Sailing Around Greece in the Fall Offers a Second Chance at Summer

Here's why autumn is the best time to sail the Aegean Sea.

Galileo Ship in the Grecia Sailin Village
Photo: Gianluca Guidi/Courtesy of Variety Cruises

"Happy is the man, I thought, who, before dying, has the good fortune to sail the Aegean Sea," acclaimed Greek author Nikos Kazantzakis wrote in his seminal book, "Zorba the Greek." It's one of my favorite quotes from one of my favorite authors, and I held tight to those words as the small boat I found myself on last month pitched to and fro in the darkness of the sea, somewhere between Spetses and Paros. As objects fell out of my closet and off the walls, I comforted myself with the thought that at least if I drowned, I'd have had the good fortune to sail the Aegean Sea.

The Galileo in Syros
Courtesy of Variety Cruises

Given the good hands I was in, perhaps I was being a touch too dramatic. Captain Yannis, a man with both decades of experience and the kind of substantial sailor's beard I implicitly trust, had certainly navigated much worse. The night before, he had invited me and my companion to his bridge, where he regaled us with stories of his long career (including a youthful near brush with death aboard a ship somewhere off the coast of South Africa). As he pointed out the constellations in the night sky, the conversation veered into philosophical terrain: the cosmos, the infinity of horizon, the possibility of alien life. Had I been on a regular cruise ship, I doubt the captain would have even had the time to say hello.

That's just one of the advantages of sailing Greece on a small boat during autumn. In early October, I set sail with Variety Cruises, a small luxury cruise ship company in Greece. A family-owned business now in its third generation, the company was founded back in 1949, when Diogenis Venetopoulos started taking post-World War II tourists on trips around Greece. Since so many of Greece's most beautiful sites — like Delos, the ancient archaeological birthplace of Apollo and Artemis — are accessible only by boat, Diogenis started renting out fishermen's boats to ferry his customers between ports. Quickly, he realized that he had found a niche: small cruises with flexible itineraries.

Cabin on board the Galileo Ship
Nikos Psathoyiannakis/Courtesy of Variety Cruises

Today, Variety Cruises has 11 boats, the biggest of which can hold 73 guests. Their cruises around Greece are up to a week long, and generally take guests to one new spot every day, docking during the day and sailing at night. "It's all about intimacy," Variety Cruises CMO Constantine Venetopoulos, grandson of Diogenis, tells me. This is nothing like a regular cruise ship — the crew learned our names within half an hour, and people quickly made friends with each other. The size of the boat meant that we could also sail to smaller ports and hidden beaches, simply dropping anchor off one beautiful cove or another.

There are many advantages of traveling to Greece in the fall. Most of the time, the weather is better than the summer — the heat has dissipated, but the skies are still candy blue and the water has retained enough heat that swimming is painless. The weather can be a bit fickle — we had to cross off Santorini and Folegandros due to extreme wind — but those kinds of last-minute changes felt deliciously adventurous. Instead, we sailed through the Sporades islands, stopping in Paros and Spetses, and stayed tight along the Peloponnesian coast, ending up in modern Greece's second capital city, Nafplio, for one day, before braving the winds to cross to the Cycladic islands.

The Sundeck on the Galileo
Courtesy of Variety Cruises
Aerial view of Grecia Sailing Village
Gianluca Guidi/Courtesy of Variety Cruises

Most people, lured by hot weather and cool waters, choose to come to Greece in the summer. Over the years, this has translated into a boom of overtourism, as island populations swell, putting a strain on natural resources. In July and August alone, Greece received over two million tourists — more than any other European country. "Of course, Greece summer — and specifically Greece in August — is very special," says Constantine. "There are so many people, tanning, swimming, partying, it's like the Caribbean of Europe. But autumn changes everything. It makes it just about the destination."

Traveling off-season is not just more relaxing (and affordable), but it's also the more sustainable choice. There's less risk of overcrowding and abusing an island's natural resources, like water. Variety Cruises is well aware of tourism's contributions to the environment — this year, it became the first cruise company to join Tourism Declares a Climate Emergency, and is committed to developing a climate emergency plan in the next year.

Kayaking and swimming from the Galileo Ship
Courtesy of Variety Cruises

Plus, traveling in autumn is easier on the locals. "You can become part of the community in autumn," Constantine adds. That's nearly impossible to do in the summer, when people are working around the clock to service tourists. But when all the tourists leave, people resume their daily habits: playing backgammon in the street, having leisurely conversations over syrupy coffees in cafes. The streets empty out. In tony Spetses, we rented electric bicycles to tour the tiny island. Initial directions were provided by a middle-aged woman hanging her laundry over her balcony, but for kilometers at a time, we were the only wheels on the road. It felt like we had the island to ourselves — an impossible situation in August.

"Time slows down," Constantine says. "The destination slows down."

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