As our Blue Star Ferry entered the caldera of Santorini, the Captain made an announcement over the public address system. He was going to slow the ferry down, he said, so that all passengers could take photographs. And then the caldera opened up before us — the ancient volcanic rim rising in a great arc from the water, the whitewashed villages clinging impossibly to the clifftops above, the deep blue of the Aegean framing everything — and every person on the deck went completely silent.
That was our introduction to Santorini. We have been back many times since. We stay for weeks at a time. We have a studio in Oia that we call our home away from home. We know the restaurants by name, the pool bars by the quality of their Wi-Fi and the dogs — the extraordinary Santorini dogs who will walk with you from Oia to Fira at dawn and hand you over to the next pack as if they have a system.
Santorini is the most beautiful place we have ever lived. Not just visited — lived.
This guide is built from years of personal experience on the island. It is honest about what the island is like, specific about what to do and where to eat and entirely personal. We have spent enough time here to know which restaurants are worth the walk down to Ammoudi Bay and which sunsets from whose balcony are the ones you remember for life. Here is our four-day guide to getting it right.
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ARRIVING IN SANTORINI
Arriving in Santorini — By Ferry or By Air
By Ferry — Our Strong Recommendation
If you have any flexibility at all in how you arrive in Santorini, take the ferry. Nothing — not a photograph, not a film, not any description in any guidebook — prepares you for the experience of sailing into the caldera. The ancient volcanic crater that forms Santorini’s harbour is one of the great natural spectacles on earth and arriving by sea means you experience it at the right scale and the right pace.
We arrived from Mykonos via Paros on our most recent trip — a classic Greek island-hopping route that gives you the beautiful harbour town of Paros before the drama of the Santorini arrival.
Ferry cost: From approximately €20–25 per person from Naxos or Paros. Book in advance through Ferryhopper for the best prices and guaranteed seats.
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By Air
Santorini has an international airport (JTR) — well connected to Athens (45 minutes) and with seasonal direct flights from many European cities. Useful if you are time-pressed but you miss the caldera arrival. Take a taxi from the airport — approximately €25–35 to Oia, €15–20 to Fira.
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Transfer from the port
The port at Athinios is approximately 12km from Oia. Pre-book your transfer — we paid $49 (AUD) per person for our most recent transfer, and it is the smoothest way to arrive. Buses and shared taxis are also available but can be chaotic in peak season.
WHERE TO STAY IN SANTORINI — OUR RECOMMENDATION
Where We Stay — Oia Old Houses
We have based ourselves in Oia every time we have visited Santorini. We stay at Oia Old Houses — a small, beautifully run collection of studios and apartments in the heart of Oia village with caldera views that we simply cannot find a better word for than perfect.
The studio we call our home away from home has a balcony directly overlooking the caldera. We have sat on that balcony at sunrise, at sunset, at midnight under stars. We have eaten pasta there. We have had glasses of wine there watching the cruise ships move silently through the water below. It has become one of our favourite places on earth.
Oia Old Houses is exceptional — the staff are thoughtful, welcoming and genuinely invested in making your stay special. On one arrival, we found flowers in our studio and freshly baked cakes and a bottle of wine. These are the touches that make the difference between staying somewhere and belonging somewhere.
Website: oldoiahouses.gr
💡 Jane’s Tip: If you are staying longer than four days — and we strongly recommend that you do — plan your activities around the cruise ship schedule. At times we counted five cruise ships in the harbour simultaneously and the pressure of thousands of visitors moving through Oia’s narrow lanes made it worth staying in and reading on the balcony. Those became some of our favourite days.
Other Recommended Hotels in Santorini
Santorini Princess Spa Hotel — Imerovigli, 4km from Fira. Outstanding 5-star spa hotel with caldera views, outdoor pool and exceptional service. Rated 9.7.
Apanemo Hotel & Suites — Akrotiri, near Red Beach. Beautiful caldera-facing complex, 3-level pool, excellent breakfast. Rated 9.5.
Oia’s Sunset — Oia village centre. Excellent value, 50 metres from the caldera, perfectly located. Rated 9.3.
👉 Compare all Santorini hotels with Booking.com →
THE 4-DAY ITINERARY
Day 1 — Arrive, Explore Oia and First Sunset
Arriving into paradise
Check in, put your bags down and do nothing for thirty minutes except stand on your balcony and absorb what you are looking at. This is not advice we give lightly — it is necessary. The caldera view from Oia takes time to process. Let it.
