We ARE going to Santorini in September and Looking Forward to It!

Sigalas is an award-winning winery located in Oia. Reserve an outdoor table at Santorini Mou in Oia for dinner and join in the fun with owner and friends playing music. Sometimes there is spontaneous Greek dancing. Have lunch below Oia at one of the fish tavernas on the wharf in Amoudi Bay. If they're performing this year go to the White Door Theater in Fira for the Wedding Show. https://www.whitedoorsantorini.com Order a flight of their wines with snacks while you enjoy the sunset from Venetsanos Winery in Megalochori.

Amoudi Bay below Oia is nice for lunch at Katina’s. Walk down the hill.

We drove up to this monastery--Monasterio Profeta Elías. Splendid views and wonderful honey that we purchased.

We hiked to Fira from Oia and took the bus back. Most beautiful hike I have ever done.

Argryos is another nice winery with a modern tasting room. You can book a tour and tasting with a some small food pairings.

Red Beach is in a dramatic setting and worth a visit - so since you're at the beach you may as well visit the nearby Akrotiri archaeological site (won't take too long - go there first). Perissa Beach with its black sand is also scenic and enjoyable.

I found Santorini to be the most unrelaxing place I've visited. The beaches were not fun at all. I do also really love the Santorini Mou restaurant, however. Be mindful of all the Instagrammers!

We took a terrific catamaran tour from Oia through the crater around to White Beach. Spectacular views, several swim stops, interesting people. Loved it.

You have received some great suggestions and all I’ll add is we absolutely loved our off season stay on Santorini and found plenty to do for the 5 days we spent there. We stayed in Firostani and walked practically everywhere. We did enjoy a couple of truly tiny museums in Fira and the wineries, but most of all relaxing and soaking up the beautiful views. We rented a car but only used it a few times. I love the title of your post. Have a wonderful time and congratulations on your retirement.

Another vote for Venetsanos Winery. We had a very relaxing light lunch and wine tasting overlooking the caldera. Another day of our trip to Santorini was spent on a Catamaran tour. Spiradakos was the sailing company, and they offer several different types of cruises. Enjoy your retirement celebration!

I'm certain you'll love Santorini, but how can you say you were there and didn't visit the site of the lost City of Atlantis? It may take archaeologists decades to acknowledge Akrotiri is the site, because they haven't found the Proof. yet. People thought Helen of Troy and Minos and the Minotaur were only myths until Troy and Knossos were uncovered in the 20th century. Akrotiri fits the Homeric stories of a city disappearing into the water.

leonard, there are a lot of people who just think that ancient sites are a boring pile of rocks. It's their loss. Akrotiri was THE Reason I went to Santorini in the first place. And I've been pursuing Piles of Rocks all over Greece in 13 trips, ever since .. you too, I expect. One of my tiny favorites, the lttle ruins of Asine fortress, outside of Nafplio, on the sea. It was Mentioned in the Iliad, as sending a boat to the Achaean's fleet. There is a tiny stony cove just there, with one taverna, and no crowds. I swam out quite a way... and found myself suddenly standing, while in deep water. ?? I looked down into the clear blue, and saw a line of flat stones coming out from the shore. ??? Could it be?

That's the kind of thrill you & I get from those piles of rocks.

Well, as a high school history teacher of 38 years, I tried to teach my charges to respect and accept the values and cultures of other people without judging them. Not only that, making an assumption without the facts is ummmmmm... I asked for people’s thoughts on what to do. You both did that kinda sorta but…your reply speaks for itself. I’m really surprised because most people on this site are helpful and extremely positive but not judgmental. Not only that, Santorini is the first place we’ll visit after flying from California so we’ll have jet lag to say the least and will need to relax. Sorry if we’re not as cultured or intelligent as you two are. I’ll work on that. I wouldn’t jump to any conclusions about a pile of rocks is this or that until a archaeologist or historian provides the evidence to prove a theory because that’s what they do.

Ken,
Great response to the posters who made it their mission to criticize your interests while vacationing on Santorini. It's your trip to spend this time on the things that you see as having value. Agreed that most people on the forum are positive & helpful. However there are a few of the self-anointed "experts" who are quite frequently snarky and condescending in their responses. Unfortunately you found one of the main culprits. Please don't let them deter you from future participation.

I’ll second a catamaran trip. It’s wonderful to view the cliffs from in the caldera and the sunset is great on the water. The whole experience was relaxing and enjoyable.