The Best of Santorini: A 3 Day Itinerary

For other articles related to our Santorini trip, you can read about how we paid for our 18-day trip to Europe, my recommendations for 24 hours in Athens or my in-depth review of hiking from Fira to Oia.

Visiting Santorini has been a dream of mine for as long as I can remember. I’ve always had a strong sense of wanderlust and felt like trips like this were so out of reach for me. When we finally had the opportunity to make it happen, we jumped at the chance. I’m so glad we did because it was one of the best things I’ve ever done. I can’t wait to share how we spent the perfect 3 days in Santorini.

Visiting Santorini, Greece

When to Visit Santorini

Santorini is in the Mediterranean so the winters are mild, but the summers can get pretty hot. Their rainy season is between November and March which wouldn’t make for a good “fun and sun” kind of vacation, but it would make for cheaper rates and less crowds. For us, visiting early June was the perfect time to go. It wasn’t too hot, but still hot enough that you want to jump into the water. It also wasn’t too crowded other than in Oia.

Don’t get me wrong – there were a lot of people; but it wasn’t overwhelming. I can’t imagine what it’s like later in the summer during July – August when tourism really kicks up. Heading there between April – June is a great way to have dryer, warmer weather and slightly smaller crowds.

How to Get There

Airport

We flew into Santorini from Italy and while there were signs for customs, you actually just exit the airport. It was a little strange and our passports don’t have the Greece stamp, but no one seemed pressed by it. The airport is small but that means the staff is small too. It took us awhile to get our luggage, but if you didn’t check any bags then you’ll be in and out in no time. I recommend scheduling a car to pick you up from the airport.

There isn’t a queue of taxis waiting to pick you up so you may end up waiting. We had some flight delays so our car had to cancel on us so we waited for a taxi. We probably waited 10 – 15 minutes, which isn’t crazy but we were eager to get going.

Ferry

When we were heading to Naxos after our time in Santorini, we took the ferry. The ferries are nice! They’re clean, they’re spacious, there is a bar. What more do you need? You will ferry in and out of the Athinios Port, which is small port and a little confusing. There’s only one port of entry, but multiple boats. Once we got there by taxi (it cost us $40 from Firostefani), we just went into the help desk to ask for instructions on which gate to go to. There are restaurants and cafes you can wait at if you have some to kill. Our ferry went from Santorini to Athens with stops at Ios, Naxos (our stop), and Mykonos along the way.

Taking a ferry is the more affordable option, but it can eat up a lot of time depending on where you’re going and if it’s delayed. I’ve heard horror stories about ferries not showing up for hours, but luckily we didn’t have any issues with that.

Where to Stay in Santorini

When people think of Santorini, they think of the blue domed buildings of Oia. However, there are so many other towns on the island of Santorini and spoiler alert – they’re a lot more affordable than Oia.

We stayed in Firostefani which is situated between Fira, the capital of Santorini, and Imerovigli. I loved Firostefani. It was quiet, but not too quiet, and had an amazing view at sunset. It was also a quick walk to Fira or Imerovigli. After taking the time to explore a few different villages in Santorini, I’d recommend Firostefani or Imerovigli for a quiet night life. If you’re looking for a little more, then Fira would be a good option.

I was overwhelmed in Oia. It was extremely crowded (especially during the day when cruises stopped at the port) and overpriced. People rave about the sunset, but you really only get a good view if you’re right at the tip of Oia. You know me – I’m bougie on a budget. I loved Santorini, but the prices in Oia aren’t worth it to me. I’d happily stay in Fira, Firostefani or Imerovigli again if we get the chance to return to Santorini.

Day 1:

Morning:

As you arrive in Santorini, you’re likely eager to get to your hotel. Who wouldn’t be? Santorini is known for the most amazing cliff and cave-style hotel rooms with personal pools and breath-taking views. You may be jet-lagged looking to get a nap in or you may just want to relax for a little bit. So what better to way to start a travel day than relaxing by pool.

If you’re staying in Firostefani like we did, you may want to check out a few different lunch places. You can also easily walk into Fira or Imerogvigli and grab lunch there.

