Five Days in Santorini

Here at Mojo and Moxie, we talk a lot about that “next stage.” The kids are leaving, or old enough to stay home alone, and you are getting ready to take some time to travel. This is the stage where you might just have the time for a trip to Greece – and for five days in Santorini!

Seriously though, when the kids are little, or even when you were in the height of busy-ness with their extra curricular activities, you probably never dreamed of a trip for just the two of you – never mind in Greece.

Well, now that that kids are heading off to adulthood, why not consider some adult time for you?

My husband and I recently did this trek, and while five days in Santorini might not be quite on your radar yet, we can both attest that it should be.

While this was a splurge trip for us to celebrate our 20 year anniversary we decided to go at an off- season time. MAY! While outside of the typical summer months it was still beautiful weather and pricing was slightly cheaper than during the height of the Summer.

Here’s a look into our five days in Santorini…


Santorini is one of the honeymoon capitals of the world so there is no lack of luxurious, romantic properties on the island.

Our only “big” decision was figuring out which of the four towns (Fira, Oia, Imerovigli, and Firostafani) we wanted to stay in. All are located on the Caldera with great views of the sunset, volcano, and those beautiful white-washed buildings. Most of the best hotels are located in these four towns.

We ended up staying in Oia (ee yah) at the Canaves Suites which we loved. It seems all hotels on island are small boutique hotels. As most of the hotels are located on the cliffs of the Caldera, they resemble whitewashed caves and make for a unique hotel experience.

Expect STAIRS 🙂 Rooms in all the hotels are accessible via a maze of staircases. You will get your workout just getting to breakfast.

Rooms were simple, white, clean and airy.

Canaves has several hotels in Oia – and every one is slightly different and special.

Armeni Restaurant

This little gem is a Santorini fav for lunch. The restaurant was only accessible from the water while we were there. The very steep steps that were previous access to the restaurant washed away last Spring. It was part of the adventure to get there and very popular.

We were picked up at the Oia harbour by speed boat, and whisked around the corner to Amoudi Bay and the delightful quaint locale set right on the water. The food was fresh – they specialized in fresh caught fish and other Greek delicacies. The service was friendly and easy going.

This is a relaxed space – and if you want to make an afternoon of it, you are welcome to lounge on the dock where they have sun chairs out for your use.

Pito Gyros

I feel like we spent our entire time in Greece looking for this place. We really wanted what WE thought was some traditional Greek street food. Pito Gyros most definitely delivered.

Pito Gyros is packed all the time and it is first come, first served – with takeout available too.

This is fast food, Greek style – and it was delicious.

You can find pita gyros, souvlaki, kebab, handmade sausages, pork steaks etc. all roasted on a charcoal grill.

We had the chicken souvlaki gyros and a couple of cold beers after a long midday hike and we couldn’t have been happier with our choice. Easy on the wallet as well! And YES – there are french fries stuffed in the gyro!!


Melitini was probably the most recommended restaurant on the Island! Both times we visited for a light / tapas style dinner we ran into guests from our hotel and people we had met on various tours. Clearly it was a popular choice among tourists and the hotel concierge!

Melitini has a beautiful roof top patio but both times we visited, we sat in the front outdoor courtyard. It was lovely and cozy – out of the cool wind of the roof top. Of course, no view in the courtyard, but a great atmosphere all the same.

Melitini features a tapas style menu with a ton of Greek favorites such as grilled octopus and fried cheese – all little plates for sharing. We loved it – and found it to be very reasonably priced as well. I guarantee you won’t find a much cheaper wine than at Melitini. 😉

With a view like this – who really cares about the food anyway?! 🙂

The best meal we had in Greece – in fact, I may consider it the best meal I’ve eaten in my life! Ovac was a gem. We couldn’t have been more thrilled that our hotel had suggested it for the evening of our 20th anniversary.

Best described as a “fusion” style of restaurant we were delighted with some of our favs on the menu. Sushi grade tuna tacos – along with an amazing selection of other sushi and sashimi for appetizers and a seafood risotto for two that was to die for.

One thing to note about the restaurants in Oia – most are focused on that unbelievable view of the sunset. And if you want to time your dinner or drinks with the sunset – this is the most busy time of the evening. It is indeed very special – and we never got sick of watching the sunset in Santorini. But – you do need to prepare for this with reservations. Also, don’t be afraid to pick spots off the “main drag.” We had amazing meals down a maze of streets and led up to the rooftop to catch “that view!”


Having not ever visited Greece before, we wanted to ensure we didn’t spend the entire time lounging at the “oh so tempting” pool bar surrounded by cavernous rocks and of course, cute pool boys!


