This August, Ally and I decided to visit Greece, a country neither of us had been to before. Of course, deciding which of Greece’s 200+ inhabited islands to visit was quite a challenge. We worried that a Santorini Greece vacation might feel overwhelmed with tourists, given that August was peak season. Still, we knew we wanted to experience Santorini’s iconic caldera views, whitewashed villages, and famous sunsets.
We decided to spend just two nights in Santorini before continuing on to other islands for a slower pace. Despite the short stay, our two nights in Santorini were quick but unforgettable. From quiet early morning exploration to stunning Oia sunsets, we enjoyed incredible views, delicious food, and a few unique adventures. Here’s how we spent our whirlwind Santorini Greece vacation before continuing on to Paros and Milos.
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Getting There
We decided to make Santorini our first stop in Greece, rather than spending an extended layover in Athens. To get there, we first flew overnight from Chicago to Athens, before continuing with a short one-hour flight to Santorini. Ahead of the trip, we discovered that our original Aegean Airlines “Light” fare for the flight from Athens to Santorini only included either an 8 kg carry-on or a personal item, but not both. Rather than paying for checked bags, we tried our luck placing €55 bids for business class tickets (only €5 above the minimum), and were thrilled when they were accepted.
The flight itself was barely an hour, but the upgrade was a worthwhile start to our Santorini Greece vacation. It included an upgraded 13 kg carry-on allowance and an additional personal item, allowing us to avoid checking bags during our layover. Additionally, we received better seats, priority boarding, and access to the Aegean lounge during our layover in Athens. Upon landing in Santorini, a priority shuttle whisked us from the plane to baggage claim. Because Ally and I rarely fly business class, we were baffled at first when the shuttle pulled away with only us and one other couple on board. However, this confusion soon turned to appreciation. We were among the first to reach arrivals, where our hotel transfer was waiting to take us into Oia Village.
Day 1: Sunset at Oia Castle
Our Santorini Greece vacation began at Katikies, one of Oia’s most iconic cliffside hotels. Built into the caldera, the property featured cascading whitewashed terraces, infinity pools, and sweeping views of the Aegean. Our room also included a small private terrace with a jacuzzi where we could relax at night. Thoughtful touches like a complimentary bottle of wine and evening turndown service added to the sense of luxury, while the staff’s warm hospitality made us feel right at home.
After checking into Katikies and freshening up, we headed to Oia Castle, Santorini’s most famous sunset spot. We chose to visit on our first night, as we knew there would be no cruise ships in port that evening. We packed the complimentary bottle of wine from our hotel, and stopped to grab a snack on our way. Wanting to compare two local favorites, we picked up chicken gyros from both Pitogyros and Souvlaki N’ Wrap. We arrived about ninety minutes before sunset, found a good spot, and enjoyed our gyros and wine as we watched the sun gradually dip lower in the sky. Even without a ship in port that night, the area was crowded, but the views made up for it.
After sunset, we stopped by Marykay’s Bar Hassapiko, Oia’s one true bar, for a pre-dinner drink. For dinner, we ate at Fino Taverna, a charming spot tucked into Oia’s alleyways. To begin the meal, we ordered the whipped feta and a serving of dolmades that Ally declared the best she had ever had. Afterward, we shared a slow-cooked lamb shank and lobster pasta, their daily special. The food was excellent, though we definitely over-ordered after our earlier snack of gyros. Full and happy, we headed back to Katikies to rest before an early start the next morning.
Day 2: The Perfect Day in Santorini
Santorini Sunrise Photoshoot
On our second day in Santorini, we woke up early for a sunrise photoshoot in Oia. We had booked a one hour shoot with Spyros Plesiotis, a local photographer we found through Flytographer. This was our first time booking a professional photographer in a foreign country, but it turned out to be one of the highlights of our time in Santorini. Spyros knew all the best spots to avoid crowds, was fun to spend time with, and captured incredible photos. As he showed us around Oia, he recommended a restaurant called Oia Oenosart as his favorite restaurant in town. We quickly bonded over this, since we already had a table reserved there for dinner later that night.
Cliff Jumping & Lunch in Ammoudi Bay
Back at Katikies after our photoshoot, we enjoyed breakfast overlooking the caldera, where Ally tried her first Greek frappé. Energized, we made the walk down to Ammoudi Bay. We followed the cliffs to the left and soon arrived at the well-known cliff-jumping area. We relaxed here for a few hours watching people leap into the water, and eventually joined in before drying off on the rocks.
