Greece Island-Hopping Series

Santorini. The whitewashed buildings, blue-domed churches, dramatic caldera views, and sunsets that seem almost too beautiful to be real.

It’s one of those destinations you see all over Instagram and wonder whether it can possibly live up to the hype. Well, I’m here to tell you: it absolutely does. And then some!

Santorini was our first stop on a 16-day Greek island-hopping adventure, and we spent four nights exploring as much of this incredible island as we could. We visited ancient ruins, discovered stunning volcanic beaches, explored by ATV, sampled local wines, and watched some of the most spectacular sunsets I’ve ever seen.

But Santorini has a reputation for being expensive. And while it certainly can be, I discovered that a little planning and knowing where to save versus splurge can make a big difference. Here’s where we stayed, what we did, what we spent, and what I’d recommend.

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Why I Chose Fira Instead of Oia

Everyone dreams of staying in Oia. It’s the postcard version of Santorini, with those iconic blue domes, winding alleyways, and incredible caldera views. And don’t get me wrong, Oia is absolutely breathtaking.

But when I started researching accommodations, I quickly realized I could get considerably more for my money by staying in Fira. I also wanted somewhere with a little life in the evenings (restaurants, bars, music, and the ability to head out for dinner or cocktails without worrying about transportation home).

Fira checked all those boxes. It also happens to be Santorini’s main public transportation hub, making it convenient for exploring by bus.

And after actually visiting Oia? I was even happier with my decision. Oia was still incredibly crowded in early October. Watching tourists drag their suitcases through narrow cobblestone alleyways and steep inclines made me especially grateful for our choice.

My advice? Absolutely visit Oia. Its views were among the best of our entire trip. But don’t assume you need to stay there to experience the best of Santorini. For us, Fira was the perfect home base.

Where We Stayed: Perla Nera Suites in Fira

We booked four nights at Perla Nera Suites, a boutique hotel about a 10-minute walk from central Fira. And I would absolutely stay here again.

We upgraded to a spacious sea-view suite with an outdoor jacuzzi, paying $974 CAD for four nights, or $487 per person. That’s about $122 per person per night. To be clear, this was a sea view, not a caldera view.

The room was beautiful, clean, and spacious, with a large bathroom and facilities to store and prepare simple snacks and drinks. Our front patio was peaceful, and the staff were excellent and accommodating throughout our stay.

Breakfast Was a Highlight

Each afternoon we chose breakfast from an a la carte menu and selected a delivery time for the next morning. Every morning it arrived right at our door. The fresh Greek yogurt and feta were absolutely out of this world! Having breakfast included saved both time and money.

The Pool and Jacuzzi: One Thing to Know

The rooftop pool had lovely sunset views, but the water was freezing during our October visit, so we didn’t swim. Our private jacuzzi didn’t get quite warm enough for me, although my cousin enjoyed it on a few evenings. Would either thing stop me staying here again? Absolutely not.

Was the Location Convenient?

The walk to central Fira took around 10 minutes with a slight incline. It was convenient for dinner and nightlife, though not somewhere we’d constantly pop back to between stops. If you have mobility limitations, it’s worth considering. Otherwise, I thought the location was ideal.

Check rates and availability for Perla Nera Suites on Booking.com

Our 4-Night Santorini Itinerary

We arrived October 5 and departed for Naxos October 9, giving us three full sightseeing days. We made the most of every minute!

October 5: Arrival and Our First Evening in Fira

Our hotel arranged a private airport van for €40 including tip, split among the four of us women travelling together. After settling in, we wandered Fira’s streets and admired our first caldera views.

We stopped for dinner at Mama’s, and the setting and atmosphere were lovely. We were a little surprised, though, that our first true Greek meal didn’t taste as authentic as some of the amazing meals we’d have over the coming days. It was a good reminder that sometimes you pay a premium for the view and atmosphere rather than the authenticity.

October 6: Akrotiri Archaeological Site and Red Beach

We walked to Fira’s main bus terminal, which was a little chaotic, to say the least! Buses serving different routes filled quickly. My advice is to ask at the kiosk and photograph the posted return timetable. Our Akrotiri bus was €2.20 each way.

We arrived near the coast and started with a cocktail on a patio overlooking the water. Not a bad way to begin sightseeing!

Next was the Akrotiri archaeological site, a Bronze Age settlement preserved beneath volcanic deposits. It reminded me of Pompeii, although no human remains have been found at the excavated settlement; some archaeologists think residents may have evacuated before the eruption. We spent about an hour exploring and found it fascinating. Admission was €20 per person.

