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Ever since watching The Sisterhood of the Traveling Pants (cliché, I know) as a teenager, Santorini had been on my travel bucket list. Those iconic white-washed buildings cascading down volcanic cliffs, the endless blue domes, the promise of spectacular sunsets; it all felt like something out of a dream. So when I finally had the chance to visit this famous Greek island in October, I jumped at it.
I’ll be honest: Santorini is touristy. Like, really touristy. It’s not the hidden gem Greek island experience you might find in places like Kefalonia or Ithaca. But you know what? Sometimes the famous places are famous for a reason. And visiting during shoulder season in October gave us just enough breathing room to enjoy the island’s beauty without the summer chaos I’ve seen in photos online.
This three-day Santorini itinerary strikes the perfect balance between active exploration and relaxation, with a healthy dose of incredible Greek food thrown in. We ate spanokopita and sipped Greek coffee from Fourni Bakery every single morning (the service was hit or miss, but those pastries were consistently excellent), hiked along dramatic cliff paths, sailed around the caldera, and ended our trip with what might have been the best seafood meal of my life.
Table of Contents
Arrival in Santorini and Getting to Oia
Fly into Santorini the night before your itinerary officially begins. Trust me on this: you’ll want to arrive, get settled, and have a proper night’s sleep before diving into your first full day. To get here, you can take a ferry from Athens (5-8 hours) or you can fly. We opted for flying – the last thing I wanted to do after being on two planes from California was to get on a long ferry ride. Check out Omio for all the transport options before you decide!
My friends and I opted to stay in Oia, the quieter and more scenic part of Santorini. Oia was a lovely, quieter vibe compared to Fira, but Fira is definitely more accessible and central. If you plan on exploring all around the island and not renting a car, Fira is the way to go.
There are a couple of options to get to Oia or Fira from the airport. You can either take the local bus (€2 for each leg of the journey) or you can pre-book an airport transfer for €15 per person (at the time of writing in 2025). We opted for a transfer direct to our accommodation.
Best Time to Visit Santorini
Since Santorini is such a popular tourist destination, I highly recommend visiting during shoulder season. The overall best months to visit Santorini are April – early June and September – October. This is when you’ll get the best hotel prices, generally warm temperatures, and fewer crowds. Swimming might be a little chilly depending on when you’re visiting, but it’s worth it to avoid the crowds.
You’re guaranteed hot summer weather from June – August but since it is peak season, crowds are heavier, and accommodation rates are high.
It’s worth noting that Santorini pretty much shuts down from end of October to end of March, so I do NOT recommend visiting during this time. Many restaurants are closed and lots of activities stop running. If you’re visiting Greece during the winter months, consider a larger island like Crete instead.
Day 1: Hike from Oia to Fira and Sunset Views
Morning: The Oia to Fira Hike
Start your first full day with the famous hike from Oia to Fira. Now, you’ll find most guides recommend doing this walk from Fira to Oia, and after completing it, I understand why. We did it in reverse – Oia to Fira – and let me tell you, there were some seriously steep uphill sections that had us questioning our decision.
The hike took us about 2.5 hours, though we definitely took our time, stopping frequently for photos and to catch our breath on those inclines. This is much more of an actual hike than a casual coastal walk, so come prepared. Wear comfortable sneakers (shout out to my Allbirds!) with good traction (those volcanic rocks can be slippery), bring plenty of water (there’s only one spot along the way to grab drinks), and slather on the sun protection. We started late morning and got absolutely baked in the midday sun, start earlier if you can, especially if you’re visiting during warmer months.
Honestly, despite the challenging bits, the views are absolutely spectacular. You’re walking along the caldera rim the entire time, with sweeping vistas of the Aegean Sea, neighboring islands, and those iconic Santorini cliff-side villages. We passed adorable little churches perfect for photo ops, spotted traditional cave houses built into the volcanic rock, and even saw the famous Santorini donkeys that transport goods along the steep paths. Every turn revealed another postcard-worthy scene.
The trail is well-marked and relatively straightforward to follow. Just keep the caldera on your right if you’re going Oia to Fira, and you can’t go wrong.
