Bucket List Redefined: A Mindful Return to the Greek Islands

In a secluded bay surrounded by thyme-scented hills and a village crowned with a medieval castle, I enjoyed serene solitude on the sparkling Aegean Sea.

Last summer marked my fifth visit to various Greek islands, including the remote Astypalea. During the pandemic, the islands' crystal-clear waters, charming white-and-blue villages, breathtaking views, and the warm hospitality of the locals provided the perfect escape I craved.

The lack of typical mass tourism last summer at popular spots like Santorini, where I used to jostle for a sunset shot by the iconic windmills even in mid-January, allowed me to reconsider my travel priorities.

As travel restrictions have relaxed since the peak of the pandemic, the vast blue of the Greek islands calls this spring and summer—inviting a shift from capturing Instagram-worthy photos to enjoying conversations with a taverna owner over a cold glass of tsipouro, the strong Greek spirit, while waiting for takeout octopus.

The southern Aegean Sea is home to two archipelagos, the Cyclades and the Dodecanese, each boasting numerous islands with distinct experiences. From the least explored to the most glamorous, here are my top four:

Astypalea, the treasure of pirates

As the ferry approached the center of this butterfly-shaped island, a fleeting doubt crossed my mind—had I truly spent 10 hours traveling from Athens, the bustling capital filled with monuments, just to find barren mountains and a lone dolphin frolicking in the waves?

That doubt vanished in an instant upon seeing the chora, or main town—a striking blue-domed church above a medieval castle, all cascading down to the sea lined with windmills and a whitewashed village.

During two lengthy weekends, I never grew weary of admiring that 13th-century castle, whether illuminated at night with the air fragrant with herbs or standing proud under the sun as I swam in the most vibrant waters I've encountered outside a South Pacific lagoon.

After exploring the remnants of the castle where villagers once sought refuge from pirates, I paused to admire the white, crenellated Portaitissa church.

An elderly woman passing by gifted me a handful of freshly picked yellow plumeria blooms she was carrying. The presence of such tropical flowers in this stark, windswept landscape adds to its enchantment.

Delos, the divine birthplace

The ancient islands' mystical allure is most potent on Delos, a small islet just a short boat ride from the vibrant Mykonos. The ancient Greeks revered Delos as the sacred birthplace of Apollo.

His sanctuary, along with the temples and mansions constructed between the 9th and 1st centuries B.C.E., forms today’s archaeological park. I spent an entire day wandering through the majestic colonnades, lifelike sculptures, suggestive fertility symbols, and intricate mosaics depicting playful dolphins and a deity riding a tiger.

Tinos, villages of pride

Nearby Tinos revels in a more recent sacredness. Its chora is home to a revered sanctuary dedicated to the Virgin Mary, where last summer masked pilgrims ascended on their knees for nearly 1 kilometer (3,200 feet) from the port. The countryside is dotted with numerous smaller churches among stone-walled terraces and dovecotes resembling intricately carved towers.

From the grandest bell tower to the simplest dwelling, Tinian villages are adorned with marble from local quarries. Pyrgos features a marble craft museum, artists' workshops, and a marble-paved square with tiny coffee tables nestled around a towering plane tree.

I particularly enjoyed driving the mountain backroads at dusk, where the only traffic was a wandering goat, and the only lights were the blue silhouettes of church crosses.

Santorini, luxurious heights

Blue lights also illuminate Santorini’s villages—but these are the infinity pools and Jacuzzis of upscale hotels carved into the rim of the volcanic island that erupted into the sea 3,600 years ago.

The 10-kilometer hike from the main town of Fira to Oia, the most upscale village perched on the caldera formed by the explosion, traverses fields of black and red lava. Among the white pumice thrive tightly coiled vines of assyrtiko, the indigenous grape that family-owned wineries like Gavalas transform into unique, intense white wines.

The eruption also buried the ancient town of Akrotiri, whose vibrant frescoes are displayed at the museum in Fira, and whose archaeological site rivals ancient Thira, which sits atop a high hill overlooking the best beaches.

On my final afternoon in the islands, I reluctantly leave the black sands and deep blue waters of Perivolos beach to catch the sunset in Oia. Couples dressed in matching white outfits and sunburned tourists hurry along boutique-lined alleyways to the western edge, filling every available space on the intersecting terraces.

Just off to one side is the small cistern-shaped chapel with a white-and-blue bell tower, featured in countless engagement photos and Instagram feeds. Local kids have repurposed it as a goal area for their soccer matches.

A heated argument breaks out as the ball flies past the bell; for a brief moment, it is framed against the Aegean Sea, where the light shifts from orange to rose.

It could easily serve as the perfect image for a cruise ship brochure—but in this moment, it’s simply refreshingly Greek.