Both Oia and Fira have good sunset views (though the best are in Imerovigli). In Fira most hotels on the caldera have a pretty direct view of the sunset. In Oia, most hotels don’t have a direct view of the sunset and you need to leave your hotel and take a short walk to see the sun set into the water.
Renting a car: Slightly easier in Fira. If you do pickup at the airport (recommended) then it doesn’t matter which town you stay in.
Closer to the airport and ferry port: Fira is about 10 minutes from the airport and 15 minutes from the ferry port. Oia is about 30 minutes from both the airport and ferry port.
Easier to explore the island from: Fira is more central and makes getting to the southern parts of the island easier and faster. This matters more if you’re getting around by bus as Fira is the hub for all bus routes on the island which means passengers taking a bus from Oia to the beaches will need to change buses in Fira (a bit of a hassle). If you rent a car then there’s not as big of a difference.
Closer to the beaches: Fira is about 15 minutes closer than Oia to the beach towns. As I say, this isn’t a big deal if you have a rental car, but makes a bigger difference if you’re getting around by bus.
ATMs are easy to find in both Fira and Oia. Both towns have grocery markets but Fira has an actual grocery store. If you need to do laundry Fira is better.
Fira vs Oia – A Comparison
Fira is up a the top, Athinios port (only used for cruise ships, not ferries) is at the bottom. To get up to Fira there’s a choice of cable car, walking, or riding the donkeys.
Looking up at Oia. Amoudi Bay (known for it’s seafood restaurants) is at the base of the hill below Oia. It’s a short walk down to Amoudi and a lots of steps back up.
The view from Fira looking north towards Skaros Rock and Oia.
View of Oia, looking northwest from Perivolas Hotel.
That’s Skaros Rock in Imerovigli which divides (to me, at least) north and south Santorini. I point it out because you can see Skaros from Oia and Fira and appears in many pictures on this page. It offers a good landmark to get your bearings.
View of Fira, looking south from Skaros Rock.
View of Oia, looking north from Skaros Rock.
View from Oia looking south towards Skaros Rock, Imerovigli, and Fira.
A view of the volcano from Fira.
The main street in Fira is a fun lively collection of shops and restaurants.
Donkeys in Fira.
The best restaurant with a view in Fira: Naoussa.
Cable car ride from cruise port up to Fira.
Donkeys on the stairs down to the port in Fira.
Sidewalk in Fira.
Looking north towards Skaros Rock from Kavalari Hotel in Fira.
Lots of cafes, restaurants, and hotels look out onto the caldera in Fira.
The main spot to watch sunsets in Oia. Bring a bottle of wine and have fun.
View of the sea from Oia.
Oia Castle is the main spot to watch sunsets in Oia.
View of church and Fira from Oia.
Best spot to watch sunset in Oia.
Large villa in Oia.
The main sidewalk in Oia (flat and stroller friendly) runs pretty much the entire length of the village (with one main interruption just past Canaves hotel).
View of Fira looking north.
If you’re looking to save money on food nothing beats a gyro. Lucky’s in Fira has the best gyros and souvlaki on Santorini but there are several places in Oia too.
Finikia is a village near Oia. No views but it does have several cheap hotels. This is the bus stop for Finikia. All buses between Fira and Oia stop here.
Both Fira and Oia have lots of steps but the main walkway in Oia is flat and much better for getting around with a stroller.
Amoudi Bay below Oia. Great seafood restaurants and there’s a good swim spot here – no beach you just jump from the rocks.
Fira is busier than Oia but there are still plenty of quiet spots in Fira.
Oia Castle with Thirassia (another island that forms part of the caldera ring) in the background. This is the most popular spot to watch sunsets in Santorini.
Lioyerma pool in Oia. Nice size and good views. It’s the only “public” pool in Santorini and nice if your hotel doesn’t have a pool. No fee, you just have to buy something to eat or drink. Strangely, it never gets all that busy.
Looking south towards Fira. Fira is roughly up the cliff from the first (closest) ship.
A sidestreet filled with shops in Fira.
The foot path between Fira and Oia. From Fira to Imerovigli you’re largely walking on town sidewalks. North of Imerovigli it’s more like a dirt path.
Imerovigli is about half-way between Fira and Oia and has the best views of any town along the caldera (because of it’s higher elevation).
Perissa is the best beach in Santorini. It’s definitely easier and closer to get here from Fira than Oia.
Atlantis Books in Oia is a fabulous little bookstore in Oia. Don’t miss it.
The view from Katikies in Oia looking north.
Hasapiko is the only true bar in Oia. It’s tiny but gets good and lively after midnight.
I love going to the open air cinema in Kamari. It’s quite a bit easier to do this from Fira than Oia.
Kamari is the best swimming spot close to Fira. Oia is 20 minutes farther from Kamari than Fira.
The stairs from Athinios port up to Fira.
Koo Club and Enigma are the big dance clubs in Fira. Oia has a few bars and places to drink but no clubs.
Tropical Bar (along with Franco’s) is one of the best places to watch the sunset in Fira.
It’s easy to get (happily) lost in the paths and stairwells of Santorini.
One of the highlights of a trip to Santorini is walking the footpath between Oia and Fira. It doesn’t matter whether you walk Oia to Fira, or Fira to Oia.
Another sign for the footpath along the caldera. This is in Firostefani (the village closest to Fira).
Ouzeri is my favorite restaurant in Fira. Both Fira and Oia have lots of great places to eat
Fira is the hub for buses getting around the island. If you’re in Oia and want to go anywhere on the island (besides Imerovigli and Firostefani) then you have to switch buses in Fira.
Fira is busier than Oia through the day but quieter than Oia during the sunset. Oia is the most popular town on the island to watch the sun set but unset views from Fira are still pretty great.
Fira has far more nightlife, bars, and clubs than Oia.
There’s plenty of shopping in both Fira and Oia – but Fira definitely has more shops and more variety.