Greece: Santorini

Where to stay: Oía, Fira

What to see/do: Santorini Town, Akrotiri, wine tasting, boat tours

Perhaps the most famous of the Greek Islands is the island of Santorini, also known by its ancient name of Thira. This jaw dropping island that we see today was created in the 16th century by the eruption of a volcano whose caldera flooded due to the eruption with waters of the Aegean, creating the steep cliffs and striking views that we know and love today. The towns of Santorini are built high atop the steep cliffs of the caldera and offer some of the prettiest views and spectacular sunsets of all the Greek islands.

When staying in Santorini, Oía is the hottest spot on the island for dining, shopping, nightlife, etc. It’s also home to the small port made famous by the movie The Sisterhood of the Traveling Pants. You’ll be in awe by how the city is built, clinging to the cliffside with its white facades and blue rooftops. It’s truly a sight to behold. While this island is incredibly beautiful, fair warning, it’s also incredibly packed with tourists at nearly all times of the year which can make navigating the narrow pathways difficult and a bit claustrophobic, not to mention getting a single photo without a person in the shot is, well, impossible. That being said, there’s no better place to watch the sunset over the Aegean than the Oía steps.

While on the island, if you’re a history/anthropology buff like me, you absolutely must rent a car or scooter and make the short journey to the other side of the island to visit the ancient town of Akrotiri. The incredibly well preserved Minoan settlement can trace it’s earliest roots back to the 5th millennium BC as a small fishing village, but expanded significantly by the 3rd millennium BC when it had become an important trade center and processor of copper and pottery. Much like the ancient city of Pompeii, Akrotiri was engulfed in ash during a 16th century eruption and left perfectly preserved protecting the structures, pottery, and even murals that are still visible to this day. Surprisingly enough, not a single human remain has been found during the excavations meaning that a timely, and orderly evacuation was carried out, saving many, if not every resident from the destruction of the volcanic blast. The site is protected by an equally impressive structure that was built over and around the remains of the village to protect it from further weather damage. You can get a chance to view the many rooms, work areas, elaborate drainage systems, and artifacts when meandering through the raised walkways that allow visitors a birds eye view of the impressive ruins. You may even see some archeologists actively working on the dig site.

While you have a rental car, I suggest touring the small island and taking in some of the other sites the island has to offer. On the eastern side of the island, not too far from Akrotiri is Ancient Thera, where you can wander around the ancient ruins nearly decimated by the eruption and take in the views from a different vantage point of the island. The ruins include an agora, stoa, theatre, temple of Apollo, grotto dedicated to Hermes & Hercules, gymnasium, courtyard, and commander’s headquarters. You may also check out Santorini’s Monastery of Profitis Ilias, built atop the highest point of the island and surrounded by vineyards. It’s prime location near the center of the island makes for some absolutely incredible views.

The island is rather small compared to some of the other Cycladic islands and, without stopping, you can tour around the island in about 45 minutes but there’s virtually endless historical sites, eateries, small neighborhoods and towns about the island to keep you entertained for hours, not to mention some incredible hiking. Something we found interesting about Santorini was the abundance of small caves built all over the island. Archeologists have identified these as cave dwellings built to house the impoverished dating about as far back as the earliest inhabitants of the island and were in use, in some cases, up until the 20th century and even today, as some have been converted into lavish hotels for well-to-do tourists. They make for some incredible exploring and photo opportunities.

Whether you’re into cocktails on the caldera, ancient ruins on the hilltops, or simply relaxing in the sun, Santorini offers a little bit of everything for everyone and will make a truly memorable experience no matter the time of year you visit. Unlike many of the other islands that become sleepy during the winter months, Santorini stays a bustling tourist hotspot throughout the year so you’ll never be short on things to see and do.