Afternoon: Exploring Fira and Lunch at Taverna Romantica
You’ll know you’ve made it to Fira when the path starts to blend into actual streets and the energy shifts from peaceful hiking trail to bustling town center. Fira is definitely the livelier part of Santorini with more shops, more restaurants, and more people. After our hike, we were ready for food.
We stumbled into Taverna Romantica and ended up having one of our favorite meals of the trip (is there a such thing as bad Greek food though?). Our waiter was delightfully quirky, and the food was absolutely stellar. We ordered the fish, moussaka, and octopus, and every single dish was perfectly executed. The octopus especially impressed me: it was tender with a beautiful char and simple seasoning. Everything tasted incredibly fresh, which seems to be the standard in Greece, especially when you stick to traditional tavernas.
After lunch, we wandered through Fira’s town center, which is great for people-watching. The main shopping area has everything from high-end jewelry stores to tourist souvenir shops. We poked into a Greek pharmacy and browsed their selection of Greek and European skincare products, picked up some snacks, and just soaked in the atmosphere. Fira has more of a cosmopolitan energy than Oia, so if you want a livelier scene with more dining and entertainment options, this is where you’ll find it.
Evening: Bus Back to Oia and Sunset
When you’re ready to head back to Oia, make your way to the bus station in Fira. Buses run regularly between the two towns and cost just 2 euros per ride; an absolute steal compared to taxis and Ubers, which are ridiculously overpriced on the island (even split three ways, it wasn’t worth it for us).
The buses generally run on time from Fira, though we did experience some delays on other routes during our trip (more on that later). The ride to Oia takes about 20-30 minutes depending on stops.
Once back in Oia, you have one mission: find a spot for the famous Santorini sunset. Yes, it’s touristy. Yes, it’s crowded (even in October, the viewing areas fill up). But honestly? It’s beautiful, and you’re in Santorini, so you might as well do the thing.
For dinner, skip the fancy restaurants and head to Pitogyros for what became our favorite gyros in Oia (we ate gyros all three days and this is the curated best one, you’re welcome). It’s casual, affordable, and delicious and the perfect way to end your first day. Plus, after that hike and all the walking in Fira, you’ll probably be craving something hearty and satisfying.
Day 2: Catamaran Cruise and Kamari
Morning to Afternoon: Half-Day Sailing Adventure
Day two is all about getting out on the water. We booked a half-day catamaran cruise that met at 9am at the tourism office and returned around 2pm. Many tours offer sunset sailing options, but since we were visiting in October during shoulder season, we specifically chose the daytime cruise so we could actually swim in warmer conditions.
Our tour included several stops around the caldera. The first couple were about 20 minutes each for swimming and snorkeling, while the last stop was a full hour that doubled as our lunch break. The water was definitely cold in October (we’re talking about the Aegean Sea, after all), so we didn’t mind that the swimming time was somewhat limited. If you’re visiting in summer, you might want to combine your cruise morning with a beach visit for more extensive swimming opportunities.
One of highlights of the cruise was the BBQ lunch, which was genuinely delicious. You got your pick of freshly-grilled beef or chicken plus plenty of in-season vegetables, tzatziki dolmades, rice, salad and more. Simple, fresh and satisfying. I’m glad I came hungry!
Throughout the journey, the boat crew did a fantastic job pointing out landmarks and sharing information about Santorini’s volcanic history and the various beaches and coves we passed. We’d specifically booked a smaller group tour (around a dozen people) and I’m so glad I did. Some companies offer boats of up to 50 people, which are, admittedly, a little cheaper, but I’d recommend splurging for the smaller group experience if it’s within your budget. It felt more intimate and less chaotic.
A few tips: bring sunglasses, reef-safe sunscreen (lots of it) and a light cover-up. The catamaran has some shaded areas, but the optimal views and vibes are in the sun. Also, if you’re prone to seasickness like me, definitely bring pack some Dramamine. The Aegean can get choppy and someone else on our boat was sadly unprepared for that.
Evening: Kamari Beach Town
After our cruise ended around 2pm, we had the rest of the afternoon and evening to explore. We hopped on the bus to Kamari, a beach town on the eastern side of the island that offers a completely different vibe from Oia and Fira.
