Santorini is More than Blue Domes and Instagrammable Spots
Food & Wine
I had very high expectations of Santorini based off drool-worthy images I found online and dozens of guides I'd read before I visited. And to my surprise, I was very disappointed... BUT, only because it took me a day to re-adjust my 'travel lenses' and let the island dazzle me with its beauty rather than trying to get that perfect sunset pic.
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Where to stay
Vedema, a Luxury Collection Resort, Santorini
Within the medieval village of Megalochori, this special resort takes inspiration from its ancient setting, with peaceful rooms, a prized wine cellar and authentic spa.
$100 food / beverage credit.
Breakfast daily for two guests per bedroom.
Upgrade & extended check-in/out based upon availability at check-in.
Canaves Oia Boutique Hotel
This honeymooner go-to is a dreamy mix of whitewashed suites, cliffside infinity pools, and views across the Aegean.
$100 food / beverage credit.
Upgrade whenever possible.
Secret View Hotel
A hidden oasis of tranquility and comfort, providing guests with an exclusive and enchanting escape in a stunning location.
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Day 1: Oia sunset & dining
Before the trip: I suggest studying the island on the maps and familiarizing yourself with the distance between your hotel and the places you want to visit. I say this because no matter where your hotel is located, you will end up driving around to see all the main attractions.
Things to note: The island has only two main roads that connect the towns and most of the streets that go into the town itself are one-way - you should allow for extra time when getting from/to your destination. For this very reason, you should not rent a car to save yourself from unnecessary stress trying to find parking. Hotels that are located on the cliffs with that breathtaking view might now have direct access to the road and you might have to walk with your bags down quite a few flights of stairs. I would also check the 360-orientation of your hotel in case you are paying for the view just to avoid any disappointment once you're there.
Day 1: Base yourself around Oia. After the check-in have a pre-dinner swim and a drink before getting to town. In the summer sunset is around 8:30pm and the best time for walking and taking some evening photos would be from 7:00pm onwards. Most tourists will rush to the edge of town to watch the sunset and you can certainly join in too, or use that time to find yourself a good spot for dinner.
Restaurant recommendations: Fine dining at Naos or Mia's with a nice view of the town, Ammoudi Bay Fish Restaurant for an early dinner or lunch, Italian Thalami Bistro (beautiful view) or Petrosia restaurant, touristy but nice. All this is walkable even if you are based a bit off the town center and you shouldn't need to look for a taxi.
Day 2: Fira & wine tasting
Enjoy your breakfast and head down towards Black Beach area for a half day swim and lunch. You could book ahead, however, there are plenty of beach bars and restaurants for everyone's taste, and the best would be to take a taxi to the beach and choose on the spot.
On your way back, stop by a winery called Venetsanos (I recommend booking in advance) for some wine tasting and breathtaking views.
The sunset is worth staying around for and having a late dinner in Fira town. Many Santorini guides recommend booking yourself a wine tour. However, that is just a waste of time as you will spend more time driving from one winery to another speed drinking the wine rather than enjoying the atmosphere and the wines themselves. Rather, pick one to be able to experience it to the fullest. In case Venetsanos winery is not available, there is a bit more touristy option down the road called Santo Wines, or if you are not bothered by the views then Art Space Art Gallery-Winery-Museum is a truly unique spot.
Fira will be more busy than Oia with far more dining options and I recommend walking around and choosing something to your liking. Not everything needs to be pre-planned! Both Fira and Oia are overlooking the famous caldera (the volcano crater) so there will be plenty of time to indulge in the view from different points.
Insider tip: Organize a taxi pick up from Fira beforehand. The transport is well worth the planning in Santorini as there are not many regular taxis on the island and more of individual van drivers that hotels are collaborating with. If you happen to get a good one, the best would be to get their number and call them whenever you need the ride!
Day 3: Cruise
After another slow morning and hopefully tasty breakfast start your day in Oia to see this beauty in the daylight. Even though you will experience crowds if you travel during the summer, take your time to meander through the streets and check out Google map pointers for photo ops. The castle is at the very end of town and no photo can replace the feeling of standing there, witnessing how majestic Oia is.
Depending on your preference, you could either go on a day cruise or get your sneakers out and explore the caldera on foot. In case you opt out for a cruise, I highly recommend booking the private tour. Most cruise itineraries are very similar, but having in mind it is 5+ hours on the water, you are not so keen to share this ride with other 20-30 people. Again, many will advertise that a sunset cruise is better.
However, keep in mind that in that case your evening will be taken completely. You might feel like walking, on the other hand, and sampling some more views. You could start from Oia towards Imerovigli making sure to locate the Skaros Rock on the map. If you are quite fit and don't mind the sun, you could also take a transfer to Fira and then walk back towards Oia. No matter what you choose to do with your day chances are you'll be pretty wiped out by the end of it, so a quiet, low key evening will be a perfect cherry on top for this trip.
Insider tips: Santorini is way bigger than it might seem when you first look at it online. To make the most of your time when visiting it would be wise to plan your trip in advance. Since not many people are living in Santorini all year round and main stream of income is tourism everyone if focused on making their every day count. With that said, I would be cautious of paying more for services or goods than what they are worth. Don't be afraid to bargain or to question some prices if they seem unreasonable! Oh, and if you happen to be in the flying dress shoot please let me know how it went since I've heard some not-so-fun stories about it. Something about 5am start and everyone queued up in their gown waiting for their 5 minutes of glory. Perhaps it was exaggerated review that I read but you never know!
Need to Know
For more travel tips, check out Fora Advisor Carlie Khalil’s guide, 3 Days in Santorini, Greece.
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This guide is part of our ongoing series on travel to Santorini.