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Planning a Boomer Adventure cruising through the Greek Islands

Cruising the Greek islands is an incredibly popular activity for travelers of all ages. And of course, there’s good reason for that. The Greek islands are not only scenic, but also boast an immense history that goes back millennia. Did you know that there are more than 6,000 islands surrounding Greece?

Recently, guest contributor, Phyllis Rose shared her tips for Exploring Greece by Land. Now, she’s back with tips on what to see and do while cruising the Greek islands. Boomer adventures guaranteed! 

Cruising the Greek Islands on a seven-day voyage

The Greek Islands have always been synonymous in my mind with the “high life,” as in the lifestyles of the rich and famous. What surprised me on my seven-day cruise aboard the Celestyal Crystal is that these islands have been centers for the “high life” for millennia.

My seven-day Greek Island cruise included five fascinating ports of call. Discover the must-see Greek Islands both famous and not-so-famous.

Greek Islands stop #1: Delos

ancient ruins with three columns

The once thriving island of Delos is now an archaeological site filled with broken columns and statues.

The surprise started in Delos, a barren archaeological ruin inhabited only by archaeologists, guards, and cats. As far as the eye can see, broken columns and statues rise from the general rubble.

That first impression belies the fact that Delos was once a sacred site and a busy commercial port. With such an amazing history, it won’t surprise boomer travelers that Delos is on the UNESCO World Heritage list.

Discover Delos history

Legend says Zeus impregnated the human, Leto, infuriating his wife, Hera, who exiled Leto. But Zeus won, persuading Poseidon to create an island for Leto, and that was Delos.

Here, Leto gave birth to twins: Apollo, the sun god, and Artemis, the moon god. So, the island became a sacred site, visited by faithful followers.

With the help of the Delian League promoting trade to the island, Delos eventually became a shipping center with a population of 30,000.

But in 88 B.C. the island was attacked and most of the inhabitants slaughtered. Essentially, Delos disappeared until 1872 when French archaeologists began excavating, work that continues today.

ancient statue of a lion

This lion on the Terrace of Lions is a copy. The surviving originals are in the museum on the archaeological site.

Archaeological treasures to see on Delos

Of the interesting things to see, there is the Terrace of the Lions, marble lions given to Delos about 3,000 years ago. The people of the island of Naxos gave the lions to Delos to guard the Sacred Lake where Apollo and Artemis were born. The lions on the terrace are copies but the originals can be seen in the nearby museum.

There’s a theater, built about 300 years before Christ, that could seat 6500 people. You can stroll among the ruins of 3,000 shops and through the various neighborhoods.

The homes were built around courtyards often featuring intricate mosaics. You can see their plumbing system and marvel at the fact that they had indoor plumbing, definitely a symbol of the high life.

Independent tours of Delos:

Greek Islands port #2: Mykonos

view of beachside buildings

These colorful homes make up the area of Mykonos Town called “Little Venice.”

Nearby Mykonos owes its high-life reputation to ultra-rich jet setters from the 1950s like Grace Kelly, Elizabeth Taylor, and Jackie Onassis.

The main town, Mykonos Town, bustles with tourists shopping for souvenirs, dining in seafront cafes, and just strolling through town up to the iconic windmills.

upclose shot of windmills

About 100 years ago, these windmills on Mykonos ground grain into flour.

The town’s lanes are maze-like so we were pleased that Nico, our tour director, led us up to the windmills which ground grain into flour until about 100 years ago. From our perch near the windmills, we could see the colorful eighteenth century homes in the area called Little Venice. At one time, pirates stored plunder in these homes.

Back in the port, we had a Coke at a seaside cafe and enjoyed the ambiance. We watched the Aegean sun create an orange and gold backdrop for a two-masted schooner anchored in the port. That’s a high-life moment—free of charge and unforgettable.

Explore Mykonos independently:

Island cruise stop #3: Milos

all white landscape looking out over the sea

The dramatic landscape of Sarakiniko on the island of Milos is often described as a “moonscape.”

If you’ve been to the Louvre in Paris, you’ve seen the Venus de Milo, a statue of Venus with no arms. On Milos, you can see where a peasant discovered the statue in 1820. The site along a gravel pat is scenic, overlooking the sea.

The most stunning place on Milos is Sarakiniko, a gleaming and blindingly white “moonscape”. It could easily be a location for a science fiction movie set on another planet.

