Santorini is really made up of two splendid villages: Fira and Ia. Fira is more of the metropolis and Ia is the village where all of the pictures “from Santorini” are taken. Although I love Fira and recommend that you go, I would encourage you to only do a day trip (or walk there, see details later) and rather use Ia as your base.
There are so many gorgeous places to stay in Ia that I really don’t know what to tell you. My go to place had always been Alexander’s Boutique Hotel Oia (www.alexandershotel.com/hotel) and it really is a lovely place. Unfortunately, however, they seem to be expanding in to other properties and, as such, their attention to clients lacks much. And the fact that a ring was stolen while I was there, with no attempt to replace it of even apologize, makes me still question whether to return or not. So, be warned: this is a lovely hotel and the cave houses are amazing, but know that the service may be rude and unhelpful.
If you want to have some true peace and quiet, I would encourage you to stay at one of the beautiful hotels between Ia and Fira, all of which look out over the caldera and have pools to squelch the afternoon heat.
Eating is a bit of pastime in Ia and you really can’t go wrong. And because you are on the end of the island, most every restaurant has a view. So, in all honesty, the determining factor of where to go could depend on price (and what you pay for the view).
Papagalos restaurant (papagalosrestaurant.com) was an amazing find and the food perfect for both this vegetarian and my non-vegetarian friends.
Ambrosia & Nectar (www.ambrosia-nectar.com) is probably my favourite choice because the décor was soothing, the staff outstanding, and the food sheer perfection! There wasn’t a view of the caldera, unfortunately, but we sat outside, under a lovely canopy and watched the crowds go by, the sun set, and relaxed as if we were at home.
And if you want to splurge, you must go to 1800 (www.oia-1800.com). Talk about service with a view! The restaurant is on the top floor of what appears to be a very old house and truly, the views cannot be beat. And the food?! The food is beyond divine and worth every penny that this upscale restaurant will charge. If you only have one night, this would be my recommendation to you.
It may seem odd to include a bar and a wine shop under the sites section, but trust me when I tell you that you must go to both.
Meteor café (www.meteorcafe.gr) is a site to behold at the end of one of the pedestrian-only streets before the street starts to curve down to the caldera. Okay, it’s not cheap here – you are paying for the view as you do in most places – but the view is incredible, the soft jazz playing is relaxing, and when you need to just sit down, relax, or even have a drink before dinner, this is the place to go. Sure, you will find lots of other places – and I encourage you to try them all – but if you need a highly recommended place, this is where you need to go!
And if you want to check a few bottles of wine in your luggage before you go, you must visit the lama wine store (www.lamatrade.com). The owners are incredibly knowledgeable about Greek wines and didn’t steer us wrong. And, quite honestly, the prices are cheaper here than they are in the convenience stores where you will have to go for all of your other provisions.
But now on to the actual sites in Ia. Although it is a bit of cliché, watching the sunset in Ia is a site to behold. There are boats that cruise the caldera but if you don’t want to spend the money, or have the food that I believe is included, just go walk to the tip of the island, one hour before sunset, and you will see everyone standing around waiting. Not only is it a great place to people watch, but it is also a great time to have a drink and watch a truly beautiful aspect of nature.
Another thing that you must see, although not a site per se, is to walk from Ia to Fira (or the other way if you prefer): the views to the caldera are stunning, the exercise a welcomed change from sunning by the pool or on the gravel beaches, and the chance to see nature not something that every visitor to Santorini has the chance to do.
Santorini is really a place to relax and enjoy life. You won’t find museums and even venues for music, but you will find outstanding views, meet truly sweet people, and enjoy a relaxation in life that we are rarely allowed to experience.