First of all, do NOT let anyone dissuade you from your Grecian dreams. Santorini is gorgeous and if you have yearned for the blue domes, far be it from me to keep you from visiting.
But let me set you up for success here. Santorini is akin to Disney World in mid-July in terms of heat and crowds. Hot, crowded, and a lot of walking.
Everyone wants that perfect shot, the blue domes in the background, the ocean view, and the beautiful cityscape. But the truth is, you will be standing in line at every photo-op behind a million other people trying to get their perfect photo.
In order to get to Oia, the beautiful city on the hill, you have three options
1. Walk up the switchback stairs all the way up the mountain, alongside donkeys that will be leaving fecal matter on the stairs.
2. Take the donkeys, which sounds fun, unless you’re like me and spend far too much time thinking about the conditions the donkeys live in.
3. Take a gondola ride that is incredibly, incredibly, scary (what I recommend).
The best time to get to Santorini is early in the morning, and I mean REALLY early.
The cruise ships start their tours at about 0800, so I recommend trying to head up to Oia right when the gondola rides open at 0630. That may seem like a lot to ask for a vacation, but if you want to see anything without a million other tourists blocking the street, that’s the time to do it.
As the day goes on, more people will be blocking streets, crowding, and it generally becomes overwhelming. At that point, my #1 recommendation is to eat! Go sit at a beautiful restaurant with a beautiful view and eat some of the most amazing seafood of your life.
Plenty of people will tell you that the food is overrated and overpriced, and to that I say – who the hell cares. It’s still delicious.
Obviously, Santorini was not my favorite place in the world, I try to avoid crowds, but c’mon its Santorini, I had to go. Talking to locals there, I heard plenty of gripes about obnoxious tourists, and how their lives are made harder by tourists ignoring “no trespassing” signs, so get your pictures don’t be a d*ck.
My advice, go and see it, if it’s your vibe that’s great, if it’s not your vibe- go to Naxos.