Kamari is definitely touristy, but in a much more low-key, relaxed way. It doesn’t have the Instagram-famous architecture or the dramatic caldera views, but it has a lovely black sand beach, a pleasant waterfront promenade, and a more laid-back atmosphere. We wandered through some artisan craft shops and enjoyed not being surrounded by massive crowds.
For dinner, we ate at Captain’s Corner Taverna, where we had excellent fresh fish (the rest of the seafood was just okay, but the whole fish is where it’s at). The restaurant was just a short walk from the bus stop and the whole experience felt more authentic and less scene-y than dining in Oia or Fira. Plus, the prices were noticeably better.
One note about the bus back from Kamari: we ended up waiting 45 minutes for our bus, which was frustrating after a long day. The buses from Fira tend to run on schedule, but the smaller routes can be unpredictable (or maybe we were just unlucky?). Build in some buffer time if you’re planning to catch a specific bus from anywhere other than the main Fira hub.
Day 3: Lazy Day in Oia and Unforgettable Seafood Dinner
Daytime: Relaxation and Wandering
By day three, the previous days of activity had caught up to us. You have plenty of options for your final day: you could visit the ancient ruins at Akrotiri, head to one of the beaches like Kamari, or explore another village. But honestly? After two active days, we were ready for something low-key, especially since we were headed to Athens for the second half of our trip.
We slept in, had a leisurely morning at our Airbnb, and eventually made our way out to wander around Oia. I low-key forgot how nice it is to have a chill, agenda-less day while traveling. We took our time, explored the quieter side streets, browsed the endless tourist shops (because yes, Oia is very touristy), and just soaked in those famous views without rushing from one thing to the next.
The ruins at Akrotiri were on our original itinerary, but getting there from Oia requires a bit of planning with the buses, and since we were heading to Athens after Santorini, we figured we’d get our fill of ancient Greek history there. That being said, if you are interested in visiting, this day trip has great reviews and includes a visit to a couple of the popular beaches. If you’re not renting a car, this is definitely the way to go.
Evening: Armeni Restaurant – The Highlight of the Trip
Now, if you only take one piece of advice from this entire Santorini itinerary, let it be this: make a reservation at Armeni Restaurant. This was hands-down the most spectacular meal we had during our entire Greece trip.
Here’s what makes it special: Armeni is a seafood restaurant located in a small bay, accessible only by boat. They arranged for Mr. Kostas, the skipper, to pick us up from Ammoudi Bay. He arrived in a speedboat, and ten minutes later, we were pulling up to this magical little restaurant perched right on the water.
The setting alone is worth it: you’re dining literally steps from the Aegean, with the sun setting over the caldera in the background. But the food is what made it unforgettable. The owner and chef (whose name I’m can’t remember for the life of me) brought out a cooler and showed us the fish he’d be preparing for our dinner, explaining how everything was caught that day. We ended up sharing a prawns, octopus, a whole fish and a seafood rice dish, all of which were cooked to absolute perfection, followed by ice cream cake for dessert. He claimed to have the best seafood on the island, and in my experience, that was a 100% accurate statement.
The prawns were sweet and succulent, the octopus was tender even to the tips, and every bite tasted like the freshest seafood I’ve ever had. We learned during our conversation with the owner that we’d visited during the last week before Armeni closes for the season (they’re only open April through October), so we got incredibly lucky with our timing.
The whole experience— brief boat ride, colorful sunset, incredible 3-course meal, and overall vibes —cost about 60 euros per person for three courses plus drinks. It was our biggest splurge meal of the trip, but it was worth every single euro.
Important: Make reservations at least a day or two in advance. If you’re visiting during the busy summer season, book even earlier. The restaurant is small and intimate, and spots fill up quickly.
Where to Stay in Santorini
Santorini is a somewhat small island, but is fairly spread out, all things considering. Where you stay depends somewhat on your desired vibe and activities. I highly recommend staying either in Oia, the much quieter but still touristy area, or Fira, the central part and more bustling part of Santorini. Fira is home to plenty of restaurants, nightlife, and to the central bus station, making it an ideal starting point to explore other parts of the island or to take public transport to and from the airport. Oia, on the other hand, is where you’ll find the iconic sunset view points and architecture, and a is a key area for shopping – souvenirs or otherwise. Below you’ll find a hotel recommendation for backpack, budget, mid-range, and luxury options.
