Santorini may be the most famous of the Greek Cyclades islands – certainly with honeymooners and Sisterhood of the Traveling Pants fans (anyone..?) – and can therefore be super crowded and expensive. I visited in May (2023), however, and found the crowds to be really reasonable and hotel prices not too bad as it was still shoulder season. Plus, the weather wasn’t too hot yet which was great because it definitely feels like you’re on a volcanic island – not much shade!
On that note, I didn’t really grasp until I was actually there that the island is really just the rim of the “caldera” – the volcano cone – such a unique experience and it really does make for incredible views. If I went back with more time and money I would definitely take a boat tour that gets you out into the middle of the caldera, and where you can see some of the smaller islands that make up other parts of it. But even without the boat ride, there are still amazing views and more than enough to do with 48 hours or a weekend in Santorini!
Day 1 – Pyrgos & Fira
- 5pm – Take the bus out to the village of Pyrgos, just a little south of Fira. You can walk up to the top of old castle for panoramic views around the island, and maybe catch the sunset as well.
- 7pm – Grab dinner and enjoy the views of the cliffside whitewashed buildings in Fira lit up at night.
Day 2 – Fira & Oia
The main agenda today is to hike between Fira and Oia – a 10km walk that can be done in either direction, allowing for exploring both towns at either end of the hike.
- 9am – If it’s a hot day, probably best to start the hike in Oia in the morning and head back towards Fira. But if it’s not too bad, start the day with breakfast and some exploring in Fira, then do the hike towards Oia in the afternoon so you can enjoy a famous Oia sunset!
- 12pm – If you’re in Fira for lunch, you can’t go wrong with Lucky’s Souvlakis.
- 1pm – Hiking from Fira to Oia, make sure to bring water and prepare for about 4 hours of walking (moderate pace, includes some time for taking photos). Your first main stop is Skaros Rock, which is well worth a quick detour to see some ruins and great views back towards Fira. You can also go into the town of Imerovigli here if you need to find food, but the main path goes around the edge of town.
- 5pm – Arriving in Oia, take a little time to look around but if you want to watch the sunset from a restaurant, bar, or even a popular staircase (with a picnic!) be sure to snag a spot plenty early – even in May, the crowds were pretty intense.
- 7pm – There are plenty of great places in Oia for dinner, and shops open late if you want to keep exploring. Be sure to check the bus schedule if you’re headed back to Fira to confirm when the last bus runs.
Day 3 – Akrotiri and Red Beach
If you want to take a boat tour of the caldera, today could be a good day for it! But if not, you can use the buses to explore some more parts of the island.
- 10am – Get breakfast in Fira (or wherever you’re staying) and then catch the bus to the village of Akrotiri to the south. (There aren’t a lot of food options in Akrotiri.) Enjoy views of the southern part of the island, including down the highway a bit as you head further south.
- 12pm – It’s about a 25 minute walk downhill from Akrotiri to the “Red Beach.” The beach doesn’t have much infrastructure but the swimming is great, the views are crazy, and you can rent a beach chair if you like and find some snack stands nearby.
- 3pm – Catch the bus back from the area near the Akrotiri beach (where you’ll find some snack stands/restaurants).
Essentials for a Weekend on Santorini, Greece
Where to stay for a weekend on Santorini
- Fira and Oia are the largest towns with the most options (and therefore any more affordable options will probably be near one or the other). Fira is closer to the port, so might be best if you have an early morning departure and don’t want to worry too much about the bus. I stayed just outside of Fira in Katerados and found a really reasonably priced hotel (although it was shoulder season) – from there I could either walk about 20 minutes or take a short bus ride into the main part of Fira.
- Imerovigli would be another great spot with caldera views, and slightly less busy – prices probably reflect that.
- If you stay in one of the other parts of the island, it’s probably best to have a car to make it easy to get around.
Getting around on Santorini
- Taking the bus on Santorini – Santorini has a pretty great bus system, and their website has schedules and routes. I was happy using the buses to get between Fira and Oia as well as some of the smaller villages like Pyrgos and Akrotiri (and returning fromRed Beach near Akrotiri). You can pay cash when you board, or buy tickets at the main bus station in the parking lot outside Fira.
- Arriving on Milos – Note that unlike any of the other Cycladic islands that I visited, Santorini doesn’t actually have a “port town.” Ferries arrive basically at the bottom of a big cliff and you have to take a bus (or taxi) up from there. In May at least, it was easy to just walk off the ferry and on to a bus – just make sure you have some cash.
What to do about money on Santorini: I mostly used my credit card, but it was helpful to have some cash as well, primarily for bus rides. Note tipping is not particularly common but if you do want to tip you may want cash as you’ll have to make a point of asking to add a tip on a credit card payment.
Best photo spots on Santorini: You’ll see people literally lined up to take pictures along the cliffs in Fira and Oia at sunset, so that can definitely give you a sense of the popular spots! In Fira if you start down the “donkey path” to the old harbor you’ll pass a picturesque old church dome. I also really liked the views back towards Fira from near the cable car station. Red Beach was another of my favorites for photos – really such unusual color!
Want more ideas for visiting the Cyclades islands in Greece? Try 48 Hours on Milos and 48 Hours on Paros and Naxos.
You can find all my weekend itineraries for Europe here.