From there, we walked roughly 15 minutes to Red Beach. Wow. The dramatic red cliffs against the blue water were unlike anything I’d seen. Because of the rocky path, unsuitable footwear, and warnings about falling rocks, we stayed at the viewpoint instead of going down to the sand. The view alone was spectacular. Check current safety and access notices before visiting.

After lunch and a cold beer, we returned to Fira by bus, relaxed on the hotel’s rooftop for sunset, and later headed into town for dinner. We had a beautiful rooftop Italian meal at Convivium, and it was lovely. As we were finishing our desserts and our last sips of wine, we could hear music drifting down the alleyway from 2 Brothers Bar. We followed it, and found a great DJ, cocktails, dancing, and lots of laughs. There was no cover charge when we visited. Being able to walk back to the hotel was exactly why I loved Fira.

October 7: Exploring Santorini by ATV

After a day on the bus, we wanted more freedom. We walked into Santo Wheels in Fira and rented one ATV for two days. I drove and my cousin rode along. The ATV cost €65 per day (€130 for the two days) plus €34 in fuel, and we split it all between the two of us.

Once I got used to the hairpin turns, I felt much more confident and free. Parking a small ATV was super easy. It wasn’t cheaper than the bus, but having multiple stops and the ability to run on my own timetable, without waiting on a group or a bus schedule, was priceless to me. Santorini has steep roads and tight turns, so check licensing, insurance, helmets, passenger rules, and your comfort level before renting.

First up was Perissa Beach, with its black volcanic sand, restaurants, shops, and lively beach atmosphere. We settled in with a cocktail and started devising a plan for the rest of the day, and that’s when we spotted the monastery at the top of the hill. It became a spontaneous addition to our itinerary.

So up we went toward Profitis Ilias Monastery, perched on Santorini’s highest mountain. The narrow, winding mountain road tested my fear of heights, and I won’t pretend I was relaxed! We didn’t go inside, but the exterior and panoramic views were absolutely worth the nerve-racking drive.

From the mountaintop, it was back down the winding road and out to the island’s southwestern tip, where the scenery shifted from sweeping panoramas to rugged coastline at Akrotiri Lighthouse. A little food truck near the base served an unexpectedly amazing late lunch and drinks, the perfect fuel before we climbed up toward the lighthouse. Sometimes those unplanned stops become the best memories.

We finished at Venetsanos Winery around 4:45 p.m. We walked in without a reservation and enjoyed a glass of wine rather than a formal tasting, with dramatic caldera views as the afternoon light faded. After such a full day and late lunch, we skipped dinner and called it an early night.

October 8: Oia, Vlychada Beach, Gavalas Winery and One Last Sunset

Our last full day started in Oia, and I’ll admit it: the postcard is real. Whitewashed houses spill down the caldera cliffs, blue domes pop against the sky, and the cobbled alleyways open onto one jaw-dropping view after another. It’s the kind of place where you stop every few steps to take a photo, then realize you’ve been wandering for hours.

Then came another highlight, in case the view wasn’t enough! We stumbled upon a TV series being filmed right in the middle of Oia’s lanes. It was called Guarded, and it’s featured on the streaming platform Angel. Walking into a real production was one of those unplanned moments you could never put in an itinerary, and it was so cool to see.

We stopped for lunch and an Aperol Spritz. Even in early October, Oia was crowded. I absolutely recommend visiting, but I was still happy to be staying in Fira. Oia charges a premium for the postcard, and you can enjoy it on a day trip without paying to sleep there.

Next was Vlychada Beach, whose dramatic rock formations look like something from another planet. It felt quieter and more secluded than Perissa, with a restaurant for drinks and snacks. Perissa is better for a lively beach day with amenities; Vlychada is wonderful for unusual scenery and a calmer atmosphere. I enjoyed both.

Our next stop was Gavalas Winery, a smaller family-run winery that felt very different from Venetsanos. There were no sweeping caldera views here. Instead, we got an intimate, relaxed wine experience, with a flight of delicious white wines and a light snack. It was the perfect way to slow down after a full day of exploring, and we loved it. But with the afternoon slipping away and sunset getting closer, we knew exactly where we wanted to be next.

A roughly four-minute ATV ride brought us to the Heart of Santorini, where we watched an unforgettable sunset. The terrain along the cliff was rugged and uneven, so wear suitable footwear and be cautious. We never watched the sunset from Oia, and honestly, I don’t feel like we missed out. The view from the Heart of Santorini was beautiful and dramatic enough for me.

