This Family’s Epic Vacation Story Is Proof Off-Season Travel Is Underrated

This mother-daughter duo was skeptical about vacationing in Greece in November, but a simple attitude adjustment gave them just what they needed to enjoy the vacation of a lifetime.

Go. Stop. Go. Stop. The travel signals in my head were mixed, conflicting. “Are you sure you want to head to Greece this November with Kathleen?” asked my husband. “The weather could be unpleasant.”

A take-charge kind of person, my daughter quickly Googled “November weather for Athens.” “Temperatures will be slightly warmer than in New York City,” she said. “And rainfall for the month—in the two-inch range—doesn’t sound like a monsoon. As for rough winter seas, let’s hop on planes instead. We’ll have endless hot-from-the-oven, spinachy spanakopita, imagine that, and be fine.”

“You must go,” said my friend Larry, who raved about having spent Thanksgiving on Santorini. “Sunsets are among the most gorgeous in the world and the island is the legendary location of the lost city of Atlantis. It’s a paradise. All you’ll need is a warm hooded jacket.”

With his encouraging words, I booked our flights to Athens and included two Greek islands: Santorini (how could we resist such a place?) and Crete. Renowned for beaches and an abundance of ancient ruins that my parents had delighted in seeing years earlier, such as the Palace of Knossos, Crete was the furthest south of all of Greece’s islands. Translation: It has a high sun-warmth factor, a way to increase odds for a successful trip.

Go, go, go….

Sunshine and a brisk Saturday afternoon welcomed us to Eleftherios Venizelos Airport in Athens. During the next days Kathleen and I devoured the crispiest spanakopita imaginable; we ranked our favorite feta, cucumber, tomato and olive-studded salads, and tried unknown-to-us foods. No annoying lines of tourists either, as we saw sights on the Athens “A” list: from the Acropolis and Archeological Museum to the ancient Panathenaic Stadium. We poked around the ruins at Delphi, home of the famed Oracle and once considered the center of the universe.

And then came Tuesday. Heavy rain kept us dashing between museums and stores. The next day’s flight to Santorini was yo-yoed by wind gusts up to forty miles an hour, our stomachs bumping up and down, our view obscured by squalls. “I’m truly sorry,” the flight attendant said. “The storm has stalled.”

victoria wilkinson brownless/Getty-ImagesThe cliff-top town of Fira, normally a much-photographed tourist destination, was chilly, rainy, foggy… empty. Only a darker grey fuzziness differentiated land from sea. With rain streaking our faces, wind whipping our jackets, Kathleen and I edged along a cliff to our hotel and checked in for a three-night stay, the only guests. As we stepped down steep stairs toward our bungalow dug into the cliff itself, a gust of wind suddenly pushed us toward what we’d been told was a sheer 500-foot drop into the Mediterranean, still obscured by fog.

Unnerved, unsettled, we fled into the cave-like rooms. We tried to read. We heated up tea with honey to settle our queasy stomachs. Read a little more. “This isn’t how I want to spend my vacation,” said Kathleen, who hadn’t smiled in hours. “Maybe Crete isn’t experiencing the same storm. Can we fly out later today?”

Her question mirrored my own thoughts, and yet I felt trapped by commitments. We couldn’t leave. We’d just arrived. Payments for the hotel and rental car would be lost, and costly last-minute plane reservations needed. And, oh yeah, I could hear myself telling my husband, who’d thought the trip ill-advised, that we’d never actually seen Santorini’s famous views. Like the photo in our bungalow showing a white-walled Cycladic church with a brilliant blue dome overlooking the sea, one of the more than 250 churches on the 11-mile-long island. “Nope,” I’d have to tell him, “we didn’t see anything.”

“Let’s not decide right now,” I suggested to Kathleen, trying to put pep into my voice. “At least let’s give the place a day.”

“Okay,” said Kathleen.

What? Where did her change of heart, her sense of grace come from? To my surprise, and now sounding as cool as a Greek cucumber, she added: “Let’s give it a try. I just came to a realization. I want adventures when I travel—not predictable beach vacations. I want experiences that are awakening and exciting. So, if not too cold and rainy, I’d like to explore the island and see what makes people call it a paradise.

“But,” she continued pragmatically, “maybe we needn’t stay the whole time.”

