Beyond the Photo Ops in Santorini, Greece

As part of my recent week-long vacation in Greece, I visited Santorini with a friend from high school, Ismael (who, by the way, has made some guest appearances on Caffeinated Excursions in my PhillyMiami, and Nashville posts).

We knew that Santorini would be picturesque, but the beauty of its less-Instagram’ed spots is as stunning as its blue-domed churches and pastel-colored villages. There were also so many different activities to do and things to explore that we roamed the island from morning to night each day. 

Before planning a trip, you’ll want to take a look at the geography of the island:

The most famous and popular town for tourism is Oia (pronounced EE-uh), located on the very northern tip of the main island. Another beautiful town called Thira is centrally located, and both have amazing sea views as well as stunning architecture. We stayed in Oia and went to Thira for dinner one night, which is what I’d recommend doing unless you have more than a few days in Santorini.

The highlights of our trip were the amazing views, the locally-made white wine, the delicious cuisine, and the beautiful beaches. This is everything you need to know for a perfect few days in Santorini:

  1. The town of Oia
  2. Day-trip ideas (wine, sailing, and Thira)
  3. Restaurant ideas in Oia
  4. Lodging and transportation

The Town of Oia

The most striking thing about Oia is the labyrinth of stairs and footpaths that run through the village up and down the mountainside. In fact, most houses and buildings in town are only accessible via these paths, and there are no actual roads except for one that runs adjacent to the edge of town. This is why Oia is so iconic and the houses look so densely packed in pictures.

If you stay here, I recommend booking one of Oia’s traditional cave homes which have been carved into the hillside. Read more about it and see what one of them looks like in the section on lodging below.

Amoudi Bay

If you’re willing to climb down a steep trail to get to it, Amoudi Bay is a beautiful part of Oia worth checking out. The bay is surrounded by unusual red rock cliffs and once you get to the water, there are about half a dozen different restaurants that all serve seafood. Read about one of the restaurants right on the water that we ended up trying here.

This is also a great place to catch the sunset if you visit during dusk.

Ideas for Tours and Day Trips

Oia is undoubtedly amazing and beautiful, but you’ll want to be sure to check out other parts of Santorini as well. One way to do this is to rent a car (more on that below), but another good option is to book a tour or two. We did a sailing tour and a wine tour; although both were pricey, they gave us a chance to see the island’s coastline and interior. Plus, our tour guides were excellent!

Boat Tour

For our first full day, we booked a sunset sailing tour, which left from Amoudi Bay (but included hotel pick-up) and then navigated south between the various small islands to the west. The trip stopped at the south end of the island, where we saw a few different beaches before heading back north to catch the sunset.

This cruise was a great introduction to the geography of the island. Our guide told us about the volcanic history of the area as well as how all of the little islands used to be a single, large one a few thousand years ago. You’ll get the chance to swim in a hot spring if you want, and I really enjoyed seeing the vivid stratified layers of rock along Santorini’s shore.

This cruise also included a dinner that the crew cooks on board, as well as bottomless wine!

We booked the tour through Sunset Oia Sailing Cruises which seemed to be one of the most popular day-cruise companies on the island. They have a number of different options for different prices, but the one we booked cost $220 (190 €) per person.

Wine Tour

What better way to see the island than with a glass of wine in hand? This tour was another highlight of our trip because it brought us to three different wineries located in different parts of Santorini. Our guide did an amazing job of introducing us to wine production as well as how to taste and pair them with hors d’oeuvres.

If you are only spending a few days in Santorini, booking both a wine tour and a sailing tour is a great way to see a lot of the island in a short amount of time. Stunning cliffs will surround you on the boat, and you’ll get a glimpse of some of the smaller villages south of Oia that are home to the wineries you’ll visit.

There are a number of companies offering wine tours, but we booked with Santorini Day Tours and were very impressed with them. The three wineries we visited on the tour were Boutari WineryGavalas Winery, and Estate Argyros, and if you like anything you try, you can purchase a bottle to bring back home.

Boutari Winery
Gavalas Winery
Estate Argyros

This tour lasted about five hours and included hotel pick-up and drop-off. We paid $120 per person, which obviously isn’t very cheap, but I’d say the experience was worth the price.

