As a child growing up in a small midwestern town, I had a long mental list of places I wanted to visit someday.
Textbook photos of the impossibly blue seas, soaring mountains and abundant ruins — along with descriptions of its temperate climate — placed Greece on the top of that list for many years.
A few weeks ago, with a group of more than 30 Pioneer Press readers, I got to live out my dream trip with a 14-day tour of Greece’s mainland and a few of its islands.
This southern European country’s stunning landscape, deep history, delicious food and warm, welcoming people exceeded my expectations — so much so that I’m already plotting my return.
Here’s a day-by-day rundown of what we did during our Collette Vacations tour, led by our fantastic tour manager, Theodora Findou.
Days 1-2: Athens
The Parthenon in Athens, Greece. (Jess Fleming / Pioneer Press)
After a long flight, we dropped our luggage at the hotel and went for a walk in this sprawling city — a sea of pale-colored structures erected in the shadow of the ancient Acropolis.
Findou gave us a short orientation before letting us wander on our own to find coffee, lunch and it turns out, stunning ruins hidden amidst the city streets.
My husband, an archaeologist, and my 18-year-old son, who is his dad’s biggest fan, joined me on the trip, and those first few hours were special for all of us. Not only could we peep Athens’ most famous structure, the Parthenon, from where we were, but we also stumbled upon Hadrian’s Library, created by the Roman emperor in 132 A.D. Gorgeous pillars reach toward the sky on the middle-of-the-city site, which was surrounded by beautiful flowering bushes, making a picture-perfect scene.
We stopped for coffee — my son ordering his first of many, many cappuccinos (I think we created a monster), and me trying a frappe, a chilled, whipped coffee that fits the perpetually warm weather in Greece. Though I usually take my coffee black, I learned that the strong, bitter frappe needs a wee bit of sugar to counteract the strength. It’s also just what I needed on hour 24 of being awake.
We stopped in Monastiraki Square at a local restaurant for our first of many plates of souvlaki, the Greek version of kebabs. My pork was fresh and juicy and the pita pillowy and tasty.
After a quick refresh at the hotel, we got on the bus and headed to the charming Plaka neighborhood for our welcome dinner. We were seated on a gorgeous patio and treated to some live traditional folk music — and dancers! A few of our group members even got up and gave Greek dancing a try. It was a memorable start to our Greece experience.
The next morning, we were up early to beat the crowds at the Acropolis, the ancient city on a hill that’s visible from most of the city.
The sculpted lady columns of the Erechtheion, part of the Acropolis in Athens, Greece. (Jess Fleming / Pioneer Press)
We climbed up the easy side, which was still quite a workout for our jet-lagged bodies, and were treated to nearly unencumbered views of the Parthenon, the Temple of Athena Nike and the gorgeous Erechtheion, known for its sculptures of women that are actually working columns, quite a feat for the 5th century B.C., which is when most of the remaining structures of the Acropolis were built.
The Parthenon is the most impressive structure, with its marble columns standing 45 feet tall. It took 20,000 slaves to build and decorate the temple, which honors the goddess Athena, in just 15 years. It’s now off-white, but archaeologists say the original columns were gleaming white and the massive sculptures on the pediments above the columns were brightly colored, painted by artists of the time who thought white marble was ugly.
Many of those statues are, controversially, in museums around the world, but several can be found at the Acropolis Museum in Athens. We tried to get in, but the line was long, so I recommend reserving tickets in advance if you want to go.
While the Acropolis is awe-inspiring, I was equally enthralled with sights from the massive hill, including the exact spot where ancient Athenians went to collectively decide issues facing the community — the birthplace of modern democracy! We could also peep the small theater where drama first took place. We owe thanks to these forward-thinking ancient people for so many of the best parts of modern life. I couldn’t help but feel overwhelmed and grateful.
