The Best Time—and Ships—for Sailing the Greek Islands

Earlier in September, while cruising the perfectly blue waters of Greece, our vessel, the 600-passenger Seabourn Ovation, landed on the uninhabited Cycladic island of Delos, off Mykonos. There, my brother and I walked through ruins of a millennia-old trading port at the mythical birthplace of Apollo, the Greek god of light. The timing could not have been better—with fall approaching, tourist crowds were thinning out. And the temperature had already dipped from the high 90s of summer to a more comfortable low 80s, better for island exploration.

With fewer passengers onboard than usual due to pandemic limits and softer off-season demand, our shore excursion group was less than a dozen guests for our outing from the port in Mykonos. The intimacy of our group gave local guide, Amaryllis, the opportunity to provide more in-depth explanations and storytelling.

We happened to visit Delos on the same day that renowned Greek composer (and Marxist rebel) Mikis Theodorakis died at age 96 (an event marked with grief and remembrances throughout the country), and I shared that I once interviewed him for a magazine story years ago. Amaryllis replied that it was no coincidence our conversation about Theodorakis was taking place on Delos, “the island of light,” which some believe to be a spiritual place. “He is speaking to you and knows it is important to share this with me,” she said, tearing up.

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I found that traveling through Greece later in the season increases your odds for these meaningful and memorable encounters. This is the type of more personal experience you can have away from the crowds of July and August.

What to do and see in Greece in the fall

Greece can be stiflingly hot in summer—this year temperatures reached 100 degrees Fahrenheit. But Athens cooled to a more comfortable lower 80s by the first week in September, much better weather for climbing up to the ancient Acropolis.

By October, temperatures typically dip to the 70s, with the chance of rain increasing later in the month. The Aegean Sea stays warm through October, so swimming remains an option, as does taking advantage of outdoor dining and sightseeing with light breezes. On a smaller ship such as the Seabourn Ovation, which has its own watersports platform, you can take a dip in the water right from the ship, borrow watersports equipment such as kayaks, or take a fun-filled banana boat ride—all still perfectly pleasant in the fall. Beaches and sunbathing remain options, too.

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There are other advantages to Greece in fall. From mid-August to October you can catch the grape harvest on islands such as Santorini, Rhodes, and Crete—winemaking is a tradition that dates back to the ancient Greeks. If you book a hiking excursion, such as Seabourn’s Cyprus hike to explore the Troodos Mountains as part of its partnership with wellness guru Dr. Andrew Weil, you may catch some fall foliage. In the small village of Elos in western Crete, fall is celebrated with a chestnut festival featuring dishes made from chestnuts, live music, traditional dancing, and homemade liquor made from grapes and honey.

What it’s like cruising in Greece right now

I’ve been to Mykonos in previous years when at times you could hardly walk the narrow streets because they were so clogged with tourists, but that was not the case on this trip. There was no jostling to get into designer shops or tables at oceanfront restaurants. And you could pause and take photos of the picturesque, white-washed houses, windmills, and blue-domed churches without being photobombed.

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In Rhodes, my brother and I toured rooms at the Palace of the Grand Masters, built by the Order of St. John of Jerusalem, which occupied Rhodes from 1309 to 1523, with only a handful of other visitors in sight. On some summer days, with the normal gaggles of tourists, the place is so crowded that you can’t even see the mosaic floors.

There is also the fall advantage that locals, recovering from the typically busy summer season, are getting back to their lives. Folks we encountered were universally welcoming and openly expressed gratitude that we had chosen to travel to Greece.

Nafplion, the capital of Greece from 1823 to 1834, is one of the country’s most charming cities with its cobblestone and red-roofed Old Town, neoclassical mansions, squares, and parks. My brother and I hiked nearly 1,000 stone steps and up 700 feet to the towering Palamidi Fortress for unobstructed views of the city and the sea, then rewarded ourselves with mezes (Greek appetizers) such as grilled sardines, stuffed eggplant, and dips at the Arapakos seafood restaurant on the harbor. In a fine display of Greek hospitality, our waiter thanked us with a complimentary platter of fruit and a very broad smile. We were among the few patrons there.

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The best fall cruises in Greece

The big advantage of sailing around the Greek Isles by ship is that you can easily travel around the mainland coast and to several islands without the hassle of dealing with ferries, local flights, or searching for decent accommodations—the ship is your home. And what better home (albeit a temporary one) than an ultra-luxurious ship such as the Seabourn Ovation, where everyone stays in a spacious suite, complimentary champagne flows freely, and you can order caviar whenever you have a craving?

Due to the pandemic, there were only 230 passengers on our sailing, few enough to make it feel like we were on our own private yacht at times, but also a sufficient number so that we could always find at least a small dance party at night. The crew of 415 memorized all the passengers’ names and served up excellent selections at the sushi restaurant, aged steaks and lobster Thermidor in the ship’s Thomas Keller steakhouse, dishes showcasing black truffle, caviar, and other gourmet ingredients in the Restaurant, and custom-designed craft cocktails. A favorite meal was a lavish Indian cuisine buffet at the Colonnade, the vessel’s casual dining spot.

Courtesy of Seabourn

The Seabourn Ovation is in Greece into October with fares for a seven-night cruise starting from $4,500 per person. Another ultraluxury option is Regent Seven Seas Cruises with fares starting at $5,800 per person for Greece cruises on the 750-passenger Regent Seven Seas Splendor (the ship does Greece sailings through mid-November). Upscale, destination-focused line Azamara has ships sailing in Greece into November with fares starting at about $1,500 per person on the 694-passenger Azamara Quest. If you miss out on these 2021 fall sailings, Seabourn will return to Greece next year with cruises on the 450-passenger Seabourn Encore from April through November 2022, with fares from about $4,800 per person.

COVID health protocols

On May 14, Greece became one of the first countries in the European Union to reopen to U.S. visitors. At press time, fully vaccinated travelers did not have to show a negative PCR test on arrival. (You will need a test for your return flight to the U.S.) All of the cruise lines mentioned above are requiring guests be fully vaccinated.

For the Seabourn cruise, guests were required to be vaccinated and to show a negative PCR test taken within 72 hours of boarding the ship. In addition, all guests were given a rapid antigen test at the pier prior to boarding. After clearing the test (it took about 15 minutes to get the results), guests were brought into a separate pier-side check-in area and offered their first chilled glass of champagne.

All crew on the ship were vaccinated and tested regularly. While the crew wore masks, passengers were able to go mask-free. It felt like cruising did prepandemic. And with everyone onboard vaccinated and tested, it also felt, in many ways, safer than in some of the restaurants and hotels on land. In Greece, there are masking rules in museums, on public transport (including the crowded ferry we took to Delos), and in some businesses, though not in uncrowded outdoor areas. Before touring Cyprus, about 20 passengers, including my brother, were chosen randomly for an additional test at the pier.

We were also tested toward the end of the cruise and given the required proof of a negative COVID test result for re-entering the U.S. from abroad.

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