Santorini, Greece

In 2012 we traveled Spain with our friends and family for 2 weeks as we celebrated our wedding in the mountains near Madrid. It was epic, memorable and fantastically fun. More on that trip another day…

During the planning stages we threw around many options in Europe for our honeymoon… we finally landed on Santorini, Greece. We were sold by the picturesque white washed buildings, delicious foods, blue domes and cliffs.


Well, it was more beautiful in person than any internet search had lead us to believe. (when was the last time THAT has ever happened!)

We stayed in Oia at the Andronis suits in their deluxe suite with an indoor jacuzzi that you could swim to the window and watch the sunset in private. It was a dream… minus the coughing.

You see we were horribly sick. Jeff suffered from a stomach bug and I unknowingly had pneumonia and bronchitis… that I tried to self medicate with cough drops and breathing warm vapors. Needless to say, we did not take advantage of all the beauty, experiences and cuisine Santorini had to offer. So we vowed to go back. In 2016, we returned to this dream island and took advantage of as much as we could in 5 days.


So here is how to maximize your time in Santorini… while keeping time to relax.

First you need to decide where on the island you want to stay. Oia is where all the tourists flock to for the sunset. It has a totally unobstructed view and has less to offer in restaurants. Fira is the capital and is in the center of the crest. The sunset view is still breathtaking,  more to offer in restaurants and a night scene but is riddled with cruise ship people during the day. You can’t go wrong with either. We did both and enjoyed them equally.

5 Day Itinerary

Day 1: Arrival

Both times our flight from Athens had us arriving in the afternoon. We arranged with our hotel for an onsite car transfer to pick us up from the airport. It is a fixed fare and saves you the long lines waiting for a taxi. It cost us around $40 both times.

Once we arrived we had champagne and snack waiting for us in our room. We spent the rest of the day walking around near our hotel, sitting in our private hot tub and sipping on some beverages and eating at our hotel. Take a break and schedule your sunset cruise, spa treatments, restaurant reservations and winery tours at the front desk.

Speaking of which, lodging is not hard to come by. It is more like how much of a view do you want and how much to you want to spend. Everything is on the island from hotels, resorts to airbnb options.

If you are feeling like splurging has all the luxuries and amenities you could want. Located in Oia, they have a spa, pool, full bar and decked out rooms.

If you are more budget friendly but still want to splurge a little http://www, is for you. The staff is amazing, three star prices for a five star treatment. They know the island and are so happy to arrange all activities you want to do on the island. Not to mention breakfast in bed every day is included. (take me back!!!) This hotel is located in Fira with stunning views of the caldera.

Day 2: It’s wine-thirty

It is a great day for a wine tour. First time we rented a car. They are super affordable. You trick yourself into thinking its a smart idea to rent a car and drive around while doing wine tours. The roads are narrow and snake along through the island and little towns.

The safer options is to go on a group tour or hire a private car to drive you. For $75 we decided to hire a private car to take us around. We went to three very different wineries and had full tastings at each. The least touristy would be Venesanos winery. They give you a tour of how they once made the wine there and set you up with pour as you go wine tasting on the veranda. The Koutsoyannopoulos Wine Museum which is VERY touristy. Has models and mannequins taking you through the history of Santorini wine making. Cheesy is an understatement but we did learn a lot. You then cosy up to the bar for your tasting choosing to taste 3 or 5 different wines. Finally the most well known winery is Santos. Perched high on the top of a mountain the views are breathtaking and they have the wine tasting thing down to a science. You sit outside as they talk you through the wine pours. No tour here though. Assyrtiko grapes are the most common grapes on the island which is why white wines dominate the island.

Like most my wine tasting adventures… it ended in a nap and an espresso to rally for dinner. We ate at Nikolas Taverna in Fira. I will never forget that roasted leg of lamb, smelling of rosemary. We loved it so much we ate there twice. We finished our night with Ouzo. A typical after dinner liquor.

Day 3: Come sail away…

I highly recommend splurging and paying for the sunset cruise.

Depending on your price point you can rent a whole catamaran for over $1,000 USD or do what we did which was hire a small group catamaran for $180 per person. We scheduled this with the front desk but the service can also be booked here.

It was 5 hours of cruising around on beautiful blue waters with about 10 other guests. We sailed around the island stopping at the white and red beaches for a short amount of time. We anchored at the volcano so we could swim in the hot spring and walk on shore. Word to the wise: wear something you don’t mind turning red due to the clay in the water. While we were anchored, the crew grilled some delicious food. We later embarked to Oia where the Captain positioned the boat to watch the sunset. The first time we went to Santorini we decided to walk to see the sunset. The streets were flooded with people and donkeys. It was not the romantic scene you would imagine when planning your honeymoon. So, if you want romance… take the cruise.

Day 4: These boots are made for walkin’

There is a hiking/walking trail that takes you between Oia and Fira. It is important to remember that Santorini is very rocky and has a volcanic history… because of this the trail can be pretty tricky in terms of keeping your footing. The trail offers white washed buildings, blue domed churches, a few donkey run-ins and spectacular vantage points of all the beauty being in Santorini has to offer. Word of advice: bring water and wear closed toe shoes. Also like most of the island… this is NOT stroller friendly.

Once we got to Oia, we walked down to Amoudi bay for some fresh fish for lunch and a few cold beverages. There are a few small restaurants by the water that are quiet and picturesque. At this point we chose to grab a taxi to take us back to Fira for our massages.  Let’s be honest… we are always caught between being a #fitfam and a #treatyoself kind of couple.

For dinner we went to one of the top rated restaurants in Fira and requested a sunset view table. Make reservations either before you arrive or the day you get there. We went in May both times which is the beginning of tourist season and had to wait 4 days to get a table. The food lived up to the hype and it was a beautiful way to cap off our Santorini adventure. Learn more about Argo here. 


Day 5: Departure

Most hotels will keep your bags to allow you to walk around. We did some shopping n Fira, had a few more cocktails and took a private car to the airport arranged by our hotel. If you are one to get hungry, bring snacks the airport is small and choices are limited.


Santorini is well worth the effort of getting there. It lived up to the hype and is hands down one of the most romantic and picturesque places we have traveled to.

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