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Two weeks allows time to take in the must-see ancient monuments in Athens and also get a good taste of island life. Though touring the islands can be require a bit of work and some logistics, we’ve tried to minimize the wear and tear. From the must-see ancient monuments (the Acropolis in Athens, the stadium in Olympia, and the site of the Delphic Oracle on the slopes of Mount Parnassus) to the famous isles (Mykonos, with its snow-white houses and trendy all-night bars, and volcanic Santorini, with its amazing harbor and sheer cliffs) to less famous places that not all visitors know about when they come to Greece (but fall in love with when they discover them)—we're going to show you how to see all this—and also keep some time for discoveries of your own.

Day 1: Athens

Start your first day in Greece with the landmark you can’t go home without seeing: the Acropolis. The ascent through the Beule Gate and up a well-worn path is stirring, and what lies beyond is even more so: The ruins of the perfectly proportioned Parthenon and surrounding temples, summoning up the glory of classical Greece. Continue the spell with a walk through the Acropolis Museum, where the sculptures and statuary that once adorned the Acropolis temples are on display, including the magnificent Parthenon Frieze. Then stroll along the Grand Promenade, a cobblestone-and-marble, pedestrian-only boulevard that skirts the Acropolis Hill. You’ll pass the Theater of Dionysus, where the newest dramas of Aeschylus, Sophocles, and Euripides once delighted audiences. Following Adrianou (Hadrian) Street through the colorful Plaka neighborhood, then end your sightseeing by strolling around the evocative ruins of the Ancient Agora, once the business and political hub of ancient Athens. After that, it’s time for dinner, maybe beneath a shady plane tree at a long-time favorite, the Platanos Taverna.

Day 2: Athens

Begin the day with a visit to Athens’ National Archaeological Museum, with the world’s finest collection of Greek antiquities. (Depending on where you’re staying, you may want to walk at least part of the way there, best up Athinas Street for a stop at the lively, colorful Central Market.) Essential galleries are the Mycenaean Collection, with gold death masks and many other magnificent treasures of the civilization whose king, Agamemnon, launched the Trojan War; the Cycladic Collection’s enigmatic marble figures; and the Thira Collection’s colorful and charming frescoes from Santorini. Find a spot for lunch in the atmospheric neighborhoods of Plaka or Monastiraki. Then make your way along Aiolou Street for a look at the Roman Forum and the adjacent Tower of the Winds, probably the city’s most unusual landmark from the ancient world. Turn off Aiolou into Pandrossou, a pedestrian alley that was the Turkish bazaar during Athens’ 400 years of Ottoman rule; the narrow lane lined with stalls is still souk-like. Continue west through the Plaka to Syntagma Square, stopping for a coffee and pastry at Oraia Ellada (entrances on both 36 Pandrossou and 59 Mitropoleos). Relax for a spell and soak in the spectacular view of the Acropolis. A walk across Syntagma Square puts you figuratively and literally in the center of Athens, with the formidable Parliament Building rising to one side. Follow tree-lined Vasillis Sofias, the city’s Museum Row, east to the Museum of Cycladic Art for a look at the elegantly simple and symmetrical marble figures created more than 3,000 years ago. Walk north through Kolonaki—a neighborhood favored by well-heeled Athenians—to the funicular that climbs Lycabettus Hill. From the breezy summit, there are mesmerizing views of the Acropolis and across the city to the sea. The spectacle is a good send-off, as it’s now time to collect your bags at your hotel, take the Metro to Piraeus, and board the Crete-bound ferry. Boats to the island, equipped with cabins and berths for a good night’s sleep, sail from Piraeus at about 9pm.

Day 3: Crete

You’ll dock in Iraklion early in the morning—too early to do much but enjoy a coffee. So, after stashing your bags at your hotel (you probably won’t be able to check in yet) join the other early risers at Kir-Kor, a venerable old pastry shop overlooking the fountains in Ta Liontaria (the Lions) square. The treat here is bougasta, a flaky, light-as-a-feather cheese-filled pastry. Since you have a whole day to work off the calories, also try the gloriously thick Cretan yoghurt with a generous drizzle of island honey. Next, head for the palace of Knossos, the dramatic ruins that about 3 millennia ago made up the center of Minoan culture. Then it’s on to the center of town and late lunch at the Pantheon in the market (actually, it’s in an arcade known as Dirty Alley, but don’t let that put you off the excellent food). Spend the rest of the afternoon in Iraklion’s Archaeological Museum for a look at beautiful frescoes portraying Minoan life and other exuberant artifacts of this sophisticated culture. As a cooling breeze picks up in the evening, it’s time to get back into the swing of modern life, but gently so, by joining Irakliots for a stroll around the old city.