Day 3: Meteora
One of the monasteries in Meteora, Greece in the mist. (Jess Fleming / Pioneer Press)
I had been looking forward to seeing this crazy feat of 13th- and 14th-century engineering, which consists of Greek Orthodox monasteries perched on giant rock spires, since I saw drone footage of them on social media.
Unfortunately, it was pouring, so visibility, especially with a camera, was limited. Still, seeing the buildings in the mist was magical in its own right, and our local guide gave us insightful information about the monks and nuns who founded the monasteries and still live and worship inside of them.
The 900-foot-tall spires, which were originally (millions of years ago) on the edge of a sea, were formed through some unique geological magic — there’s nowhere else like it on Earth. Monks built on top of them because the spires provided isolation, and because they believed it would bring them closer to God. We saw the original “elevators” — giant rope nets — that the monks used to get materials to the top of the spires, because they didn’t initially have stairs or roads to get to the top. And we marveled at the gorgeous gilded paintings that adorn every wall of the chapels and a 12,000-liter wine barrel, because of course the monks were making wine!
After settling into our hotel, which had fantastic views of the Meteora rock formations, we had a traditional dinner at a Greek taverna, which, as we were learning, usually consists of many plates of everything from tzatziki to roasted vegetables to meat (so much meat — chicken, lamb, sausage and pork).
Day 4: Delphi
A priest works on an icon painting in his studio outside of Olympia, Greece. (Jess Fleming / Pioneer Press)
On our way out of the Meteora area, we stopped at a local art studio, where we saw a priest, his wife and his son creating gorgeous Byzantine icons, or religious paintings.
We watched their paintbrushes cruise swiftly over the canvases, using tempera paint mixed on the spot, using naturally colored powders, egg yolk and vinegar.
Many in our group purchased little paintings, which they watched the priest/artist sign for them.
Then it was off to Delphi, the main religious site for those who worshipped the god Apollo several millennia ago.
We started our visit with a guided tour through the site’s modern, gorgeous museum filled with treasures excavated after the site, which was traveled to by many in the ancient world who were looking for an encounter with the gods, was abandoned in the sixth or seventh centuries.
Columns from the Temple of Apollo at Delphi in Greece. (Jess Fleming / Pioneer Press)
Our guide explained that there used to be a fissure in the tectonic plates where ethylene and other gasses escaped from the Earth. That’s where the oracle of Delphi was, allowing a priestess to “speak to Apollo” and create prophecies, which were most likely gas-induced hallucinations.
An earthquake closed the fissure, and the site was eventually abandoned. Archaeologists began excavating it in the 1880s, discovering the site of the Temple of Apollo (and the oracle), a theater overlooking the sea, a row of treasuries (ancient banks) and a sprawling marketplace.
We finished our day by checking in to our hotel in Arachova, a town popular with locals for skiing that sports some amazing views of the surrounding mountains and valleys below.
Day 5-6: Olympia
Ed Fleming (foreground) and his son, Simon Fleming, on the original start line from the Olympic stadium in Olympia, Greece. (Jess Fleming / Pioneer Press)
My son was most looking forward to seeing the place where the Olympic games originated, but I don’t think even he could have imagined the wondrous site we would encounter.
A baby pomegranate at The Olive Temple in Olympia, Greece. (Jess Fleming / Pioneer Press)
First, though, we needed a pit stop at The Olive Temple, a local olive farm. We toured the facilities and tasted many of the farm’s flavorful, artisanal oils before being served a lovely souvlaki lunch and shopping in the well-appointed gift shop where most of us purchased oils, handmade soaps, lotions and even jewelry.
After checking in to our hotel, we were treated to a Greek dance class, where even the most left-footed among us learned some basic steps of the more than 4,000 traditional dances still practiced in the country today.
The next morning, we set out early for the ancient site of Olympia, where a tour guide brought us through a museum filled with iconic pottery, statues and most impressively, the Apollon of Olympia, statues that filled the pediments of the Temple of Zeus. The massive marble statues are mostly intact, and having them in the museum means you can walk right up to them and see the detail and artistry put into works that were originally 68 feet off the ground.