Caveland Hostel (Backpack)
Most of the Santorini hostels are located in / near Fira or in Perissa, a popular beach town. However, for ease of access, I’d strongly recommend staying in Fira, specifically at Caveland, a charming hostel in a traditional village just a 25-minute walk from Fira.
Caveland has rave reviews for a reason – it has a huge pool, plenty of common areas for socializing, free breakfast, and is incredibly clean. All these amenities, along with the incredible staff more than make up for the walk to/ from Fira.
Note: if you’re looking for a hostel where you can simply lay down in a comfortable bed that’s in the heart of Fira, consider Bedspot instead. What it lacks in its social environment it makes up for in proximity to the city.
Read Trip Advisor Reviews | Book a Stay
Asterolithos (Budget-friendly)
If you’re looking for a step up from a hostel without breaking the bank, consider Asteolithos, an aparthotel in the center of Fira. This cozy accommodation offers a variety of options that can accommodate anywhere from 2-4 people, all of which are more spacious than most of the nearby budget hotels. Plus, its location – 2 minutes from the bus station – can’t be beat, especially when walking with your luggage.
If you’re a light sleeper, pack some earplugs and an eye mask, but otherwise this is a perfect spot for those looking to explore the city.
Read Trip Advisor Reviews | Book a Stay
Callia Retreat Suites (Mid-Range)
Even though this is considered a mid-range accommodation, this adults-only accommodation is stunning, with its quintessential white-washed exterior and sparkling blue pool. All rooms have their own patios and the hotel is just far enough from Fira (a 10-minute walk) to feel extra tranquil.
When you walk in, you’ll feel like you’re staying in a luxury hotel. I cannot tell you enough how gorgeous this spot is – everything from the the modern decor to the exquisite views is picture-perfect. And yes, the beds are as comfortable as they look.
Breakfast is complimentary (and delicious) and air conditioning is a given. It’s an excellent spot for luxurious vibes at reasonable rates.
Read Trip Advisor Reviews | Book a Stay
Canaves Ena (Luxury)
If you’re looking for top-of-the-line luxury, then you must stay in Oia, specifically at Canaves Ena, one of the Small Luxury Hotels of the World. This is a honeymooners paradise, but two-bedroom suites are also available for families. With incredible sea views and balconies, each room is equipped a rain shower, ultra-comfortable beds, and plenty of space.
Of course there are plenty of amenites too – a fitness center, a pool, yoga classes, a concierge, an onsite restaurant and much more.
These amenities, along with the the incredibly friendly, dedicated customer service make it the complete luxury experience.
Read Trip Advisor Reviews | Book a Stay
Where to Stay in Oia
We stayed at Amarie Santorini in Oia and absolutely loved it. The apartment was perfect for our group of three (though it could accommodate more if you’re willing to share a bathroom with more people). What really made it special was our host, who went above and beyond. She helped arrange our airport transfers, was incredibly flexible when we had to change our arrival time, and even stocked the fridge with a few groceries for our first morning. The location was ideal: just a two-minute walk from the Oia bus stop, but not in the super hilly, cobblestone-intensive part of town. This might not sound like a big deal, but if you choose to stay here, you’ll thank me for not having to drag your luggage up and down those picturesque but punishing Oia steps. I highly recommend this accommodation if you’re looking for a comfortable and reasonably-priced apartment in Oia!
What to Pack for Santorini in October
Generally speaking, there aren’t many specialty items I’d recommend for an October visit to Santorini. Comfortable shoes are a must because those cobblestones are no check and definitely bring layers. It gets pretty chilly in the mornings and evenings, but the daytime is usually pretty warm. And depending on where you’re staying, think carefully about which luggage to bring. Cobblestones can wreak havoc on suitcase wheels.
- Backpack: Okay, look I’m not here to tell you to pack light or anything, but in the case that you are considering it, I always recommend this backpack, my favorite for carry-on travel. There’s also this larger one if you can’t pack carry-on only (no judgements). I’m more of roller bag girl nowadays but we were also lucky not to be staying anywhere that required cobblestone transport. Both backpacks are incredibly comfortable, easy to carry, and have tons of compartments for organization.
