In recent years, Santorini has become an increasingly popular destination in the Greek Cyclades. And upon visiting, I can now say that its for good reason. More than just a tropical destination, the sheer drop of the cliffs and the mass of white dwellings that seem to stack on top of one another, seemingly on the precipice of rolling into the waves below, is an astonishing sight to behold.

For the purposes of travel: the island can be divided into three main areas: southern, middle, and northern.


Our first night on the island was spent in the southern town of Perissa, home to a black sand beach typical to volcanic islands.

The larger and more tourist-laden towns of Fira and Oia are towards the middle and northern tip of the island respectively, so eating in the southern parts can be make for more of an authentic and economical Greek dining experience.

Perrissian locals swear by Fratzeskos Fish Tavern by the main beach of town.

Make sure to stop by for an early dinner (7pm by Greek standards), or make a reservation during the busier summer months.

Dakos, left, made of soaked dried bread or barley rusk, topped with chopped tomatoes and feta, drizzled with olive oil and oregano. Small dishes meant to be shared in Greece are known as mezes, similar to the Spanish tapas. This particular mezes was definitely one of my favorites during the trip. A must-try.

Right, Tirokafteri, known on their English menu as 'spicy hot cheese dip,' is actually a slightly spicy dish of grated feta cheese meant to be eaten with bread. A delight if one wants to get away from the typical dips of Greece.

Ah, yes, my first octopus dish in Greece, left. Chewy yet tender, juicy and flavorful, my only problem with this dish was its size. More please!

The Greek islands are known for their seafood. In particular, fish tavernas are known for serving up some of the freshest, tastiest grilled fishes in the world. Beware though, freshly grilled fish do not come in fillet form, so better practice de-boning your own fish before you go.

Fried marida fishes, left, and no, the cat was not part of our meal. It and its friends did, however, enjoy quite a few of these small fishes alongside our table.


For a digestif, hit up the ironically named but incredibly lively Tranquilo for a drink, or two, or three. Who's counting in the Cyclades?


Day two, or our first full day in Santorini, started with us missing a tour to the volcanoes and hot springs on the nearby islands. (Note that there are indeed two ports on Santorini, the Old Port is located in Fira, and requires a cable car ride to get down to. The New Port is where most cruises and large ferries dock, accessible by car via a winding road.)

So, Day 2 actually began with a trip to Pyrgos, a small village in the middle of the island. Known for a monastery perched on top of this mountainous region of the island, its known for some spectacular panoramic views and sunrise/sunsets.

My first donkey sighting in Greece. These animals are typically used by residents to carry loads up and down the island's steep and winding pathways.


About a 15 minute walk from the town of Pyrgos is an island favorite for tourists - the Santos Wine Winery. Its rather repetitive name aside, this winery boasts some of the most spectacular views of the island, and some killer wine, of course.

The restaurant in the winery features an outdoor seating area and patio lined with glass enclosures that look out into the endless Aegean sea and surrounding cliffs of the island.

The winery offers tours of the its facilities in conjunction with a 6, 12, or 18 flight tasting. The tasting flights can be shared, so I suggest splitting it between at least two people for the 12 and 18 glass options. They pour with quite a heavy hand here in Greece, a great thing but might mean you may not be walking out of the vineyard after an attempt to finish 18 glasses alone.

Time for the main attraction. We went full-steam ahead for the 18 wines flight, seen below. For a morning snack (ok, I'll admit this was breakfast), try the Santo Taste mini platter. The cheese and the tomato dip were heavenly to pair with the wine.

Verdict: all the whites and reds were excellent (not that I know much about wine). Some were drier than others, with sweeter reds towards the end of the flight, blending into the selection of port and apertifs to conclude. The ports were heavy and quite sweet, so if you're not big on sweet wines, maybe skip the 18 wine flight and opt for the 12 instead. But hey, when in Greece...


