The Ultimate Santorini Itinerary: A First Time Visitor’s Guide + The 11 Best Things To Do In Santorini, Greece
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Oh, Santorini…the magical island that needs very little introduction and will sweep you off your feet the second you lay eyes on it. The island that boasts jaw-dropping caldera views, picturesque white-washed villages, dramatic volcanic cliffs and colorful beaches, just to name a few. There is so much this stunning island has to offer, it can be hard to narrow down the best things to do in Santorini, Greece. If you only have a short amount of time (hello, fellow island hopper!), don’t fret! You can easily plan the perfect 2 or 3 days in Santorini itinerary that will still fulfill all of your fantasies!
The fabled white-washed buildings and blue domes, scalloped alongside those breathtaking volcanic cliffs that contrast perfectly with the deep blue and turquoise hues of the Mediterranean Sea, attract thousands of visitors from all over the world each year.
From the glimpse of a just a photograph, one is astutely aware of a certain magic exuding from the iconic white and blue facade that seemingly captivates your soul and draws you in, almost as if it were in invitation. It’s no wonder why Santorini is one of the most popular tourist destinations of all the Cycladic islands, as everyone who has gotten a taste of that magic longs to experience the reality of it for themselves.
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Where To Stay In Santorini
Oia
Oia (pronounced ee-a) is probably the most famous, picturesque town in Santorini. It’s situated along the northwestern tip of Santorini island, and is best known for its beautiful, famous blue domes and white-washed cliffs that are filled with charming cave houses, traditional Cycladic homes, and luxurious hotels.
Although Santorini can get pretty crowded during the day (especially at sunset!), it is a fairly mellow and quiet town overall. For this reason, this is usually the prime honeymoon location! If you are looking to stay somewhere with more of a nightlife, Oia may not be your best option, as there are only a few bars and cafes open late.
I stayed in Oia during my time on Santorini, and loved every minute of it! We stayed at Delta Suites in a cave house (when in “Rome”, right?!), and were blown away by how amazing it was! Not to mention, the incredible view from our hot tub on the cliffs overlooking the Aegean Sea! We woke up one morning and watched the sun rise from our porch, and it took our breath away!
Budget Oia Hotel ($)
Mid-Range Oia Hotel ($$)
High-end Oia Hotel ($$$)
For more places to stay in Oia, click here.
Fira
Fira, located on the west side of the island, is the capital and commercial center of the island. On the caldera side, it offers an incredible view of the volcano and another one of the most breathtaking sunsets I’ve ever seen!
Fira is overflowing with amazing restaurants, cute shops, cafes and hotels, and has a much more energetic vibe compared to Oia. It’s also the spot to be if you want the bustling nightlife scene. There are tons of bars, lounges, and clubs that frequent visitors until the early morning hours, some of which have several levels of patios and balconies! If you’re spending more than a couple days on the island, this may be a good place for you to base your stay!
Stay at the stunning B&B, Le Petit Greek, when in Fira! The views of the caldera from that balcony are unbelievable!
For more places to stay in Fira, click here.
Nightlife in Fira
- PK (Palia Kameni) Cocktail Bar – Has three levels overlooking Santorini and the caldera, serving the finest cocktails, local wine and champagne
- Enigma Club – Offers 3 different rooms and bars where you can dance all night, or relax and kick-back in their outdoor courtyard
- Franco’s Bar – Boasts gorgeous panoramic caldera views, and is known for playing classical music at sunset (the venue that established classical music on the island). Serves champagne, a wide variety of wines and delicious cocktails
- The Koo Club – One of the most popular clubs in Santorini and plays house, trance, progressive and Greek types of music
- Club 33 – Go here if you want to listen to Greek music
- The Highlander – The island’s only Scottish bar, however, the music ranges from fun dance party beats to mainstream pop and even rock
Imerovigli
Known as the “Balcony of the Aegean,” Imerovigli is located on the highest point of the caldera cliffs–about 300 meters above sea level–offering the best sunset and caldera views. It is much quieter and peaceful than Oia and Fira, making it the perfect choice for a more secluded and laid-back holiday.
The famous attraction of the village is the huge rock called Skaros that was once one of the five fortresses of Santorini (and the most important one). It used to be an lookout post providing security from pirates!
To discover where to stay in Imerovigli, click here.
Firostefani
About a 15-20 minute walk from Fira, Firostefani is the place to stay if you want to be close enough to access the hustle and bustle of Fira, but far enough away to have a bit more privacy and tranquility. Even though it’s considered a separate village, it is actually an extension of Fira.
