Staying in Santorini in Sept 26-29

Akrotiri is a good option. Sun sets directly opposite from there and the rooms cost half the price. Plus, you can walk to the charming village and ancient ruins as well as the stunning Red and White beaches.

Look at a map! https://www.mapsof.net/santorini/thira-island-santorini-map All over the world the sun sets in the west .. this doesn't change that much. If you don't like the prices in OIA, try Firostephani ... I've brought newcomers to Santorini at least 6 times, and they always love the views from FIrostephani ... it's right on the cliff edge, like OIA, but is about 30% cheaper for similar accommodations. Browse booking dot com for your dates, to compare - https://www.booking.com/city/gr/firostefani.html

Other advantages:

• Firostephani is just on north fringe of Fira, easy to walk there down the rimside path in 20 mins or so, for shops, museum, cafes, nightlife -- but it's away from the hubbub. Tours ignore -- busses whiz right by - so its plesantly calm both day & night.
• Sunsets in OIA Can be Mob Scene (see this montage) https://tinyurl.com/4js8e8t8 whereas u can enjoy serene sundown dinner (at sane prices) at a FIrostephani place like this - https://santorinidave.com/santorini-restaurant-remvi
• Served by N-S bus, so u can get around w.o. car rental (ask yr hotel about bus stop/schedulelL)

Of course OIA is a must-see -- but at the right time! Either catch 8 am bus or splurge on taxi to get there early, so u can enjoy strolling enjoying views, taking pix. At about 10 AM the cruise crowds and large tour-bus armies "invade" and and jampack the narrow lanes - like NYC TImes Square subway@rush hour! When they arrive, you leave... to explore other parts of isle. The only other time OIA crowds let up is between about 3:30 (when last tours go) and 6:30 (when fresh crowds arrive to stand around waiting for sunset) . Another way to enjoy sunset relatively crowd-free is to book a wine-tasting visit at a winery with a view.

Janet,
Of course I know that the sun sets in the west and of course I looked at a map. Looking at the map, it looks like the hotels/Airbnbs all point south because it curls up at the top of Santorini. That is why I am confused about it. Do those hotels in Oia have great sunsets or just great views of the Caldera?
Thanks for the additional information,

Our stay in Firostefani was picture perfect, and we enjoyed the sunsets every evening while having a glass of wine on our terrace, so I would recommend that location. It was also easy walking to numerous restaurants. We did visit Oia, and it was a madhouse with all of the cruises in port, so we were happy with our decision not to stay there. Our hotel was a great value when I compared it to other accommodations, and the service that Maria provides was phenomenal. https://www.lithies.com/

Thanks Travelbug79. I ended up booking an Airbnb in Firostefani. Can't wait.

It's definitely expensive! Nearly caused me to second guess our entire trip. I finally just gave in and booked the Belvedere in Firostefani. I did a ton of research and it seems to be the best for our purposes (we are 3 adults which made it challenging too). Yes, don't stay in Oia .. from what I read and saw on Youtube Firostefani is away from the crowds but close enough for the views.

If it is your desire to watch the sun drop below the horizon from your BnB in Firostefani you will not succeed. In late September the sun will be setting behind the small island of Thirassia on the other side of the caldera from Santorini, and Firostefani is not at a high enough elevation over the sea to provide that view. But you will have an excellent caldera view. In Oia you will be able to see the sunset from Esperas Santorini, Fanari Villas, Marizan Villas, Canaves Oia Epitome, Oia Castle Hotel, Domus Solis Villa, Old Castle Oia, Theodora Suites and Oia Mare Villas. Another good area for that view would be in Megalochori, on the cliff south of the ferry port of Athinios.

Lee,
Thanks so much for answering my question correctly. This is what I was afraid of. I wondered if the sun would be too far over for us to enjoy it from Firostefani. I will look into the ones that you suggested in Oia. Thanks so much.