Our original plan for a Greek island vacation was a multi-week sailing trip hopping from one beautiful place to another on a catamaran with friends in tow. Then I got pregnant and the idea of flitting around the Aegean Sea no longer seemed wise. So we narrowed our focus to one island: Santorini.
We chose very, very well.
The small island had everything we wanted including beautiful vistas, deep blue water, friendly people, fascinating history and delicious food. I love the Caribbean – my husband and I got engaged there – but I think the Greek islands might give them a run for their money.
Here are a few of our favorites from Santorini.
Where to stay: Oia
There are several towns on Santorini and most folks choose to stay in Fira, the largest town closest to the airport. Fira has a lot to do, including plenty of restaurants and nightlife and it’s close to some of the other sites on the island. But if you want something more romantic or relaxing, stay in Oia. It’s smaller, but still packed with wonderful restaurants, good shopping and gorgeous views. The sunsets are incredible because, unlike Fira, it has views to the west. And thanks to Santorini’s excellent and affordable bus system, you can hop a bus to Fira every 20 minutes.
One of the many beautiful sunsets in Oia.
I wish I could take credit for finding this fantastic hotel on my own, but it came highly recommended by two friends who spent their honeymoon there. It’s in Oia, a smaller town on the northern tip of the island that’s a more romantic alternative to Fira. Esperas is made up of suites carved into the ancient cliff side cave houses and it overlooks the caldera while still having a fabulous view directly west. Ammoudi Bay, where lots of boat tours take off and some amazing fish restaurants are located, sits directly below. The staff is incredibly helpful, the rooms are comfortable and the pool deck is the perfect place to waste an afternoon. Their sunset view is so good that tourists come from all over the island to stand outside Esperas’ front door and snap photos. As a bonus, they serve fantastic Greek yogurt and local honey for breakfast.
View up the cliff from the Esperas pool deck.
One of the great things about vacationing on a Greek island is you can have a beachside holiday and still get a hit of culture if you want. There is so much ancient history right under your feet. There are plenty of museums and archaeological sites to visit in Santorini, but we focused on Akrotiri, a village that was destroyed around 2,000 BC by volcanic ash. Like Pompeii, the ash preserved the village so that when it was first discovered in 1967, entire buildings, paintings and ceramic jars were still perfectly in tact. It was a highly developed society with beautiful art, multi-story buildings and indoor plumbing – all before Rome got off the ground.
The site is at the south end of the island, so you’ll need to get a bus there unless you take a guided tour — and I highly recommend a guided tour to get the full story. We were really pleased with Akrotiri Santorini Guided Tours. Our guide did a great job of providing us background on Akrotiri that helped us appreciate the ruins when we saw them. They also picked us up at the Oia bus station and dropped us off in Fira, where we ducked into the Museum of Prehistoric Thira, which houses all the art and objects found in Akrotiri.
Part of the Akrotiri ruins. They thoughtfully built a roof over it!
Santorini Wine Tours
Even though it only rains about 30 days each year in Santorini, the island manages to grow produce including cherry tomatoes, white eggplant and grapes. Lots and lots of grapes. We heard that two-thirds of the island’s land is covered in grapevines.
And all those grapes get used to make wine, something the folks in Santorini have done for 2,000 years. I’d never heard much about Greek wine before our trip, but we figured it would be a fun afternoon out to take a wine tour. Nick tasted, I spit, and by the end of the day we learned that there are some truly delicious whites and dessert wines being made here.
Santorini Wine Tour did a great job of providing us with both the history of wine making and grape growing in Santorini as well as a look at three different family-owned vineyards. The tastings were generous, the wine was delicious and our guide was fantastic.
Our guide shows us the grapevines in Santorini, which grow in a wreath shape close to the ground. It protects the grapes and allows the vines to absorb the dew.
Sunset Oia boat tours
My husband loves nothing more than being on the water. Early in our relationship, he took me deep sea fishing in North Carolina mostly to see if I could hang. Luckily I reeled in a marlin before giving into seasickness or I don’t know if our relationship would have lasted. So we couldn’t have gone on an island vacation without going out on the sea.
Our package at Esperas came with a boat tour with Sunset Oia, so we didn’t do a lot of research. When we showed up at the dock in Ammoudi Bay, we were a little worried we’d inadvertently signed up for a booze cruise. We were one of the oldest couples there and certainly the only one that was pregnant. It was only 10 a.m., but the crew of the catamaran told us the wine would be flowing freely all day.
Luckily once we got out on the water, it turned out to be a chill four-hour tour. We visited the volcanic islands, the sulfur springs, the Red Beach and the Black Beach before snorkeling and eating a surprisingly delicious barbeque lunch on the boat. It was a nice way to see parts of the island that would normally require us to take a long bus ride and then hike in.
All in all, it’s a good option for folks who just can’t do the hiking (pregnant ladies, older folks, small children) or people who don’t want to hire a boat on their own.
The sulfur springs in Santorini. The yellow water is the sulfur.
Restaurants in Oia:
Thalami: A cute little taverna on the cliff side with nice views of the water and reasonable prices. The perfect dinner? Stuffed peppers to start and the moussaka for your main. It was the best Greek food we had the whole trip. The experience was made sweeter by the manager, who offered me a seat while we waited for a table. “My wife is pregnant too,” he said. “You don’t need to stand in line.”
1800 Restaurant: Fine dining in an old mansion from, yes, the 1800s. Their menu puts a new spin on classic Greek dishes, and the romantic rooftop is the perfect setting.
Melitini: Adorable little tapas place with a roof deck and laid back attitude. Their small plates menu makes it fun to try a little bit of everything and give yourself an introduction to the local favorites.
Niko’s Gyros: Folks told us these were the best gyros on the island, and I think they’re right. The pork gyros and Greek salad were so good we had the exact same meal there twice. This place is a bit hard to find. TripAdvisor says it’s in Fira, but it’s actually in Oia near the bus station. Look past the place with the sign that says “Best Gyros in Santorini” and you’ll seek Niko’s, a white building with a green circle logo that says “Oia.” You can eat in at the covered patio or take away.
Lolita’s Gelato: This place is the No. 1 rated restaurant in Oia, and I can see why. It’s delicious gelato, period. Not just delicious for Greece, but plain old delicious. The flavors aren’t super inventive, but everything tastes wonderful and none of them have that chemical, overly sugared after taste that bad gelato is known for (I’m looking at you, gelato purveyors of Dubrovnik. Yuck!). We went here almost every night for dessert and were never disappointed. As a bonus, the staff is young, cute, friendly and generous with the free samples.
Lolita’s Gelato in Oia. Their signature flavor is Greek Viagra.