When you are ready, put on comfortable shoes and spend the afternoon exploring your neighbourhood. Oia’s lanes are narrow, whitewashed and endlessly photogenic — you will want to find the routes, the good cafés, the small galleries and the blue-domed churches before the crowds arrive in the morning. This is also the time to make dinner reservations for later in the week — the best restaurants fill up quickly.
The Santorini sunset
Oia’s sunset is the most famous in Greece and the crowds it attracts confirm that its reputation is fully deserved. Arrive at your chosen spot early — the clifftop fills up considerably before sunset and positions at the castle (Kastro) and along the caldera wall are taken an hour or more ahead.
If you are lucky enough to know someone with a private balcony — we spent one unforgettable sunset on the balcony of a cargo captain named George who was born in his house above Oia and whose son runs the restaurant below — the caldera at golden hour is something you simply cannot photograph well enough to do justice to.
For your first evening, we recommend dinner in Oia itself rather than the walk down to Ammoudi Bay — save that experience for when you know the island better.
💡 Jane’s Tip: On evenings when sunset is particularly spectacular our Scottish friend Martina — who has an extraordinary network across Oia — has been known to lead guests to private balconies for the best views. Ask around. People on this island are exceptionally generous.
Day 2 — The Oia to Fira Walk at Sunrise
Start at 6:30 am. This is non-negotiable.
The walk from Oia to Fira — or Fira to Oia if you prefer — is 10km and takes approximately 3 to 3.5 hours at a comfortable pace. It is one of the great walks in Greece. It is also, in our experience, one of the great walks in the world.
We set off at 6:30 am. The sunrise was extraordinary — the caldera lit from below as the light came up, the islands appearing one by one from the dark water, the windmills casting long shadows across the path. We were almost entirely alone.
Then the dogs appeared.
Santorini’s famously friendly village dogs have what appears to be a structured arrangement for accompanying walkers on the Oia to Fira path. Amelie was waiting for us at the gate at the start of the path — she had apparently been doing this for some time. Koukola joined us near the bakery. They walked with us, ranged ahead, checked back, kept us on the right path when we took wrong turns — once with a few small strategic barks, once by simply turning around and leading us down the correct route.
As we approached Fira, Amelie turned back towards Oia. We briefly panicked about what to do with Koukola if she followed us all the way into the bus station. Then two Americans walking the other way appeared and Koukola joined up with them without a backward glance. And then a pack of six dogs — apparently the Fira contingent — appeared and took us the rest of the way into town.
We have walked this path three times. The dogs have been different each time, and the arrangement has been exactly the same.
Practical details:
- Distance: 10km one way
- Time: 3 to 3.5 hours
- Difficulty: Easy to moderate — some uneven paths, gentle climbs
- Start time: As early as possible — 6 am to 6:30 am for sunrise conditions
- Return: Local bus from Fira back to Oia — approximately €2, runs regularly
- What to bring: Water (essential), sunscreen, comfortable shoes, camera
💡 Jane’s Tip: Have breakfast in Fira after the walk — you will have earned it. The town is extraordinary in the early morning before the cruise ship crowds arrive. Walk the caldera rim, visit the Orthodox Metropolitan Cathedral and have a proper Greek breakfast overlooking the water.
Afternoon — Lioyerma Pool Bar
After the walk and Fira breakfast, take the bus back to Oia and spend the afternoon at the Lioyerma pool bar. For a small fee per person per day, you have access to the pool and all facilities. It is a genuinely excellent deal and the views from the pool over the caldera — particularly on the days when morning fog lies over the water and the islands appear to be floating — are extraordinary.
On one of our visits, a fruit and vegetable man arrived poolside mid-morning. We bought beans, tomatoes, onions, grapes and bananas — a full bag — for three euros. He gave us a recipe with the beans:
Boil water until very hot. Add beans and boil for no more than three minutes. Meanwhile, mix olive oil with lemon juice, salt and pepper. Toss the cooked beans immediately into the mixture. Eat.
We had it as a starter that evening. It was one of the best things we ate in Santorini.
