An Essential Greek Itinerary

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Greece, almost incomparably rich in history and culture, earns its reputation as a hedonistic paradise decorated with idyllic beaches, stunning clifftop vistas, and hospitable locals. A typical tour of the country—including Athens and a few of the Cycladic islands—isn’t merely an introduction; it’s a program that many Greece-lovers repeat every season (at some point from spring to autumn), and for good reason. The mix of bona fides from antiquity, a sociable environment, and carefully curated relaxation is heady.

Athens—which today is modern and easy to navigate—has been a major city and a seat of civilization for more than 3,000 years. Located on the mainland, it’s the largest metropolis in Greece and home to more than a third of the country’s population.

Even a short stay here can prove indelible. Start by keeping two words straight: the Acropolis and the Parthenon. The former is the hilltop citadel that lords over the city; the latter is the Acropolis’s star attraction. It’s a steep climb up but not a long one, and soon you’ll find yourself stepping on white stones from antiquity and gazing up to the Doric columns of the 2,400-year-old former temple. It is one of the world’s most instantly recognizable monuments, and even though the Parthenon has suffered numerous cycles of damage, repair, destruction, and restoration, its architecture awes and astonishes. 

Also intriguing is the Porch of the Caryatids (maidens) at the Erechtheion temple. These enigmatic women appear to hold up the temple’s roofline with their heads—and after so many centuries, the burden must have proved too great: today, these caryatids are impressive replicas, the originals having been painstakingly transferred to the 12-year-old, very modern Acropolis Museum down in town. 

Once you descend from the hilltop, the Plaka neighborhood—which sits below the eastern and northern sides of the Acropolis—will beckon with tavernas, bars, and shops. Its winding, pedestrian-only pathways presage those found in villages in the islands that follow Athens on this itinerary. But in this old historical neighborhood, the architecture is neoclassical and more typically European compared with the whitewashed, earthy island style. Partly because utility cables are all underground, Plaka is great for shutterbugs and is, overall, a pleasant place to wander off for an ouzo—a sweet, anise-flavored aperitif with a high alcohol content (around 40 percent) that is ubiquitous in Greece.

Worthwhile archeological sites that are less known than the Acropolis are scattered throughout Athens, reminding you of the ancient city’s vastness and influence. Among the best of them is the stunningly symmetrical, all-marble Panathenaic Stadium; you can climb the stairs here to catch a glimpse of the Acropolis. And time permitting, stop by the Temple of Olympian Zeus, which captures the imagination; though the gates and the magnificent columns are all that remain, they stand formidably in a grassy field under a (usually) cobalt sky.

The Exotic Cyclades Islands

To tour Athens, even for a few days, is to come face to face with one of the world’s oldest and most influential civilizations; the experience delivers a fine foundation before you jet off to the other Greece—one that is wilder and rugged in landscape and sybaritic in lifestyle. That would be the arid, exotic Cyclades islands, which lie to the southeast of the city in the Aegean Sea. 

Santorini—which has launched a million postcards, calendars, and Instagram photos—is an island you have to visit. It is also the most remote of the Cyclades, due south of its sister islands. Despite Santorini being one of the most photographed places on Earth, nothing quite prepares you for its breathtaking, sui generis beauty. 

When people refer to Santorini, they are really talking about the west side of the semicircular island’s northern, counterclockwise curl. This is the caldera edge. Above the caldera, architects don’t build much on the soil, because the volcanic ground is too soft and porous. In Fira, the island’s capital, you see that resourceful locals have built homes and businesses into the cliffs. 

This topographical challenge is partly why Santorini, which some imagine is the lost city of Atlantis, is so stunning. On the rounded caldera edge, the boundary of a collapsed volcano, a specific architecture has taken shape: a jumble of whitewashed cave houses that descend, in cake-like layers, to the lip of the cliff. All the white is punctuated by a brilliant blue that pays homage to the sparkling Aegean Sea: first, Santorini’s iconic, cerulean-domed churches, and second, a series of glittering pools, some of which begin inside homes, half-covered and grotto-like, only to flow out into the sunshine to show off their beauty and ingenuity.

Any visit to Santorini should begin in Fira and end in Oia, about seven miles to the north, with time in the middle for the lovely and sleepy Firostefani and vertiginous Imerovigli. Fira features a charming indigenous architectural feature: doorways that seem to float. Leading to bars and restaurants, they are like doors to nowhere, framing the sea. Because the establishments are typically downstairs, arranged in descending open-air terraces, the doorframes are like freestanding sculptures. 

In Fira, you can get happily lost in the tangle of pedestrian paths. Expect to be waylaid by numerous boutiques carrying fashions in gauzy linen, and cotton summer shirts and dresses. White House is a landmark for such textiles, for men and women; many of the women’s fashions evoke the Greek-goddess look, for modern-day Athenas. And there’s always a café for a quick snack—for example, the dip on every menu, tzatziki, which is concocted from salted strained yogurt, cucumbers, garlic, and olive oil. 

Fira is now so sprawling that it’s hard to discern the line between that town and Firostefani. But then the latter reveals itself: there is a main pathway that features tavernas and shops, but mainly this is a quiet residential stretch of white villas. You can spy villas with museum-quality artifacts surrounding their pools, antique busts, and the like. North of Firostefani is Imerovigli, the highest and most vertically oriented of the towns. Its views, especially in the direction of the flat-topped Skaros Rock that rises from an unmissable outcropping, are astounding. (You can even hike out to the rock with moderate exertion.) Finally, at the northern end of the caldera sits Oia, drawing tourists like magnets to its scenic staircases, cave hotels, blue domes, clifftop cafes, and sunset vistas. Oia contains all the best architectural features of the other three towns, distilled.