To discover where to stay in Firostefani, click here.
What To Do In Santorini:
1. Watch The Sunset in Oia
Although this is probably the most popular spot to watch the sunset (expect large crowds), it is something you surely cannot miss!
If you are staying in Oia, my advice is to make dinner reservations (in advance) at a restaurant that offers views of the sunset–make sure you request a table with a view! This way, you don’t have to fight off the crowds, and you can enjoy the unobstructed glory of it all at a private table, glass of wine in hand, ready to soak it all in.
The most popular place in Oia to watch the sunset is Oia Castle. If you choose to watch the sunset here, make sure you arrive early! The crowds on top of the castle get insane!
We arrived to Oia Castle earlier before the sun began to set, and people were already hanging out there to hold their spot!
I’ll give you a little secret, though…I may, or may not, have hopped over the other side of the wall on the far end of the castle (where you’re technically not supposed to go) to get these awesome photos and to enjoy the scenery away from all the people. Oops…but I don’t regret it one bit. 🙂 If you do this, though, just be very careful! There’s no ledge or railing as you can see from my picture above.
If you aren’t staying in Oia, the best way to get there is by bus, ATV, rental car, or hiking (more on that, next). NOTE: If you are renting a car, parking is very limited in Oia, so make sure you get there several hours before sunset! Swarms of people flock to Oia close to sunset, making it very difficult to even walk, much less find a parking spot!
P.S. It’s super fun (or, rather, intriguing) to watch Santorini almost turn into a ghost town immediately after the sun is completely set (or at least that was the case for us in October). Almost immediately after, all the little ants go marching (red and black antennas waving ♪♫) right back where they came from, leaving you questioning in the quiet abyss of the abandoned alleyways if they were ever really there to begin with. (Or was it just a dream?)
The sunset was also breathtaking in Fira!
Dinner with a sunset view:
- Argo (Fira)
- Ambrosia (Oia)
- Lauda (Oia)
- Strogili (Oia)
- Petra Restaurant (Canavas Oia)
- Skala (Oia)
- The Red Bicycle (Oia)
- La Maison (Imerovigli)
- Sphinx Wine Bar Restaurant (Fira)
- V Lounge Cafe & Cocktail Bar (Fira)
Or, watch the sunRISE in Oia from two of my favorite breakfast spots, Vitrin and Melenio Cafe!
- Vitrin Cafe Creperie
Melenio Café:
Offers stunning views of the water, and everything is made from scratch using local ingredients (plus, its delicious)!
2. Hike From Oia To Fira/Fira to Oia
Unfortunately, with the way our time was scheduled in Santorini, we didn’t have time to do the hike from Fira to Oia. However, I’ve still added it to my list because I’ve heard from multiple sources that it is a MUST if you love hiking and you have the time! I can only imagine how incredible the views are! (If I ever go back to Santorini, this will FOR SURE be on my list!)
The route takes you along the caldera, the crescent-shaped volcano that is now separated from the island by the Aegean due to a volcanic eruption around 1620 BC. The hike itself is about 6 miles (taking around 3 hours if you’re walking at a leisurely pace), and is said to be a moderate difficulty level (not a walk in the park, but not too difficult either).
Don’t worry, though, with plenty of photo-ops along the way, there will be plenty of time to rest and take a water break if needed!
TIPS: Make sure to pack water, as there aren’t really any places to stop for a drink along the way, and try to go as close to sunrise as possible to avoid the mid-day heat (and to watch the sunrise – duh). Also, you don’t have to hike back if you don’t want to! There are buses or taxis at each end to get you back to where you came from.
3. Visit The Local Wineries
Wine making in Santorini dates back thousands of years to the 3rd millennium BC! So, if you love history and enjoy wine, this is a no-brainer (ammiright!?)!
Oia Vine Art
Oia Vine Art was my favorite little wine bar (and I think the only one?) in Oia! Some locals recommended it to us, and we would never have known about it had they not! It was tucked in one of the back alleys and scattered with locals when we visited on our last night. They had an amazing selection of Greek wines from all over. I absolutely loved the vibe here, and would highly recommend it if you are staying in Oia! (It’s one of the few bars that stay open late!)
Venetsanos Winery
One of the best views of all the wineries!
