This is the perfect 3 or 5 day Santorini Itinerary! With everything you need to see in Oia, Fira, Imerovigli and so much more! Hike, take a caldera cruise, head down to Ammoudi Bay, and eat some of the best Greek food! If you plan to visit Santorini, you’re going to want to read this itinerary!

blue domes of oia

Santorini, Greece!

I can’t even begin to tell you how long visiting the Greek islands has been on my bucket list. After Italy, Greece was the next European destination that my husband and I have always wanted to visit. We went right at the tail end of June. That definitely meant that tourist season was kicking off in full swing! 

I will say that every Greek island – Naxos, Paros, Milos, Santorini, Mykonos, etc. has a completely different feel. Though Mykonos was absolutely beautiful, it was also a lot more fast-paced with a LOT more partying. Santorini was way more my vibe than Mykonos. It has a much more laid back feel, and I definitely see why so many people choose this destination for their honeymoon!

ammoudi bay

Greek words to know:

Though we didn’t come across any local Greeks that didn’t speak enough English for basic communication, it’s always nice to be able to greet someone in their own language! So here are a few easy words to learn:

  • Kalimera (Kaaali May-Rah) – Good Morning
  • Kalispera (Kaali Spay-Rah) – Good Afternoon/Evening
  • Efharisto (Ef-far-Eestho) – Thank you!
across from Castle of Oia

What is the best time to visit the Greek Islands?

If you’re looking to go island hopping or stay on one island for the entirety of your trip, here are a few things to keep in mind when you’re planning on what time of year you want to visit:

  • Peak Season: Starting mid June, all of July till the end of August
  • Low Season (aka best time to go): Beginning of September through October. Some people do suggest going in May and April. However, I would think the water would be significantly colder and the evenings would be on the chillier side, especially if you’re staying in Oia.
blue domes of Oia

Getting to Santorini:

  • By Ferry: There are ferries that run from between the greek islands so it’s a great way to go island hopping! Check with the hotel you are staying at to see if they offer free transfers to and from the ferry or the airport terminals.
  • By Airplane: Santorini Airport is another way to get to Santorini. I planned our Santorini itinerary so that we’d take a ferry from Mykonos to Santorini. Then take a flight back to Athens.
random bougainvillea on the way to dinner in Oia

Things to know when you’re planning a Santorini Itinerary:

  • Where to stay Fira (aka Thera) is where most of the affordable accommodations are located. You’ll be able to find something in an array of budgets. Oia is at the tip of Santorini and has limited accommodations but it boasts spactacular caldera views. Limited spacing + beautiful views definitely equals a higher price tag. Limited accommodations also means that you’ll need to book your trip further in advance. Plus, a luxury hotel with a sunset view will undoubtedly be more sought after. We stayed at a moderately priced hotel (it definitely wasn’t the most expensive.) I booked out hotel 4½ months ahead of our trip. I checked back a month later and they they were completely sold out for our dates but then. Keep in mind a lot of these cliff view or caldera (volcano) view hotels only have 10-12 rooms to begin with, so in this case, the early bird definitely gets the worm.
  • Just because you stay in Fira doesn’t mean you can’t venture out! Plenty of people add a day trip to Oia on their Santorini Itinerary, instead of spending the big bucks on hotels in Oia. The trip is easily doable within 60-90 minutes depending on how busy the roads are. You can rent a vehicle or take the bus. Peak season and peak hours (like if you’re heading to Oia for the sunset) will take you longer. My recommendations are to plan for that!
  • Cruise ships dock in Fira, not Oia So unlike the issue we ran into in Mykonos where the cruise ships and ferries docked right there, Oia doesn’t have that problem. So that means that most of the morning hours in Oia are relatively calm. It’s usually around midday that the cruise ship crowds and the day adventurers from Thera descend on Oia. If you can budget to stay in Oia, I do believe it’s worth it to be able to have those hours to yourself before the crowds thicken.
  • There is a bus that runs between the towns If renting a car isn’t your thing and you still want to day trip to other towns, the bus is a great way to get there. For roughly ~2 euros/trip you can easily go between towns. Anees stopped by a coffee shop early one morning to pick up cappuccinos for us and met a guy that took the first bus into Oia from Thera for the day. Keep in mind the the buses will be packed during the midday hours as most people will want to travel between towns around that time, so the guy was smart to get into Oia nice and early!
ammoudi bay
us before dinner one evening

