Oia

Known for being an excellent place to go for a swim and to fill up on the freshest of fish, spend the day at Ammoudi Bay, located just below Oia. The seafood is incredibly good and you’ll have your pick of fish taverns. I’m particularly fond of grilled octopus!

Oia at sunset is one of the most magical things I’ve ever experienced. While it gets extremely crowded, this is something you don’t want to miss. While there are many vistas to watch from, one particular favorite is from the Oia castle.

Alternatively, if you’re wanting to beat the crowds and you’re an early riser, sunrise is just as beautiful! The colors might be a bit softer, but you won’t melt from the heat or have to make your way through throngs of tourists to find a good vantage point. Remember that the sun won’t rise from the same spot where it set—so you may need to locate other prime spots for viewing.

We didn’t do a catamaran tour while we were in Oia, but it seemed like it would be a pretty spectacular thing to do! Some companies offer full day tours that end in the harbor around sunset, which sounds quite magical to me.

The true charm of Oia is found when exploring it on foot! Wander around and discover all the nooks and crannies of the cute little town. You’ll find lovely whitewashed alleys, picturesque staircases, and gorgeous bougainvillea framing doorways.

As charming as Oia is, I would highly recommend getting out and exploring the whole island! Renting at ATV and going on a self-guided tour is quite the adventure. You’ll need to get an international license to do so — check the guide for more instructions!

In 2002, several college students who were visiting Greece had a fantastic wine-fueled idea…they wanted to open a bookstore. The bookstore is quite enchanting with its painted decorative mural of books out front, and a staircase that descends down into the shop. The store, which resembles a cave stacked with books (mostly in English, but they also have Greek, French, Italian, German, Spanish, and Chinese on offer). If you’ve ever been to Paris, it may remind you a bit of Shakespeare and Co.

Does tasting local wines sound like the perfect activity to you? You can find wine tasting tours around the island or make a stop at one of the many wineries. Santo Wines (on the other side of the island from Oia, by the ferry port) is a pretty well-known stopping point, and if wineries with epic views are your calling—don’t miss this one! You’ll want to make a reservation, for tastings or a meal, in advance.

Put on your hiking shoes and trek from Oia to Fira. The hike is roughly three to five hours and you’ll have stunning views of the ocean as far as the eye can see. Once in Fira, you can find the Three Bells and Skaros Rock.

In both Oia and Fira, you’ll find a bunch of small artisan shops and boutiques featuring local crafts. Take the time to peruse and admire all the skilled handiwork!

Oia (and Santorini as a whole) has churches in spades. From ones carved into the cliffs to blue-domed churches overlooking the caldera, you could spend hours (and likely days) in awe of these gorgeous architectural delights.