Santorini Dreaming

Standing on the edge of the world, my heart swells with gratitude. The wind at my back nudges me forward towards the slow, oozing sun beams that seep across the evening sky as the sun is slowly pressed into the horizon.   Santorini feels like a world for the Gods, a place that us mortals could only touch in our most beautiful dreams.  But here I stand, awake with feet planted firmly, a witness to miracles, on the edge of a great expanse.  

Santorini is among my favorite places that I've ever traveled to.  It's beautiful, the food is fantastic, fresh and healthy, there are an array of magical places to stay for every budget, you have sea-side activities and even a little bit of historical sight-seeing.  Whether your traveling for your honeymoon, a relaxing getaway, or a celebratory family trip, Santorini is hard to beat.

Traveling here is relatively easy because it's one of the few islands with an airport.  We flew directly from New York to Athens and then took a small flight from Athens to Santorini.  

Many people choose to visit the Greek islands by boat, making several stops over the course of a week or two.  However, we chose to base ourselves for a full week in Santorini with 2 additional days in Athens at the end of our trip.  I'm so glad we did it this way because there is actually quite a lot to do in Santorini and it gave us enough time to fully experience the island, while avoiding the hoards of tourists descending from cruise ships like locusts swarming the plains.  

If you plan to see Athens, and you should, I recommend doing it at the end of your trip.  You will need more energy for sightseeing there, and it's HOT.  So visit the islands first to recoup from the jet-lag and then save 2 days at the end for the really touristy stuff!

Where to Stay:
With so many large villas on the island, Santorini is a great destination for larger groups.  I traveled with my entire family in celebration of my mom's 60th birthday, so there were 8 of us in total.  There are a number of lovely villa's on the island with enough rooms for all your guests to stay together, but I can't imagine any are more beautiful than Villa Erossea.  

This 5-bedroom, luxury villa is located in Imerovigli, which lies just between the two main towns of Oia and Fira.  It's a bit quieter here but still very convenient, and directly faces the Caldera, giving you some of the most breathtaking sunsets in the world.  We absolutely loved our stay here.  The space is beautiful, the view was awe-inspiring, and the service was warm, personal and some of the most attentive that I've ever experienced.  

The private pool and hot tub are one of the best things about this villa.  Looking out over the caldera, it's difficult to ever want to leave the comforts of your own terrace.

I'm also still dreaming about the incredible breakfasts that were always waiting for us each morning on the patio.

Once you are ready to leave the relaxation of your villa, one of the must-do's in Santorini is a day spent in the gorgeous town of Oia.  Head there in the late morning and plan to spend some time walking around, popping into the many local shops and wandering the narrow streets.  When you're ready to sit down for a long lunch, there are a handful of delicious places.    

Walking the streets of Oia with my beautiful mother.

One of my favorite restaurants for lunch in Oia is called Candouni.  It's a family-owned casual place located in the back streets, away from the many tourist traps.  The food here was absolutely delicious, healthy and extremely fresh.  We had an array of incredible dishes from fried zucchini, a classic Greek salad and Octopus stewed in traditional green sauce.

Another must-do activity in Santorini is a walk down to Amoudi Bay, followed by lunch or dinner at The Amoudi Fish Tavern.  It's very important though to wear good walking shoes with a lot of traction!  We unfortunately did not receive this tip, and the walk down was extremely steep, slippery and hot.  We had to move pain-stakingly slowly in order to avoid slipping and we still all ended up with blisters.   But once we made it, we were rewarded with the most delicious lunch! Order the octopus here too.  You'll see the day's fresh catch stretched out and drying in the sun.

On another day during your stay in Santorini (ideally when it's not too hot out) plan to do the hike from Imerovigli to Fira.  If you want a longer hike, you can walk all the way from Oia to Fira but it takes 2.5 hours, so bring some water.  The sights along the way are breath-taking and we stumbled upon another restaurant with delicious food called Aegean!  Make sure to try the potatoes.  They are crispy, salty, deliciousness that you will dream about long after you leave.

