Visit Oia

Oia is the most famous village on Santorini, known for its whitewashed buildings, blue domes, pedestrian streets, and sunsets. It’s on the northwest edge of the island and extends for about 1.2 miles (2 kilometers) along the edge of the caldera. The narrow streets and buildings are carved into the hill and built into niches and caves of the caldera.

You need to visit Oia, first and foremost, just to see this stunning town. Every alley and staircase brings you to another breathtaking vantage point. Make sure you see the ruins of Oia Castle, also called Fort Londsa, with a true 360-degree view of Santorini, the other islands, and the caldera.

You need to see the sunset at least once from Oia.

Other places to visit are the old windmills and at least one of the 70 whitewashed churches in the town. You can also visit the Naval Maritime Museum, a restored 19th-century mansion that displays rare figureheads, ancient nautical charts, seamen’s chests, old maritime equipment, and historic photographs, letters, and documents.

You also need to walk down to Amoudi Bay for great views of the town and the caldera, but the walk back up is rough, so any of the restaurants on the bay can call you a taxi.

The Fira to Oia Hike

Hiking from Fira to Oia (or Oia to Fira) takes you along the rim of the caldera through the villages of Fira, Firostefani, Imerovigli, and Oia. The hike can take about two hours if you’re walking at a steady pace and don’t stop very often. But the whole point of this hike is to stop and enjoy the views, so it can take as long as you want it to take.

At roughly 6.5 miles (10.5 kilometers), the path alternates from sidewalk to cobblestone to dirt path. Terrain wise, the walk isn’t difficult, but it’s long, and parts of the trail are uphill. Make sure you have plenty of water, and in the summer, you should start early in the day or the late in the afternoon to avoid the peak heat.

The route is well-marked and well-traveled, so you don’t need to go with a tour group, but guided tours (some of which include additional excursions or stops) are available if you’d like. One option is Fira to Oia: Guided Walking Tour.

This trail isn’t meant for strollers or bikes. Entering “Fira to Oia” on Google Maps will give you a walking route that skips some of the best views. You should stay on a footpath almost the whole time. If you’re walking on a road with cars (except for one short stretch between Imerovigli and Oia), you’re doing it wrong and missing out on some stellar views.

Sail around Santorini

As impressive as the caldera is when you’re standing on its edge, looking down at water where land used to be, you also need to see the caldera from the water.

There is an abundance of options for sailing around the island – yacht tours, private tours, group tours, etc. If you’re visiting Santorini as part of a cruise, then you’re already going to get those looking-up-at-the-island views, but taking a smaller boat around the island is still something to consider.

Some tours go to different beaches around Santorini, some boats visit the other islands, some tours stop so you can swim in hot springs, and some boat anchor so you can eat dinner on the water and watch the sunset.

I did the Santorini Platinum: Luxurious Small-Group Catamaran Cruise, but you can find a cruise around the island that suits your budget, time frame, and interests.

Hike to Skaros Rock

Skaros Rock is a conical peninsula with a large rock formation on the top near the town of Imerovigli that was once home to a castle that protected the island from pirates. Ruins of the castle can still be seen on top of the rock.

It’s about an hour walk (round trip) to and from Skaros Rock from Imerovigli, but that’s not including any exploring you do on and around the rock once you get there. You can detour to Skaros Rock from the Fira to Oia hiking trail, or you can explore Skaros and Imerovigli as a separate excursion.

Skaros Rock protruding out from the town of Imerovigli

Start at the Grace Santorini Hotel in Imerovigli, go past the Church of Agios Georgics, and then you’ll see the path to Skaros. You’ll climb down for a while, then come to another church at the base of Skaros Rock. You can take a steep path up to the top of the rock, but the views from the base of the rock are spectacular if the climb isn’t for you.

A Food and Wine Tour

Thanks to its rich volcanic soil, Santorini is renowned for its vineyards, fava, cherry tomatoes, and other produce and crops. You can do a food tour through one of the island’s 18 wineries, or there is an abundance of tour options to choose from on Trip Advisor and Santorini Tours.

I did the Eat & Walk Santorini Food Tour through Airbnb, which included wine, beer, and olive oil tasting in addition to an abundance of local dishes. This tour also doubled as a walking tour of the town of Fira. Find a food and wine/beer tour in a town you want to visit with the culinary emphasis you’re looking for, then sit back and enjoy.