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It’s Fall, so now is the time to start stashing those coins and planning for your summer vacation. If you’re wondering where to go, look no further than Greece.

The city of Santorini, which won the “Reader’s Choice Award for Best Island in the World 2016″ and was lauded as the “World’s Best Trip” by Travel and Leisure in 2016, actually lies inside of the largest volcanic crater on earth. 3500 years ago, one of the most powerful eruptions in history sunk the center of Santorini into the Aegean Sea, leaving a half moon crescent shaped island built on layers of volcanic rock and sloping cliffs that plunge majestically into the sea. You could go to Greece and visit only Santorini, exploring the world’s most beautiful sunsets and your life would be damn near complete…but you’d be selling yourself short. Go to Santorini for the views…the wine, the history, but there is so much more to the Greek Islands than Santorini (and fine Greek men) so get out and see some Greece.


All international flights from the U.S. land in Athens, Greece’s largest city. If you have time, venture out into a city that Conde Nast Traveler voted one of the Best Places to Visit in 2017. A must: a visit to the Acropolis, Greece’s famous ancient ruins, dating back to the 4th century B.C. where Athena and Poseidon battled it out for namesake rights to the city. Located in the middle of the city, it is accessible enough to visit on your own. If you’re staying overnight, The King George of Athens  has everything you’d expect from a hotel of this name. Located in the city center with tastefully decorated rooms, oversized marble bathrooms, and rooftop dining with the view of the Acropolis are just a few things that made this my hotel of choice.

If you’re bypassing Athens for island hopping, there are about 20 daily flights during the high season–April to October. A quick 45 minute flight, and you’re landing in Santorini, whose beauty resembles snowcapped mountains thanks to the mandate that only whitewashed houses may be built here. Santorini’s cloudless blue skies, sparse vegetation, where the mountainous coastline meets the turquoise waters of the Aegean Sea, make the rumors that this is Plato’s lost Atlantis entirely plausible. Regardless, it’s clear that you’ve found paradise.

WHERE TO STAY: Fira (pronounced Thira) is the bustling part of the island where cruise ships dock. Take a stroll up Angiu Mina Street towards the cable car, climbing 587 steps or ride a donkey up from the old port. If you prefer an easy walk, start at Gold Street, wandering through cobblestone paths and corridors where you will find souvenir shops and jewelers selling colored stones that Santorini is famous for. Make sure to comparison shop as you can bargain for the high priced baubles. Fira has shopping, art galleries, and eateries tucked in every corner overlooking the Aegean. Even during the tourist season, Fira is so damn charming, you won’t feel overwhelmed.

Andronis Concept is a wellness spa and boutique hotel located in Fira. If you can splurge, book a room with an infinity pool overlooking the Aegean.

Oia (pronounced “Ia”) Santorini’s other main town is located about 6-8 miles from Fira is easy to get to by hiking trail, or by taxi or bus. This picturesque village, located on a cliff overlooking a volcano and the Aegean, with its blue domed churches is one of the most photographed vistas in the world. Merchants and traditional whitewashed houses and churches nestled among cobblestone corridors give this seaside village its charm.


You can’t really visit Santorini without experiencing the beauty of the Aegean. Captain Ted of Santorini Sailing  will take you on one of his company’s yachts on a shared or private day or sunset cruise. All itineraries include drinks and meals cooked onboard and time to swim in various bays. Sailing in the middle of the world’s largest volcanic crater surrounded by hot springs, various red, black and white beaches dotted with mountainous lava rock is unlike anything you’ve experienced. All sailing trips end at “The Beach,” Captain Ted’s private beach where you will be attended to by some VERY handsome Greek servers as you sip cocktails, light fare, or desert.

Akrotiri is one of the most important ancient sites in Greece. Around 1627 B.C., the volcanic eruption sank part of Santorini into the sea and buried an entire town. In 1967, archeologists began to unearth the ruins of what is rumored to be Plato’s Atlantis, consisting of an office square, marketplace, homes, frescoes, pottery and artwork under 37 miles of volcanic ash, giving you a glimpse of Greek life in the Bronze Age.

Greece is famous for wines, so leave time to visit Venetsanos Winery which overlooks the port from the cliffs of Fira. You can book a tour, or a balcony table with breathtaking views before hopping on the ferry to Sifnos, your next island.

SIFNOS is gaining in popularity among Americans, but this Greek gem has always been a European favorite. Sifnos and Santorini are only 2.5 hour apart by Fast Ferry but the lush green gardens, vegetation and sandy beaches sets them worlds apart. The island is famous for olive oil, garbanzo beans, thyme and honey, grown by many villagers in their own in their gardens.


Sifnos is the place where you can really get your beach on, whether lounging at the beach near the port of Kamares, wandering through shops, dining at waterfront cafes, or swimming at the lazy beach enclave of Platys Gialos. Widely recognized as the best restaurant on Sifnos, Omega 3 Restaurant and Wine Bar is where you go for the food and wine and stay for the beach. The chef trained at New York’s famous Per Se Restaurant and brings an international flare to traditional Greek dishes. Think Zucchini Carpaccio with pinenuts and manoura cheese, Red Snapper ceviche with pesto and red pepper jelly, and Sea Bass ceviche.

Sifnos’ city center, Apollonia has great shopping and eateries and comes alive after dark with bars staying open until 5. Although its landscape lends itself to hiking, beaching and chilling, Sifnos’ beauty is in its simplicity. The hotels, while not fancy are clean, and AirBNB is booming, so don’t leave Sifnos off your list because you’ve never heard of it. Here, you’ll get your best glimpse into life on the Greek islands: potters handcrafting ceramics and residents congregating around the town’s communal ovens on Saturday nights preparing the traditional Garbanzo Bean soup for Sunday meals. If people make the place, then Sifnos is heaven. A national officer of the government brought me a caldron of Garbanzo Bean because I mentioned it was a favorite, and a tour operator gifted me a bottle of handpressed olive oil from his garden as a departing gift.

After a few days on Sifnos, the Fast Ferry will get you back to Athens in about 3 hours, as you prepare to head home from one of the best trips of your life.

My trip wouldn’t have been the same had Petros from Hellenic Holidays hooked up the ultimate Greek itinerary. Let Petros help you plan your Ultimate Greek Summer Vacation.


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