We were a silly sight—our colorful plumage of clothing consisting of long-sleeved shirts under hooded sweatshirts, and puffy vests, pashminas and gloves. And thus warmly adorned, we sped off on adventures:

… Up a rocky hill to ruins at ancient Thira. With the rain easing, we drove to the southern side of the island and then climbed up rugged switchbacks. To reach the old hill-topper village with the remains of a few houses and the agora, or market, we had to inch cautiously over a thin slippery land bridge with an unsettling 1,200-foot precipice on one side and a jagged slope on the other.

“Can you believe this?” asked Kathleen, exhilarated by crossing safely. “We’re retracing steps Greeks made thousands of years earlier, perhaps daily since their farms were on flat land along the sea far below.”

… To another cliff-side village, Oia. Despite more showers, we stayed another day and ventured to Oia. A friendly woman corralled us on a deserted street and in excellent English asked, “Would you like to attend my church’s feast day?” The tiny Greek Orthodox church she attended was the size of a very large American kitchen. Several dozen black-clad women were singing and talking in one corner, more people than we’d seen in the entire town. They pressed glasses of sweet red mavro wine into our wet hands. Showers lifting, we stepped back outside and marveled at the town’s precarious perch on the cliff’s edge.

“The earthquake of 1956 caused immense damage,” said the woman, pointing to abandoned cliff cave houses, known as skafta. “It was the Aegean’s largest quake of the twentieth century. It wasn’t as damaging, of course, as the volcanic eruption of 1650 BC that blasted out the center of the island, but homes crumbled, some tumbled into the sea, and yet as before our lives somehow went on.”

As we imagined such an occurrence, the woman disappeared into the church. She emerged carrying two platters. “Try these buns,” she said. They were filled with a pocket of crispy sesame seeds. Her hospitality was like a warm embrace of friendship, especially when she added, “The seeds will bring you good luck.”

… To black sand beaches. Red sand, too. The boarded-up restaurants and villas along the beach didn’t bother us. The wonderful upside of this emptiness meant the beaches were ours alone. In damp black sand our footprints edged deeper.

… To VERY leisurely meals. No reservations needed. At a restaurant named Poseidon, on our third night (yes, we stayed the full time and did see Fira’s iconic blue-domed church), we waited and waited, and waited some more, for dinner: artichoke-stuffed squid and grilled grouper with a tomato-olive sauce. “The chef is now back,” our waiter explained sheepishly. “Your dinner will be out shortly. The chef was busy studying something beautiful.”

Seeing our puzzled look, the waiter then confessed, “He went out for a smoke, saw a beautiful girl and began to flirt until the owner started to yell and, and, and….”

Suddenly, Kathleen laughed. Instead of reprimanding the waiter impatiently, she leaned back and smiled, and out came a loud, happy sound. A joyful laugh.

Courtesy Elinor Allcott Griffith, GettyAn attitude adjustment into grace, I realized, had been happening since our arrival. My daughter had shifted into a “going-with-the-flow” mindset. She was the one leading me. As she explained later: “You know Mom, you can’t live a positive life with a negative, critical mind. I’m learning that Greek people have their own wonderful sense of time and priorities.” The tables had truly turned. After an initial struggle with the messy weather, Kathleen had helped dispel the layer of gloom clouding my thoughts, my mood. Her own sense of grace contained a valuable realization about the unpredictability factor in travel—and life. Her new view: try to deal gracefully and affably with whatever happens.

Several days later on Crete, sunny and warm as anticipated, we continued to relish the off-season travel pleasures of uncrowded beaches, museums and historical sites. In driving merely half an hour out of the modern city of Irakleio, for instance, we visited the Palace of Knossos—in essence, time traveling back to around 1700 BC, or so it felt because again we were virtually the only ones there. Well, and the ticket-taker and four strutting, trilling, iridescent blue-green plumaged peacocks.

“Give me a pinch,” said Kathleen. We were now facing a charging bull, actually on an ancient fresco. “I can’t believe we’re in the same palace once visited by Grandma June and Grampa John,” she said. “I’m so glad we traveled to Greece in the off-season.”

Grace surrounds us. The challenge is to let go of anxieties and worries, the tendency to complain, that can hover nearby like a Greek fog. A sunny disposition—your sunny disposition, wherever you are—can let grace shine and clear the air for everyone. That and a hooded jacket!

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Originally Published in Reader's Digest International Edition