Afternoon:

Booking a sunset winery tour for your first day is a great way to finish your day of relaxation. We booked this tour with Get Your Guides and absolutely loved it. Our tour guide was Stratos and he was so knowledgeable about the area and all of the wines. I loved having a guide and someone to drive us around so we could try a few different wineries, but you could also just go to a winery on your own as well.

Santorini is known for white wines. I’m not typically a white wine fan, but absolutely loved the wine. Through our tour, we went to 3 different wineries – Avantis Wines, Hadzidakis and Santos Wines. Each winery had their own ambience and vibe to it.

Avantis Wines

We absolutely loved Avantis. We were supposed to get to Santorini early in the morning, but didn’t end up arriving until close to 4 PM because of some flight delays. This meant we had to go directly to the winery to meet up with our tour group. The winery staff were so friendly and offered us a complimentary glass of wine while waited for everyone to arrive.

The wine here was our favorite and the small plates they brought out were delicious. The winery itself is a bit in the middle of nowhere and doesn’t have a great view, but the internal design was perfect. It gave strong luxury winery vibes and it kind of felt like something that could be in Southern California. I’d recommend checking out Avantis if you have time or even just trying some of the Avantis wine at a restaurant while you’re out and about in Santorini.

Hadzidakis Winery

The next stop on our winery tour was Hadzidakis Winery. This winery was cool because it was in a cave and we could see into the wine making process, but it was our least favorite wine. We had small plates here as well, but they were mostly just things like fruits, nuts, etc. One of the things I really liked about this winery was how family-oriented it is. Some of the wine labels were created based on drawings from the owners’ daughter when she a little girl. I thought that was really sweet.

Santo Wines

The final winery on our tour was Santo Wines. This was the “sunset” portion of our winery tour and it did not disappoint. We had an amazing seat and view for sunset. The winery is quite large with ample terrace seating and a good view of the caldera. Each person in our table had their own little charcuterie board to go with their different wines as well.

If you’re planning to go to a winery on your own, make sure you call and make a reservation. If you’re wanting to do one at sunset, Santos Wines is the way to go. I loved going to the wineries on our first day because then we knew what kind of wine we wanted throughout the rest of our time in Santorini. We ended up buying a bottle of the Avantis when we grabbed a few items from a mini mart near our hotel.

Evening:

We ate a lot of small plates at each winery. Some people thought the tapas were enough to get by for the night, but we still wanted to grab dinner afterwards. After a long day of traveling, we were tired, hungry and not interested in spending a lot of time finding the right place for dinner. I should have had a list of options; but I read reviews about the winery tour with people saying they didn’t need to eat dinner afterwards so I didn’t think about it. We ended up getting a few recommendations from the front desk of our hotel and were not led astray.

We had dinner at Aktaion in Firostefani and loved it. The owner was so sweet and friendly. We had a great conversation and even better food to go with it. They were celebrating their 100 year anniversary!

Day 2:

Morning:

Fira to Oia Hiking Trail

Start your morning off with a sunrise hike from Fira to Oia. All of the villages between Fira and Oia are connected through a trail that is fairly easy to walk through while you’re in a town. We hopped on the walking path from Firostefani where our hotel was and headed towards Oia. The hike is about 6.5 miles and will take a few hours to complete.

We took a detour from the trail down to Skaros Rock. This probably adds roughly 45 minutes to an hour onto the hike, but was worth it in my opinion. It gives you a great view of Santorini. If you opt for this hike, which I definitely recommend, make sure to pack a bookbag with some waters, a bathing suit, towel and change of clothes for the next activity in Oia – Ammoudi Bay.

I wrote an in-depth blog post on our hike from Fira to Oia that you can read about here. It’ll provide a ton of tips, tricks and insights into the hike.

Afternoon

Lunch in Oia

Once you get to Oia, you’ll definitely be ready for some lunch or at least a snack. We had lunch at Pelekanos because I read that it had a good view. I also knew that it put us a little closer to Ammoudi Bay where we wanted to head to next. We got something light – just a salad and a smoothie. Both were great and the view was as good as Yelp reviewers promised.