The wind and waves erode the volcanic rocks giving them their whiteness and  making them look like snowdrifts whipped into artistic formations. Swimmers, divers, and hikers find this a fascinating place.

Our last stop before returning to the ship was at the Mouratos Bakery to sample a traditional watermelon pie—thin like a pizza with a semi-sweet watermelon topping.

Have fun in Milos on your own:

Greek Island stop #4: Santorini

view of the santorini coast

The coast of Santorini as seen from the capital of Fira.

Santorini is the most dramatic of the Greek islands due to a volcanic explosion in 1630 B.C. After the volcano blew out its innards, it collapsed in upon itself, creating the caldera or volcanic crater, surrounded by a crescent-shaped island.

The main towns and villages sit atop the volcanic ridge, accessible by tour bus, donkey or cable car. Our first day we went up by tour bus and drove along the ridge to the town of Oia which is about 250 feet above the sea.

Here you’ll take fantastic photos of the white-washed, blue-domed churches with the bright blue waters of the caldera in the background. It’s also a high-end shopping destination, featuring art galleries and jewelry stores,

The second day on Santorini, we visited the archaeological site at Akrotiri, a city buried by the volcanic eruption in 1630 B.C. It’s a sprawling site which has been excavated since about 1967.

view of the santorini coast

The coast of Santorini as seen from the town of Oia.

Unlike Pompeii, Italy, where the volcanic eruption of Vesuvius in 79 A.D. caught the populace off guard, the Akrotiri residents had enough warning to flee the eruption. Thus, no human remains were found. As you tour the site, you’ll see archaeologists at work.

Both days, we had lunch in the capital city, Fira, at lovely restaurants overlooking the caldera. They were wonderful places to rest, enjoy some moussaka, and soak up the beautiful scenery. There are numerous restaurants with views. Don’t even think about eating where there is no view.

A quick cable car ride took us down to the port where we caught the tender to our ship. That night before sailing to Crete, we looked up at Santorini, where the lights of the towns and villages crowned the ridge like Christmas lights—another high-life memory.

Explore Santorini on your own:

Greek Island Stop #5: Crete

people in front of a greek church

The Church of St. Titus in Heraklion, Crete, where the skull of St. Titus is kept in a silver reliquary.

Our last stop was Crete, the largest Greek island and home of the archaeological site, Knossos, which some call Europe’s oldest city. At the archaeological site, you can see the remains of the palace of King Minos, who according to mythology had Daedalus build a labyrinth which was home to the Minotaur, a half-man and half-bull creature.

An Athenian prince, Theseus, sailed to Crete to fight the Minotaur in the labyrinth. King Minos’s daughter, Ariadne, fell in love with Theseus and devised a scheme for him to navigate the labyrinth. She gave Theseus a ball of string to unwind as he went into the labyrinth so he could find his way out. He killed the Minotaur and then he and Ariadne fled the island to get away from her angry father.

an ancient building with fresco of a bull

A painting of a bull can be seen on the ruins of the palace at Knossos. Bulls were sacred to the Minoans.

Bulls were sacred to the Minoans. In the archaeological site, you’ll see a fresco of a bull on the palace wall. Nearby is a stone slab shaped into two horns, known as the horns of consecration.

From other palace frescoes, now on display at the Archaeological Museum of Heraklion, you can learn about the Minoan sport of bull-leaping. One fresco shows three people, one grabbing the bull’s horns, one sailing over the bull’s back, and the third one having just landed behind the bull.

After immersing ourselves in ancient history, we were ready to explore Crete’s capital, Heraklion, which has lots of places to shop. We strolled along the 25th of August Street, featuring shops in an outdoor bazaar-like setting with all the magnets and easy-to-carry-home souvenirs you could want.

Here we also saw the Church of St. Titus which houses the skull of St. Titus in a silver reliquary. Also of note is the Venetian Loggia of the Town Hall. Although it has been renovated over the centuries, the loggia dates to 1620.

Our high-life tour of the Greek islands had come to an end. We sailed away with a new appreciation for these dramatic islands that have drawn not only the rich and famous, but also modern-day travelers sailing Homer’s “wine-dark sea” into the mists of history and mythology.

Visit Herkalion on your own:

What to pack when cruising the Greek Islands? Donna recommends:

It’s hot in the Greek Islands, especially during summer cruises. To look good but beat the heat, pack a few of Donna’s favorites:

More Greek Island fun

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