Plan your tours for sure, but don’t miss some r n’ r at the pool. The Greek people are lovely and the service at our hotel was beyond amazing. We so enjoyed getting to know the staff, and learning a little about their lives in Santorini.

We scheduled a few tours, and added in an incredible hike in order to see the most of the island in our short time there.


When you think of Greece, you probably don’t really think of wine. BUT – being the wine lovers we are, we thought a wine tour anywhere can’t really be a bad thing!

And it wasn’t!

We spent 4-ish hours touring around the island with our knowledgeable sommelier and a few other wine loving tourists. We got the chance to visit 3 different, unique wineries and taste some interesting wines.

Was the wine the highlight of the tour? Probably not – but we have been spoiled with trips to Tuscany and Napa which are hard to beat. BUT – it was a great day, enjoying the company of other people, learning about Greek culture and their approach to wine making.

We would recommend this tour as another interesting way to see the island of Santorini as well. We booked with Santorini Wine Roads. Loved our guide and enjoyed the tour.


You can’t go to Santorini and not see it from the water. So whether you choose the 5 hour sunset cruise like we did, or the day trip it really is a “must do.”

The cruise we opted for started about 3 hours prior to sunset, with a focus on getting you in the water. Find it HERE. Swimming and snorkelling, sailing past the volcano, and visiting the hot springs were all a part of the tour. We visited Santorini in May, so although the weather was beautiful, the water was still too cold for lil’ old me 🙂

I enjoyed watching the “guys” turn blue as they bravely hit the water – and would imagine this trip would be so refreshing in the heat of the summer. Not particularly a “group activity” person, this cruise was actually amazing. The staff was great – knowledgeable and safety conscious but also fun with lots of stories to tell.

Typically on these types of tours, the food is not really anything to write home about. I can honestly say, the food was delicious – fresh bbq’d chicken, lamb and beef, traditional Greek salads, humous and pita and of course their yummy Tzatziki. As you can imagine, drinks were plentiful.

The sunset cruise started at a port quite a distance from our hotel – but ended at the port just below us, so that was an additional bonus because by the end of the evening, you are starting to feel chilly for sure. I would recommend bringing long sweats, and sweatshirts etc because once the sun goes down, it is COOL.

Also, as a note. All the sunset cruises end at the same place – which coincidently has the most perfect views. So, you will be surrounded by boats all doing the same thing as you. This of course, is not really bothersome in itself, BUT causes a major traffic jam upon disembarkment.

There is a lottery system for boats approaching the dock – and if you are the last boat in, you could possibly be sitting out on the water for an additional 1 – 2 hours.

For some reason, the Greek Gods were smiling on us the day we went, and we won the first boat in spot. The captain couldn’t stop talking about it, so I am assuming this is a rare occurrence. Don’t say I didn’t warn you…


Of all the memories I have of our time in Santorini, this jaunt between Fira and Oia will forever have my heart. My husband and I love to keep active, and the hotel suggested we might like the 10 km hike between the two beautiful towns set on the cliffs of the Caldera.

We are so glad they did.

I do have to say, that I use the word “hike” loosely. Really, it is more of a walk – nicely carved out – easy to follow and a trek many on vacay take advantage of. The views are some of the best in the world, and you will be in constant awe.

We took the 10 minute cab drive into Fira and explored the town a little prior to finding the pathway. Fira is where all of the cruise ships come in – so we spent a little time watching the ships, and marvelling at the size and quantity of ships in the harbour.

The hike takes anywhere from 2 – 5 hours, and goes through the villages of Fira, Firostefani, Imerovigli, and finally into Oia. Allan and I treated it like a work out once we had explored Fira, and made it in under 2 hours – but we were hauling!

Hike from FIra to Oia
Bring water and a backpack – not a ton of places to stop on the way – especially if you leave early!

I can honestly say, this is the most beautiful way to see and appreciate the Caldera, and this beautiful island. You will not be disappointed.


If you love to work out – and a good sweat, skip the gym. The towns provide you with a gym all on their own! We ran a good 5 / 6 km each day and ended at Amoudi Port. Look up – look waaaaay up. Climb that hill, (or run it) around the donkey poop and the instagrammers. You will be rewarded when you are done 🙂

You can take the hill on your own…
Or with a little help from the local Ass… 🙂

As you might be able to tell, we loved every moment of our trip to Greece. You can’t go wrong in Santorini. Bring your camera – be prepared to be awed.

**For info – we booked our trip through travel agent “extraordinaire” Jolene Williams – who arranged everything for use through her contacts at Hellenic Tours. She is a Virtuoso agent and was able to get some perks and upgrades for us – and was there if we had any questions or problems.

If you are loving our travel blogs – check out Danni’s Five Days in Los Cabos

Mojo and Moxie



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