Santorini had been sitting at the top of my travel bucket list for years. I had saved countless photos to Pinterest, watched more Instagram reels than I care to admit, and built this island up so much in my head that part of me wondered if it could actually live up to the hype. Spoiler alert, it absolutely did. From the moment we pulled into Oia (overnight flight exhaustion and all), I was completely obsessed. The blue domes, the cave hotels, the caldera views, the sunsets, somehow it all felt even better in person.
But I also quickly noticed that how you experience Santorini makes a huge difference. Things like where you stay (many argue this doesn’t matter, I’ll never be one of them) transportation, and even dinner reservations can completely shape your trip. A little planning ahead meant I got to spend less time stressing about logistics and more time pretending I lived in a cave hotel for a few days. In this post, I’m sharing the exact Santorini itinerary I would recommend after experiencing the island for myself, including plenty of the little moments that ended up becoming some of my favorites.
Santorini Itinerary
One thing I definitely underestimated before visiting Santorini was just how spread out everything is. On a map the island doesn’t look very big, but getting from place to place takes longer than you might think. Which is exactly why I think staying in Oia completely shaped our experience, and I would make that same decision again in a heartbeat. Being able to enjoy the village early in the morning and later in the evening, while spending the busiest hours relaxing by the pool, ended up being one of my favorite parts of the trip.
While the big sights are incredible, some of my favorite memories were the slower moments, coffee at Meteor Café, sunset Aperol spritzes at Saint, wandering around after dinner, and lingering at Santo Wines way longer than we originally planned. That’s exactly the approach I took with this itinerary. Yes, you’ll hit the famous spots, because they’re famous for a reason. But hopefully you’ll leave enough room to slow down too, because those chill moments ended up being some of my favorites.
Where Is Santorini Located
Santorini is located in the southern Aegean Sea and is part of Greece’s Cyclades islands. It’s famous for those iconic whitewashed villages perched high above the water, dramatic caldera views, and volcanic beaches that make it feel unlike anywhere else I’ve visited. Even though the island looks fairly small on a map, it feels much bigger once you’re there. Between Oia, Fira, the beaches, wineries, and smaller villages, there’s a lot more to explore than I expected before my trip. It’s also very easy to reach, with regular flights and ferries connecting Santorini to Athens and other popular Greek islands.
Is Santorini Worth Visiting
Absolutely. I know Santorini sometimes gets labeled as “overrated” or “too touristy”, but after finally experiencing it for myself, I think that’s usually because people aren’t seeing the island at its best. Some of my favorite memories had nothing to do with checking off sights. They were the quiet mornings in Oia, afternoons spent hiding out by the pool, cocktails at Mary Kay’s Bar, and dinners that lasted for hours (in a good way.)
Does Santorini get busy? Of course. But with a little planning and a slower pace, I found it to be every bit as beautiful as I’d dreamed for years. The blue domes, the cave hotels, the sunsets and the wineries all felt even better in person. If you’ve had Santorini sitting on your Pinterest boards forever like I did, I’d say it’s absolutely worth experiencing at least once.
When Is The Best Time To Visit Santorini Greece
Something I noticed while planning my trip is that the time of year you visit Santorini really shapes the experience. Weather, crowds, prices, and even the overall vibe of the island can feel completely different depending on the season. If I had to pick my ideal months, I’d personally choose May, September, or very early in October. Those shoulder season months just seem to offer the perfect mix of beautiful weather, fewer crowds, and slightly lower prices, which is exactly how I like to travel.
Spring (April-May)
Spring is one of the times I’d most love to visit next. The weather is beautiful, everything is starting to reopen for the season, and the crowds are still relatively manageable. You’ll also generally find lower hotel prices compared to the busy summer months.
Summer (June-August)
Summer is peak season, which means hot weather, packed viewpoints, and lots of cruise ship traffic. It’s lively and everything is open, but it’s also the most expensive time to visit. If you’re traveling during summer, I’d definitely recommend booking hotels and dinner reservations well in advance.
Early Fall (September-October)
This timeframe always gets my vote. This is when we visited, the first week of October to be exact, and I absolutely loved it. The weather was still warm enough for pool days and Aperol spritzes at sunset, but the crowds felt much more manageable than peak summer. I really felt like we got the best of both worlds, and prices had started to come down a bit as well.
Winter (November-March)
Winter is the quietest time on the island, and probably not a time I personally would visit, but still an option for some. Many hotels and restaurants close for the season, but you’ll find the lowest prices of the year and a much slower, more local atmosphere. Just keep in mind that ferry schedules and tourist services are more limited.
How To Get Around Santorini
Getting around Santorini is actually pretty straightforward, but there isn’t just one perfect option. The best way to get around really depends on your itinerary and how much of the island you want to see.
