Santorini Stay, Fira or Firostefani?

Stay in Oia. That’s my advice.

Depending on your budget -
I might suggest Imerovigli for caldera views and very quiet evenings. This is the "higher priced spread" but did not seem as expensive as either Oia or Fira when I was researching. It's a bit further north of Fira - but on the caldera and path to Oia. We stayed at Zenith Blue for 3 nights (late Oct 18) and had a nice time and breathtaking view from the room and hotel deck/pool area. Used the local bus to explore. Had/do plan to revisit and stay there with family in 20/21/22/???.

Or Kamari - on the So E edge of the island - nearer the airport. Generally less expensive but with a bit more "real-ness" about it. Stayed 3 nights {Dioskouri Art Villas} in May '19 with friends (rented a car to get around one day). Lots of fun beachfront restaurants and several family rest. a few blocks in.

From both -there are busses or rental cars you can hire by the day- that will get you anywhere on the island.

No matter where you stay - make certain it is near a town and/or has a bus stop nearby. There appeared to be many hotel/rentals to the SW (on the road from Fira towards Akrotiri) and the road between Kamari and Oia that were out in the center of "no where". Then you would need either a rental or to get to know a "cabbie" really well.

While the island can be tourist crowded - it is stunning and an experience unique in all our travels. One highlight in Imerovigli was occasionally hearing thuds on our room ceiling and then realizing it was people walking on it to get their "selfie" with the caldera below.. Turned out - our headboard was actually dug into the rock below the main footpath. IMHO - the caldera edge is the heart of the Japanese wedding portfolio photography world. Amazing and fun to watch the hoopla!

We stayed in Firostefani in the fall of 2017. Why did we choose this location? It has the same Caldera view as Oia, it's away from the cruise ship crowds, quiet evenings, short walking distance to restaurants with views, 15 min. walk to Fira (walking path is especially scenic at night), & public transportation to Oia, Imerovigil, etc.

We took a guided day tour that included Akrotiri Archaeological Site, Red Beach, Perissa for lunch & swim, winery, Megalochori, Oia.

Ditto what Janis wrote about Firostefani. Small place, much less crowded or touristy than either Fira or Oia, but still plentiful diverse restaurants and shops nearby. Great sunset views, without the masses of people in Oia. Although it maybe some years before Oia has masses of tourists again.
PS: I took the same island tour as Janis did, it was really great, I enjoyed Megalochori so much that I returned by public bus and spent most of the next day there, lovely small town great lunch!

Oia is a hike not a walk from Firostefani. We stayed in Oia and hiked to Fira through Firostefani. It took us most of the morning but then we took a lot of pictures. We then took the bus back to Oia.

We actually planned to stay in Firostefani but found a air bnb that worked for us in Oia. Oia is more beautiful but also is less centrally located and restaurants tend to be more expensive. Fira is busier and more commercial than either.
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We had 3 nights in Oia back in Spring 2016 and enjoyed it. Definitely better than Fira IMO.

Depends on several things. I think it's more like 20 minutes from the center of Fira to Firostefani. And as pointed out above, you can't really 'walk' to Oia from there (you can hike, but it's a couple hours hike). So if you plan on taking buses to other places on the island, like Oia, or the archaeological sites, or to the hill towns in the center of the island (and all of those are very worthwhile) then you might be better situated in Fira itself. Budget is another issue. If you plan on public transportation to/from your hotel to either the airport or ferry port for arrival/departure then Fira. If you can afford taxis then it doesn't matter as much. And budget for the hotel itself. In Fira there is a larger variety of prices. But no question Firostefani is more 'charming' and quieter.

Thanks to all of you who responded to my post. Your opinions are a valuable resource to our planning for a trip that we hope we can take sooner than later. All the best to all of you in your future travels.

We visited Santorini in October and stayed in Firostefani at Lithies Traditional Homes for three nights. Ithttps://www.lithies.com/about_us The "Eros" home was a perfect size for the two of us. It was a great location; easy walking distance to some terrific restaurants and the view of the caldera was magnificent. Maria manages the property and she will ensure that you have a magical stay, as nothing is too much trouble for her guests. Breakfast served on your patio, wine and snacks in the afternoon, transportation to and from the airport, concierge services and reservations...she does it all. We found Oia to be an absolute madhouse with hordes of tourists to the point that it is difficult to walk in some places. We did have dinner there one night at sunset with a table on the edge of the caldera thanks to Maria securing us a reservation. Santorini is not to be missed!

We stayed in Oia in May, 2019 and really enjoyed it. Staying in Oia gave us the opportunity to enjoy it in the morning before the crowds arrived. We stayed from a Friday to a Monday because there were fewer cruise ships docking on the weekend. During the day we could take the bus from Oia to Imerovigli and walk downhill to Firostefani and Fira. One day we took the bus from Oia to Fira and then Akrotiri which was very worthwhile. When we returned to Oia in the afternoon we could enjoy the pool by our hotel and not get involved with the crowds. We made a reservation at a restaurant called Oia Gefsis in the evening, so that we could watch the sunset from the rooftop terrace of the restaurant and then walk back to our hotel. The views in Oia are spectacular and there are no powerlines there to get in the way of photography. They also do not allow loud music at night. Whether you stay in Fira or Firastefani or Oia. a trip to Santorini is magical and unforgettable.

Stay in Oia. The Filotera Villas in Oia is one of the most memorable stays from my 2 week trip to Greece in 2018.

https://www.filoterasuites.com/