Back in Ammoudi Bay, we snapped a quick picture of the octopus sun-drying in front of Sunset Ammoudi Restaurant. However, we chose to actually eat lunch at a different Ammoudi Bay restaurant, Dimitris Ammoudi Taverna. Here, we grabbed a front-row table, just inches from the water. Waves occasionally splashed our feet as we sipped wine and dined on tomato fritters, grilled octopus and a fresh-caught sea bass that we hand-picked from the ice cooler. The octopus was average, but the fritters and sea bass were excellent. To finish, we split an affogato, giving us fuel for the steep climb back up the steps.
One Last Oia Evening
We spent the remainder of the afternoon lounging by Katikies’ infinity pool, a welcome retreat from Oia’s crowded streets. Later, we walked to Canaves Sunday’s Veranda bar for sunset drinks. To our surprise, we had the bar nearly to ourselves and were given a daybed with unobstructed sunset views. Sipping neon-colored cocktails as the sky lit up over the caldera was an unforgettable experience.
Dinner at Oia Oenosart exceeded even our high expectations. We shared the risotto “spanakorizo,” a perfectly cooked flap steak, and a bottle of orange wine from Santorini’s Venetsanos Winery. However, the highlight of the meal was the grilled octopus carpaccio delicately dressed in vinegar sauce (the best octopus of our trip). Dessert was a standout too: a lemon cream and biscuit creation layered with crisp phyllo and paired with lemon sorbet. With Charlie Chaplin films projected on the patio walls and local artwork for sale inside, the restaurant had a creative, welcoming vibe. We left with full stomachs and a photo of Oia’s street cats taken by a local photographer, a perfect souvenir to remember the night.
Day 3: A Quiet Morning and Departure
On our final morning in Santorini, we rose early once again to explore Oia before the crowds arrived. We revisited a few of the hidden corners that Spyros had shown us during our photoshoot and wandered into some new alleys on our own. The quiet streets and soft morning light made it one of the most peaceful moments of our trip. Back at Katikies, we enjoyed one last breakfast overlooking the caldera before checking out. Soon after, our transfer took us to the ferry port, where we boarded a boat bound for Paros, the next stop on our Greek adventure.
Final Thoughts on Our Santorini Greece Vacation
We were pleasantly surprised by how much we enjoyed Santorini, even in the middle of August. The island didn’t feel nearly as crowded as we feared, especially when we ventured out early in the morning. Those quiet hours, when Oia’s streets were still empty and bathed in soft light, became some of our favorite moments. While we were excited to continue on to Milos and Paros, our time in Santorini gave us iconic views, memorable meals, and a few unexpected highlights that made the stop more than worthwhile.
Know Before You Go: Tips for Your Santorini Greece Vacation
Wake up early to beat the crowds. We loved exploring Oia early in the morning, when the streets were quiet and bathed in soft light. Setting an alarm made all the difference, and we often had entire viewpoints to ourselves. Not only did this give us a peaceful start to the day, but it also made for the best photos.
Check cruise schedules in advance. While Santorini recently limited daily cruise passengers, the city’s busiest times are still heavily dependent on the ships in port. We made sure to plan our evening visit to Oia Castle for a night with no overnight cruise ships. While it was still busy, planning ahead helped us avoid the heaviest crowds. A quick look at the port schedule can significantly improve your experience.
Views vs. food. The restaurants with the best views don’t always offer the best meals. Some of our top dining experiences were in more modest settings. We recommend enjoying golden hour from Oia castle or a hotel sunset bar, then grabbing a late dinner afterward.
Use transfers or taxis: Driving and parking around Santorini can be stressful, particularly in the height of summer. We arranged transfers through our hotel and were grateful not to deal with rental cars or crowded lots. The rides were quick, comfortable, and stress-free, letting us focus on the scenery.
Embrace the pace: Afternoons can be crowded and hot, so we learned to slow down. Instead of fighting through the busiest hours, we relaxed at the infinity pool during peak times. Saving our exploring for mornings and evenings let us enjoy the island without frustration.
Frequently Asked Questions About Santorini Greece Vacations
How many days do you need in Santorini?
We found two nights was just enough to see the highlights, though three to four nights would give more time to relax and explore. If you want to include day trips, plan for a longer stay.
When is the best time to visit Santorini?
Spring and fall (April–June and September–October) bring pleasant weather and fewer crowds. We visited in August and while it was busy, early mornings and careful planning made it perfectly manageable.
Is Santorini expensive?
Santorini is one of the pricier Greek islands, especially for accommodations in Oia with caldera views. That said, we balanced splurges with casual meals like gyros and still felt we had a great experience.
What’s the easiest way to get around?
We relied on hotel transfers and taxis, which kept things stress-free. While renting a car is an option, parking is limited and the roads can be crowded in summer.
Is Oia Castle worth visiting for sunset?
Yes, but be prepared for crowds. We’re glad we did it once, arriving early and snacking on gyros and wine while we waited. With that being said, we probably wouldn’t rush back, as other viewpoints and bars offer more relaxed sunset experiences.
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