The village of Oia is on the northeastern tip of the island. Arguably the most scenic village of Santorini, this is the place to go if you're looking a postcard perfect shot of the sloping white houses against the backdrop of the Aegean.

Why are houses painted white in the Cycladic islands?

It started for practical reasons, as white reflected most of the harsh summer sun, and therefore insulated the houses from the heat.

Rumor also had it that during the beginning of the 20th century, many diseases befell the people of the Greek islands, and whitewash was one of the cheapest and effective disinfectants of its time - contributing to the enduring color schematic of the houses.

After 1974, a law decreed that all new houses had to be painted white, memorializing the picturesque towns.

Today, however, other light pastel colors are allowed, such as shades of beige and pink, seen above.

The locals like to say that there are more churches than houses on the island, and that's because churches receive free electricity which surrounding dwellings can take advantage of.

There are many hotels, and restaurants in the village of Oia. Even in the off-season, however, they will easily run you a few hundred dollars are night. Best to line your pockets before you come a-sailing to this island.

Fun fact about windmills in the Cyclades. Many of them have been renovated as guest houses on the inside, so you can usually stay in one, if you so desire.

A port in the town of Oia.

Snack break: here in Greece, a midday snack of (more) octopus, and tiropita, layers of fine phyllo pastry wrapped around decadent cheese, fried, drizzled with honey, sprinkled with sesame and sunflower seeds. 'Nuff said.

Gorgeous. Simply gorgeous. Nothing more to say.

Even in October, one can work up a sweat climbing up and down the cobblestone paths around town under the bright Mediterranean sun. Stop by Lolita's for satisfying scoops of gelato. Seen here: decadent chocolate and peanut butter cream. Yum.


Driving nearly the entire length of the island, we headed south towards Red Beach, a popular tourist destination near Akrotiri known for its red cliffs and coarse, rocky beaches.

The unique formation of black sand against the backdrop of red cliffs is caused by the volcanic nature of the entire island.

Travelers and locals alike enjoy hunkering down on the rocky beach to swim and sunbathe for the day. If it were warmer and we had more time, I'd have joined them. Just beware the boats that ferry passengers to and from the beach's smart port.

If we had more time, I'd also have stopped by the ancient ruins in Akrotiri. But as with Delos, it seems it wasn't meant to be this trip. Plenty coming up in Athens, presumably.


After the Red Beach, take a car to the proximate Faros Lighthouse for some sweeping views of the sea, and if you're in time, catch the sunset.

But if you are early, stop for dinner at Taverna Giogaros, recommended by a local as the restaurant of 'the best fisherman on the island.'

Indeed, neither the food nor the view disappointed. Definitely make a reservation during tourist season or if you're coming in during 'normal' dinner time, which is 8 or 9 pm here.

Left, fried eggplant, and right, bougiourdi, a delicious combination of feta cheese, tomatoes, green pepper and onion slices, heated into a ceramic-ensconced delicious, gooey concoction.

Fried calamari - hands down the best calamari I've ever had. I would go as far to say I've never had calamari before I had this. Tender and chewy squid enshrined within a perfectly fried, crispy, crunchy, croissant-like shell. I would come back to Santorini just for this.

More octopus, because you can never have enough. Less tender than the one we had at previous night's dinner, but delicious nonetheless.

Grilled red snapper, delightfully flavorful skin grilled to a crisp perfection, paired with a perfectly balanced olive-lemon-butter sauce.


Faro's Lighthouse offers a great vantage point from which to see the sunset.

Though most tourists will gather in Oia for this time of day, the southern tip of the island can also has its own (less crowded) charm to ring in the end of another day in Santorini.

Beautiful.


Day 3 started with a sunrise: seen from Pyrgos.

Then, onwards to the Old Port in Fira, the second of the two cliff-side towns on the island. Stop to pick up a locally made souvenir from a street vendor: perhaps a (sea)sponge or some volcanic rock/pumice?  