That evening, my cousin surprised me with an early birthday dinner at Volcano Blue in Fira. I’d actually been planning to splurge on a caldera-view dinner, so the timing was perfect. The seafood and shrimp pasta, wine, caldera views, and exceptionally attentive waiter made it a lovely final night. One thing to be aware of: the shrimp arrived with the heads attached, and every shrimp dish we had in Greece came that way. Not exactly my preference! But the pasta was delicious.

October 9: Goodbye Santorini, Hello Naxos

Perla Nera Suites arranged a private transfer to the ferry port for €50 including tip, split among the four of us. And just like that, our four nights were over. Next stop: Naxos!

Getting Around Santorini: Bus vs. ATV

Both worked for us. For exploring one area, like the Akrotiri ruins and Red Beach, the bus was inexpensive and a no-brainer: our round trip cost €4.40 per person (€2.20 each way). But the ATV gave us the flexibility to stop anywhere we wanted, as many times as we wanted, on our own timetable. We weren’t waiting on a group or a bus schedule, which made it much easier to fit multiple beaches, viewpoints, and wineries into one day.

Our ATV cost €65 per day, plus €34 in fuel for the two days, split between the two of us. It’s a splurge compared with public transport, but one I was happy to make. Transportation wasn’t part of my original Greece budget, so it came out of my spending money. Check rental requirements and road safety before choosing it for yourself.

Is October a Good Time to Visit Santorini?

Based on our October 5–9 experience, absolutely! We enjoyed plenty of sunshine and warm sightseeing weather, though wind made some evenings chilly. Pack layers.

Fira still felt lively, with restaurants, shops, and bars operating, and Oia was busy with tourists. The one downside was swimming: our hotel’s pool was freezing, and the jacuzzi wasn’t warm enough for me. But for exploring beaches, wineries, villages, and viewpoints, early October worked beautifully.

What 4 Nights in Santorini Actually Cost Me

Santorini has a reputation for being expensive, but you can balance splurges with smart savings. Here is exactly what I spent, in Canadian dollars per person, October 5–9, 2026. My Greece budget covers accommodation, food and drinks, and activities, so I’ve kept those separate from transportation, which wasn’t part of my original budget.

All figures reflect my personal spending, with costs paid in euros converted to Canadian dollars. Transportation wasn’t part of my original Greece budget, so I paid for it from my spending money and kept it separate to keep the budget comparison clean. Food & drinks excludes our Volcano Blue dinner, which was a birthday treat from my cousin. The hotel and ATV were shared between two people; private transfers were shared among the four of us. International flights and inter-island ferry tickets are excluded and covered in my complete Greece trip budget article.

Want to see how Santorini fits into my whole trip? I compare what I planned with what I actually spent across all five destinations in my complete Greece trip budget article.

See the full Greece trip budget: What 2 Weeks in the Greek Islands Actually Costs a Canadian

Santorini Save vs. Splurge: What Was Worth It?

Where We Saved

Staying in Fira instead of Oia gave us better accommodation value, walkable nightlife, and easy access to buses. Even with our sea-view suite upgrade, we landed at about $122 per person per night with breakfast included, which saved both time and money. Using the bus for our Akrotiri day cost just €4.40 round trip.

Where We Splurged

My planned splurge was a caldera-view dinner. Then my cousin surprised me with an early birthday dinner at Volcano Blue, so that one never touched my budget. Best surprise of the trip! The splurges I did pay for: the two-day ATV rental (€65 per day) and fuel (€34 total), split between the two of us, which I loved for the freedom it gave us, and the wineries, an experience I was happy to spend money on.

That’s really the point: you don’t have to choose between a budget trip and a memorable one. Save where it makes sense. Splurge where it matters.

How Many Nights Do You Need in Santorini?

Four nights gave us three full days and enough time to see a lot. But in a perfect world, I’d have stayed five nights. That extra day would have let us slow down and explore even more.

We’d originally planned the famous Fira-to-Oia hike, but chose to prioritize exploring other parts of the island instead. The hike would have taken a significant chunk of our day. I don’t regret the choice, but I’d consider it next time.

Did Santorini Live Up to the Hype?

Absolutely. Santorini was everything I imagined and more: the dramatic caldera, iconic Oia, volcanic beaches, wineries, and unforgettable sunsets. Yes, Oia was crowded even in October. Yes, some experiences were expensive. And yes, we ran out of time to see everything.

But I loved it. If I went again, I’d still choose Fira, I’d happily explore by ATV again, and I’d try to squeeze in one extra night.

You don’t need the most expensive caldera-view hotel or someone else’s perfect itinerary to have an incredible experience. Some of our favourite memories came from an unexpected food truck, a spontaneous night out, and simply sitting with a glass of wine enjoying a view we’ll never forget.

That’s my kind of travel. Save where it makes sense. Splurge where it matters.

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