By: Jane Foster

Knossos. Elafonissi. Delos. Oia. Vlychada. Psarou. Symi. We’ve organized a potent array of Grecian wonders into three easy itineraries that include some superstars of the ancient world, little-trod beach gems, well-known-but-worth-it cliffside havens, and entire islands just under the radar. On Crete, the seat of the ancient Minoans and a world unto itself, we delve into lovely Venetian-era port towns and a sprinkling of remote beaches where merely wading through the turquoise water is an event. On Santorini and Mykonos (in the Cyclades), which continue to cast a spell over international celebs and merrymakers, we find the stunning sunsets are worth the hype and Psarou Beach is actually more paradisiacal than Paradise Beach. In the Dodecanese chain of islands, where Rhodes still reigns with the majesty bestowed by the Crusaders, there’s much to be gained by venturing out to Symi, Leros, and Patmos, where sites like the Cave of the Apocalypse are really old hat and untouched villages beckon with low-key charm.

Tourism is still Greece’s No. 1 industry—hardly surprising considering the Greeks’ well-known flair for hospitality—and after the 2004 Olympics, the services for tourists are smoother and sleeker than ever. Recent updates to the transport systems have made it easier to navigate the new Athens airport and metro. Mykonos hotels have adopted a white minimalist look and added luxurious wellness centers. On Crete, all-but-abandoned rural farmhouses have been reborn as eco-friendly agritourism centers. Likewise, in medieval Rhodes Town, historic buildings have been converted into small hotels, many furnished with Ottoman-style antiques. And modern Greek taverna fare, a lighter and more experimental version of the original, has been gaining a foothold in chicer destinations.

But perhaps just as appealing as what’s changed is what’s remained the same: Age-old traditions like Easter lamb roasts, grape and olive harvests, and saint’s day celebrations are still big to-dos, attracting participants of all ages. This heady mix makes for an undeniably crowded high season, but don’t despair. Our three trips will steer you to both marquee attractions and lesser-known treasures, so you’ll end up on a perfect island, in a perfect bar, watching a perfect sunset, after another perfect day.

Crete

Enjoy an abundance of riches, from ancient ruins to stunning beaches.

With rugged mountains soaring more than 8,000 feet, a staggering 650 miles of coastline, and remote, sandy beaches giving way to deep-blue water, Greece’s biggest island offers a bit of everything. While showcasing vivid landscapes, it also claims a fascinating history tracing back more than 5,000 years to the world’s first known “leisure civilization,” that of the ancient Minoans. The Minoans were followed in succession by the Greeks, Romans, Byzantines, Ottomans, and Venetians. Each culture left its mark—from the enthralling Minoan frescoes at Knossos to the charming Venetian-style port towns of Chania and Rethymno. Today, agritourism, aimed at visitors interested in nature and farm life, is a burgeoning enterprise. Our one-week itinerary traverses the island from west to east along the main northern highway, stopping in its four major towns, Chania, Rethymno, Iraklio, and Agios Nikolaos, with detours to several magnificent beaches, a world-class archaeological site, and a legendary gorge.

Start in the northwest, in Chania, once Crete’s capital and regarded by many as Greece’s most beautiful city. With the White Mountains visible in the background, the mottled facades of Chania’s old town curve around a lovely harbor, graced by a 17th-century mosque and a lighthouse. Near the harbor, pedestrian-only cobbled streets are filled with boutique hotels, stylish eateries, and shops with handcrafted items. Book a couple of nights at Casa Delfino (Casa Delfino Theofanus 9, Chania; from $251/night in summer; 30/282-108-7400, casadelfino.com), a former 17th-century Venetian palace with 22 rooms and suites, all including marble bathrooms. Or try Casa Leone (Thotokopoulou 18 at first side street, Chania; from $155/night in summer; 30/282-107-6762, casa-leone.com), a five-room, family-run boutique hotel; some rooms come with balconies overlooking the harbor. For dinner, try Tamam (Zambeliou 49, Chania; entrées from $9; 30/282-109-6080), for eastern Mediterranean mezedes (small plates of appetizers) in an Ottoman hammam, or friendly Portes (Portou 48, Chania; entrées from $8; 30/282-107-6261), which serves typical Cretan dishes like lamb with egg-lemon sauce.