Dinner in Thira

If you’re going to stay in Oia, consider going to Thira for dinner and drinks one night. Thira is the capital of the island and has a little more to offer than Oia in the way of nightlife. Located about a twenty-five-minute drive south of Oia, it’s also an amazing place to see the sunset.

Thira may look similar to Oia, but it has a more lively vibe to it, especially at night.

We ended up trying a nice restaurant called Argo, which specialized in seafood and had an enormous outdoor seating area overlooking the bay to the west. If you’re a fan of escargot, order the snails here as an appetizer; they were delicious!

After dinner, we wandered the town and stopped at a few places for drinks. Two Brothers was definitely the loudest and most rowdy one and felt like a college bar with strong drinks.

A couple on our boat tour recommended PK Cocktail Bar, so we headed there afterwards. They have a heated outdoor terrace and the cocktails were top notch. If you only want to do one bar in Thira, this is the one to go to!

Restaurants in Oia

Thira isn’t the only place with good food options; Oia also has a bunch of excellent restaurants. Because our wine and boat tours included meals and snacks, we only got a chance to try two places in Oia, but everything we had was delicious.

For dinner on our first night, we tried Sunset Ammoudi. It ended up being a bit overpriced, but they have a bunch of tables that are so close to the water that you could fall in if you’ve had a few too many glasses of wine! This made it a great place to watch the sunset while eating.

As you might guess, they mainly have seafood on the menu.

For lunch the next day day, we tried Nikos Place Gril House, which had excellent souvlaki and gyros.

Their sampler appetizer was also great for tasting a variety of Greek flavors.

If you’re looking for a good cup of coffee in the morning, try Meteor Cafe. It’s a cute and cozy little place with a great view. It appeared to also be a bar, but it was my favorite place to get coffee first thing in the morning.

Another good place for drinks in Oia is called Marykay’s Bar. It’s also pretty cozy, but they have a huge list of original cocktails and the ones we tried there were delicious.

Additional Info


It’s probably not going to be cheap, but if you can find one within your budget, consider staying in one of Oia’s traditional cave houses. We stayed at this home and our host was so nice and hospitable that she spent a good half hour at check-in telling us her favorite spots around Santorini.

It’s incredible that these cave homes are built into the rocky hillside, and this one even had a cellar that was used to collect rainwater in days past.


Getting to Santorini by Plane

Flying to Santorini from Athens was easy and the journey only took an hour. We booked on Expedia with Sky Express. A one-way ticket from Athens cost 100 Euro.

Leaving by Ferry

Instead of flying, we left Santorini by passenger ferry, although I’m sure a round-trip flight from Athens to Santorini would be as straightforward as a one-way. However, the ferry was an interesting experience that you should consider too.

We booked our tickets through Direct Ferries, but by October, the boats weren’t departing from Santorini every day. Book in advance and don’t miss your boarding, because there may not be another one for a while! Our tickets cost $40 per person.

If you’re curious about the ferry experience, read about it on my other blog post here [coming soon]!

Getting Around on the Island

In order to move around the island, you can either hire taxis or rent a car. In most cases, I think it would be more economical to rent the car, which for us cost 40 Euro per day, while a taxi between Oia and Thira (about a 25-minute ride) cost 30 Euro. We rented a car for one day from Drossos Car Rental and ran into no problems.

On to the Next Island...

By the time we had boarded our ferry and were waving goodbye to Oia, it was clear that Santorini is as magical as we hoped it would be. However, the island is home to so many more beautiful places than the few famous spots that have taken Instagram by storm in recent years. Early autumn proved to be the perfect time to avoid the summer crowds without having to give up the sun and warmth. Personally, I can’t wait to go back to Santorini one day!

After staying in Oia, we headed off to the much quieter island of Milos, which was a completely different experience. Read about it here, or check out my general overview of Greece here [coming soon]! Thanks for checking out my post on Santorini!

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This Post Has 3 Comments

  1. Sreedhar

    A must visit some day 🙂 🙂 Lovely!!

  2. Joanne

    Santorini is so beautiful. I’d definitely visit Amoudi Bay. Just love the red rocks.

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