Sailing Seasons in Greece: When to Go & What to Expect

Home to over 200 inhabited islands and thousands of rock islets, along with a lacy mainland coastline, Greece has long drawn sailors to its shores. Mariners from ancient times to the present day, among them Homer’s Odysseus and pilot book authors Rod and Lucinda Heikell, offer endless inspiration for yacht charterers.

This Eastern Mediterranean nation is the ultimate European summer yacht charter destination, beloved for its historical sites and traditions, crystalline seas and hearty cuisine. Above all, Greece is renowned for its warm hospitality.

The Greek islands, in particular, rank among the world’s best sailing grounds. What really sets them apart is the fact that each one is unique. Divided into six distinct groups and two standalone islands, the landscapes vary from the rugged Cyclades to the verdant Ionian. Even the hues of the water change. Around Santorini, the country’s best-known island, the deep waters of the Aegean appear royal blue, whereas Skiathos’ bays are sapphire-colored.

Greece’s yacht charter season runs from May to October with variable weather and sailing conditions, depending on the month. Here’s our guide on when to visit the islands and what to expect:

What Type of Yacht to Charter

Hellenic Yacht Masters’ Club founder and president Captain Dimitris Maroulis says that motor yachts represent 95 percent of yacht charters, while sailing yachts correspond to the remaining five percent.

“Most charterers prefer motor yachts so that they have the luxury of being able to visit more destinations,” he says. “Sailing yachts are also great boats to charter. They have a different appeal. When the sails are up, there is silence, and you’re closer to the sea.”

For avid sailors who enjoy the physicality and thrill of hoisting sails and relying on the wind to power the vessel, charter options include classic gulets and sleek performance yachts.

The Best Size Yacht to Charter

Maroulis recommends chartering a yacht between 131 feet (40m) and 197 feet (60m) for Greek waters. This size range is capable of handling the prevailing northwesterly winds of summer, which can be quite strong.

“Smaller yachts are also great, but when it’s a little rough in the Aegean, they’re not as comfortable. There is less pitching and rolling,” he says. Larger yachts offer more space and amenities, Maroulis points out.

“Due to our marina infrastructure … yachts larger than 197 feet (60m) don’t have many berthing options in the islands, or have to tender guests ashore,” he says.

When to Visit: Seasons on the Islands

The Mediterranean yachting season kicks into gear in May, while some charterers choose to arrive in Greece as early as April. When planning your yacht charter, consider where you plan to sail in Greece and with whom, along with the sort of experiences that interest you.

Spring and Early Summer

In spring, many of the islands, particularly in the lush Ionian and Sporades, are carpeted in wildflowers. Even the Dodecanese and North Aegean, whose landscapes tend to be rocky and scrubby, come alive in a burst of color. The sunny but moderate weather makes this an ideal time of year for hiking and touring ancient sites without the crowds. June sees long, languid days and nights.

Peak Season

August is peak summer travel season but also the liveliest time to be on the islands. Festivals featuring music, dance and art exhibitions abound, along with panegyria, feast day celebrations held in towns and villages. For the most popular islands, like Santorini and Mykonos, restaurant and bar bookings need to be made in advance.

Ideal Times to Charter: Weather and Cruising Conditions

Maroulis, whose roots lie in the Sporades island of Skopelos, recommends chartering in May, June, September or October. “The season starts in May in the East Mediterranean because the weather is really nice. The sea starts warming up and it is calm,” he says.

“Guests receive first-class services in every aspect during May and June, including marinas, dining and private guided tours. These are not the busiest months,” Maroulis says. He also enjoys cruising in early fall for the same reasons.

While July and August are the hottest months of the year, the northwesterly winds known as the meltemi arrive just in time to temper the heat. Most common in the Aegean, particularly in the Dodecanese and Cyclades, Maroulis describes the meltemi as “nature’s air-conditioning”.

“The Cyclades and Dodecanese are mostly bare and rocky. The land absorbs the heat all day and then releases it like a barbecue,” he says. Maroulis explains that the winds slowly appear at sunrise, strengthen during the day, then ease at sunset. At night, there is much less wind.

Exploring Greece’s Island Groups

The Cyclades

Famed the world over, the Cyclades convey the picture-perfect image of the Greek islands: whitewashed sugar cube-shaped homes, deep royal blue seas, and effortless cosmopolitan style. Showstoppers Santorini and Mykonos top the list of most desirable destinations, while Milos and Paros draw beach devotees.

