Oh, Santorini. A dream, picturesque island in the middle of the Medditerrean that everyone should experience at least once. When I pictured our Greece trip where I could finally relax after three years in graduate school while working full time, this was it.
Where to Stay
We stayed at Vallais Villas, a small hotel with seven suites available and the best views, staff, and seriously, the most amazing breakfasts possible. Every morning, you wake up and call the front desk, and within 15 minutes, they will bring up a hot breakfast for you to enjoy on your private balcony (that also has a hot tub).
Every day on Santorini seemed unreal, and it started with breakfast.
Vallais Villas is based in Imerovigli (Uh-Meer-Oh-VIG-Lee), a little town between Fira and Oía (EE-uh). Fira? Walkable. We walked to Fira several times, which is woven into the cliff with restaurants, cafes, shops, and even art galleries. I will note that Santorini is technically one big cliff… and it is not flat. Be prepared to walk up and down and hike your way through the island! It’s 100 percent worth it, but sturdy shoes are a must (so maybe leave the $2 Old Navy flip-flops at home).
Now, walkable to Oía? Not so much. You can do it, and it’s a well known hike, but we personally did not make it during this trip. There are also buses on the island to get between Fira and Oía, if you don’t feel like walking. We technically ended up taking a bus to Oía unintentionally… buses on Santorini sort of run on their schedule and rules, so be mentally prepared before taking one. Taxis are available on the island as well (no Uber) and come in handy! Just make sure you’re not overpaying – a local told us that anything more than 20 euros is too much, even if you’re going from one end of the island to the other.
Overall, we loved staying in Imerovigli – it was less crowded (read: cheaper hotel prices), and nearby restaurants were amazing (check out Blue Note, Aegeon Restaurant, and Argo). You also get an amazing view of both sides of the island and are right next to a great hiking trail up to Skaros Rock.
What to Do
Unlike Mykonos, Naxos, Crete, and most of the other Greek islands, Santorini is not known for its beaches. Their famous Red Beach has actually been closed off by the government for years and is not recommended for visitors.
So, what’s the best way to experience the Aegean Sea? By catamaran! Santorini Sailing Tours offers catamaran sunset tours where you can sail around the island and swim in various spots, including the hot springs by the sunken volcano (the caldera). It is a once in a lifetime experience.
Halfway through the tour, the staff will also prepare a huge spread for dinner with shrimp, barbecue chicken, pasta, tzatziki, and more. It was the best time we had on our entire Greece trip – so much so that we have zero photos of the tour, because we were so busy taking everything in! Oh, and beer and wine is included.
And of course, no vacation is complete without a wine tour. Our travel agent booked another sunset tour with Santorini Wine Tours, and we lucked out with getting a semi-private tour – the only other people were another couple (who ironically went to my high school – what are the chances!).
We visited three estates on Santorini including Artemis Karamolegos Winery; Avantis Winery, which had the most amazing atmosphere and mediterrean vibe; and Venetsanos Winery, which also has a small museum on its wine history – after all, it was the first industrial winery on the island!
Santorini’s native grape, Assyrtiko, is an unusual white wine. It has a high acidity, which I sometimes don’t like. The different tastings at the wineries were either a hit or miss for me – Venetsano’s wines were a bit too acidic for me, but Avantis had the most refreshing citrus wines with one also tasting of honey!
We did skip out on Santo Winery, which is probably the most well known winery on the island, but our sommelier noted that Santo is usually packed and more “commercial” than the others. Venetsanos was next door and offered the same amazing views! Perfect place to end the tour and watch the sunset without the crowds at Santo.
Santorini is a picture perfect vacation, and I know we’ll be back someday to enjoy it beyond the four days we had here. But Santorini was not my favorite part of our trip – haaave you heard of Crete?