Things to Know about Oia

  • How to pronounce Oia: Oia is pronounced EEE-YAH.
  • There are no taxis in Oia! Wait, I take that back, there are no vehicles allowed in Oia! Visitors can take a taxi up to the post office and then you’re on foot from there. If you day trip from Fira, don’t worry, there are parking lots near the post office where you can park your car and explore Oia by foot.
  • There are a LOT of stairs in Oia Cliffside I can’t tell you how many older couples I saw struggling to get to their hotels. There are a ton of steps down the cliffside of Oia. If your hotel is located on the cliffs, you’ll need to walk up and down the steps to get to and from Oia Town unless you plan on hunkering down and not leaving. Keep in mind that the steps are often slippery and uneven. Just something to consider if you do have relating mobility issues.
  • Wander right after sunrise! It’s so peaceful in Oia right after sunrise. It’s quiet and sleepy and the views are waiting for you without any lines. If you’re looking to get that perfect picture with the domes in the background, this is the time to get it! Waking up before everyone else was one of my favorite highlights from this trip. You’ll definitely see a few brides in their wedding attire or couples taking pictures with professional photographers but the lines are no where near as long as they are around midday.
  • Make dinner accommodations in advance Add making dinner reservations to the list of things to do when you start making your Santorini Itinerary for the trip. If it’s peak season, you’ll want to make your dinner reservations for any restaurants you really want to eat at well in advance. One thing I found a bit interesting is that the restaurants in Ammoudi actually charge a 10-20 Euro fee/per person for booking. This is of course reimbursed to you on your bill when you eat there, but it is something to keep in mind.
  • The walkways are always crowded Once it’s 10 am the crowds are out and about! The walkways on Oia are quite thin and the crowds are wild during peak season. And remember, we’re all on foot. So if you’re trying to make it to a reservation, leave plenty of time to get there.
cliffside oia
sunset ammoudi octopuses hanging
kastro oia houses

Beaches to add to your Santorini Itinerary:

  • Red Beach: A very narrow strip of a beach that will undoubtedly be very crowded if it’s peak season when you visit. If you do head to this beach, don’t plan on spending the day there, it’s just not that kind of beach.
  • White Beach: Whatever you do, don’t try to drive here. This is a beach that’s only accessible by a boat taxi. You can take the taxi right from Red Beach and it runs every 30 minutes so getting back and forth is easy.
  • Black Sand Beach: There is more than one beach in Santorini that has black sand. Perissa Beach is the one I heard the most about when I talked with locals. It’s a beach covered in black sand and black pebbles.
  • Ammoudi Bay: If you’re looking for a sandy beach, this isn’t it. But if you’re looking for a place to go put your feet in the water, there’s definitely a place to do that here. Add this to the days itinerary for when you plan on dining down in Ammoudi Bay!  This was one of my husbands favorite experiences to be able to go swim in the beautiful aqua and deep blue waters of the Aegean Sea. Highly recommend adding to your Santorini Itinerary!