Out of town, some remote beaches are worth a trip. For something really special, drive 40 minutes west to Kastelli (also known as Kissamos) and take an excursion boat to the fine white sands of Balos, overlooking an emerald-green lagoon. Or head an hour and a half by car southwest of Chania to Elafonissi, where a long, curving, white-sand beach faces a rocky islet, reached by wading through the turquoise waters. Stop for lunch near the mountain village of Vlatos at Milia (Vlatos; entrées from $9; 30/694-575-3743, milia.gr), a delightful agritourism center renowned for its organic specialties. If you’re in good shape and enjoy hiking, a popular venue near Chania is the steep-sided Samaria Gorge (Chania prefecture; 30/210-331-0392, visitgreece.gr), to which local tour companies provide day trips. The challenging 10-mile descent takes you from Xyloskala in the White Mountains, through pine forests into a deep, rocky canyon and eventually to a black-sand beach on the sunbathed south coast (where a ferry can await your return).

An hour east of Chania lies the university town of Rethymno, home to an impressive 16th-century Venetian waterside fortress, one of the island’s only surviving Ottoman minarets, and a harbor ringed by seafood restaurants. While summer is high season, the resident student population keeps Rethymno’s bohemian bars and informal tavernas buzzing the rest of the year. In the old town, check into one of the seven suites at Avli Lounge Apartments (Xanthoudidou 22 at Radamanthios, Rethymno; from $275/night in summer; 30/283-105-8250, avli.gr), with beamed ceilings and marble or mosaic-adorned bathrooms. A restaurant under the same management, Avli (Xanthoudidou 22 at Radamanthios, Rethymno; entrées from $25; 30/283-105-8250, avli.gr), serves upscale Mediterranean cuisine in the leafy courtyard garden of a 16th-century Venetian villa. Alternatively, continue 27 miles east along the coast to Enagron (Rethymo; from $100/night in summer; 30/283-406-1611, enagron.gr), an agritourism center in the village of Axos, where visiting guests can stay in traditional stone cottages.

Iraklio, Crete’s capital since 1971, lies 50 miles east of Rethymno. Not as pretty as Chania or Rethymno, it often hosts visitors en route to Knossos Palace (Iraklio; $8; 30/281-023-1940, odysseus.culture.gr). Built by the Minoans 4,000 years ago, this site was partially reconstructed (some say over-reconstructed) in the early 1900s. Grouped around a vast courtyard, the royal apartments and the throne room are not to be missed. For an overnight stay in Iraklio, try the GDM Megaron Luxury Hotel (D. Beaufort 9, Iraklio; from $231/night in summer; 30/281-030-5300, gdmmegaron.gr), with 58 modern rooms and suites, and a top floor bar-restaurant affording views of the harbor. For dinner, you can’t do better than Kounies (Sofokli Venizelou 19, Iraklio; entrées from $12, 30/281-030-1448), where chefs prepare lamb and chicken at an indoor barbecue area within the open-plan kitchen. While there, visit the south coast town of Matala (about 1 hour and 40 minutes away from Iraklio by car), renowned for its golden-sand beach backed by cliffs with caves, where a small hippie community, including the singer then known as Cat Stevens, lived in the 1960s and 1970s.

Some 41 miles east of Iraklio, the former fishing village and modern-day holiday resort town of Agios Nikolaos can become overrun by travelers on package tours, but may be worth visiting if you also want to venture to Elounda, 10 minutes by car to the west. This town, perched on Mirabello Bay, started out as five tiny hillside villages but is now an upmarket resort with some of Greece’s most luxurious hotels. If you feel like splashing out, stay at Elounda Gulf Villas & Suites (Agios Nikolaos; from $610/night in summer; 30/284-109-0300, eloundavillas.com), a family-run modern facility with an intimate atmosphere. Last but not least, drive 60 miles east of Agios Nikolaos, to Crete’s eastern coast for a day on Vai; lined with straw umbrellas, it’s home to Crete’s largest natural palm grove. The beach, a nature reserve, is pristine, but it can get crowded.

Getting There and Around
Crete has two main airports, in Iraklio and Chania, served by flights from Athens. There are regular ferries and catamarans from Athens’ port, Piraeus, to Chania, Rethymno, and Iraklio. A rental car is recommended; Avis (avis.com) and Hertz (hertz.com) have offices at both airports, while Eurocar (eurocar.gr) can deliver and collect cars from anywhere on the island.