The archaeological site, which we wandered after the museum, is a marvel. We imagined Greek athletes training in the vast facilities for events like archery, boxing, running races, chariot races and more. Our son smoked my husband on the original “track,” where runners would start from one line of marble (still intact!) to another and back again, unlike today’s ovals.
Our guide explained that all of the original Olympic games were designed to train soldiers for battle. In this way, she said, they could avoid war. Because how best to stay out of a fight? Be the most prepared so no one messes with you. At least that’s the theory, then and now.
For lunch, we attended a cooking demonstration in town, where an Aussie woman who married a Greek man showed us how to make her husband’s family recipes, including cheese pie and tzatziki. For the latter, she enlisted the help of my reticent teen, who eventually warmed to the idea and has even made the tasty yogurt sauce since we’ve been home.
A sunset from the terrace restaurant of the Hotel Europa in Olympia, Greece. (Jess Fleming / Pioneer Press)
That evening, we had a delicious dinner at the hotel’s outdoor terrace, where we witnessed one of the most spectacular sunsets I have ever seen.
The next morning, before heading to our next destination, we made a few stops. First was to visit Klio, a small local honey producer, who gave us a rundown of how beekeeping began, what it’s like to keep bees now, and of course, samples of her products. After sampling, most of us bought some of her floral, delicate honey and beeswax salve.
Then we hit a small ouzo distillery, which makes some of the best of the anise-and-other-spice flavored spirit I have ever tasted. We were running out of room in our suitcases by then, or I would have purchased more than the small bottle we took with us.
Days 7-8: Nafplio
Bougainvillea vines line the streets of Nafplio, Greece. (Jess Fleming / Pioneer Press)
Before this trip was on my horizon, I had never heard of Nafplio, but the charming seaside resort town was a great place to spend a few days.
We spent some time wandering around town, poking into shops, admiring the flowering-vine-lined streets, sipping coffee and sampling gelato before hitting a seaside restaurant for dinner. Fried anchovies, crisp Greek sauvignon blanc and a swordfish souvlaki were highlights. My son was also enthralled with a few of the many, many cats wandering around (this is true all over Greece) and even fed a few of them some of his salmon steak.
The next day, we took a brief bus ride to Mycenae, an iconic site once ruled by King Agamemnon.
First, we stopped outside the city walls at the Tomb of Clytemnestra, named for Agamemnon’s wife, who according to legend murdered her husband after he sacrificed their son (Greek myths aren’t known for their happy endings). It’s unclear who was actually interred there, but the tomb itself is in excellent condition and shows the ingenuity and dazzling architectural abilities of the Myceneans.
Pioneer Press readers check out the inside of the Tomb of Clytemnestra in Mycenae, Greece. (Ed Fleming / Special to the Pioneer Press)
The tomb’s entrance is a long hallway of brick, and when you enter the imposing doorway, the space opens up into a beehive-like room that seems impossibly taller than it is. It’s an optical illusion, our guide explained. The tomb also serves as an echo chamber of sorts — you can stand on one side of the giant structure and speak in a normal voice and the sound travels around the sides of the tombs and reaches those on the other side.
We took a brisk tour of the on-site museum, aided by our local guide who pointed out many of the treasures found within the city, including a replica of the controversial Mask of Agamemnon. Many scholars think this solid gold funeral mask was planted in a Mycenean grave site by German archaeologist Heinrich Schliemann.
The author and her son at the Lion’s Gate entrance to the ancient walled city of Mycenae, Greece. (Ed Fleming / Special to the Pioneer Press)
The city itself, built on a hill and hidden behind enormous walls, was a major center of Greek civilization in the second millennium B.C. and is characterized by its famous Lion’s Gate entrance, which my husband was giddy to see in person.
We walked the site’s well-preserved streets and imagined what it must have been like to live in this bustling city full of artisans, craftsmen, religious scholars and royalty.