The Ionian Islands

Off Greece’s western mainland coast lie the Ionian islands, beloved for their turquoise seas, white pebble beaches and fir-studded hillsides. The tranquil waters make this one of the country’s most attractive yacht charter destinations. Venetian influences abound in the Ionian, from Corfu’s intriguing old town to the vibrant neoclassical homes of Kefalonia.

The Dodecanese

To the southeast lies the Dodecanese, a collection of islands large and small. Traces of Roman, Byzantine, Ottoman and Italian rule are visible in carefully-preserved architectural treasures. Stroll the cobblestoned streets of Rhodes’ Unesco World Heritage-listed medieval Old Town, once ruled by the Knights of St John. Rock climbers flock to Kalymnos to tackle challenging routes with Aegean views from above.

The Sporades

Along Greece’s east coast lies the Sporades, a fertile assortment of islands, four of which are inhabited. Cruise your way between Mamma Mia filming location Skopelos, Skiathos, Alonissos and Skyros, whose Linaria marina is minuscule yet well-equipped. Pine trees, wild olives and oak trees generously cloak the land, while the sea is a dreamy shade of ultramarine.

The North Aegean

Few yacht charterers venture to the North Aegean, a cluster of islands with golden hillsides, silver sand beaches and an unwavering traditional character. Samos, the birthplace of Pythagoras, features excellent museums and far-flung fishing villages. Miraculous mastic gum is gathered from trees that grow only in the south of Chios, while Greece’s best ouzo is produced in Lesvos.

The Argosaronic Isles

Just a few nautical miles from Athens lie the Argosaronic isles. Aegina, a favorite weekend getaway for Athenians, and elegant Hydra have long drawn artists. Grand captains’ mansions line the seaside of sophisticated Spetses, where superyachts drop anchor for a night on the town at stylish restaurants and bars.

Crete

Not often thought of as a yachting destination, Crete is a world unto its own. Its southerly location ensures a longer warm weather season. Heraklion is home to a must-visit archeological museum and the Palace of Knossos, where the Minoan civilization flourished. Spinalonga islet, a former leper colony in the Gulf of Elounda, is a fascinating place to visit before cooling off in the cerulean waters that surround it.

Top-notch Services

Up until a decade ago, Greece didn’t possess the infrastructure that superyacht charter clients required, Maroulis notes. “Now, Greece offers high-end services in most islands and on the Athens Riviera,” he says.

“Brands like Four Seasons and One&Only Resorts offer services, such as premium dining that charter guests want. Besides the geographical beauty that Greece offers with its variety of islands, now the infrastructure is there.”

Santorini, Mykonos, Syros, Corfu, Tinos, and Kos offer a wider range of services for guests, Maroulis notes. “These islands have airports which make them easy to reach,” he says.

Docking and Anchoring

Where docking at a marina might not be possible or feasible due to lack of berths, Greece offers plenty of attractive anchorages.

Yacht charterers can locate designated areas where they can safely anchor on nautical charts, Maroulis says. “Every island has beautiful natural bays and coves, where you can drop anchor and stay overnight,” he says. Dinghies allow easy access to the shore. “You can anchor anywhere you want except for some areas that are prohibited due to the existence of Posidonia oceanica (protected seagrass endemic to the Mediterranean), underwater wrecks or cables,” he says.

Coves and bays in the south of an island are well-protected and calm, Maroulis notes, since 98 percent of the winds in Greece blow from the northwest or northeast.

Events Worth Planning Around

Greece’s islands host a plethora of exciting cultural events, showcasing tradition and innovation, artists local and international. Most are staged in July and August.

In June, Spetses hosts the Spetses Classic Yacht Regatta, organized by the Yacht Club of Greece, featuring a spectacular array of classic yachts, schooners and lateens. The highly-regarded Molyvos International Music Festival takes place on Lesvos in August. It showcases the talents of established and emerging classical musical artists.

Naxos’ 17th-century Bazeos Tower plays host to the Naxos Festival in August. Highlights include Greek music and theatre performances. Crete stages Dance Days Chania in July and August, an international contemporary dance festival featuring local and international acts.

Also in July and August, the Andros International Festival breathes life into an open-air theater in stately Andros’ capital Hora, with music, dance, theatre and visual arts.