Read our Crete Travel Guide for even more in-depth destination and trip-planning advice!

The Cyclades

On Santorini and Mykonos, drop-dead gorgeous scenery is just a backdrop for the fun.

Lying in the south Aegean Sea between mainland Greece and Turkey, the Cyclades provide the classic images of Greek islands—clusters of whitewashed houses built into sunbathed outcrops rising from a deep-blue sea. Santorini is probably the most dramatic of all the Greek islands, with eye-catching reddish-brown and black cliffs overlooking a unique sea-filled, volcanic caldera. And cosmopolitan Mykonos attracts international celebrities who flock to its hedonistic nightlife, smart hotels, and south coast beaches. Plan to stay at least three days on each of the two islands—and consider adding on a side trip to the relaxed, family-centric isles of Milos and Santos. 

Santorini
Santorini took on its extraordinary look when a massive volcanic explosion blew off a huge piece of the island some 3,600 years ago, forming the caldera, a 32-square-mile crater, filled with dark-blue water. Its two most stunning settlements, Fira and Oia, lie on the west coast atop sheer cliffs rising 1,000 feet above the caldera. The key word here is romance—these villages, offering stunning sunsets, provide an unforgettable backdrop for couples of all ages. Santorini draws visitors from the world over, including bold-faced names like Goldie Hawn and Kurt Russell.

Fira, the island’s capital and largest town, is a labyrinth of white cubic buildings. Most visitors base themselves here for its stellar selection of caldera-view hotels and the pedestrian-only alleys packed with jewelry stores and boutiques. Fira heaves with tourists in the summer, some from cruise ships docking in the tiny harbor of Skala, which can be reached from Fira with a descent of 580 steps. Thankfully, most ships depart by sunset, and as the town lights up for the evening, it’s sheer magic. Stay at the friendly, low-key Enigma Apartments & Suites (Fira; from $256/night in summer; 30/228-602-4024, enigmahotel.com) for accommodations including a kitchenette and a balcony or veranda with a caldera view.

Begin the evening in Fira with an aperitif at Franco’s (Fira; 30/228-602-4428, francos-bar.com), where sublime sunsets are visible from the terrace. For dinner, book a table at Selene (Fira; entrées from $18; 30/228-602-2249, selene.gr), whose creative Mediterranean dishes include baked sea bass wrapped in a fava crepe. Or, walk 10 minutes out of town to Vanilia (Firostefani; entrées from $15; 30/228-602-5631, vanilia.gr) in Firostefani, also overlooking the caldera, to dine on classic Greek taverna fare in an attractive garden. Nearby, socialites and celebrities flock to Fira’s most-talked-about nightspot, Koo Club (Fira; 30/228-602-2025, kooclub.gr), where you can stop for a nightcap in the palm-filled courtyard or hit the dance floor.

Santorini’s top cultural attraction, ancient Akrotiri (odysseus.culture.gr), a 5,000-year-old Minoan settlement, is closed for maintenance, but its artifacts, including impressive frescoes, are displayed at the Museum of Prehistoric Fira (30/228-602-2217). Devote your second day on Santorini to a boat excursion around the caldera from Skala, or, to avoid the hordes, charter a yacht, a splurge of about $150 per person for a group of six. In the middle of the caldera rise the uninhabited lava islands of Nea Kameni and Palea Kameni. The former is a semi-active volcano, with a smoldering crater, while the latter offers thermal mud springs suitable for bathing. For lunch, sail to the tiny island of Firassia, which provides fantastic views of Santorini.

Eight miles north of Fira, find Oia, possibly Greece’s most photographed village. Its winding streets are lined with traditional white houses and blue-domed churches. Take a taxi from Fira to this community of bohemian artists and writers with sophisticated hotels and eateries. A smart splurge, Perivolas (Oia; studios from $665/night in summer; 30/228-607-1308, perivolas.gr) is the top choice for an overnight stay. Its rooms are beautifully restored, 17th-century cave dwellings—vaulted spaces excavated out of a rock face and embellished with antiques and sea-view terraces. For dinner, Ambrosia (Oia; entrées from $33; 30/228-607-1413, ambrosia-nectar.com) serves Mediterranean dishes (try duck in red wine and cherry marinade) on a caldera-view terrace. If you’re up for a trek, follow the 214 steps down to the tiny harbor of Ammoudi, where the waterside Katina (Ammoudi harbor, Oia; entrées from $12; 30/228-607-1280), a moderately priced taverna, serves fresh fish.

