We arrived with big plans for sunsets and beaches, but it was a tiny, tucked-away village and its fragrant vine leaves that became the highlight of our 4 days in Santorini.
With iconic caldera views, technicolour evening skies and of course, the famous blue domes, Santorini is one of Greece’s most popular destinations. But, it was the moments away from the island’s biggest hotspots that stayed with us. Think quiet villages, eucalyptus-lined lanes and some of the best food I’ve ever eaten.
This 4 day Santorini itinerary will guide you to balance the big-ticket sights with the quieter moments that are guaranteed to make your trip unforgettable.
Where to stay in Santorini?
Where to base yourself is always one of the biggest decisions. Many people flock straight to the iconic Oía, but prices here can be sky high and the narrow streets crowded once the cruise ships and day trippers arrived.
After a few days of browsing and intense discussions, we took a recommendation from my parents who’d visited Santorini the year before and chose Pyrgos, a small hilltop village they swore we’d love. Spoiler alert: they were right.
Pyrgos is centrally located, giving you easy access the entire island (especially with a hire car), it still has plenty of food options to enjoy in walking distance and it’s wonderfully atmospheric at sunset. Fewer crowds – just as beautiful.
We checked into On the Square’s Suite with Heated Tub and absolutely loved our stay there. The apartments are relatively new, so were offered at a really good price for the beautifully spacious room, plunge pool and patio for sunbathing. As always, I used Booking.com for my Level 3 Genius perks!
If you want somewhere a little closer to Oía and Fira, or with a caldera view, the village of Imerovigli comes highly recommended too.
Your perfect 4 day Santorini itinerary
Day 1: Arrive in Santorini
We arrived in Santorini right on schedule at lunchtime and walked just a few steps from the airport to collect our hire car – more on that experience later. After driving straight to Pyrgos, we checked into our gorgeous apartment and, stomachs rumbling, followed a recommendation of our host to try lunch at the wonderful Kavatza Santorini.
Centrally located in Pyrgos by the popular Johnnie’s bar, Kavatza is a fairly new place that transforms fast-food gyros into freshly made versions that’ll take a little longer to create, but are well worth the weight. Accompanied with a Greek salad and an ice cream, it made for the perfect start to the trip.
If you’re energetic enough to head straight out and about, you could explore the town’s castle for a couple of hours. Instead, we decided to make the most of our sunny terrace and spend a few hours unwinding, cat-napping and reading by the pool. We had a big two weeks ahead of us!
For dinner, we’d been recommended Kantouni, a restaurant at the foot of the castle with great service and an extensive menu. We dove straight in with the good stuff: cream cheese croquettes with fig sauce that’ll make your mouth water, the first of many many stuffed vine leaves, meatballs with a spicy tomato sauce, tomato fritters garnished with capers and authentic Greek yoghurt and finally, a fried Cretian gruyere we probably could have lived without but sounded too good to miss.
Is your mouth watering yet? Well, just so you know, they also own a dessert place next door, Kantouni Sweetery, that we may have frequented more than once…
Day 2: Oía, Fira & Perissa
Refreshed after balcony beer and early night, we were up early to enjoy Oía without being crushed by selfie sticks. Or at least, we’d try our best!
Arriving at around 8.30am, we spent a blissful hour wandering around fairly quiet streets. Sure, most of the shops and restaurants were just opening up, but it was worth it to feel a taste of Santorini before us visitors crowded in. We grabbed a quick spinach pie for breakfast at Passaris Bakery – where we spotted the locals heading – and contemplated walking down the hill to Ammoudi Bay. The prospect of the steep walk back put us off that!
Before we knew it, there were queues forming for the best dome viewpoints – and by the way, you’ll only find about the three famous domes here. There are more in other towns which really surprised us! By 10am, it was already significantly busier and we headed out.
Next stop – Fira. I didn’t have any expectations from Santorini’s lively capital but honestly, it was absolutely packed. By that time, the two cruise ships were well and truly in so we couldn’t really enjoy the narrow lanes without fighting our way through backpacks, fridge magnets and groups taking up the entire path. It’s well worth a visit, but time it better than us and be ready to make an escape when it all gets a little much.
For us, that escape was Perissa Beach. Here, the vibe was utterly laid-back, with plenty of restaurants offering free sun loungers if you ordered food or drinks. Desperate to get our toes in the Aegean, we ate at the ~ok Aquarius, then spent a few hours lounging on the black sand beach.