A second must-see island is Mykonos. While Santorini is best explored on foot, you’d be wise to rent a car to check out Mykonos’s world-famous beaches (Elia, Super Paradise, and Psarou top the list) and beach clubs (Nammos, Skorpios, Jackie O’). If you spend the day at one of these hotspots, you’ll quickly grasp the island’s international, hedonistic, pansexual reputation.  

Mykonos’s main town, referred to as Chora or Mykonos Town, is one of Europe’s most instantly distinguishable places. Its characteristic whitewashed labyrinth of pedestrian alleys, set off by brightly painted blue doors, red shutters, and profusions of pink bougainvillea, is intoxicating. Inevitably, you end up waterside, in the area known as Little Venice, where the festive bars overlook the bay, a small pebbly beach, and a row of oft-photographed windmills, set commandingly on a hilltop. Like Oia in Santorini, Little Venice draws throngs for its sunsets.

If you have time to experience at least one other island aside from the famous twosome of Santorini and Mykonos, consider Paros, which is close, convenient, and impressive. The capital and main port, Parikia, is attractive and navigable, but it is the bayside Naoussa, with its cafes and tavernas running alongside pedestrian lanes, that delivers the holiday ambiance. While Paros is chic and hardly undiscovered, you can still find serenity and solitude here. It is possible to grab a swim off a white-sand beach, emerge to grab a table at a taverna (which may or may not have much of a menu), and ask for the day’s catch. 

Two experiences distinguish Paros and make it highly recommendable. The first is Kolimpithres, a vast bay on the north end of the island that is almost completely closed off—so it feels like a lagoon. Calm, clear, and shallow (around four feet deep even at its center), the bay has tiny sandy coves tucked away here and there, with beach lounges available for rent. The island’s other unusual feature is its proximity to Antiparos, which you can easily reach by car ferry from Pounda, on the west coast of Paros. Tiny and lightly populated, Antiparos is lined with pristine beaches.

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Traveler Fast Facts

WHAT IT IS:

Athens, the Greek capital, is a must-see destination for its ruins. It is also the jumping-off point for a visit to the Cyclades, a group of sunbaked Greek islands in the Aegean Sea that are known for their global jet-set popularity, lucid waters, and distinctive architecture. Of these, Mykonos and Santorini are the most heavily visited, while Paros offers a quieter ambiance without losing any of the scenic qualities of the others. 

CLIMATE:

Athens and the islands enjoy a Mediterranean climate; the Cyclades, like many Mediterranean resorts, are mainly open for business during “the season.” Visitors may begin to trickle in by March and April when conditions are spring-like with daytime temperatures in the 60s. In June the crowds come, remaining until August or early September. (Daytime temperatures are in the 70s and 80s during this stretch.) During the October shoulder season, when hotels and restaurants start to close, the weather can still be glorious, in the 60s and 70s during the day.

GETTING THERE:

Athens International Airport is served by every major U.S.-based airline, including American, United, Delta, and JetBlue, plus international carriers such as KLM, Lufthansa, Emirates, Iberia, Swiss, British Airways, and Air France. As premier luxury destinations, Athens, Mykonos, Santorini, and Paros all accommodate private jets.

WHAT TO KNOW BEFORE YOU GO:

Greece was one of the first European countries to open to American tourists during the COVID-19 pandemic, and it continues to welcome them; many travelers have enjoyed the capital and the islands throughout the summer of 2021. That said, conditions can change rapidly. As for entry restrictions, no quarantine is required, but entrants 18 and over must show one of four documents: proof of full vaccination at least 14 days prior to travel; a negative PCR test no older than 72 hours; a negative antigen (rapid) test no older than 48 hours; or documentation by a health care professional of recovery from COVID-19 within the previous two to nine months. In addition, submission of an online Passenger Locator Form is required before entering Greece. For re-entry into the U.S., a negative COVID-19 test is required. For more information, visit the website of the U.S. Embassy in Greece.

Perhaps even more so than Italy or France, Greece is a casual place that can be negotiated with ease. The country depends on a tourist economy, and virtually everyone you might encounter speaks perfect English. When scouting out the various archeological sites or climbing the stairways that define Santorini, comfortable shoes are a must.

Traveler Report Card

ACCOMMODATIONS:

In Athens, the Grand Bretagne (A), a Luxury Collection Hotel, is not only one of the city’s poshest lodging options; it’s also perfectly situated in Syntagma Square, with many rooms offering direct views of the Acropolis. In Santorini, the Grace Hotel(A), now managed by Auberge Collection, boasts one of the island’s best infinity pools, with unbeatable views of Skaros Rock and the Aegean. This property will likely persuade visitors that although Oia is a must-see, it’s preferable to actually stay over in Imerovigli. Mykonos’s Elia Beach is blessed with several hotels that are part of the Myconian Collection brand; dotting the hillside, they look like adorable villages rather than hotels, and the most exclusive property is the Myconian Villa Collection (A+). Some accommodations boast private pools and Jacuzzis with a view.

CUISINE:

A top choice in Athens is Papadakis (A+), where celebrity chef Argiro Barbarigou serves up kakkavia fish soup, sautéed prawns with feta, and portokalopita (orange pie), made with yogurt and olive oil. The views from Blue Note (A+) in Santorini are so prime that the cuisine doesn’t even need to be as good as it is—but the grilled octopus and gruyere saganaki (pan-fried cheese) are to die for. Tucked away in a small square in Mykonos Town, Paraportiani Tavern (A) offers family charm and hearty dishes like lamb with okra in tomato sauce (the meat falls right off the bone) and fresh-baked pastitsio, a kind of Greek lasagna. In Little Venice, Galleraki (A) is arguably the most sophisticated place to take in the scene over a bottle of Ktima Alfa, a smooth, local white wine.