Destination 02: Santorini
Most people will smirk or dub you as unoriginal for visiting the popular island of Santorini. They will scold you for being a “tourist” or lacking any imagination, and speak with certainty that you will regret not choosing a more obscure or off-the-beaten-path type of destination. I, myself, couldn’t disagree more. The splendor of the small town, Oia, mesmerized me with the crisp, whitewashed rooftops, turquoise blue waters and breathtaking sunsets. My days were spent exploring the city and getting to know the locals. I was fascinated with the people and their sense of peace and contentment. Some had never left the island, yet spoke of their simple days with pride and joy. I eagerly searched their faces for a glimmer of disdain or longing for extravagance, but I never found it. All I could see was a sly smile in their eyes, as if they knew a secret that the rest of us would be lucky to learn.
When night fell, I would plunge down 300 stone steps to my favorite restaurant, Sunset on Amoudi Bay, for their famous lobster pasta. As I made the decent, I would pass small cave houses pristinely tucked into the crevasses of the hilltops and catch glimpses of families and friends sitting around a table eating, drinking and laughing the night away. Their doors were swung wide open, welcoming guests to stop in and pull up a chair. The air was filled with love and a magical allure that was intoxicating.
I felt overwhelmed with serenity and gratitude as I sat on our spacious Airbnb porch, overlooking the magnificent caldera, watching the lights from each nearby outpost dance in the dark sky.
Although Santorini is extremely romantic and probably the place most people think to go on for their honeymoon, I went with my friend Jane and still had a blast. Below are my top tips and recommendations, mostly for the town of Oia. I plan to explore more of the island on my next visit:
Things to Know
Stay in Oia: It's the most crowded and expensive town in Santorini, but it's also the most picturesque part of the island with optimal vantage points for catching those famous Santorini sunsets.
Live like a Local: Although there are many gorgeous hotels, if you want more of a local experience, rent a cave house on Airbnb. If you book in advance you can score great deals. Our spacious home had amazing views and was located right in the heart of Oia. The owner, Leandros, is a legend and gave us many great tips for exploring his hometown.
Take a Boat Trip: Take a yacht tour around the island - this is an absolute MUST! We booked with Santorini Yachting Company which was honestly the highlight of the trip. You can choose form a few different tour and boat options for day or sunset. We opted for the semi-private Lagoon 52 sunset tour which was an unforgettable experience. It's 150€ a person (or around 1,000€ for a private tour which makes sense for groups up to 8 people where you can split the cost), and includes open bar, lunch, towels snorkling gear and complimentary transfer to and from your hotel. The guys who run the boat are hilarious, and they make sure you have the best time by playing fun music on board and taking you to all the main points of the island. Santorini isn’t known for it's beaches like some of the other Greek Islands, so taking a boat tour is a great way to be on the water and work on your tan.
Visit: Atlantis Books in Oia. It’s a world famous bookstore that is so cute and charming. It's the perfect place to get your summer reading material.
Wine Tasting: Santorini is famous for it's local wine, espcially the Assyrtiko white wine. There are plenty of wineries to visit, but the best thing to do is book a wine tour so you can visit a few different wineries and not worry about driving. Book in advance.
Sunset Watching: This is a huge event in Santorini, especially in Oia. If you are planning to watch the sunset in Oia, you need to make sure you secure a prime viewing spot. Below are my suggestions for where to post up and get the best insta worthy pics:
Option 1: Book a dinner reservation at Santorini Sunsets restaurant (don't get this Sunset restaurant confused with the Sunset restaurant that is at Amoudi Bay). The name says it all, because this restaurant’s patio provides an unobstructive view of the sunset. Book in advance.
Option 2: Book a dinner reservation at one of the restaurants on Amoudi Bay (see below). You won't be high on the hills, however, the views at sea level are just as stunning. This is probably the least crowded option.
Option 3: Secure a prime spot on top of the Byzantine Castle Ruins (we did this). You will need to arrive at least a couple hours before sunset as the streets will be flooded with pushy tourists ready to get their cameras clicking. If you despise huge crowds and chaos, this probably isn't the option for you. However, if you get a spot early enough, it can be a fun experience. Bring a bottle (or two) of wine, make new friends and prepare to watch the most beautiful sunset your eyes will ever see.
Restaurants/Bars
Sunset Ammoudi Taverna at Amoudi Bay: This was my favorite restaurant in Santorini. The lobster pasta is to die for! It’s a massive plate so make sure to share amongst friends. The tzatziki here is also extra creamy and delicious. The overall food and vibe are A+.
Taverna Katina at Amoudi Bay: Another great restaurant at Amoudi bay (right next to Sunset).
Melitini: Casual place with delicious food, especially the octopus. It’s a family run restuarant, cooking up authentic Greek recieps that have been passed down from generation to generation. They also have a nice selection of local beers - my favorite was the Donkey Yellow. Prices are very reasonable for Oia. Go for lunch, sit on the roof and enjoy the view.
Skala: Our airbnb host recommended this place but we didn't have enough time to go. We walked by and views were amazing, the vibe was fun and the food did look delicious.
Red Bicycle: Another recommendation from Leandros - on my list for next time.
Lolita’s: The best gelato place on the island with a backdrop wall that is perfect for selfies. We came here often.
Hasapiko Bar: Practically the only bar in Oia. It's where all the locals go. We ended up dancing the night away with our fun servers from Sunset at Amoudi Bay.
