6 Days in Santorini
Why Santorini
When you think about Santorini, you probably think of the beautiful pictures you see on social media. However, Santorini is so much more than that. It was the pictures that initially brought us there the first time, but it was the warm people and the culture that brought us back for a second trip.
I try to learn as much as I can when I go somewhere. I love talking to the local people, asking questions, and learning about their culture and history. Even though we had been to Santorini before, my eyes were open in a new way this time after not being able to travel for so long due to Covid.
Traveling During Covid
The first time we went to Santorini, we stayed for 3 days as part of a bigger trip to Greece. This time because of Covid, we only went to Santorini and stayed for 6 days. It was nice to have a balance of relaxation time and time to explore.
At the time we went, if you were vaccinated you didn’t need a Covid test before going to Greece. You just needed one coming back to the U.S. We purchased at-home tests through our airline that we were able to do in our hotel room through a facilitated tele-health visit, which was super easy and results came in 15 minutes. A lot of hotels will also help you book a test if this isn’t an option for you.
Overall, we felt very safe in Santorini. Most activities and restaurants were outdoors and many establishments required their staff to wear masks. We brought masks with us on our excursions and if we felt like there were too many people around, we would put them on. All the tours we booked were private so that we wouldn’t be in big groups of people. We also went in September after Labor Day, which helped with the crowds.
The 5 Best Things About Santorini
The People
Of all the places I’ve traveled, the people in Greece are my favorite. They are warm, generous and so grateful that you have made the trip to their country. The economy in Greece is dependent on tourism, so the people there want nothing more than for you to enjoy your trip. Because Santorini is such a popular tourist destination, many of the people working there come just for the busy season to make money and then when Santorini closes down in the cooler months, they travel home. While they always have a smile on their face, remember that many people there are working 12+ hour days without breaks, often 7 days a week during the tourist season. Be kind, be respectful, and don’t forget to tip them. They are grateful for just a small amount of gratuity, but we always like to give as much as we can for their hard work and kindness.
The Food
Santorini has some of the freshest and most delicious seafood in the world. There’s nothing better than sitting by the sea eating a beautiful piece of fish that was just caught earlier that day. A lot of restaurants will let you go see the fresh fish selection and pick out what you want. Some other popular and traditional dishes in Santorini are Sagnaki: fried cheese covered in filo pastry drizzled with honey, Tomatokeftedes: small tomato fritters, Fava & White Eggplant. Because of the volcanic soil in Santorini, everything from the produce to the wine has unique, rich flavors that you won’t experience anywhere else.
The History
Do yourself a favor and book a tour in Santorini. It’s the best way to truly see the whole island and learn about the culture and history, especially if you haven’t been before. (More information below about booking a tour.) There is an old saying about the island: “There are more churches than houses, there are more donkeys than people, and there is more wine than water.” If you’re going to Santorini just to take Instagram pictures, you’re missing out on so much of the experience and what makes this place special. Ask questions when you’re talking to the locals. They love sharing stories and fun facts about the island.
The Sea
A friend once told me that there is no bluer water than in Greece. The color is truly breathtaking. There is something therapeutic about being in the Aegean Sea. It is so special and healing. The best way to see the water in Santorini is to take a boat tour. You can swim in the volcanic waters and the views of the island are spectacular.
The Views
The shape of the island was created by a volcanic eruption in the 16th century BC (and the volcano is still active today). This is why the views in Santorini are unlike anywhere else. It is definitely worth splurging on a hotel or Airbnb with caldera views so you fully experience the landscape. You will never see a more beautiful sunrise or sunset in your life.
About Our Hotel:
We stayed at Charisma Suites in Oia both times we traveled to Santorini. We love the staff there and the location is magical. The hotel has undergone some significant changes since our last visit with an additional pool, a restaurant and more suites. Our first time we stayed in a basic suite on the lower level of the hotel. The second time we did 3 nights in the windmill suite and 3 nights in a private pool suite.
All the rooms are absolutely gorgeous and they all have caldera views. The hotel also has an incredible breakfast included that is delivered to your balcony every morning. The hotel is full service, with a 24 hour concierge. They will help you with restaurant reservations, activities, as well as transportation throughout your stay.
——-—Our Itinerary ———
Day 1
We arrived in the afternoon, relaxed and settled into our hotel room. Then we headed down to beautiful Amoudi Bay for dinner at Sunset Tavera. We had an early reservation at 6:30 so we could have some daylight and fully enjoy the sunset. They have the most incredible Lobster Pasta that we had to come back for twice. The sauce recipe has been a family secret for 41 years. Make sure you request a table by the water for the best views when you make a reservation. Also, see if George is there! He’s our favorite waiter. Tell him Greg and Michele sent you.