- Comfortable sneakers: A few years ago, a friend of mine introduced me to Allbirds, these awesome wool sneakers that don’t make your feet sweat (even if you wear them without socks) and now I own several pairs and styles. They’re made of Merino Wool, which explains the magic behind them. They’re cute, they’re functional, and they’re comfy AF. You can wear them to hike up a mountain or to explore a new city. They’re my go-to travel shoes and if they get dirty, I can throw them in the wash. If it were to rain, I’d pack my totally waterproof Vessi sneakers instead.
- Travel Insurance: Yes, you need travel insurance for if things (hopefully don’t but often do) go wrong. I’ve been sick, needed stitches, crashed a rental car, had cash stolen and have dealt with luggage delays. Let’s just say I’ve learned my lesson about travel insurance the hard way. My go-to insurance is World Nomads cause they’re awesome and easy to deal with. Be sure to check out the different plan options to pick one that’s right for you!
- VPN: For those of you who don’t know, a VPN (virtual private network) is a service that allows you to securely and privately route your internet through a server. Basically, it makes your internet think you’re in one place when you’re in a different one. Why do you need this? Well, if you want to access your bank account or any secure online account, the sites get super sketched out when you’re in a foreign country. NordVPN is my go-to because it works even in countries where VPNs are blocked. Yay for internet security!
- eSim: If you don’t have a free roaming plan on your phone, get an inexpensive eSIM for your trip so you’re never without service.
- Power bank: I don’t know if I’m a phone addict or what (jk, the answer to that is an unfortunate but resounding yes) but I legit don’t understand how people can travel without a power bank. You’re out and about all day and using your phone to navigate, take photos, and who knows what else. I always carry my Anker PowerCore while I’m out. It’s light, holds multiple charges, and charges phones quickly. Win!
- Portable Travel Strip (optional): If you’re one of those annoying people charging your phone, laptop, and camera at the same time (read: me), bringing a small travel strip along makes powering your devices that much more efficient. I know I’m extra. Sorry, not sorry.
- Sun Protection: Whether you’re planning on booking that Catamaran adventure I mentioned or going on that hike-disguised-as-a-walk, make sure to pack your favorite sunglasses, sunscreen, hat, and sandals.
Practical Tips for Visiting Santorini
When to Visit: I can’t recommend October enough. Yes, it was still fairly busy, especially for sunset viewing and when cruise ships were in port, but it was nothing like the summer crowds I’d seen in photos. The weather was still warm enough for swimming (though the water was chilly), and we rarely felt overwhelmed by tourists. I would not want to visit during peak summer season. If it was that crowded in late October, I can only imagine what July and August are like.
Getting Around: If you aren’t planning on renting a car, the bus system is your friend. At 2 euros per ride, it’s incredibly affordable and covers all the major areas of the island. Fira is the central hub, so most routes connect through there. Buses from Fira tend to run on schedule, but routes from smaller towns can be unpredictable. Taxis and Ubers are okay in a pinch, but they’re definitely priced for tourists.
Food: Don’t miss Fourni Bakery for your morning spanokopita and Greek coffee fix if you’re staying Oia. We went every single day. Also, embrace the taverna culture. Some of our best meals were at casual, family-run spots rather than the fancy restaurants with caldera views.
Currency: Greece uses the Euro and at the time of writing this post (November 2025), the rate was about USD $1 to 0.87 euro. Credit cards are widely accepted and there are plenty of ATM machines for withdrawing cash.
Expectations: Go into Santorini knowing it’s a tourist destination through and through. This isn’t an off-the-beaten-path Greek island experience. But if you visit during shoulder season, stay in a good location, and balance the must-do activities with downtime, it’s absolutely worth visiting. Sometimes the famous places are famous for good reason.
The island delivered exactly what I hoped for: dramatic views, excellent food, a mix of activity and relaxation, and yes, that Sisterhood of the Traveling Pants magic I’d been dreaming about since I was a teenager. Three days was the perfect amount of time to see the highlights without feeling rushed or overstaying our welcome.
Tell me: have you ever been to Santorini? If not, has this post inspired you to visit or do you prefer lesser-traveled destinations?
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