👉 Book Santorini walking tours here →
Day 3 — Sunset Caldera Catamaran Cruise and Wine Tasting
Morning at leisure
After two full days of walking and exploring, Day 3 earns a slow start. Breakfast on your balcony. A morning at the pool. A long lunch of Greek salad, olive oil drizzled on fresh stone-baked bread with thick-sliced local tomatoes and a cold glass of Santorini Assyrtiko. This is what we came here for.
3 pm — Sunset Catamaran Cruise on the Caldera
We thoroughly enjoyed our sunset cruise, and it is one of the experiences we recommend without reservation to every visitor to Santorini. Departing at 3 pm, the cruise takes you past the Indian Head Mountain and Venetian Lighthouse into the caldera, visits private bays for swimming and snorkelling, passes the volcano and the famous hot springs, and positions you perfectly to watch the sunset from the Aegean Sea.
The combination of being on the water looking up at the whitewashed villages on the clifftops as the light changes through the afternoon is a completely different perspective on Santorini — and one of the most beautiful things we have seen anywhere.
Most tours include hotel pickup and drop-off, which makes the logistics completely seamless.
💡 Jane’s Tip: Book the sunset cruise as early as possible in your planning — these sell out weeks ahead in peak season from June to September. If your preferred date is sold out when you check, keep an eye for cancellations.
👉 Book the Santorini Sunset Caldera Cruise with BBQ here →
Alternative afternoon: Private Wine Tasting Tour
If you prefer land to water, Santorini’s wine country is extraordinary, and a 5-hour private wine tour with a sommelier is one of the great afternoon experiences on the island. Santorini’s volcanic soil produces wines unlike anywhere else in the world — the mineral-rich Assyrtiko white is arguably the best white wine in Greece and the sweet Vin Santo dessert wine is exceptional. Three wineries, twelve varieties, local cheese and olives.
👉 Book the Santorini 5-Hour Private Wine Tasting Tour here →
Day 4 — Ammoudi Bay Dinner at Dimitri’s and the Full Island Bus Tour
Morning — Full Day Bus Tour of Santorini
For your final full day, we recommend the island bus tour — the most efficient way to see the highlights of the wider island, including the Red Beach, the ancient site of Akrotiri, traditional inland villages and the monastery of Prophet Elias on the island’s highest point.
The tour also includes time in Fira and Oia — if you have been based in Oia all week, seeing it from the perspective of an organised tour gives you a different understanding of the island’s geography.
👉 Book the Santorini Full Day Bus Tour here →
Evening — Dinner at Dimitri’s, Ammoudi Bay
Save Ammoudi Bay for your last evening. The walk down from Oia — roughly 200 steps descending the cliff face — is manageable and beautiful. The walk back up is the tough part. Worth every step.
Dimitri’s Taverna at Ammoudi Bay is our favourite restaurant in Santorini for seafood. Sit as close to the water as possible. Order the sea bream and swordfish if they are on the menu. Watch the fishing boats come in. This is one of the great dinner settings in Greece and the food matches the view.
Address: Ammoudi Bay, Oia, Santorini
Booking: Essential in peak season — book several days ahead
💡 Jane’s Tip: The walk back up from Ammoudi Bay after dinner is steep. Take your time, wear sensible shoes and do not do it in the dark without a torch on your phone. The path is well-worn but unlit. Please do not take the donkeys — there is an active movement to end their use as tourist transport and we fully support it.
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WHERE TO EAT IN SANTORINI — OUR PERSONAL RECOMMENDATIONS
Where to Eat in Santorini — From Someone Who Has Eaten Here Many Times
Roka — Oia (Our Absolute Favourite)
Address: M. Mpotsari 6, Oia, Santorini
Website: roka.gr
Roka is a hidden gem. Not hidden in the sense that nobody knows about it — it is regularly full — but hidden in the sense that it sits down a small lane in Oia away from the main drag and rewards people who seek it out rather than stumbling upon it.
We have eaten there twice. The first time with friends Alex and Marissa — four starters, four mains, two desserts, two litres of wine and raki. The total bill for four people was 111 euros. The food was authentic Greek cooking of the kind that reminds you what Greek food actually is before the tourist versions got in the way. It was one of the great dinner evenings of our entire time on Santorini.
The second time we tried to book, it was full. Book early. Always book early. We managed to get a booking the following day.
Dimitri’s Taverna — Ammoudi Bay
The seafood restaurant at the base of the cliff at Ammoudi Bay. Outstanding fresh fish — the sea bream and swordfish are exceptional. The setting directly on the water is extraordinary. More expensive than Roka but the experience justifies it. Book in advance.