Days 9-10: Mykonos
Stained glass evil eye art in Mykonos, Greece. (Jess Fleming / Pioneer Press)
We had heard much about the chaotic loading and unloading of the ferries that travel throughout Greece’s many islands, and this was the day we got to experience one for ourselves.
Hundreds of travelers line up with their luggage and are herded onto the boat in mere minutes. Findou instructed us to stay together while she flagged down a worker who helped us put our luggage all in one place before heading up to our comfortable seats. Getting off the ferry is just as wild as getting on, but we all managed without losing any of our belongings.
It was all worthwhile, though, because Mykonos is, in a word, stunning.
The whitewashed buildings, winding mazes of narrow streets — built that way to confuse invaders — and colorful flowers and accents enchanted us as much as the bright blue Aegean Sea in which the island is situated.
Seafood souvlaki in Mykonos, Greece. (Jess Fleming / Pioneer Press)
Most of us stopped for lunch at a seaside restaurant where my husband ordered seafood souvlaki, served dangling from a sizeable metal hook, and we had our first taste of delicious Santorini wine (more on that later).
After a lovely dinner at the hotel, we were ready for bed, because the next morning, we were taking another boat to the nearby island of Delos, a major religious site where, mythologically speaking, Apollo and Artemis were said to have been born.
The small, rocky island was considered to be one of the most important ports in the ancient world, because of its proximity to Greece, Turkey and Africa. The massive temples and palaces of rich merchants that were unearthed since the island was mostly abandoned in the century before Christ show the amount of wealth that was concentrated here.
The ruins on Delos island in Greece include many nearly intact statues. (Jess Fleming / Pioneer Press)
Archaeologists are still uncovering parts of the island in one of the most extensive digs in the Mediterranean. The gorgeous stonework, mosaics, statues and temples are well-preserved and popular with tourists, so I’d recommend getting on the early ferry if you plan to visit.
That evening, we wandered through the maze of Mykonos looking for a place to eat until we stumbled upon an adorable little place called Cocotte, where we sampled some vegetarian dishes like giant beans, white eggplant and fried cheese, in addition to a carafe of the house wine, which was just $11 for a liter!
Days 11-14: Santorini
One of the many blue-domed Greek Orthodox churches on the island of Santorini, Greece. (Ed Fleming / Special to the Pioneer Press)
After another exciting ferry ride — we felt like experts at this point — we landed on one of the most beautiful, and popular, islands in Greece, Santorini.
The sizeable island was once round, until a volcano erupted and created the now crescent-shaped archipelago, which consists of four islands, the largest of which is Santorini.
Our gorgeous hotel was in Fira, the biggest city on the island, and after dropping our bags there, we were off to Oia, the village at the tip of the island best known for a series of blue-domed churches, often photographed with a backdrop of the almost equally blue sea.
A chicken gyro from Pitogyros in Oia on Santorini, Greece. (Jess Fleming / Pioneer Press)
My chef friend who had been to the island recommended a place for fresh gyros, so we booked it there as soon as we were set loose. Unfortunately, Pitogyros, a tiny spot with a tiny patio, is not a secret. Locals and tourists were lined up, waiting for takeout or tables. We waited nearly an hour for a seat, but were rewarded with the best gyro I have ever tasted. The fluffy, fresh pita was stuffed with chicken (they also have other meats) cooked on a spit and shaved so that the caramelized bits are present in every bite. Like many gyros in Greece, there were also french fries inside, along with ripe, juicy tomatoes and a generous helping of tzatziki. It was worth every second of that wait.
Because we waited so long, we had time for only a quick jaunt through the town before we had to meet the group to return to the hotel. I’d like to spend more time in Oia, but also, the crowds there are so crazy that it was Fira that captured my heart.