Santorini’s volcanic soil supports rich vineyards producing some of Greece’s best white wines. On day three, take a taxi or a bus to SantoWines (Pyrgos; 30/228-602-2596, santowines.gr) and try its specialty, Vinsanto, a velvety dessert wine. For an afternoon on the beach, avoid overcrowded Kamari and Perissa, and head to the smooth gray sand of Vlychada.

Mykonos
Mykonos was the first Cycladic island to embrace tourism in the 1960s, and is now undoubtedly the most cosmopolitan and expensive of all the Greek islands. Base yourself in the port and capital, Mykonos Town, renowned for its glamorous nightlife, design hotels, and modern Greek tavernas. Built into gentle slopes that descend to a picturesque harbor, the old town is a maze of cobbled streets packed with whitewashed cubic houses sporting blue wooden shutters and draped in bougainvillea. Mykonos is loved by visitors from all over the world, though Americans and Europeans tend to predominate.

Stay at the peaceful Semeli (Mykonos Town; from $447/night in summer; 30/228-902-7466, semelihotel.gr), offering a splendid hillside location with great sea views, as well as a Mediterranean restaurant adjacent to an outdoor pool. The slightly more funky, 1960s-inspired Ostraco Suites (Mykonos Town; from $435/night in summer; 30/228-902-3396, ostraco.gr) has 21 all-white rooms and suites plus an outdoor pool. For dinner, try the friendly Mamacas (Mykonos Town; entrées from $15; 30/228-902-6120, mamacas.gr), serving unpretentious modern taverna fare in the heart of Mykonos Town. Trendy Gola (Periferiakos-Drafaki Street; entrées from $20; 30/228-902-3010, gola.gr), set on a hillside above town, is the place for upmarket modern Italian.

Mykonos nightlife is unashamedly exhibitionist, brimming with see-and-be-seen bars and clubs. For sunset cocktails, try Caprice (Lambrou Katsoni 8; drinks from $11; 30/228-902-2177, caprice.gr), overlooking the water in Mykonos Town. Late at night, head to the harborside to El Pecado (at the harborfront; 30/228-902-6747), where Argentinian tangos play into the small hours, or Pierro’s (Matoyanni Street.; 30/228-902-2177, pierrosbar.gr), a gay cocktail bar dating back to the 1970s and renowned for its drag shows.

The best beaches, along the south coast, are served by water taxis from Mykonos Town. The most talked-about are Paradise and Super Paradise, but they can get rowdy. Instead, head for the pale golden sand of Psarou Beach, which is more upscale and offers excellent water sports facilities. Have lunch at Nammos (Psarou Beach; entrées from $8; 30/228-902-2440, nammos.gr), a favorite with celebrities; its deck leads right back onto the sand.

For a cultural diversion, take a boat from Mykonos Town to the uninhabited island of Delos (Archaeological Museum of Delos; Delos; $6; 30/228-902-2259; odysseus.culture.gr), a UNESCO World Heritage Site known for the ancient Sanctuary of Dionysus.

Milos and Sifnos
Unlike their neighbors, these two Cycladic isles have a relaxed, family-centric vibe. It doesn’t hurt that they’re less trafficked and more reasonably priced, either. Connected to Santorini by ferry (two to four 2-hour trips weekly), Milos is blessed with silvery sand beaches, including Kleftiko and Gerontas, and striking rock formations. In Adamas, the handsome capital, Villa Notos (from $160/night in summer; 30/228-702-2193, villanotos.gr) offers studios and apartments with handcrafted furniture. In the fishing village of Pollonia, the luxurious Melian Hotel & Spa (from $203/night in summer; 30/228-704-1150, melian.gr) boasts all-white rooms.

Unspoiled but rather upscale Sifnos is known for its pretty coves and ceramics (daily ferries connect Milos to Sifnos). The port, Kamares, has an ideal beach for kids, while popular Platis Gialos is one of the longest beaches in the Cyclades. In Apollonia, the funky Patriarca Boutique Hotel (from $195/night in summer; 30/228-403-2400, patriarca.gr) occupies a restored 17th-century house, while the nearby charming Niriedes Hotel (from $229/night in summer; 30/228-407-1530, niriedeshotel.gr), by Platis Gialos, has a sea-view terrace where breakfast is served.