The Lioyerma Pool Bar — Oia
Not strictly a restaurant but the pool bar where we spent many afternoons has genuinely good food — Greek salads, fresh bread, mezze. At a small fee for a day for pool access, it is also one of the best value experiences on the island.
Eating at home — our caldera balcony
For a significant portion of our longer stays in Santorini, we ate on our balcony — fresh bread delivered by Anna each morning, local produce from the supermarket and occasionally the fruit and vegetables from the poolside vendor who appeared with extraordinary produce for three euros. There is something deeply satisfying about eating pasta on a terrace overlooking the caldera at sunset with a glass of local wine. We recommend it highly.
FREE THINGS TO DO IN SANTORINI
Free Things to Do in Santorini
The Churches of Santorini
Santorini has over 600 temples and churches — a number that becomes less surprising when you learn that many were dedicated by sailors’ families giving thanks for safe return from the sea. The island’s Catholic community numbers around 500 people and the Catholic Cathedral in Fira has been there since 1823. The Orthodox Cathedral is equally beautiful and the small blue-domed churches scattered throughout Oia are among the most photographed images in all of Greece.
On our walk from Oia to Fira, we passed multiple churches just as morning light was catching the blue domes — photographs we have tried and failed to adequately describe to people who have not seen them.
Wandering the Alleyways of Oia
There is no better free activity in Santorini than simply getting lost in Oia. The bougainvillaea clinging to whitewashed walls. The blue doors. The cats sleeping in patches of morning sun. The caldera appearing unexpectedly at the end of a lane. We have done this dozens of times and find something new every time.
The Windmills
The windmills of Oia cling to the clifftops and are some of the most distinctive features of the island’s silhouette. Several have been converted into accommodation or incorporated into restaurants. The views from beside them over the caldera are excellent at any time of day.
Sunrise over the Caldera
We think the sunrise is better than the famous sunset. Yes, the sunset crowds are smaller at sunrise — dramatically so — but more than that, the quality of the early morning light over the caldera, the islands appearing from the dark water and the silence of the village waking up around you is an experience that the sunset crowds never get.
BUDGET SECTION
How Much Does Santorini Cost? — Our Real Numbers
Santorini is not cheap. We say this having stayed there many times and loving it completely. Here is what you can realistically expect to spend:
Getting There
| Transport | Cost Per Person |
|---|---|
| Ferry from Mykonos (fast ferry) | From €50 |
| Ferry from Naxos or Paros (fast ferry) | From €50 |
| Flight from Athens | From €30–80 |
| Transfer from port to Oia | €25 per vehicle |
Accommodation Per Night (per room, two people)
| Option | Cost Per Night |
|---|---|
| Budget studios | From €80–120 |
| Mid-range hotels | From €150–250 |
| Luxury caldera-view hotels | From €300–600+ |
| Peak season (July–August) | Add 30–50% to all prices |
Activities
| Activity | Cost Per Person |
|---|---|
| Lioyerma pool bar day pass | €7 |
| Sunset catamaran cruise with BBQ | From €70–90 |
| Private wine tasting tour (5 hours) | From €80–120 |
| Full day island bus tour | From €35–50 |
| Fira walking tour with wine tasting | From €30–45 |
| Oia to Fira walk | Free |
Food and Drink
| Meal | Approximate Cost |
|---|---|
| Greek salad and wine at local taverna | €15–25 per person |
| Dinner at Roka (our experience) | ~€27 per person including wine and raki |
| Dinner at Dimitri’s Ammoudi Bay | €35–50 per person |
| Breakfast at café | €8–15 per person |
| Local wine by the glass | €5–10 |
| Supermarket (self-catering evening) | €15–25 for two |
💡 Jane’s Budget Tip: The supermarket in Oia is genuinely good — well stocked with local produce, excellent Greek yoghurt, fresh bread and good local wines at reasonable prices. Self-catering some meals on your balcony significantly reduces costs and is one of the great pleasures of staying in Santorini rather than just visiting it.
FAQ SECTION
Frequently Asked Questions — Santorini
Is Santorini worth visiting?
