Where to stay, eat & go in Santorini

For the last destination of our summer 2018 europe tour we wanted to head south and go to one of the most beautiful places in the world -- Santorini which is arguably the most popular of the cyclade islands.

This was my second time visiting Santorini and I couldn't wait to come back to see the breathtaking sunsets and picturesque white and blue architecture.

Both times I’ve been to Greece have been in peak season (June) and it gets pretty hot (think high 80s) so make sure you bring the appropriate clothing and sunscreen.

Where to stay

On this island there are a few different villages to stay in. I’ve stayed in both Oia and Fira which have different vibes depending on what you’re looking for.  I preferred staying in Oia but glad I experienced a different part of the island the second time around.

  • Oia is located on the northern part of the island high up in the Caldera.  The village is carved out of the cliffs and there are a lot of cave homes and structures there.  The village is charming with many local boutiques and restaurants with views of the deep blue Aegean sea and volcanoes in the distance.  Oia also has one of the best views for watching the sunset.

  • Fira has the same winding streets and white stone architecture.  It’s located on the coast in the middle of the island. Fira is a good option if you’re looking for a more vibrant nightlife - Oia dies down after dinner.  

Accommodations in Santorini book up fast and can be pricey.  You need to do a lot of research to make sure the hotel or Airbnb you’re staying in is up to your standards.  My first trip we stayed in a great Airbnb and most recently stayed at hotel Kalisti.

What to do

Santorini has a relaxing vibe - you can easily spend your days enjoying the amazing views, eating amazing food and exploring the cute villages. Here are a few planned activities I would recommend looking into during your stay.

  • Wine tour: Santorini has a handful of wineries. Doing a small group wine tour was a great way to see 3 different ones with a knowledgeable guide and with transportation included. We did the first tour of the day and went to Gavalas, Boutari and Estate Argyros.

  • Catamaran Sunset Cruise: There are a few different tour companies and package options for a catamaran cruise. We went with Sunset Oia and chose the platinum option which was a semi-private tour.  This is a great way to see the island from the water. There were 3 stops (red sand beach, white beach and the hot springs) before ending at the caldera to watch the sunset from the water.

  • Hike from Fira to Oia: You can hike from Oia to Fira to vice versa, it’s a 6.5 mile trek but was one of the most memorable experiences from our trip. Given the time of year we went, we started our hike around 7 AM to avoid the heat.  It took us about 2.5 hours to get to Oia but can take up to 5 depending on how fast of a walker you are. The views were amazing but note that it wasn’t easy. Make sure you have water, gym shoes, and workout clothes since you will work up a sweat!

  • Domaine Sigalas: I highly recommend visiting this winery and I’ve made a point to visit this both times in Santorini. It’s a locally owned winery.I recommend the full tasting menu which can be shared with 2 people vs. ordering your own.  Order some of their delicious food. The winery is located outside of Oia and you’ll need to make arrangements to get a ride to/from.

Where to eat

Greece is known for its rich Mediterranean cuisine and Santorini’s vicinity to the sea means fresh delicious seafood.  Expect to eat a lot of greek salads (consisting of feta cheese, tomato and cucumber, no lettuce), fish, octopus and more feta cheese that I swear tastes better in Greece than in the US. Also, don’t miss out on getting a mocha frappe in the morning - they are so good!

I would recommend looking up reviews for restaurants on TripAdvisor and work with the concierge of your hotel to make reservations.  Here are a few I would recommend:

  • Melitini: cozy little restaurant off the main path in Oia. The food was really good and I would definitely come back here.

  • Ammoudi Fish Tavern: we didn’t actually get to a chance to eat here, but it was recommended if you want to eat down in Ammoudi Bay.

  • Pelekanos: make sure you sit on the rooftop! Great views of the water and Mediterranean cuisine.

  • Domaine Sigalas: if you’re going for a wine tasting, recommend going around lunch time to enjoy the yummy food.  We got the saganaki, taramasalata, dolmades leaves and octopus and all were amazing.


I hope you get to experience Santorini and if you do, leave a comment below on some of your favorite things to do and places to stay!


Xoxo, Syd