Rental car
If you’re planning to explore a whole lot of the island, renting a car is probably the option I’d recommend for that. It gives you the flexibility to visit beaches, wineries, smaller villages, and all those viewpoints you randomly stumble upon and immediately pull over for because, somehow, every view in Santorini is prettier than the last. Parking can be a little tricky in places like Oia, especially around sunset, but overall it’s one of the easiest ways to see more than just the main tourist areas.
ATV
ATVs are everywhere in Santorini and definitely add to the fun island atmosphere. They’re especially popular for beach hopping and shorter distances, and I know a lot of people absolutely love them. Personally, I don’t know if I’d trust myself enough to drive one around those winding cliffside roads, but that’s just me. They can be a really fun option if you’re traveling light and want a little extra adventure.
Public bus
The public bus system is probably one of the best deals on the island. It’s inexpensive, easy to use, and connects major areas like Oia, Fira, and the airport. We actually used the bus to spend a day exploring Fira while staying in Oia, and I was pleasantly surprised by how easy it was. The ride itself only costed a few euros, and the bus dropped us just a short walk from everything we wanted to see. The only downside is that buses can get crowded, especially during peak season, so I always like building in a little extra time.
Taxis
Taxis are another easy option, although they’re a bit limited on the island, especially during the busiest months. We used taxis a few times during our trip, including getting to and from Santo Wines for sunset, and had no issues at all. Once we found a driver we liked, we actually kept his card and called him again later in the trip, which made things super simple. If you’re visiting during summer, I’d definitely recommend arranging airport and port transfers ahead of time. It’ll save you a lot of stress, especially after a long travel day.
How Many Days In Santorini Is Enough
One of the questions I get asked most about Santorini is how many days you really need, and after visiting myself, I think 3 to 4 days at the absolute minimum, with 4 days being my sweet spot. That’s exactly what we did, and I honestly wouldn’t change a thing.
Four nights gave us enough time to experience the big highlights without feeling rushed. We explored Oia and Fira, enjoyed sunset drinks and long dinners, spent time relaxing by the pool during the busiest part of the day, and still had room for things like Santo Wines and wandering around with no real agenda, which ended up being some of my favorite memories.
If Santorini is part of a larger Greece itinerary (it was for us!), I think 3 to 4 nights is perfect. But if it’s your main destination, I could easily see spending a full week here! There are plenty of beaches, wineries, boat tours, and smaller villages to explore, and I feel like this is one of those places where slowing down only makes the experience better.
What To Do In Santorini Greece
While there are plenty of iconic sights and excursions to choose from, something I realized after visiting Santorini is that you don’t need to pack every second of your day with activities. Of course, there are a few experiences I think are absolutely worth prioritizing. Here’s what I’d personally put at the top of the list:
Watch the Sunset in Oia
Everyone talks about the sunsets in Santorini, and after experiencing them for myself, I totally understand why. One of my favorite evenings was grabbing pre-dinner cocktails and then lingering over dinner while taking in those famous sunset views. The cruise ship crowds are definitely real, but timing and reservations make all the difference.
Book a Sunrise Photoshoot
One of the best decisions we made was booking a sunrise photoshoot with @franko_photographer. Not only did we get incredible photos, but we also got to experience Oia and the iconic blue domed churches before most people were awake. Afterwards, we grabbed breakfast at Meteor Café and eased into the day.
(People always ask how we get photos without anyone in them. The answer is almost always the same, wake up early!)
Stay in a Luxury Cave Hotel
If I could splurge on one thing again, it would be this. Staying in a cave hotel completely shaped our experience, and I highly recommend it if it’s within your budget. Between Old Castle Oia and Oia Spirit, I don’t think I would have loved the trip nearly as much without those pool mornings and caldera views.
Relax by the Pool or Beach
As much as I loved exploring, I also loved slowing down. We purposely spent the busiest hours relaxing by the pool and I stand by that strategy completely. If you’re craving a beach day, you’ll find plenty of options on the other side of the island, including the famous black sand beaches in Perissa and Kamari, along with Red Beach.
Visit Santorini Wineries
Santorini is known for its volcanic wines, and visiting a winery was easily one of the highlights of our trip. We spent an afternoon at Santo Wines sharing a charcuterie board and watching the sun slowly begin to set. Safe to say, neither of us was in a hurry to leave.
Explore Fira
While we stayed in Oia, I loved spending a day in Santorini exploring Fira. We took the bus over, grabbed lunch, did a little shopping, and wandered through Atlantis Books (definitely pick up a travel book here). If you’re feeling ambitious, the famous Fira to Oia hike is another popular way to experience both villages.
Dine in Ammoudi Bay
Dinner in Ammoudi Bay ended up being one of my favorite meals of the entire trip. Sitting right by the water with fresh seafood and a glass of wine felt like peak Greek island energy.
