Best 7-Day Greece Itinerary: Islands, History & Culture

Gods without heads mark the Odeon of Agrippa entrance. Columns line the streets, casting shadows across the dusty ground. You will be in Ancient Agora, walking through more remains and ruins. While the Acropolis was the land of the gods, the Agora was the empire’s business and political hub. Grasp its history with your local guide before a mid-morning visit to the National Archeological Museum. Nowhere else in the world has such an impressive collection of ancient artifacts with gold death masks in the Mycenaean gallery, expressive marble figures from the Cycladic era, and Thira frescoes that hint at where you are heading this afternoon. Your guide will help you explore the highlights before you grab your luggage and head to the airport.

Santorini is five hours away by unreliable boats or just 50 minutes by flight. Touch down and transfer across the island, the vineyards and orchards leading to a sublime cliff-dominated coastline. You will be staying in Oia, the largest of the famous blue and white towns but also one that is relatively quiet, as nearby Fira is much busier with tourists. Oia is where Santorini’s visitors come to watch the sunset, and you will have a private view on your terrace perched above the old town and the Aegean Sea. Spend the evening strolling Oia, without a guide, a plan, or a map. This mazy little town has a treat on every corner, and the food is sublime, almost anywhere you dine.

Vineyards flicker in the morning breeze while orchards are punctuated by the faded grandeur of stone outhouses. A road twists through the valley, and slowly you approach a winery. The vines are old, and the terroir is volcanic here, creating a wine that even the Ottomans allowed during their prohibition period. The wine is acidic and dry, lots of citrus on the nose, and a lingering earthy finish. Pair it with some Santorini food delicacies, and you have a dreamy morning, complemented by a dreamy view over the island. Continue your private tour of Santorini in Akrotiri, a 5,000-year-old town that is still being excavated from volcanic dust. Frescoes have survived, along with ceramics and alleyways of three-tiered stone houses.

You will now be in the northeast of the island, and enjoy your lunch on the coast before an hour or two to wander, or take some time for a nap on Red Beach. The afternoon is dedicated to blue and white villages, those that Santorini is famous for. Explore Pyrgos and listen to how the church bells sing in harmony. Delve into Fira with your local guide, descending steps to small taverns and a microbrewery. You can then choose to walk the cliffs back to Oia, or travel by boat. Either way, you can gaze up at a stunning volcano, so iconic with its perfect shape and impression of nature. Evenings are quiet in Oia, and once more you can watch the sunset from your private perch.

Santorini’s history starts to make sense from the air. Beneath helicopter propellers, you can see the volcanoes and rugged ash fields, appreciating how civilizations have come and gone through the whim of nature. The island also makes sense on a catamaran, just in a completely different way. Cruise slowly beneath the cliffs with turquoise water all around as wind ruffles the sail. Tiny beaches hide beneath the cliffs, cut off from the land while caves impress more of Santorini’s volcanic history, visited by swimming or perhaps kayaking from the catamaran. Hot springs appear at a small islet in the Aegean, the water is not that hot but very refreshing on a warm afternoon.

After the bird’s-eye view, you now get a glimpse at the island’s rugged exterior. It doesn’t take long before there are no other boats in view. The captain lays anchor, and you drift off in the sun-loungers or go swimming in placid pools of blue-green water. As evening draws near you’re sailing back to Oia, enjoying a setting sun from the deck. Gradually the town’s lights turn on and perhaps the moon comes out to play, a peaceful scene that leads into your third night on Greece’s favorite island.

Although there are ferries to Crete, it is far better to fly as the schedules can be inconsistent. An early flight means you can be exploring Knossos before the early-afternoon crowds descend. This centerpiece of Minoan culture is now a maze of rough rock and rugged ruins, the stone surrounded by trees in a peaceful valley. Palace remains are the major highlight, the evocative state of ruin suggesting their true age. Standing before the ruins, you can appreciate that populations were thriving on Crete more than three millennia ago, long before visitors came for the coastline and beaches.

Heading into bustling Iraklion you can take your lunch in the Pantheon, which is not an ancient temple, but a lively market that’s stuffed with great food, so if you want to dine like the locals, this is where you come. Refresh and energize with a cafe stop on Ta Liontaria square, Venetian sculptures the backdrop to a thick, gloopy coffee. Staying in Iraklion, you can delve into Crete’s Archeological Museum. It is not as extensive as in Athens but is very detailed in its portrayal of Minoan life. After all the sights, it will be back to the Greek tranquility, and you will be staying just outside Ellinika, a small resort town that twists elegantly along the waterside.

Take it even slower today. The rhythm of the islands starts with a late breakfast and continues at a siga siga pace until sundown. It will be an especially slow rhythm in rural Crete, away from the tourist resorts, as this is an island with treasures that should be savored and that’s what you do today, the guide takes you on a scenic drive to the Lasithi Plateau. Orchards and cultivated fields cut a picture across the valleys, with strange hills casting shadows upon them. Windmills are dotted around while small, whitewashed villages are so sleepy you might not see a single person on their streets.

Hidden around here you find Psychro Cave, considered the birthplace of Zeus, if you can imagine that a god has a birthplace. There is a superb rural restaurant out here, perfect for a lunch that can last for over three hours. Eat, relax, eat some more. Drink, eat some more, wait for the heat of the afternoon to slip away. And only now do you finish the meal, perhaps after 4 pm. Complete the day trip on the Elounda peninsula, where the water is fresh and placid, back-dropped by palm trees, and the odd crucifix-topped church. Like yesterday, you will spend the night near Ellinika, enjoying a final evening of simple island pleasures.

There is a really early flight back to Athens this morning. Some may say too early, but it is worth it as you get to include one more magnificent attraction. Delphi is high in the mountains, a city of ruins mostly untouched by time. Temples are back-dropped by rugged peaks as the amphitheater gazes down upon an often mist-filled valley. Sculpted figures give you the eye while the Temple of Apollo suggests a grandeur that can rival the Athens Acropolis. This alluring place is ancient Greece at its very best, full of mystery and magic for your final day on vacation.

Driving back from Delphi is part of the experience, the road twisting through sublime mountain vistas, each corner a potential photo. You will reach Athens by 7 pm after the private tour, perfect timing for a final evening in Plaka. Relax on the hotel rooftop, wander the lively streets, dine on classic Greek fare, and glimpse up at the floodlit Acropolis. One week will have flown by in some senses, yet the country’s serenity ensures it feels like a break as well as an active adventure.

After a free morning, you are transferred to the airport for your outbound flight.