Day 2
We headed to Fira (the capital) for a day trip. It’s busier than Oia and feels more like a city. It’s fun to walk around, shop, stop for some wine, eat lunch and people watch. We enjoyed an amazing lunch at Kaliya restaurant overlooking the caldera. Their octopus dish was delicious. Then we enjoyed the late afternoon by our private hotel room pool and ate dinner on our balcony while watching the sunset.
Day 3
We had a tour that we booked with Santorini Day Tours and requested Ted as our guide. He was our guide during our first trip to Santorini and we had kept in touch over the years on social media. When we came back this time, we surprised him and booked a tour under a different name. He picked us up at our hotel and was shocked to see us. It was so special and the warmest welcome.
Santorini Day Tours will customize your tour to see whatever you want. Because we had been to the island before, we had some new places we wanted to check out as well as some places we wanted to go back to and experience again. We did a walking tour in Pyrgos: a quaint village with adorable cafés, charming restaurants and places to stop for coffee. It’s also full of rich history that your guide will share as you walk around and explore. We also went to Megalochori (which means big village), home to historic mansions and the famous Gavalas Winery where we had a tasting and met some of Ted’s local friends.
Then we finished our tour at Art Space Winery, a place we went to last time we had visited. This winery is truly unique, not only with incredible wines but it is also an art gallery, displaying work of local artists in the wine caves. Greg and I bought one of the bronze olive tree statues last time we went. You’ll meet Mr. Antonis, the winemaker, who has created his own unique methods of harvesting his grapes. You will never taste wine like this in your lifetime. Ted is studying to be a wine expert under Mr. Antonis so we had a rich and educational experience while tasting some of the most magnificent wines in the world. And of course, we shipped a case home to ourselves of our favorite ones.
Day 4
We took a boat tour that we booked with Santorini Catamaran Sailing. The first time we came we did a group sunset tour, but this time we did a day tour that took about 5 hours. The group tour we did last time was less expensive, and a lot of fun, but because of Covid we did a private one this time. The company provides transportation to and from your hotel (both for group and private tours).
The boat staff takes you all around the island, stops for swimming a few times and cooks a traditional Greek meal for lunch on the boat. There is also local wine and beer provided. This was one of the highlights of our trip. We also loved our captain and boat guide (Theo & Harris). They were such wonderful people who also shared a lot of Santorini’s history with us during the trip. The lunch Harris cooked for us on the boat was his grandmother’s chicken recipe, which was so special and delicious.
After the boat trip we went back to our hotel, swam in the pool and freshened up for dinner. We ate at Roka, one of our favorite restaurants on the island. It is so charming, family owned and the food is incredible. Our favorite dishes are the Greek Buffalo Burrata, The Mushroom Ragout and the Greek Handmade Pasta.
Day 5
We spent the day walking around Oia exploring and shopping. Make sure to stop at the famous Atlantis Bookshop. They have signed and first editions of some of the most famous books of all time. I always buy a Greek cookbook when I go. We had a lovely lunch at Lotza and then went back to our hotel to swim and relax before dinner.
Dinner was at Metaxi Mas in Pyrgos. We hadn’t eaten there before and were blown away. The food was so good and the service was also excellent. The meal was surprisingly inexpensive. We actually thought they had made a mistake on our check! For dessert, they gave us a complimentary Greek cheesecake, which was easily the best cheesecake I’ve ever had in my life.
Day 6
I booked us a sunrise photo shoot through Flytographer. Our photographer was “Alex in Santorini.” It was an early morning, but so worth it. During the sunset time in Oia when most people want to take pictures, the streets are packed. During the sunrise, you see completely different colors, the streets are empty and it feels like you have the whole island to yourselves. It’s romantic and a completely unique experience. Alex was also awesome. We had so much fun with him and loved how our photos came out.
Then we headed to the Black Sand Beach in the afternoon where we met Ted (our tour guide friend) for a swim and dinner. Black Sand Beach is a super fun day outing. We went to Seaside where they have gorgeous cabanas with beachside service. The water is beautiful and warm. It was a great way to spend our last afternoon on the island.
We ate dinner at the Seaside Restaurant. There is a little spot on the beach to shower and change clothes before dinner. Seaside Restaurant was such a nice surprise. They had an extensive menu, featuring fresh seafood with an Asian fusion twist. Everything was so delicious. Don’t miss out on their famous Truffle Tart and the Crispy Salmon entree.
Until Next Time
And then, the sun set on our time in Santorini. We woke up the next morning at 6am for our departure. As we walked up the hotel steps to leave, I turned around to say goodbye to our beautiful caldera view. The sun was starting to rise as if it was giving us one last glimpse of Santorini’s beauty before we had to go. Our favorite driver, Demetrius, picked us up and brought us coffees from his favorite place (I’m not kidding about how wonderful the people are)! We sat in silence on our way to the airport, taking in our last Santorini sunrise.