Getting There and Around
Santorini and Mykonos both have airports served by regular flights from Athens. You can also reach these islands by ferry or catamaran from Athens’ port, Piraeus. Through the summer, high-speed catamarans connect the two via the nearby island of Paros (Paros to Santorini, 75 minutes; Paros to Mykonos, 40 minutes). Don’t bother renting a car—taxis and buses are abundant.

Read our Mykonos or Santorini Travel Guides for even more in-depth destination and trip-planning advice! 

The Dodecanese

An Eastern-inflected island chain offers bustle and solitude

Close to the Turkish coast, the Dodecanese Islands had a turbulent history due to their strategic position. In the 14th century, the islands were ruled by the Knights of St. John, a religious military order affiliated with the Crusades, that constructed the mighty fortress of Rhodes Town as its main base on the largest island of the chain, Rhodes. The Ottoman Turks captured the islands in the 16th century, then the Italians seized them in 1912. The islands were reunited with the rest of Greece in 1947. Today, an intriguing mix of Eastern and Western cultures is still apparent in their architecture, food, and customs.

Rhodes, where you’ll most likely start your trip, teems with visitors (predominantly Americans, Europeans, and Russians) from spring through autumn. Yet staying there two days is worthwhile for the magnificent battlements and the charming town of Lindos. But it’s the smaller islands of Symi, Leros, and Patmos that can provide a sense of timeless calm.

Rhodes
On Rhodes, devote the first day to the impressive, UNESCO-listed old town, located within a massive fortress and ornamented with Ottoman minarets. Its pedestrian-only medieval streets can be packed, but visit the monumental Palace of the Grand Masters (Ipoto Street, old town; $8; 30/224-102-5500, odysseus.culture.gr). Inside, a museum dedicated to the history of the island serves as the entry point for walking a section of the city’s walls, overlooking terra-cotta rooftops and the sea.

Right in the old town, check into Marco Polo Mansion (Agiou Fanouriou 40-42, Rhodes Town; from $141/night in summer; 30/224-102-5562, marcopolomansion.gr), a 15th-century Turkish home with an interior courtyard garden and eight rooms furnished with antiques and textiles from Morocco and Turkey. For dinner, try Auberge Bistrot (Praxitelous 21, Rhodes Town; entrées from $20; 30/224-103-4292, bistrotrhodes.com), also in the old town, for sophisticated French Mediterranean cuisine served in a medieval courtyard.

Take one of the plentiful buses or taxis 29 miles southwest of Rhodes Town to Lindos, whose diverse attractions include a sweeping cove with a sand beach, a medieval fortress enclosing an ancient Greek temple, tightly packed whitewashed mansions, and streets paved with pebble mosaics. Although Lindos is full of day-trippers, a night at Melenos Lindos (Lindos; from $486/night in summer; 30/224-403-2222,  melenos-lindos.com) is blissfully romantic. This mansion, renovated in a 17th-century architectural style, has 12 suites, each with a private terrace for sea gazing. For dinner, the hands-down favorite is Mavrikos (main square, Lindos; entrées from $8; 30/224-403-1232), which has been cooking up homey Greek classics like grilled octopus since 1933.

Symi
North of Rhodes, the small rocky island of Symi (a 45-minute trip by hydrofoil from Rhodes Town) deserves its reputation as one of the gems of the Dodecanese. We recommend staying there overnight. Unspoiled Symi Town is comprised of two settlements: the port of Gialos, where visitors arrive, and the hillside Horio. Gialos is set in a steep-sided fjord, surrounded by the pastel-colored 19th-century mansions of Horio, and the two are connected by stone steps. Stay in Gialos at the Aliki Hotel (Akti Gennimata; from $166/night in summer; 30/224-607-1665, www.simi-hotel-aliki.gr), a charming waterside mansion, and dine at nearby Mythos (by the harbor; entrées from $9; 30/224-607-1488), which serves delicious mezedes. From Gialos, water taxis shuttle visitors to the pebble beaches of the east coast. Of these, Symi’s Agia Marina gives onto sapphire-blue water and a tiny island, while Nanou is set in a sweeping bay backed by cliffs. Water taxis also run to the southern tip, where Symi’s top cultural attraction, the huge 18th-century Panormitis Monastery (30/224-607-1581), presides.