Day 4: The South Coast of Crete & Rethymnon

On Day 4, you’ll head west to Rethymnon, but rather than taking the speedy National Road along the north coast of the island, go off the beaten path and head south across the mountains to the Messara Plain, some of the most fertile agricultural land in Greece. Set your sights on one of two beaches near the resort town of Matala—Red Beach, reached by a 20-minute hike south over a headland from Matala, and Kommos, a long stretch of sand just north of town. After a swim, head north and west again, with a leisurely amble through the scenic Amari Valley, a panorama of vineyard- and orchard-covered mountain slopes beneath the snow-capped peak of Mount Ida. On a high plateau just to the north of the valley, the ornate Arkadi Monastery is a patriotic landmark for Greece, the scene of a bloody fight against the Turks in the 1860s. Then make the half-hour drive down to the coast and Rethymnon, an inviting place to dine and spend the night amid an exotic maze of Venetian and Turkish houses, mosques, and a massive seaside fortress.

Day 5: Chania

It’s a short drive west from Rethymnon to Chania, only 72km (45 miles), but there’s no hurry—you’ve got time to make a detour onto the Akrotiri Peninsula, jutting into the Cretan Sea just east of Chania. The lands at the northern tip of the peninsula are the holdings of three adjacent monasteries. The most remarkable is the 11th-century Monastery of Katholiko, where St. John the Hermit and his followers lived in caves. A steep path leads past the hermitages and ends at the sea, where you can end your pilgrimage with a swim in a paradisiacal little cove. Then it’s on to Chania, one of the most beautiful cities in Greece. Settle in for 2 nights—we recommend Doma, an outpost of traditional Cretan hospitality, and the Porto Veneziano, so close to the water that you’ll feel like you’re on a ship. Then find a spot on the western side of the harbor, maybe the terrace of the Firkas, the waterside fortress the Venetians built—and take in the view of shimmering sea and waterside palaces. A good place for dinner is the Well of the Turk, tucked away beneath an exotic minaret.

Day 6: Samaria Gorge

The longest gorge in Europe, the Samaria Gorge is one of the most traveled places in Crete, but crowds of eager hikers don’t detract from the spectacle of its narrow passageways and sheer steep walls. Copses of pine and cedar and a profusion of springtime wildflowers carpet the canyon floor, where a river courses through a rocky bed. The hike ends with a well-deserved swim in the Libyan Sea. The easiest way to visit the gorge is on an organized tour. Chania’s Diktynna Travel is notable for its small groups and knowledgeable and personable guides. Trips leave Chania early, around 8am, and return at 6 or 7pm.

Day 7: Moni Preveli & Iraklion

You’ll be heading east again today, to Iraklion to spend the night before boarding a morning boat to Santorini. Take the day slow and easy. First stop along the north coast is the pretty town of Vrisses, which rests its fame on thick, creamy yogurt, topped with local honey and savored at a well-shaded cafe table alongside a rushing stream. Just outside of the town in the village of Alikambos, the Church of the Panagia houses some of the finest fresco cycles in Crete. Continue on the north coast highway, then detour south through the mountains to the isolated monastery of Moni Preveli, a beautiful place with a bloody past: its monks led rebellions against the Turks in the 1820s and during World War II hid Allied soldiers from the Germans. Palm Beach reached by a steep path from the monastery grounds, is one of the most lovely stretches of sand on Crete. You’ll be in Iraklion in time for an evening walk along the ramparts of the Koules, the mighty, wave-lapped fortress built by 16th-century Venetians.

Day 8: Santorini

Take an early boat to Santorini. You’ll probably be leaving around 9am and traveling by a high-speed hydrofoil. Though the airplane-like cabin is enclosed, try to wedge your way onto deck as the boat sails into the deep harbor with its high lava-streaked cliffs, created by a volcanic eruption around 1500 B.C. Sailing into Santorini is one of the world’s great travel experiences. Once you’ve checked into your hotel (or, if it’s too early to do do, at least leave your bags there), walk a portion of the 10km (6-mile) path that follows the top of the cliff from Fira to Ia, affording a bird’s-eye view of the outrageously blue waters and clusters of white houses perched on top of the cliffs like a dusting of snow. From stops along the caldera you can catch the bus to the southern end of the island and Ancient Akrotiri, Greece’s version of Pompeii—a well-preserved Minoan-era town that was buried in that same 1500 B.C. eruption that shaped modern Santorini. Adjoining the site is Paralia Kokkini (Red Beach), carpeted in red volcanic pebbles and perfect for an afternoon swim and nap. Come evening, take the bus back up the island to Ia, where watching the sunset is a celebratory event accompanied with a glass of wine. Then head down to Ammoudi, the little fishing port below Ia, for a seafood dinner at Katina’s or another waterside taverna.

