Our Guide to Santorini, Greece

Santorini has been the number one destination on my bucket list, since I was 14 years old, and saw ‘The Sisterhood of the Travelling Pants’. Like all consumers of fine cinema, I’ve rewatched the films with my girlfriends over the years, and said ‘I’m going to go there someday’. Lucky for me, my husband made all those dreams come true and took me to Greece last week.

Santorini is everything I hoped and thought it would be, and even more impossibly beautiful in person than it is in photos. Today, we’re sharing where to stay, play and eat on one of our favorite islands.


-Secret Legends in Oia

This hotel only has eight suites and is build right into the cliff in Oia. Each room comes with a private wading pool that has a view of the Caldera, and they bring giant trays of breakfast to your room every morning.

If this hotel isn’t in your budget, make a point to try to stay somewhere in Oia – it’s by far the most convenient and beautiful place to stay in Santorini.


-PitoGyros Traditional Grill House

Our favorite restaurant (and the cheapest!) in Oia. We ate here four times in three days, and I’m still dreaming of the gyros. They don’t take reservations, so be prepared to wait in line.

-Lolita’s Gelato

It’s not Italy, but it’s pretty darn good and open late.


Good food, but an even better view of the sunset.

-Sunsets Oia

The best sunset view in Oia, and some of the best food. Make sure to make reservations months in advance.

-Sunset Ammoudi

Delicious seafood right by the bay – seriously the water is inches away from your table.



The prettiest village in Santorini, with the classic ocean views against white blue, topped buildings. Spend hours here getting lost and drinking in the views.

-Ammoudi Bay

You can walk down the 250 steps, and then pay to take a horse back up, or take an ATV down. Either way, Ammoudi Bay isn’t to be missed for its crystal clear water and great dining.

-Rent an ATV

ATV is by far the best and easiest way to see the island. You NEED to rent transportation – Santorini is a lot bigger than you think, and you won’t have as good of an experience without transportation.

-Cliff jumping

When you’re at Ammoudi Bay, head to the rocks on the left – you’ll find a rocky trail that will lead to a makeshift beach. Really just a collection of rocks people sun themselves on – you’ll then be able to swim out to another island that used to house a church, which is where people cliff jump from.

-Red Beach

Red cliffs meet vibrant water for a stunning beach.

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