Where we stayed:

We stayed at the Oia Mare Villas Hotel. The rooms have an amazing cave-like feel to them and many of them come with a private hot tub. Keep in mind that getting there does mean going down A LOT of steps. And the first day that we got there, I was shocked. The hotel does provide transfers to and from the port/airport, and a porter that will meet you at the top and carry your luggage down to the hotel for you. Breakfast was included and the staff was extremely friendly and very helpful. They definitely went above and beyond during our stay and especially when it came to booking a quad for a day trip we wanted to make to Fira. 

oia mare villas
peach juice and a caldera view
view from Oia Mare Villas

Things to do in Santorini:

  • Check out the Blue Domes of Oia (Church of Agios Spyridonas) Come early if you can! During the day, there was always a lineup here. However in the morning there’s usually only a few people around. There are a lot of private homes located close by, so I do suggest being quiet!
  • Castle of Oia: This is a renaissance-era castle that people flock to in the evenings to watch the sunset in Santorini. Keep in mind that you’ll need to plan ahead and arrive at leave 60 minutes before the sunset to grab a good spot. If you plan on passing this area around sunset, just don’t! People are blocking every side of the walkway and it’s near impossible to get by. Nonetheless, it is a must-do for your Santorini Itinerary!
  • Kastro Oia Houses:The instagram famous iconic orange buildings in Santorini. 
    • PRO TIP: Come early! This place is packed during the day and the only time you’ll be able to snag a picture without someone photobombing is early in the morning.
  • Ammoudi Bay: Is a small port tucked below Oia. They have 4-5 seafood restaurants along the water and you’ll definitely want to make a reservation for them if you plan on going during sunset. Though the sunset isn’t visible from any of these restaurants, diners flock to them to taste the delicious fresh catch from the sea including the iconic octopuses that hang out to dry along the water. 
    • Many boat tours of the volcano and the hot springs actually start down by the water. 
    • There are 300 steps that start at the Kastro Houses that you can take down to get here. 
    • Keep in mind it does get very hot midday, so I recommend going before or well past noon. Bring a big bottle of water with you!
    • You can also hitch a ride down from a donkey. However, this isn’t something we did. 
    • Wear good shoes! The donkey’s do create quite a mess up and down the stairs so close-toed shoes with a grip on the bottom are preferable.
    • PRO TIP: If you don’t want to walk the steps back up after dining at the restaurants in Ammoudi, ask your waiter to hail a taxi a few minutes before you plan to leave. We asked two separate restaurants on two different occasions to do this, and they both were happy to help. The taxi fair was ~20 Euros up to the top if I remember correctly, but it definitely beats going up 300 stairs after a big meal!
  • Wander Nikolaou Nomikou: This is the main street in Oia. It’s very busy starting around 10 am but there are tons of cute shops and instagram-worthy photo spots everywhere!
  • Take a catamaran cruise and visit the hot springs: there are options to take a private, semi-private, or a group catamaran cruise to visit the hot springs and view the volcano. Sunset cruises usually depart around 3 pm and end shortly after sunset.
  • Hike from Oia to Fira: if you’re going during the summer months, I can’t stress enough that you need to start earlier in the day so that it doesn’t get too hot on the trail. This is a 6.2 mile hike that will take you anywhere from 2-5 hours to complete depending on your fitness level.
    • I suggest stopping in Imerovigli on the way there to check out Skaros Rock.
    • If hiking isn’t your thing, you can drive to the same stops you plan to make along the way to Fira.
  • Check out Skaros Rock in Imerovigli: this is a fortress that was build in the 15th century. Great views of the Caldera.
  • Visit the Three Bells of Fira: The only bells you’ll see in Fira! These are located along the cliffs on the western side of Santorini. Getting that iconic picture can be a little difficult though. The path is a bit hidden and you’ll need to look for a signs along the walking path that point up and to the left.  Don’t be surprised when the viewpoint my picture is across from a parking lot. 
three bells of Fira
Santorini sunset

Where to Eat in Santorini:

I’m going to split this up into two parts – Oia and Thera so that you can grab just what you need for your Santorini Itinerary.