Giant pottery found at the site of Akrotiri on the island of Santorini, Greece. Intact grains, pomegranates and olives were discovered in the pots, which were located in a shop that had a window to sell to customers walking through the streets. (Jess Fleming / Pioneer Press)
The next morning, we took a short bus ride to the archaeological site of Akrotiri, a Pompeii-like city that was buried by a volcanic eruption. The Bronze Age (16th century B.C.) site, which is still being excavated, was incredibly well-preserved by volcanic ash. Inhabitants must have known from previous experience that an eruption was coming, because no human remains were found at the site, and very few valuable artifacts were found, leading archaeologists to believe that a mass evacuation took place.
The site is covered with a permanent structure to keep out the elements as archaeologists continue their work. It’s invaluable to have a guide, which we did, to point out parts of the settlement that non-historians might have difficulty deciphering, including a second-floor latrine that was basically a stone throne with a hole in the middle.
The museum for the site, which is in Fira, is a must-see, not only because of the gorgeous pottery and other artifacts that were found at the site but also because of the lower level, where you can see up close the frescoes that once adorned the elaborate settlement. Luckily, it was within walking distance of our hotel, so we visited the next day.
Colorful frescoes were rescued from the walls of the ancient site of Akrotiri, Greece, which was incredibly preserved because of being covered in volcanic ash. (Jess Fleming / Pioneer Press)
After Akrotiri, we stopped at Venetsanos, a winery with some of the best views on the island.
An employee described the three wines we tasted, which are made from grapes grown on the island. Because Santorini is so dry and windy, clever Greeks figured out how to weave the vines into basket-like bushes, which remain close to the ground. This helps the grapes stay hydrated — the lava-rich soil retains even the tiniest bits of water that fall on the island — and also protects the vines from strong winds.
The crisp, minerally, slightly saline Santorini white was our favorite, but the lighter red they produce is also worth seeking out. Not many of us were fans of the traditional sweet wine, which is made from grapes left to dry partially in the sun.
That evening, we walked through the sleepy village of Megalochori, which had a lovely art gallery where I bought an evil-eye necklace. The artist who made it took my payment from her studio space in the back of the “building,” which consists of rooms built into little caves. She did a brisk business that night, as many of us were enamored with the affordable artwork and jewelry, made by local artisans.
A whole sea bass on the island of Santorini, Greece. (Jess Fleming / Pioneer Press)
We ended the night with a fantastic dinner on one of the island’s famous black beaches. Course after course poured from the kitchen, served, as usual, family style. Greek salad, tomato fritters using the island’s famous tomatoes, grilled talagani cheese, served with a bright tomato marmalade, grape leaves, yellow split peas (and more) were followed by the main course of our choice. Many of us had the perfectly seasoned, ridiculously fresh sea bass. And some of that delicious Santorini wine, of course.
The hotel pool of the Santorini Palace Hotel at night. (Ed Fleming / Special to the Pioneer Press)
The next day we were on our own, so we visited the Akrotiri museum and wandered around town, doing a bit of shopping before returning to the hotel to spend time at its gorgeous pool, where many of our fellow travelers were lounging in the shade, taking a dip in the chilly water or having a nosh and a drink at the bar tables.
For dinner, we walked back into the city, where we dined at Pelican Kipos, on its spectacular terrace that is covered with all kinds of vegetation, from giant cacti to vibrant flowers. My husband and I kept it light with another smattering of fresh vegetarian dishes, but my son opted for the souvlaki, as he knew his days of eating Greek meat on a stick were numbered.
It was the perfect relaxing last day on the island after a busy tour.
Pioneer Press readers at the Venetsanos winery in Santorini, Greece. (Courtesy of Theodora Findou)
The next morning, after a quick flight to Athens, we checked into our hotel before meeting for our farewell dinner, at a taverna across the street. There were many, many delicious courses and many toasts — in Greek, cheers is “yamas!” — as we bid farewell to this magnificent country.
Want to travel with Jess?
We are currently promoting our summer and fall 2025 trips.
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