If you like talking pictures and want to visit Greece, Santorini is the place to go. This little city of 50,000 is often overcrowded from May to the first half of September with more than 3 million annual visitors. So I would recommend going during the off or shoulder (the time between high and off seasons) seasons. In Santorini, this is begins in late September and runs until April. An additional benefit at this time is the prices will also be lower for lodging.
The main city of Oia (pronounced eee-a) is expensive during the high season but if you can afford it, it’s worth the spurge. Here you’ll find the small cobblestone paths and lots of stairs between the shops, restaurants and hotels. The large blue Domes you see in all the photos are located in Oia and you can get lost walking the paths. We got up early one morning to take photos. There were already a lot of girls running around in beautiful dresses posing for photos. Ah, the advent of Instagram.
Oia also faces southwest and hundreds of people come out each night to cheer as the sun dips into the ocean each night. Definitely grab a glass of wine and stake your spot out ahead of time on the westward facing part of the island.
We stayed at VIP Suites. Depending upon the time of year, the cost could be outrageous, dipping down to the respectable in the off season. If you want to stay in the hotel with the blue pool so often found in photos, it’s called Canaves Oia Suites. 
Our room overlooked the buildings on the west side and provided us with a private patio and a beautiful view to watch the sunset. Checking in was a pain as we went to the address for the room and the Internet mapping systems don’t work well here as the streets are really just walking paths and close to each other. After wasting around an hour trying to find the place and a phone call, we realized we were supposed to pick up our keys in a totally different spot. Lesson learned, read your instructions closely.
Also, if you’re wanting to see the whole island, you’ll need to rent a car, quad or motorcycle. We opted for a car at the last minute while at the airport and could have saved a lot of money if we reserved one ahead of time. As it was, we ended up with a convertible Mini Cooper. It was pretty cute and totally worth the higher expense.
Santorini has main three beaches for swimming. You can drive to red beach. Parking there is a pain and you half to walk over a hill to get to the beach or you can do what we did and park below and pay $10 for a shuttle boat to take you to three beaches, Red, White and Black beaches. When we went, you couldn’t get off at Red Beach because they were afraid of falling rocks but you could get on the boat if you were already swimming there. White Beach has black sand so maybe a name change is in order but there are white rocks here. Black Beach offers black landscapes and black sand. All of the beaches have swimming and are rocky getting into the water.
Santorini also is known for riding the donkeys from the bottom of the port (This is where all of the cruise ships come in) to the top of the hill. There are booking sites available but I would just negotiate when you get there.
There is a sky tram/cable car that will also take you up and down. We rode it down and then walked up the 587 steps back up the hill. What they don’t tell you is that for each step up, there is really 3 steps across so in reality you’re walking about 1,700 steps through donkey dung. 
Its’ okay when it’s dry but you need to watch your where you walk. Just beware of the donkeys going down. If there is shade, move to the sunny side of the path. The donkeys almost ran me over when I moved to the shade to get out of the way. The walk was a terrific work out and my ass is tighter for it. Living on the side of a hill really works your butt.
Also, if you’re taking a ferry from the island to another and using a car service to get there, know that everyone has to drive down the same hill to drop you off. The traffic on the switch- backed road was backed up, reminding me of LA traffic. It took us three times longer than we expected.
The island is also known for its wine. There are a few wineries spread throughout the island. The vines actually grow on the grown instead of trellises because of the wind. We opted to just order local wines when we went to the restaurants. Speaking of food, if you’re staying in Oia and want a seaside view for dinner, reservations are highly recommended.
Santorini has been on my bucket list
since I first heard about it 15 years ago. While we were only there a couple of days, I took more than 700 photos, most of these turned out beautiful and it’s going to be hard to decide which ones to print. There is a reason it’s so popular, it’s because it’s beautiful. Have a terrific time, relax and breathe. Cheers and ahh…..
Sunsets are proof that everyday can end beautifully. –Found on a wall in Santorini, Greece