Walking from Fira to Oia is one of Santorini’s highlights. Hike along the rim of a caldera, explore the towns of Oia, Imerovigli, Firostefani, and Fira, and enjoy some of the most beautiful views of the islands. If you go the entire distance, you will walk just over 10 km (about 6 miles). The walking path is a mix of paved, pedestrian streets and dirt hiking trails. It’s a hilly walk with little shade, however the weather should be mild in May and it is not a difficult hike. Along the way, you also have the option to make a detour out to Skaros Rock. This is an outcropping of rock located near Imerovigli. If you add this on to the walk, it will add another 45 to 60 minutes to the hike.
Wine tasting in Santorini has grown up in recent years and no place has demonstrated it more clearly than the cafe and tasting area at Santo Winery. With a world-class view from high above the famed caldera, this is a very worthwhile stop during your adventures on the island of Santorini. The location is a terrific place to view the sunset, offering a different angle on the caldera. There’s a sizable parking lot on-site, and Santo is accessible via buses from Fira, Perissa, and Akrotiri. Daily wine tours are offered for €12 per person, two tastings included; tasting flights range from €18 to €55. Call after 9:30am to make reservations or book online.
A hidden gem we discovered in 2014, Franco's is tucked away high up in the village of Pyrgos. Quaint, with a spectacular rooftop views, fresh food, and excellent service. The walk up through the village is spectacular, but a bit of a climb. Well worth it for this local favorite, especially during sunset.
Remains of a historical Town that was abandoned prior to the Volcano erupting on the Island of Santorini. This 11th century BC Dorian settlement includes remains from Hellenistic, Roman, and Byzantine periods. Fantastic views from the top of all the Island on a clear day. Well maintained & signposted spots of interest. Entrance cost is around 4 Euros.
Cine Kamari is one of the best outdoor cinemas in Europe. Watch a movie outside as the sun sets and the sky grows dark. Wine, beer, and simple snacks available. Tickets cost €8 and it’s cash only at the door and at the bar. All movies are popular current movies in English with Greek subtitles. Doors open at 8:30pm. Movies start at 9:30pm. There’s a bus stop directly across the street with buses back to Fira.
The home of the island’s in-demand Donkey beers is well worth a stop. Sample the Yellow Donkey (hoppy golden ale), Red Donkey (amber ale), the Crazy Donkey (IPA), the White Donkey (wheat with a touch of orange peel), plus the Lazy Ass lager. All are unfiltered, unpasteurised and extremely palatable. There are free tastings for visitors.
The Atlantis Bookshop in Santorini is one of my favorite bookstores anywhere. Definitely stop in for a visit (and support the store by buying something) if you’re in Oia. It’s on the main footpath that runs through town and pretty much marks the end of the Fira to Oia hike. The owners and staff are smart and helpful and love to help customers find a great book (or a good gyro) so feel free to start a conversation. The shop is on your left as you’re walking north (towards the sunset). But it’s small and easy to miss – just ask any store owner, “Bookstore?” and they’ll point you in the right direction.
Yazz Bar is located at the end of Perissa Beach. A popular beach bar in the area, the Yazz is full of action that lasts well past midnight in the summer days. The bar offers some of the most amazing smoothies and cocktails on the island. Great live music.