Santorini remains one of the most breathtaking sights on earth, but the "hidden gem" I first fell in love with twenty years ago has certainly grown up. With cruise ships and crowds now a permanent part of the caldera landscape, the secret to a perfect Greek escape isn't just about showing up—it’s about doing it right.
Getting Around: Scooter or ATV for the wind in your hair.
Where to Stay: Oia for the views and vibes.
Whether you’re a first-timer or a returning traveler, these six battle-tested recommendations will help you bypass the "conveyor belt" of tourism and find the soul of the island I keep coming back to. From the best sunset perches to the most rewarding cliffside treks, here is how to do Santorini right.
A private deck overlooking the caldera is a must.
1. Stay in Southern Oia
For the ultimate caldera experience, aim for the southern end of Oia. It will give you an amazing view of the sunset without the crowds. If you can find a hotel with a private deck, at the end of a road, book it. You will be able to enjoy the stillness in the air and the spell of the sunset.
Hotels at the center and northern part of Oia are also amazing but the sunset will likely be obstructed and the buzz of visitors from the entirety of the island will be heard overhead as the streets and buildings are terraced to face the caldera.
2. Navigate by Scooter or ATV
Rent a scooter or ATV. The island has gotten more strict and now requires scooter renters to have an international motorcycle license. ATVs require you to have previous experience driving an ATV on an island. There have been quite a few accidents, some fatal, due to the larger crowds and countless tour buses that have arrived. Hopefully, you have a license or experience because there is nothing better than driving around the island with the wind in your hair, from beach to beach. If an ATV or scooter isn’t for you, a mini car will fit the bill.
3. Ammoudi Bay for Sun and Sea
Visit Ammoudi Bay for swimming, cliff jumping, and lunch. There is a cliff jumping spot on a rock about 200 feet from the end of the road. It looked like a lot of fun from where I was sitting...Once you’ve built up an appetite, grab a table at one of the restaurants and order some white wine and fresh grilled fish. Taverna Katina is delicious!
4. Enjoy the Deep Blues at Perissa Beach
Spend the day at Perissa Beach. Choose a chair and umbrella in front of a restaurant. Many chairs are free to use if you order a drink or food from the restaurant. Order from your server whenever they stop by your beach chair.
5. Dine with a View in Oia
Have dinner in Oia. There are a number of delicious restaurants in Oia because competition is fierce. If you want to catch the sunset glow against the caldera during your meal, book Floga 45 minutes before sunset. If that’s not important, try Kyprida or Santorini Mou. Santorini Mou has a soulful, "old Santorini" vibe. Its owner provides live entertainment nightly, making for a dinner that feels like a celebration among friends.
6. Hike from Fira to Oia
Hike the 6 miles from Fira to Oia. Travel North (Fira → Imerovigli → Oia). This ensures the iconic white-washed windmills of Oia stay in your line of sight the entire time, rather than having the view at your back. Start early to beat the intense Mediterranean heat and the midday foot traffic. About halfway through, make the detour to Skaros Rock in Imerovigli. This conical rock formation was once a medieval fortress; climbing out toward the tip feels like standing at the edge of the world.