Since I can’t possibly give you a description of this winery better than their explanation on the wineries’ website, I’ll just leave it with you here…
“Where The Sky Meets The Sea And The Earth Greets Life Force, Where The Vines Bestow Their Fate To The Sun And The Soul Surrenders To The Senses, Where The Wind Shapes The Cliffs And The Disobedient Mind Seeks For The Pure And The Unexplored, Is Where Venetsanos Winery Is Formed, Into The Nature.” –Venetsanos Winery
Yup.
Santo Winery
Santo Winery is a beautiful, modern winery that offers stunning views on their terrace of the caldera and cliffs. They also have a restaurant on-site in case you want to pair some food with your wine! Tours are offered daily!
Argyros Estate
This winery (and the following), came highly recommended by a friend of mine who is a certified sommelier (he’s a WSET Level 3, and on unit 2 of the DipWSET). AKA…He knows a LOT about wine! I always trust his wine recommendations, so if you want to taste some incredible wines on the island, you can’t go wrong with Argyros and Gaia!
P.S. If you have an instagram account and love fine wine & food, make sure to follow him! His handle is @attorneysomm, and I can assure you that you will want to live vicariously through him (and learn a lot along the way)!
Gaia Wines
Kapari Wine Restaurant (Imerovigli)
Dinner (+wine, of course) with a view! If you’re staying in Imerovigli (or just happen to be there for dinner), make sure to book a reservation and watch the sunset!
Heliotopos Wine Bar (Imerovigli)
Another wine bar with stunning sunset views of the caldera! You can’t go wrong with any of these!
4. Eat, Explore & Cliff Jump in Ammoudi Bay
I loved Ammoudi Bay so much, I would have spent a whole day there if I had time! Ammoudi Bay is located at sea level below the cliffs of Oia, and is a MUST in my opinion (whether you are staying in Oia or not)! It is so cool to take in the scenic views from a different perspective–situated right along the edge of the coast, versus the arial view you experience high on top of the cliffs in Oia.
Trekking Down to Ammoudi Bay
I say trekking, because this is no “walk in the park” (especially the hike back up)! To be a little more clear, when I say trekking, I do, in fact, mean you might be dodging donkey poop and descending/climbing the insurmountable steps that may or may not feel like they’re actually leading you to your doom. HOWEVER, do not let that stop you, because (1.) I was *slightly* kidding, and (2.) it was some of the most stunning views I’ve ever seen!
Just make sure–unlike we did–that you let all those fishies you ate down below in Ammoudi Bay fully digest BEFORE you make the climb back up to Oia! (HAH! Fail…)
Also, you do have the option to ride a donkey up or down the steps to save you from the journey on your own, if you so choose!
Where To Eat In Ammoudi Bay:
Sunset Taverna Amnoudi Bay (website)
Katina Fish Taverna (website)
Dimitris Ammoudi Taverna
Dimitris is another notable waterfront seafood restaurant I’ve heard recommended in Ammoudi several times! I didn’t get a chance to eat here, as I visited the two mentioned above, but I know this one would have been just as amazing!
Tip: Order the Lobster with Linguini!
Cliff Jumping in Ammoudi Bay
Follow the steps down to Ammoudi Bay. Once you get to the bottom down by the water, with the town behind you, take a left and walk past Sunset Taverna Restaurant.
Once you walk past Sunset Taverna, you will see a pathway that should be marked with a (beware of) falling rocks sign. This is the pathway that takes you to the cliffs–follow it around the bend.
You may have to climb over some rocks here and there, but you will eventually see the rock/cliff not too far out in the middle of the water. Note: You have to swim out to get to that rock!
Fun Fact: If you are a fan of the movie, “The Sisterhood of the Traveling Pants 2,” You will see the rock that they jumped from in the movie as you are walking the path (before you get to the cliff jumping rock in the water)!
There should be a stairway on the backside of the cliff that lets you access this area to jump from the same spot as they did in the movie. (I didn’t get a chance to jump from either cliff, as the water was really cold when we went in the end of October, but I definitely would have if the water wasn’t so icy!)
**As always, use good judgement and be very careful when jumping from any cliffs! I’ve heard that you need to get a running start to jump out and avoid the rocks below, if you jump from the same cliff that they did in the movie. You also don’t have to jump from the highest point if you don’t want to, as there are lower jumping points if you feel more comfortable there.**
5. Rent an ATV/Quad Bike and Explore the Island
What better way to explore an island than renting a 4-wheeler and cruising around the island, off-roading with the wind blowing through your hair!?
Renting an ATV is actually pretty cheap and easy, and only requires a regular driver’s license to do so. It’s a super fun way to get around and explore areas that aren’t accessible by bus.