Leros
Northwest of Symi, Leros (a little more than a 3-hour voyage by catamaran) remains relatively undeveloped; enjoy its radical architecture and idyllic beaches for one or two days. Of Leros’ two ports, you’ll probably arrive at Agia Marina, which is guarded by an imposing medieval castle. From here, buses and taxis run to the other port of Lakki, notable for its monumental rationalist style of architecture, a relic of the ’30s, when Mussolini wanted it to serve as a model town and naval base. Station yourself in the low-key village of Alinda (reachable by taxi), home to Leros’ best beach, a long strip of pale golden sand. Just a 5-minute walk from the seafront, Hotel Archontiko Angelou (Alinda; from $128/night in summer; 30/224-702-2749, hotel-angelou-leros.com) is a stately 19th-century villa set in a leafy garden. In the early evening, return to Agia Marina to feast on simple Greek taverna fare at Restaurant Milos (waterfront, Agia Marina, Leros; entrées from $12; 30/224-702-4894).

Patmos
Northeast of Leros is the unspoiled but sophisticated island of Patmos (a 50-minute trip by catamaran), known for its religious sites. Spend at least two days in Grikos, a fishing village with a long sandy beach 3 miles southeast of Skala, a 19th-century port town. Stay at the Petra Hotel (Grikos; from $348/night in summer; 30/224-703-4020, www.petrahotel-patmos.com), a boutique hotel with 12 rooms and suites that can be reached by local buses or taxis. For dinner, reserve a table on the terrace at nearby Benetos (Sapsila Street; entrées from $23; 30/224-703-3089, benetosrestaurant.com). The Greek-American owner-chef Benetos Matthaiou, has earned a cult following with his modern approach to Mediterranean cuisine.

Patmos’ tiny capital, Hora, is made up of 17th- century mansions clustered around the indomitable walls and towers of the Monastery of St. John the Divine (Hora; 30/224-703-1234, odysseus.culture.gr). A UNESCO World Heritage Site, the 10th-century monastery’s courtyards and arcades are blissfully tranquil, and its walls are decorated with richly colored Byzantine frescoes. Walk along a cobbled donkey path to Patmos’ other UNESCO religious site, the Cave of the Apocalypse (Hora; 30/224-703-1234), which lies on a hillside halfway between Skala and Hora, and is believed to be where St. John made his home and wrote the Book of Revelation in the 1st century AD. 

Getting There and Around
Direct flights from Athens serve Rhodes several times a day. Also an overnight ferry travels from Athens’ port, Piraeus, to Rhodes or Patmos. From Rhodes, daily high-speed catamarans and hydrofoils run through the Dodecanese all summer, so the region is particularly suitable for island-hopping. Taxis and buses are plentiful throughout the islands and are the best way to get around on them.

Jumping Off in Athens

Since you’ll most likely connect in Athens to flights or ferries to the islands, spend a couple nights there for a fine introduction to Greece, complete with ancient monuments and vibrant nightlife. From the airport, take a taxi to the city’s center, where you may catch sight of the symbol of Athens, the Acropolis (30/210-321-4172). Note that the entrance ticket will also provide access to other major sites, including the ancient Agora.

Stroll through Plaka, the city’s oldest residential quarter, made up of cobbled streets. Crowned by three ancient temples, the Acropolis has the magnificent 5th-century BC marble Parthenon as its centerpiece. No matter when you go, there will be crowds, but don’t miss the much anticipated New Acropolis Museum (newacropolismuseum.gr, 30/210-924-1043), a high-tech, all-glass structure designed by Swiss-French architect Bernard Tschumi and scheduled to open in June 2009.

For Acropolis-view rooms, book the smart Electra Palace (from $203/night in summer; electrahotels.gr) in Plaka, which has a roof terrace with a pool. In the nightlife district of Psirri, the design hotel Fresh (from $140/night in summer; fresh hotel.gr) boasts a minimalist interior and a rooftop bar-restaurant.

Go to the Michelin-starred Varoulko (entrées from $27; varoulko.gr) to savor some of Greece’s most creative seafood dishes while admiring the Acropolis from a spectacular rooftop terrace, For traditional taverna fare, stop at Psaras (entrées from $19; psaras-taverna.gr), one of Plaka’s oldest eateries, with wooden tables on the whitewashed steps leading up to the Acropolis.

