Michael & Kendra found the best place to stay in Santorini is Oia. Discover their week of sailing, wine tours, Greek food, and amazing sunsets!
Oia, Santorini
Activities in Oia
If you’re wondering where to stay in Santorini, we highly recommend staying in Oia, at the northern tip of the island. It’s called the island’s most romantic town and is known for it’s stunning sunset views. We found a lot of great activities and restaurants below.
Santorini Food and Wine Tours
The Santorini Food and Wine Tour offers food and wine pairings at several wineries across the island. Our guide Phenix picked us up from a central location in Oia and drove a group of 6-8 of us all over the island. She is American, but has lived in Oia for years, so she gives a really interesting perspective on everything. Santorini really only grows white grapes, so be prepared if you are a red wine drinker. There were a couple of good reds at the last winery, Domaine Sigalas. The wine and tapas were so good there, Michael and I walked back the next day for more.
Santorini Sailing
We did a semi-private daytime tour on a catamaran with Santorini Sailing. We were lucky to only share with one other couple on a huge boat, so it was like our own private tour. The views are beautiful and the water is so blue; it is unlike anything I’ve ever seen! The captain gave us some great historical information about the island of Santorini. We also enjoyed a tasty and large BBQ feast on board and had unlimited amounts of soda and alcohol! We were able to get close to the volcano and experience the hot springs at the base. The hot springs are currents of warm water in the ocean due to the volcano in the caldera – super cool! Highly recommend this tour!
Walking tour through Oia (self-guided)
Oia is a beautiful pedestrian city with winding cobblestone sidewalks, perfect for wandering on our last afternoon. It’s the best area to stay in Santorini. There are plenty of shops and restaurants (and yummy gelato!) to experience. There’s also a pathway to the Byzantine Castle Ruins, which are crowded, but an interesting thing to see as you are walking through. I also recommend walking down to Ammoudi Bay and riding the donkeys back up to the top.
Ammoudi Bay
Sunset in Oia
If you’re not sure where to stay in Santorini to see the best sunsets, it’s Oia! This attraction brings the crowds to Oia in droves! We went to Lioyerma Cafe and Pool Bar 2 hours before sunset. This is a great place to spend the day if your hotel doesn’t have a pool. The service isn’t great, but it was very busy so it was understandable. The views were totally worth it!
Restaurants in Oia
Anemomilo’s Taverna
Anemomilo’s Taverna was the BEST PLACE WE ATE!!! This came recommended from our wine guide, Phenix. It’s a very pretty restaurant, but located in an area that doesn’t have a view. Tavernas are authentic Greek family restaurants, which was unique for us. At Anemomilo’s they literally walked us back to the kitchen to show us what they were serving. We ended up with chicken kabobs and the best moussaka in the world! I highly recommend ordering lots of food and trying as much as possible!
Ammoudi Tavern
Our meal at Ammoudi Tavern was reserved through our hotel and it was our only pitfall. We aren’t the biggest seafood lovers, but are always up for trying it when it is fresh. This place is definitely fresh – fishermen bring in fresh catches every day. However I don’t care for pointing at raw fish in a case and having it thrown on a grill. I prefer a well cooked fish with no scales, no bones and no eyes. My husband ordered a fish that came with all three so it wasn’t very appetizing. I had the lobster spaghetti, which they are known for, but I wasn’t impressed. You must eat on Ammoudi Bay and watch the sunset, but I would pick a different place.
Paradox Thai Food and Bar
We went in Paradox for a mid morning snack before our wine tour. It was not crowded so I was initially weary about the quality. However we ordered the egg rolls and we still talk about them to this day – amazing! It’s located in Oia on the main driving road.
Skala
We enjoyed breakfast at Skala, but it wasn’t particularly memorable. We liked it because it was close to our hotel.
Pito Gyros
Pito Gyros has delicious gyros and fries! Great for quick and cheap lunch! Not a lot of seating inside so be ready to enjoy standing – totally worth it. Located in Oia, near the main driving road.
Where to Stay in Oia
Chelidonia Villas
It’s important to know where to stay in Santorini with the best views, and the hotels in Oia are known for just that. We wanted to stay in the pedestrian only city of Oia in a traditional cave hotel with spectacular views, but we were on a budget. Chelidonia Villas was perfect! Many of the hotels in Oia offer pools or private hot tubs, but are very expensive. We decided we didn’t need that since we had a private patio with chairs where we could soak up the sun and just enjoy the views.
We found Chelidonia Villas to be the right price, and in a great location near a few restaurants. Our villa was two bedrooms, one (beautiful) bathroom, a private patio, and a small kitchen where we would make coffee in the mornings. (Note there are a ton of stairs to get to and from the villas, which is typical in Oia.) The owner, Erika, was super communicative via email and checked on us once during our stay. We actually arrived one night earlier than expected and they were able to accommodate us.
Transportation in Oia
My husband is in the airline industry so we took many roundabout flights to get to and from Santorini. The staff at Chelidonia Villas booked our airport transfers (at an additional fee of course). Transportation for the wine tour and boat tour were part of the package when booking those trips. Otherwise we walked everywhere since we were staying in Oia. It’s very walkable; there are plenty of restaurants, sights and shops that were all walking distance. Cars are not allowed in Oia – only one road in and out – so we didn’t worry about renting a car or having to find taxis. If you’re wondering where to stay in Santorini where it’s easy to get around, Oia is the place.
Where to stay in Santorini – Oia Travel Tips:
Best time to visit – May was a very good time to visit. It did get rather chilly around sunset so I recommend bringing layers. The water is pretty cold if you are planning a beach day or boat day. We did get in the water on our boat trip to experience the hot springs.
Packing – We walked a ton, and Oia is all cobblestone, so don’t waste precious luggage space on heels or wedges!
Accessibility – There are also a lot of stairs so hit the StairMaster before your trip to get into shape!
Language – A lot of English is spoken however it is very broken and sometimes hard to understand. We didn’t learn any phrases before we arrived, but we did just fine.
Dining – As with any European country, eating out is a long affair. We often had to ask for the check or go find someone to pay.
Voltage – You need a voltage converter, however my curling iron fried anyway while we were there, so don’t bring your best hair tools. I sported a side braid and a pony most of the time since it’s very windy!
Allergies – There are stray cats all over, so beware if you are allergic. My husband is, but he didn’t seem to have too much trouble.
Other travel guides you might like:
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Rome, Tuscany, Naples & Sicily, Italy – 2 Weeks in Italy: Rome, Tuscany, Naples & Sicily
Paris, France – 5 Days in Paris: Explore All the Iconic Paris Sights
London, England – The Ultimate 5 Day London Itinerary
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