6. Discover The Real Atlantis (Akrotiri)
Over 3,600 years ago, a catastrophic volcano erupted on Santorini causing a large part of the middle of the island to collapse and disappear into the Aegean Sea, forming the caldera we now know today.
This volcanic eruption is one of the biggest in recorded history, happening around 1,600 BC, taking with it what is assumed to have been the lost city of Atlantis (according to legend).
Although the ancient Minoan civilization is said to have been wiped out by the effects of the volcanic eruption, you can explore and discover some of the remains of the old villages in the Akrotiri Archaeological Site on the island. Head there for a glimpse into the past, and to discover for yourself if the lost city of Atlantis just might be the ancient Minoan settlement that once thrived on the island.
7. Visit The Akrotiri Lighthouse
Located on the southern tip of the island near the ancient city of Akrotiri (across from Oia), the Akrotiri Lighthouse offers stunning views and is a perfect spot to watch the sunset after a day if exploring.
Rent a car or quad bike to explore this hidden gem and get away from all the crowds, if you have time. Although it is not as popular as Oia, the scenery isn’t any less stunning!
8. Explore Pyrgos Village
Pyrgos is the best-preserved medieval settlement on Santorini, located in about 7 and a half kilometers south of Fira, that was once the capital if the island until the early 1800s. The traditional village was strategically built at the heart of the pre-volcanic land, at the foot of Mt. Profitis Ilias, offering stunning panoramic views of the island!
Another plus (in my opinion) is that Pyrgos is not swamped by tourists and sunset chasers alike, as other more famous locations on the island are. It’s more of a lesser-known, off-the-beaten-path hidden gem that is less advertised–making it all the more charming and intriguing.
9. Visit The Beaches
Santorini may not be known for having the absolute best beaches, as they are more composed of tiny black pebbles rather than soft sand, but they are still worth a visit if you have time!
Ammoudi (scroll back up to #4 to see more of Ammoudi Beach), Perissa, Perivolos, Kamari and the stunning Red Beach (pictured above) are considered some of the best beaches on Santorini and are the most talked about, but these are not the only ones!
Tip: Make sure to wear closed toed shoes when visiting Red Beach (try to avoid thongs or sandals), as it can be very slippery on the rocks and they can get very hot!
The other beaches that are said to still be worth a visit include Vlychada Beach, Koloumbos, Katharos, Monolithos, Eros and Vourvoulos Beach.
Too many beaches, too little time! (Well, for me at least!)
10. Sail Around The Island
One of the best things you can do in Santorini is to tour the island via boat!
Many of the tours will take you around to the most scenic parts of the island, the caldera, and even stop off at some of the famous beaches so you can swim and snorkel!
Check out this small group catamaran cruise or this 4-hour sunset wine tour to start the search for your perfect tour!
11. Get lost in time at Atlantis Books
Atlantis Books is one of the most enchanting bookstores a traveler, or literary lover, could ever stumble upon (well, that, and Shakespeare and Co. in Paris). Its walls are adorned with famous quotes from renowned authors, the ceiling is painted with the bookstore’s own history and timeline, drawn out as if it were a work of art, and filled with books stuffed floor to ceiling from all places and time.
It was actually started by two young American men who were vacationing in Oia during their Junior year studying abroad at Oxford University, back in 2012. About halfway through their stay, they had quickly read through the books they brought with them to their dismay. As there was no sign of any book store in Oia, and a trip to Fira turned up fruitless as well, they found it quite impossible to replenish their reading material. Thus, the idea of opening their own bookstore on the island was born.
If you’re strolling through the center pathway that runs through Oia, you’ll spot this hidden little gem across from the old town hall. The books are mostly in English, but you can also find Greek (of course), German, French, Spanish, Italian and Chinese. The literature is expertly selected, and also includes things like special editions, maps, posters, etc.
After the time it took to get the business running and fulfill their dreams and visions, Atlantis Books became a local and international institution. The fact that there is nothing else quite like it on the island is what helps make this amazing place so enchanting. It will captivate you!
…Until next time, Santorini! ♥
In the end, though, words and photographs still just don’t do this dreamy island justice. Santorini truly is something that has to be seen (with your own eyes) and experienced to fully grasp the glory of it all. It will leave you speechless, dumbfounded by the beauty and magic that surrounds this incredible place nestled in the Cyclades.
So, if you haven’t had the opportunity yet to experience the island first-hand, what are you waiting for?
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