The path from Imerovigli to Fira

How gorgeous is my mom!

Lunch at Aegean Restaurant!  I want to go back!

If you do decide to base yourself in Santorini like we did, you can still do day trips to a few nearby islands.  We chose Santorini Luxury Trips for our private trip to Ios and sunset tour around the island of Santorini.  It was spectacular and I highly recommend using them if you decide you'd like to add a few days on a boat to your itinerary.  The captain was friendly and knowledgeable, and the crew made the most amazing lunches for us on board.  

Ios is known as a party island like Mykonos, but it also has a charming little port town and some of the most beautiful beaches in Greece.  It's one of the islands nearest Santorini and so is easily reachable for a day excursion.  All of the islands are very different from each other, so it's worth trying to visit more of them in the future if you can.  

Relaxing on the boat while heading to Ios.

Arriving in Ios

Lunch made fresh on the boat.

The beautiful island of Ios 

The main port town of Fira, is also worth a visit, but be prepared for heavy crowds and touristy shops.  It's not as quaint and charming as Oia, but if you're in Santorini, you should see it.  There is a beautiful area to walk by the sea and even a few interesting museums.  

For historical sights, definitely visit Ancient Akrotiri.  This pre-historic excavation is impressive and gives you an awe-inspiring sense of what we were capable of thousands of years ago!  It's also on a completely different part of the island and so gives you another opportunity to get to know Santorini.  Afterwards, have lunch at Mextasimas Taverna on your way back to your hotel.

If you're like me, staying healthy while you travel is important.  Luckily, Santorini has some beautiful areas where you can go for a run amongst the stunning surrounding scenery.  Near Imerovigli, there is a gorgeous trail leading to Skaros Rock.  It's one of the most beautiful areas of the island and is the perfect place to go for a run.  When you reach the peak, choose a rock for a 30 minute meditation.  It gets really windy though, so be careful. 

When it comes to fine dining in Santorini, there is no shortage of gourmet restaurants.  However, most of them we found to be very disappointing.  We had much better meals at the more casual, local restaurants.  On the gourmet end, The Athenian House was very good though and offered impressive views.  This is a great choice for a celebratory sunset dinner during your trip.

Photo credit: @hannah_claire

Another restaurant worth visiting is Botargo in the old town of Pyrgos.  The food, unfortunately, needs a lot of work.  However, the space and the view are so impressive that it's actually worth the rather disappointing meal (and as an obsessive foodie, I don't say that often).  So go for an aperitivo with snacks before dinner so you don't arrive starving.  Ask for a table on the terrace, order a great bottle of wine and just plan to have a simple meal while you take in the majestic surroundings.  

Pre-dinner drinks next door to Botarga.  The view is much more impressive from Botarga, but it was too dark when we got there so I don't have any great photos for you unfortunately. :(

In Fira, there is much hype about Koukoumavlos.  However, the dishes here are very hit or miss.  My impression is that they are trying too hard to be avant-guard, combining strange ingredients and flavors.  Often, it just doesn't work, but a few things were surprisingly good.  Flavor aside, each dish is it's own little work of art.  And if you like to be adventurous, this is a restaurant worth experiencing.

I still dream about Santorini.  Especially now as I face treatments for breast cancer, when I'm feeling stressed and scared, I often hold Santorini in my mind to cultivate the sense of awe and calm that I felt there.  It is certainly among the most beautiful places on earth, so don't be surprised to see instagrammers at every turn.  (It's almost impossible to take a bad photo here.)  So pack a great camera for this trip, take in the sights and capture all of the memories of the incredible experience you are sure to have.  Here are some of my favorite captures taken by my instagram husband, Nico Bossi. :)

And finally, I leave you with a word of advice that I am learning during my 2nd battle with cancer.  Life is a miracle, and this world holds so much magic.  See it.  Explore it!  The memories made during those beautiful times will help carry you through when things get hard.