Three Days in Santorini

Oia Santorini

Planning a visit to Santorini? There’s plenty you can do in just a short time. Let me show you how to make the most of three days in Santorini.

I’ve dreamed of visiting Greece since I was a kid—dreams that included whitewashed cliffside villages with staggering views to the sea. Finally, a few days after arriving in Europe in May, I made my way to Greece for the first time. I spent three days in Santorini in the village of Firostefani before settling in on the quieter island of Sifnos.

blue-domed church in Santorini

I typically steer clear of tourist-packed places. I’ll skip an important site rather than stand in line, and I far prefer meeting and meshing with locals than talking to other ‘Mericans. I can stay home and do that. Santorini is known to be bursting with foreigners all summer long, so I wondered whether I should visit at all. I’m so happy I did.

In early May, the Santorini tourist season is just getting into gear. There are enough people around and places open that it feels lively, yet not quite crowded. In other words, it’s perfect. And the pinch-me-I-must-be-dreaming beauty of the place is enough to make you swoon. Even if you’re not there on a romantic getaway, Santorini makes you fall in love—with the island, with the wonders of nature, with the Greek culture, with life.

Sunset in Santorini

Want to make the most of your three days in Santorini? Follow my itinerary and you’ll experience some of the best that the island has to offer—a perfect mix of exercise, exploration, relaxation, and ridiculously good food.

Arrival

You’ve arranged for an airport transfer through your host, Santorini View Studios, a family-run accommodation perched directly on the edge of the caldera. Sure enough, a smiling guy named Andrew is waiting to whisk you off to Firostefani, filling you in on bits of island insight during the 15-minute drive. His mother, Georgia—with whom you’ll feel like old friends immediately—meets you at the pedestrian entrance to Firostefani. And while Andrew hefts your luggage, Georgia leads you to your first glimpse of the to-die-for view. Your personal balcony is right there and you’re tempted to do nothing at all but sit, stare, and feel your heart skip a beat.

First peek Santorini View Studios

You’re travel-hangry, however, so after unpacking and freshening up it’s time to eat. It’s still early by European dinner standards, but that works in your favor. Head a few doors down to To Briki where you snag a seafront table, no reservation required. Order a glass of wine and far too much food, a chance to taste a bit of everything and pack the leftovers to go for a later snack.

Greek salad from To Briki
Fava from To Briki
Grilled haloumi from To Briki

Next, wander the charming streets of Firostefani, getting a feel for the place and picking up essential supplies for your three days in Santorini. And by essentials, I mean bottled water (the tap water is too salty to drink) and good Greek wine. Before heading back to your studio, stop into Onar, the highly recommended restaurant next door, to secure your front-row sunset-timed table reservation for tomorrow night’s dinner.

By now it’s 7:00 p.m. and time to settle in and watch the sun go down. Pour some wine and let the colors of paradise surround you, deepening as the sun hits the sea. When you’re hungry again, bring out dinner, round two. Watch the village lights begin to twinkle. Once the temperature drops, find the fleecy blanket in your bedroom and snuggle up again outside, sipping wine and gratitude until you’re ready for bed.

sunset in Santorini

Day 2

After a perfect night’s sleep in your cliffside studio, pull on the lush terry robe and settle back on your balcony as homemade breakfast is served. There’s a plethora of food and you’ll want to fuel up. You have a big day of hiking ahead.

View to Oia from Firostefani
wildflowers along the caldera trail
Fira to Oia trail view

The 10-kilometer trek to Oia—Santorini’s most picturesque village—is best done in the morning before the sun beats down. You could cover it in under two hours, but with all the stops to ooh and ahh and snap photos galore, plan for three hours on the trail.

little church on the way to Oia
wildflowers, Santorini
donkeys, Santorini

Once in Oia, spend the early afternoon exploring alleys, climbing up and down steps, and finding increasingly beautiful views. Stop for lunch at Lotza, then wander back through town, popping into some of the many boutique shops. (Mov & May is the place for a unique, sexy-yet-sophisticated summer dress.)

stairs and more stairs
watch dog, Oia
Lotza for lunch
local beer at Lotza
tzatziki at Lotza
Greek salad at Lotza

Pick up the pace on the return hike home, burning calories in advance of another feast. Make one final pit stop just before reaching Firostefani—this time to the trailside boutique Under a Fig Tree, where you’ll be tempted by the beautiful Park House handmade leather bags, along with every other thing.

Under a Fig Tree

After 20k of hiking, it’s time to shower up and head to Onar for a delectable dinner and another perfect sunset. The restaurant’s rooftop (accessed from a staircase at the corner of the dining room—your friendly waiter will show you the way) is where you’ll want to be at just the right moment for a postcard-worthy photo opp. Linger over dinner, because there are simply too many menu items you won’t want to miss, including dessert and a local Vinsanto. Finally, happily full and fatigued, roll around the corner to your studio and drift sweetly to sleep.

Tomato balls from Onar
Greek salad from Onar
Mushroom risotto from Onar
yogurt mousse from Onar
view from Onar

Day 3

Another beautiful breakfast on the balcony awaits. Savor it slowly, as the world around you wakens and you prepare for the day. This time you’re headed to Fira, just a short 1-kilometer stroll along the cliff. The town is made for wandering, and you’ll find plenty of stairs and laneways to discover, packed with shops and cafes for every budget and taste.

Breakfast on the balcony at Santorini View Studios
walk to Fira

But today’s true gem awaits another 4k down the road: Santo Winery. You can walk there and get a look at the local side of Santorini while working up an appetite—there’s a sidewalk almost the entire way. Or hop on the bus or take a taxi. Just be sure to get there for a luxurious afternoon spent wine tasting (I recommend the premium reds flight), nibbling on local cheese and olives, and more I-must-be-dreaming caldera views.

Santo Winery spread
Patio at Santo Winery
another Santorini view

Once you’ve soaked up your fill of wine, cheese, and beauty, make your way back to Fira. Wander about as your wine buzz wears off, perhaps stopping into a cafe for a mud-thick Greek coffee. Or say hello to the donkey packs on the stairs to the old harbor, waiting to haul tourists around. As afternoon shifts softly to evening, find local favorite Lucky’s Souvlaki. Order a takeaway dinner to tote back to Santorini View Studios and spend your final evening—you guessed it—back on your balcony. Because right here right now, there’s no better place in the world to be.

donkeys and steps, Fira
Lucky's Souvlaki
Felafel pita from Lucky's Souvlaki
Sunset dinner on your balcony

Departure

Pack up early, then indulge in another delicious lingering breakfast while wrapped in your robe. Your three days in Santorini has felt like 30, given how relaxed you feel. Breathe in the beauty around you. Commit the sensations to memory. Snap a few more photos of the hilltop village and the sparkling sea below. Say a heartfelt farewell to your wonderful hosts, with promises to return. Chances are, you will.

Santorini sunset


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