande Bretagne (guests can use both hotels’ facilities). The King George has a small gym with Finnish sauna, and the lobby’s exclusive Valmont boutique has high-end cosmetics as well as a perfumery. Emphasis at the award-winning Tudor Hall restaurant is on seasonal ingredients and slow cooking, with local wines carefully chosen to complement the dishes. With a location right on Syntagma Square, views of the Parliament and Parthenon are a matter of course, and all of Athens is within easy distance.

Guidebooks often lack the practical pieces of advice that could save travelers some rather unpleasant moments, in the Greek Islands one such nugget of wisdom I missed in my reading was that after a late night fueled by Ouzo it is not ideal to ride in a high speed ferry. Thankfully the ferry ride from Mykonos to Naxos is a short one at under an hour. I was greeted at the terminal by part of the family that runs Hotel Grotto, a small retreat perched on the edge of the Aegean sea that would be my home while in Naxos. After weeks competing for beach chairs and being corralled down tight marble alleys in some of the more frequented islands, Hora (also known as Naxos Town) proved the perfect place to relax and experience Greece at a slower pace. Upon arriving to the hotel, the bags were taken out of my hand and replaced with a glass of wine made by “Pappa” along with local olives as I was led out to the pictured patio. The view from patio of the hotel is of the Portara, believed to be the beginning of the Temple of Apollo dated back to 530 BC and is an ideal spot to pack a picnic from the local grocery, and watch the sunset before heading into town for the night. On the walk back to the hotel rising above the town is The Venetian Castle Kastro. During the day it serves as a museum offering tours, on Sunday nights after sunset it hosts traditional music and dance made easier by the accompaniment of Kitron,a liqueur indigineous to the area.

The large, leafy patio of this mezze restaurant in bohemian Exarchia was once the local schoolyard. Now cozy couples and animated gaggles of friends gather beneath the flowering bowers to enjoy some of the most honest and comforting food in town. Order as many dishes as you can fit on the table and share them all. Rather than traditional Greek fare, the menu is a tasty Mediterranean pick-and-mix. Try the cracked wheat salad with green apple, mint, and dried figs; meatballs seasoned with cinnamon and clove; and mini lamb kebabs. The high-ceilinged, well-lit classrooms make charming dining rooms in cooler weather. Service is unfailingly friendly and relaxed.

A school-turned-mezedopoleío serves delicious meze including bakalyaro (walnut-crusted fish fillets) and pita topped with yogurt and smoked eggplant. Bonus: a patio surrounded by bougainvillea.

Located in Messinia’s Mediterranean area, this popular beach is most well-known for its distinct “omega” shape. Locals and visitors come here to lap up the waves, admire the dunes, sunbathe on soft sand, hike, and bird watch. Other attractions located above the beach include Nestor’s Cave, the ruins of Old Navarino Castle, and the tomb of Thrasymedes (Mycenaean period). As you climb, you’ll enjoy aerial views of the Divari Lagoon of Gialova, Navarino Bay, and the olive tree-littered Peloponnesian Hills. Interestingly, Voidokilia Beach is believed to be the place mentioned in Homer’s Odyssey, where Telemachus (son of Odysseus and Penelope in Greek mythology) was greeted by King Nestor—who is thought to have used the beach as a port during ancient times—when searching for his father. For a guided experience, Navarino Outdoors offers a bike tour of the beautiful Voidokilia, with time to swim and enjoy views of Gialova Lagoon.

Also known as Old Navarino Castle, Paleokastro—built by the Frankish ruler Nicholas II de St. Omer around 1278—is located above Voidokila Beach in Messinia’s Mediterranean area. Make sure to bring your camera, as a trek to the castle awards panoramic views of the Ionian Sea, the city of Pylos, Voidokilia Bay, the Romanou-Petrochori beaches, Gialova Divari lagoon, the olive tree-lined Peloponnesian Hills, the Sykias chanel, Sphacteria island, and Navarino Bay. When hiking, you’ll be taking the same path as you would to reach Nestor’s Cave, a popular cave in Greek mythology.