Yes — without question. We have been back multiple times and stayed for weeks at a time. Santorini is one of the most beautiful places we have ever been and the combination of extraordinary landscape, excellent food, genuinely wonderful local people and that caldera view — which never becomes ordinary no matter how many times you see it — makes it worth every euro. It is not cheap, and it is not uncrowded in peak season. Go anyway.
Is 4 days enough for Santorini?
Four days is enough to experience the highlights — the Oia to Fira walk, a sunset cruise, the wine country, Ammoudi Bay and the villages. But Santorini rewards longer stays significantly. When you have more time, you settle into the island’s rhythm, you find your pool bar, you make friends, you discover which mornings the fog lies over the caldera and makes the islands look like they are floating. We always stay longer than planned. We always wish we had stayed longer still.
When is the best time to visit Santorini?
May, June, September and October are the best months — warm enough for swimming and exploring, less crowded than the peak summer months and more affordable. July and August are the hottest and most crowded — cruise ships fill the harbour daily, and Oia becomes extremely busy. We visited in September and found it still busy but manageable. The shoulder months give you the real Santorini.
How do I avoid the cruise ship crowds?
Check the cruise ship schedule — your accommodation can tell you which days have the most ships in port. On heavy cruise ship days (we have seen five ships simultaneously), plan to be at the pool or your balcony during the busiest midday hours and head out in the early morning or later evening when the day trippers have gone. This is the insider approach, and it transforms the experience.
Is the Oia to Fira walk suitable for all ages and fitness levels?
The walk is 10km and takes 3 to 3.5 hours. It is not strenuous — there are no steep climbs — but it is long and can be hot. We strongly recommend starting at sunrise (6 am to 6:30 am) when the temperature is cool, and the light is extraordinary. Comfortable shoes are essential — the path is uneven in places. We have walked it with people in their sixties and seventies without any difficulty. The return bus from Fira is easy and inexpensive.
Is the Santorini sunset in Oia as good as it looks in photos?
Yes. We say this knowing how rarely the answer to that question is yes. The famous Oia sunset is genuinely one of the great natural spectacles of the Mediterranean. Arrive early for a good position. The castle (Kastro) and the caldera wall paths fill up an hour or more before sunset in peak season.
What is the best restaurant in Santorini?
In our personal experience, Roka at M. Mpotsari 6 in Oia is the best. Authentic Greek food, exceptional value, genuinely wonderful atmosphere. Book in advance — it fills up. Dimitri’s at Ammoudi Bay is the best for seafood with an extraordinary setting. Both are personally recommended from multiple visits.
Should I base myself in Oia or Fira?
Oia. Every time. Fira is the island’s capital and is well connected, livelier and slightly more affordable — but Oia’s setting, the caldera views, the quality of the restaurants and the village atmosphere are in a completely different category. The bus between Oia and Fira runs regularly and frequently so you are not isolated.
Can I drink the tap water in Santorini?
No — tap water in Santorini is not recommended for drinking. Bottled water is widely available and inexpensive. This is normal throughout the Greek Islands.
Is Santorini suitable for older travellers?
Very much so — with some considerations. Oia and Fira have narrow, sometimes steep cobbled lanes that require comfortable footwear. The walk down to Ammoudi Bay (and back up) is steep. The caldera view hotels often have steps. That said, we have seen travellers in their eighties thoroughly enjoying Santorini at a relaxed pace — caldera views from a balcony, wine tours, boat cruises and long slow lunches are all completely accessible. The key is choosing accommodation wisely and not trying to rush.
CONCLUSION
Why We Keep Coming Back
There was an evening — one of many — when we sat on our studio balcony in Oia as the last light faded over the caldera. The cruise ships had gone. The village had settled into its evening self — quieter, more genuinely Santorinian. The lights were coming on in the restaurants below. Someone somewhere was cooking something that smelled extraordinary.
Duncan had a glass of local white wine. I had the same. We did not talk much. There was not a great deal to say.
This is what Santorini does to you if you let it. It slows you down to its own pace. It makes you realise that the best version of a holiday is not about how many sights you see but about how many moments you actually inhabit. The caldera at different times of day. The dogs that walk with you at dawn. The vegetable man at the pool who gives you a recipe for beans. The cargo captain who opens his balcony to strangers because he loves the view and wants to share it.
We will go back. We always go back.
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Have you been to Santorini? Did you do the Oia to Fira walk? Did the dogs walk with you? We would love to hear your Santorini story — leave a comment below.
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