(Yes, there are a lot of stairs, but I promise they’re worth it! Just don’t ask me while actively walking up them)
Take an Excursion
Even after four nights, there were still a few things left on my list. A catamaran cruise or boat tour around the caldera are two of the most popular excursions, and Skaros Rock is another beautiful viewpoint I’d love to experience next time. If you’re renting a car, you’ll have even more flexibility to explore different corners of the island and add a few more adventures to your itinerary.
Whether you want to eat drink and relax or fill your days with sightseeing, it’s hard to go wrong when you visit Santorini. It’s one of those bucket list destinations that somehow exceeded every expectation I had.
Santorini Greece Itinerary
If you’re wondering how I’d personally spend 4 days in Santorini after visiting myself, this is almost exactly what we did, and I truly wouldn’t change much. One thing I loved about our trip was that we never felt rushed. Santorini is one of those places that deserves to be savored, not speedrun. Here is my ultimate Santorini itinerary:
Day 1: Arrive and Settle In
After an overnight flight from the US and flight from Athens to Santorini, we were exhausted. I purposely kept our first day easy, and I wouldn’t change a thing.
Morning & Afternoon
- Arrive in Santorini
- Check into your hotel in Oia (highly recommend a cave hotel, like the ones we stayed at!)
- Unpack and freshen up
- Relax and recharge from travel (we immediately took a quick nap and I don’t regret it one bit)
Evening
- Wander around Oia
- Take in those first caldera views
- Enjoy a casual dinner (highly recommend Pitogyros)
- Early bedtime (Trust me, you’ll appreciate saving your energy for the days ahead.)
Day 2: Sunrise Photos and Sunset Dinner
One of the best decisions we made was scheduling our sunrise photoshoot with @franko_photographer for our first full day. The rest of the trip felt extra relaxing knowing we’d captured some awesome shots right off the bat.
Morning
- Sunrise photoshoot (this is how we get all those crowd-free photos everyone asks me about!)
- Explore Oia without the crowds
- Discover the best viewpoints (it was actually nice getting our bearings around the village right away with the help of our photographer)
- Grab breakfast afterward
Mid-day
- Relax by the pool at your cave hotel (this became one of my favorite parts of the trip)
- Enjoy the views
- Take it slow
Evening
- Get dressed up
- Sunset dinner reservation (I highly recommend booking these well in advance, even in shoulder season)
- Evening stroll through Oia
(Not a bad way to spend a random Tuesday.)
Day 3: Explore Fira and Dinner in Ammoudi Bay
Mornings in Santorini are elite. I said what I said.
Morning
- Wake up early
- Wander Oia before the crowds (my favorite time of day on the island, hands down)
- Breakfast and coffee at Meteor Café (still dreaming about these views)
Afternoon
- Take the bus (OR wake up extra early to hike) to Fira
- Shop and explore (I actually found prices to be better here than Oia)
- Grab lunch
- Wander the side streets and viewpoints
- Stop by Atlantis Books (they even stamped our travel book for us!)
Evening
- Head down to Ammoudi Bay
- Dinner at Sunset Ammoudi (one of my favorite meals from the entire trip)
- Stroll back through Oia after dark (yes, there are a lot of stairs. yes, they’re worth it.)
Day 4: Pool Morning and Wineries
Possibly my favorite day of the trip.
Morning
- Sleep in a little
- Enjoy one last slow pool (or beach) morning (we purposely hid out during the busiest hours and I stand by that decision)
- Take in those last caldera views
Afternoon
- Head out to enjoy the day at some Santorini wineries
- Wine tasting and charcuterie (highly recommend booking a tasting experience at Santo Wines for sunset!)
Evening
- Stay for sunset (we ended up lingering way longer than planned because neither of us wanted to leave)
- Enjoy one final dinner overlooking the caldera
- Pack up to head to the airport or ferry port in the morning (we were off to Mykonos next!)
By the end of our time in Santorini, it somehow managed to exceed every expectation I had. I hope this itinerary helps you plan a trip that feels a little less overwhelming and a lot more enjoyable. If you’re anything like me, don’t be surprised if you’re already plotting your return before you even leave the island!
If you’re still planning your trip, I also have a few other Santorini guides that might help:
- Read my guide on How Many Days in Santorini to figure out the perfect length for your trip.
- Check out How to Get from Athens to Santorini for everything I learned while planning our own journey.
- If you’re looking for even more things to do while there, check out my complete list of What To Do in Santorini.
- If you’re looking for even more recommendations, my complete Santorini Travel Guide covers where to stay, restaurants, and plenty of additional tips.
You can also follow along on Instagram at @sierrainthecity, where I’m usually sharing hotel stays, travel tips, and plenty of proof that my camera roll still hasn’t recovered from Greece. As always, if you have any questions or if Santorini is next on your travel list, I’d love to hear from you in the comments below!