Chartering a Sailboat in the Greek Islands

If you’re prepared to take up the challenge, sailing is a rewarding way to explore the Greek islands. Aboard a chartered sailboat you can plan your own route, choosing where and when to stop, whether for a night in a buzzing harbor town or for a day in a deserted cove. But be aware that sailing is not for the faint-hearted; even on a luxurious yacht, you’ll be exposed to the elements.

For people with little or no sailing experience, we recommend the Ionian Islands. Situated off the west coast of the Greek mainland, the Ionian Sea affords easy navigation, with light to moderate winds throughout summer. The majority of charter companies on the Ionian Islands are based on Corfu or Lefkada. We suggest any of the following: the Moorings (moorings.com), Kiriacoulis (kiriacoulis.com), Cosmos Yachting (cosmosyachting.com), or Ocean Nomads (ocean-nomads.com).

Charter a vessel bareboat (if at least two in your group are qualified sailors) or skippered. A skipper can arrange activities like scuba diving and wine tastings. Your daily schedule couldn’t be simpler: Breakfast and lunch are normally eaten aboard. If you don’t want to cook, the charter company can supply a hostess who will shop for provisions, prepare light meals, and clean the cabins.

By the time you reach the night’s harbor, you’ll probably be ready to dress up and dine out—your skipper can recommend favorite tavernas or even arrange a beachside barbecue. From $3,800/week for a group of six with an experienced skipper.

Making it Happen

GETTING THERE
By Air North America to Greece: Delta, Continental, and the Greek carrier Olympic (olympicairlines.com) offer daily direct flights from New York to Athens. Delta also flies directly to Athens from Cincinnati, Atlanta, LA, and Salt Lake City. US Airways offers a direct route to Athens from Philadelphia. Within Greece: Olympic, Aegean (aegeanairlines.com), and Sky Express (skyexpress.gr) all fly between the islands. Prices vary considerably depending on demand, which peaks in August. Reserve several months in advance if you’re traveling during high season to be assured of a seat.

By Ferry / Hydrofoil / Boat Piraeus, Athens’ port of departure for the islands, lies 7.5 miles southwest of the city center, and can be reached by metro or taxi. Navigating Piraeus is a bit of a challenge, even for Greeks. It’s a big port, and there are no hard and fast rules for the dock a boat will depart from. Arrive about an hour early to find your boat (last-minute changes are not unknown). Reserve one or two weeks in advance if you’ll be traveling by catamaran or hydrofoil or desire a private cabin on a ferry. Ferries normally sail regardless of weather, while catamarans and hydrofoils can be canceled due to strong winds, which are quite common in the Cyclades in August.

ITINERARIES
Flying is faster, but for many people part of the pleasure of visiting the islands is journeying across the sea and arriving by the water.

Cyclades to Dodecanese There are no direct flights from Mykonos or Santorini to Rhodes; all airline routes involve stops in Athens. Take a Blue Star ferry (bluestarferries.com) from Santorini to Rhodes (7 hours, 40 minutes). GA Ferries (gaferries.gr) and Lane Lines (lane.gr) also connect Santorini to Rhodes but sail via Crete, making for a long journey (approximately 17 hours).

Crete to Cyclades High-speed catamarans are the best option. Hellenic Seaways (hellenicseaways.gr) sails from Iraklio on Crete to Santorini (1 hour 45 minutes) and Mykonos (4 hours 40 minutes). Alternatively, take a Lane Lines ferry from Santorini to Sitea (5 hours 10 minutes) or Agios Nikaloas (6 hours 40 minutes) on Crete.

Dodecanese to Crete Aegean Airlines and Sky Express both fly between Iraklio on Crete and Rhodes Town (50 minutes). Otherwise, a Lane Lines ferry sails from Rhodes to Agios Nikolaos on Crete (9 hours 10 minutes).

WHEN TO GO
To avoid the high season (July–August) crowds, visit in shoulder season (May–June or September–October). In June and September especially, the weather is sunny and the sea warm enough for swimming, but without the crowds.

 

Read our Greek Islands Travel Guide, or individual Guides to Crete, Mykonos, or Santorini for even more in-depth destination and trip-planning advice!