While Santorini doesn’t have the best beaches in the Greek Cyclades, this one came with lovely views of the cliffs and clear turquoise water, so it’s a great spot for enjoying the coast if you’re sticking to Santorini only.
Sunbathing complete, we headed back to Pyrgos and up through the castle to Franco’s. We’d actually only intended to have a drink here but, having unintentionally secured one of the prime spots for sunset, we decided to order our main meal too. Watch out – it’s windy enough up here to blow a glass off your table, as I learned the hard way!
Day 3: Boats, beaches & villages
Now look, I won’t lie – we fumbled day three of our four day Santorini itinerary.
With big plans for boat trips elsewhere, our biggest regret is not taking the classic catamaran tour to the caldera and hot springs. So do me a personal favour and book yourself onto a boat trip in Santorini to round off your last full day in style.
Instead, we started the day by driving to Red Beach, one of Santorini’s most famous. It looks pretty cool, with the cliffs a striking red that gives the beach its name, but honestly we didn’t think it was worth the hype. There’s very little shade and again, you’d be better seeing it from the water on a boat trip.
After an hour or so, we decided to head back to Perissa for lunch at Chilli’s beach bar but something still wasn’t hitting the mark for us.
Here’s where we saved the day.
We made a spur of the moment detour to Megalochori and this quiet village became one of our absolute highlights. We wandered shady alleys, admired the town’s bell-topped archways and then stumbled across Traditional Kafeneio Megalochori.
With just us sat at this authentic taverna, we devoured an oregano-topped Greek salad and the freshest vine leaves of our time in Greece – zesty, perfectly rolled and served with creamy, fresh tzatziki. It was like discovering our own secret part of the island and we never wanted to leave.
In contrast, dinner turned out to be a more glamorous affair. The Greek tapas at Madame Sousou (another Pyrgos gem) were calling and with unparalleled sunset views, we decided to give it a go. With artichoke hearts for me and tender beef cheeks for my husband, accompanied by a starter of fresh cherry tomato fritters, we were in our element and feeling semi-healthy along the way.
As we ate, a newlywed couple arrived for dinner and the whole restaurant burst into applause – one of those moments you can’t plan for, but create a really memorable experience. I can only imagine how beautiful their wedding photos turned out with the view just outside as the sun went down.
Day 4: Ancient Thira
On our final morning, we spontaneously drove up the winding hill to Ancient Thira. If you have a car, I’d highly recommend doing the same as it is steep to walk.
Again, I wasn’t really sure what to expect as we paid the €10 entrance fee, especially because the main site is pretty hidden from the ticket office. But a walk around the corner and wow, the ruins of this ancient city will take your breath away.
Considering its windy, mountaintop location, the site is vast and contains tons of useful historical placecards so you can learn more about what the buildings were used for. We overheard a couple of tour guides too and think it’d be really beneficial going with an expert if you’re a history buff.
After an impressive morning, it was time to tackle the ferry port. After dropping our hire car back – breathing a sigh of relief as we did – we took a taxi and were glad we left ourselves with plenty of time. The road down is a steep, single lane with heavy traffic and buses navigating tight corners; an easy recipe for missing your boat.
Luckily, we hopped out just in time to board Blue Star Delos to Naxos, and the adventure continued!
Steal my two week Cyclades island hopping itinerary
Practical tips for 4 days in Santorini
Car hire
Having a car is almost essential for exploring beyond where you’re staying, unless you’re happy taking tours everywhere. Just be careful with who you book through. Our experience with Volta4U was frustrating, due to hidden payment restrictions and extra insurance charges – always check the small print.
Cruise ships
Check the cruise schedule before planning your visits to Oía and Fira. You won’t thank yourself visiting in peak time!
Catching a good sunset
Santorini sunsets are legendary for good reason but don’t feel pressured to battle the crowds in Oía every night. Central spots like Pyrgos offer equally stunning views with a fraction of the people.
Our 4 days in Santorini were the perfect introduction to the Cyclades. Yes, it’s busy but with a little planning, you can carve out moments of peace and authenticity that make it magical. For us, it wasn’t just about the sunsets or blue domes, but the scent of eucalyptus, cuisine filled with flavour and unexpected discoveries.
I hope this itinerary gives you the balance of iconic sights and hidden gems to spend the perfect 4 days in Santorini!
Laura x
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