  • Ammoudi Fish Tavern: Zucchini blossoms, shrimp appys, and freshly grilled fish. There’s no denying that Ammodi Fish Tavern is one of the nicest seafood joints in Ammoudi Bay! Make sure to ask a waiter to hail you a taxi if you want to skip taking the steps back up to the top of Oia.
    • Ammoudi Fish Tavern, Ammoudi Bay, Santorini, Oia, Ammoudi 847 02, Greece
  • Sunset Ammoudi By Paraskevas: This was the second place we went to down in Ammoudi Bay and if I had to pick for next time, I’d skip this one. The prices are somewhat similar to the Ammoudi Fish Tavern, however, the customer service, and the food quality just isn’t as great, in my opinion.
    • Sunset Ammoudi by Paraskevas, Ammoudi Bay, Oía 847 00, Greece
  • Skala Restaurant: This was one of those restaurants that didn’t live up to the hype for me. The interior was a bit meh but the food was decent. I really enjoyed the vegetarian moussaka here but I’d skip the spanakopita next time – not the best!
    • Skala Oia 847 02, Greece
  • Lolita’s Gelato: When the temps are up, a gelato a day is a must! I tried the pistachio gelato here and countless other flavors.
    • Lolita’s Gelato, Oía 847 02, Greece
  • Skiza Cafe:This place has takeaway coffee, dessert, and is a great little spot for breakfast.
    • Skiza Cafe, Οία, Thira 847 02, Greece
  • Paradox: If you’re looking to take a break from Greek food, this is the place to check out. After being in Greece for 10 days, I needed to veer for just a second so I can appreciate all that Greece has to offer. This place has great Thai food and we especially enjoyed the shrimp satay stir fry!
    • Paradox Main Street, Oía 847 02, Greece
  • Karma: A really unique restaurant situated close to the post office. This place has a really unique vibe. We tried the fava beans here, the tomato fritters, and a whole fish which was absolutely magnificent!
    • Nik. Nomikou 11, Oía 847 02, Greece
  • ROKA: One of the best dinner’s we had on our whole trip! The fried gruyere cheese crusted with almonds served with pepper honey was really good, so was the chocolate hazelnut tart, and black truffle mushroom risotto!
    • Be sure to make reservations, this place is HOT! You’ll be allowed to a stay a maximum of 2 hours on a reservation.
    • Roka, m.Mpotsari 6, Oía 847 02, Greece
  • Pitogyros: A simple place to grab a gyro! They have chicken, pork, and even a vegetarian option loaded with lots of French fries and a cabbage slaw.
    • Pitogryos Oia 847 02, Greece
  • Piatsa Souvlaki Grill House: Another gyros and souvlaki place right by the bus stop to Fira. 
    • Vegetarian friends, this one has a vegetarian gyros made with meatless meat and it was delicious!
    •  Piatsa Souvlaki Grill House Oia, Bus Terminal, Oía 847 02, Greece
meatless gyros in Oia
vegetarian moussaka
greek salad
feta wrapped in phyllo with honey and sesame seeds
tomato fritters with white sauce


These are the restaurants that came up the most during my research. I’ve only been to two of these! 

  • Greek Bites
  • Argo Restaurant
  • Metaxi Mas: I hear this is a cheese lovers paradise!
  • The Athenian House (Imerovigli)
  • Falafeland: We stopped by for a quick wrap here and it was really good. But a fair warning, when they say spicy, they mean SPICY!
    • Δανεζη Μιχαηλ, Thira 847 00, Greece
  • The Family Bakery: try the Trigona here. It’s a honey coated crispy shell filled with cream and crushed pistachios. Sadly, they were out when we went!
    • Επαρχ. Οδ. Φηρων – Ορμου Περισσης, Μεγαλοχωρι, Σαντορινη 847 00, Greece
  • Svoranos Bakery: Try the cheese and spinach pie here

And that brings my Santorini Itinerary to a close! We had the best time on the Greek Islands this year! As always, if you’ve been and have recommendations, please feel free to leave them in the comments below!

down by ammoudi bay
This is the perfect 3 or 5 day Santorini Itinerary!