Day 9: Naxos

A morning or early afternoon departure will give you the nice part of a day on Naxos, the largest, greenest, and most scenic island in the Cyclades. (The boat trip from Mykonos takes about 1 1/2 hr.) For a close-to-perfect island retreat settle into Villa Marandi, set in seaside gardens a couple of miles outside Naxos Town. Studios Kalergis is another nice choice, with attractive units hanging over Agios Yeoryios (St. George) beach at the edge of Naxos Town. Spend some hours relaxing before setting out for an evening walk out to the Portara, an unfinished ancient doorway above the harbor. Then follow the steep lanes into the hilltop Kastro, the Venetian fortress and the neighborhood of tall houses that surround the walls. It’s an atmospheric setting for a meal at Lithos or Taverna to Kastro.

Day 10: The Tragaea Valley & Naxian Beaches

Rent a car for a day to explore Naxos, with its appealing mountain valleys and long stretches of sand. In the garden of an estate in Melanes outside Naxos Town, you’ll find a 6th-century B.C. kouros, a huge marble statue of a beautiful youth. Villages on the lower slopes of Mount Zas, the highest mountain in the Cyclades, preserve the rhythms of agrarian life. Apiranthos, with marble streets, is especially pretty, and Taverna Lefteris is a good stop for lunch. To the south, near Sangri, some columns and walls of a Temple of Demeter, goddess of grain, still stand amid fertile fields. Just to the east is a string of sandy beaches that bring many northern Europeans to Naxos. Skirt the sands on small roads to find the most appealing spot; your best chance for finding a cove to yourself is at Pyrgaki, the southernmost beach on this stretch of coast but only 21km (13 miles) from Naxos Town.

Day 11: Mykonos

You’re island hopping in earnest now. In season you have a good choice of morning boats from Naxos to Mykonos, where you’ll arrive just after noon. Check into your hotel—our top choices would be in or just outside Mykonos Town, because this old Cycladic port is so beautiful and so convenient to the rest of the island. For hedonistic and stylish luxury, it’s hard to beat Cavo Tagoo, while the in-town Carbonaki gets high marks for good-value comfort and lots of charm. Now it’s time to hit the beach (aside from partying, this is the island’s favorite pastime). To see the most of the island in your short time here, rent a car—you’ll only need it for 24 hours. Paradise and Super Paradise are the island’s legendary beaches, but Agios Sostis on the north coast is much less crowded and just as beautiful, with warm, crystal-clear water washing the soft sands. You can get a late lunch at Kiki’s, a simple beachside taverna. In the evening, succumb to the Cycladic charms of Mykonos Town (better known as Hora), with its wooden balconies hanging from white cubical houses and outdoor staircases lined with pots of geraniums. A drink on a seaside terrace in Little Venice shows off the island’s worldly appeal.

Day 12: Delos

Begin the day with another swim at one or two of the Mykonos beaches that help put this all-too-popular island on the map for beaches. You might want to drop by Paradise and Super Paradise just to see the scene, but for some quieter beach time, drive out to Kalo Livadi (Good Pasture), a beautiful stretch of sand at the end of a farming valley, or Panormos, a dune-backed crescent edging a bay on the north coast. Wherever you choose to go, be back in Mykonos Town in early afternoon to return the car and catch a boat for the short crossing to nearby Delos. In ancient times this little outcropping was the most famous island in Greece—birthplace of Apollo, a sacred religious sanctuary, a flourishing trade center, and headquarters of the Delian League, the confederation of Greek city-states. As you step ashore and see such famed antiquities as the Terrace of the Lions, it soon becomes clear what all the fuss was about. The last boat heads back to Mykonos about 4pm, so plan your trip to allow 2 hours or so on the island—and remember to bring sunscreen and a wide-brimmed hat.

Days 13 & 14: Hydra

A morning boat from Mykonos will have you back in Athens by midafternoon. But don’t pack your island togs away just yet. For one last fling, turn right around and board a hydrofoil at Piraeus for the idyllic Saronic Gulf island of Hydra, about 2 hours away. You’ll arrive in plenty of time to check into your hotel and then have dinner near the harbor, maybe at To Steki. The next morning, you’ll have one more carefree island day to hike, swim, and roam through Hydra Town. A trip by water taxi to the beach at Ayios Nikolaos nicely shows off the rugged shoreline. Boats to Piraeus run frequently, from around 7am to 8pm, so you can time your return to Athens in the evening of Day 14 or morning of Day 15 accordingly.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.