The Old Port of Fira requires either a short cable car ride to get down from, or a donkey ride. For those who want to walk the winding path down to the port: be warned that you'll be sharing the road with donkeys, who are not led by anyone as they carry passengers up the hill.  

Before boarding the boat, a stop for some breakfast: right, no - I did not come all the way to Greece to eat hash browns. For breakfast, that's Saganaki, because nothing wakes one up in the morning like two large chunks of delicious, gooey fried cheese.

Right: Tomatokeftedes, fried tomato balls native to the island. Chopped tomatoes mixed with onion, herbs, salt and flour, pan fried in olive oil to form a crisp shell. The delicate balance of sour (tomatoes, seasoning), and umami (olive oil, fried) proves to be an intrigue to the palate, especially for breakfast.

Finally, a satisfying portion of octopus that I've been waiting for the whole trip. (No - that's not a portion of what they serve here, just some freshly cooked octopus left out to cool by the owner, but hey, one can dream).

Greek omelet, featuring everything. Chorizo, onion, tomato, and more, this should be top of any breakfast-eater's list when in Greece.


Finally, time for the volcanoes and hot springs tour. Board a traditional ship that will take you to two of the nearby islands for the two agenda items on the tour - a must-do if one has a half day free in Santorini.

Get ready for some spectacular views of the island's coastline and the ocean as the boat pulls away from shore.

Sailing on the sea provides a great vantage point to see the towns of Fira and Oia from below.

Cruise ships dock off the piers off the Old Port, and ferry their passengers to the shallower waters.

As we approach the first stop, get ready to change into swim wear for the hot spring. Note that there's not direct way to access the spring from the boat, one has to jump from the deck and swim abut 100 meters (200 feet) to the 'springs.'

After a somewhat arduous swim, I arrive in the patch of sulfur-infused water to discover that its rather more lukewarm than hot. In October, one may want to think twice about the swim if sensitive to the cold, as the seawater isn't particularly warm either during this itme of year.


Santorini was created out of one of the largest volcanic eruptions ever recorded in human history.

The island's entire eastern side, its cliffs and the ocean below, is part of a massive caldera with nearby Nea Kameni island serving as the crater of the super volcano.

It's name used to mean 'circle,' the shape of the once-larger island that encompassed the islands near Santorini and the original caldera.

The climb up to the largest erupted crater of the volcano can be a bit of a hike, but worth it for the view from the top.

After the large eruption, large section of the island sank into the ocean, creating the dramatic cliffs seen on the east side of the main island (seen in background below). Today, the eastern shores of Santorini and its surrounding islands form the largest caldera in the world.

After the volcano, its back on the boat and straight back to the Old Port. All in all, a worthwhile 2-3 hours spent sailing the Aegean.


To avoid the lines at the cable car station for a ride back up to the actual town of Fira, we opted for the authentic Greek experience of riding on a donkey.

Word of advice: hang on tight during the trip. These donkeys are not led by anyone, and follow one another up the winding path. Sometimes, with a mind of their own, they can pick up speed to overtake the pal in front of them, brushing dangerously close to a fellow passenger atop another donkey in the process.

However, the trip offers some spectacular views of the ocean, the path, and the port below. But seriously, hang on tight, because these donkeys will start trotting without prior notice, and sometimes you get errily close to the steeper side of path.


Back up in the town of Fira, we were once more treated to generous, sweeping views of the houses, cliffs, and water below.

Definitely make time to stop for a coffee (read: a drink) at any of the cafes or tavernas lining the narrow pathways of town.

Find one by the cliffside, and you can likely sit and enjoy your drink with an awe-inspring vista.

View from the side of this particular café/restaurant. Try one of their signiature cactus cocktails, seen above.

The Three Bells Church of Fira, below left. One of the most famous blue-domes of Fira - follow the signs to find the best vantage point.

So long, heavenly Santorini. You'll be missed.