Another lunch option would be to head over to Ammoudi Bay for some great seafood on the water. There are a few resturants to choose from. I’ve heard great things about Ammoudi Bay Fish Tavern from friends and family who have traveled to Santorini.

Ammoudi Bay Cliff Jumping

After lunch, go ahead and head down to Ammoudi Bay (if you’re not there already.) There are 300 steps taking you down to Ammoudi Bay. If you’re not ready for those kinds of steps after hiking all that way, you can always take a taxi. It’s nice to see the sites on your way down to Ammoudi Bay and it’ll help you work off your lunch before CLIFF JUMPING.

Cliff jumping in Ammoudi Bay is a must-do if you’re in Santorini. It can be a little confusing to get to though. Once you get down the stairs, you’ll want to go left and cut through the restaurants. Once you’re through all of the restaurants, just follow the path to the populated area. It’s a little rocky, but manageable. We even saw kids on the other side. I would recommend wearing shoes not sandals due to the rocks, steps, and donkey poop. You may also want water shoes for swimming in the bay. I ended up cutting my foot on a rock while swimming in the water.

For the cliff jumping, you’ll need to swim out to the to ledge across the water. If you swim on the left side, you’ll see stairs that will take you up the ledge. The cliff jump is about 20 feet high. I was a little scared so we waited until we saw a few other people go and pop back up before we tried it ourselves. I’m so glad we did it. It was a ton of fun and something that I probably won’t get the chance to do again.

Once you’re done cliff jumping and sun bathing at Ammoudi Bay, you can head back. There are donkeys that will take you up the 300 stairs, but I think that’s pretty cruel. We opted to walk them. You can also take a taxi back to to the top if that doesn’t appeal to you. Either way, head back to your hotel to enjoy the rest of the afternoon lounging around your hotel. I’m sure there is a great pool or view you want to soak up there.

Evening:

We were pretty exhausted from our day out and about. Instead of going to a restaurant, we opted to grab some quick souvlaki and wine on the way back to our hotel and enjoy it on our patio while watching the sunset. We were glad we did the winery tour on the first day because we ended up picking up Avantis wine since we enjoyed it so much the day before.

Day 3:

Morning

We used the morning of our third day in Santorini to relax and really enjoy the hotel we were staying at. We had a great pool with a good view so we wanted to make sure we spent time there. It was also our 2nd anniversary so we wanted to take the day slowly rather than pack it full of things to do. We ate breakfast at our hotel then hung out by the pool until we were ready for lunch.

Afternoon:

For lunch, we took the walking trail over to Fira. It was a fairly quick walk, but like with our hike the day before, there wasn’t a ton of coverage from the sun. It was hot! Once we got to Fira, we headed straight to Lucky’s Souvlaki. I read that it was the best souvlaki in all of Santorini so I had to try it. Let me tell you, it did not disappoint. We loved it!

You go into the restaurant, place your order, and then circle back around and get in line. It can be a little confusing and we didn’t realize the order when we first got there. When you walk in, you’ll see two people – a chef and cashier working in tandem. When we were ordering, we didn’t know exactly what to get, but Lucky was so helpful. He helped us order the best combination to try a little bit of everything. It was delicious and I can definitely believe they have the best souvlaki in town. Seating is limited, but there are some tables across the street that you can stand around as well.

After lunch, we explored the town of Fira. It’s bigger than Firostefani, but less crowded than Oia so we loved that. There are a ton shops with knick knacks and your basic touristy items, but there were a lot of authentic and amazing finds as well. We loved wondering the streets, getting lost in the alleys and finding new shop and businesses. We ended up stumbling upon an AMAZING ice cream spot that I would 10/10 recommend. There were really unique flavors and ended up being one of our favorite spots.

If you’re up for it, once you’re done exploring Fira, you can do another hike to see the Three Bells of Fira. It’ll take you 588 stairs (which are numbered) to get down to it. We were not up for it after the day we had before, but we walked a little of the way down, checked out the view and then headed back to our hotel to get ready for our anniversary dinner.

Night

We wanted to splurge a little bit for our anniversary dinner. We tried to be economical for most of trip, but we were in Santorini and it was our anniversary. There is no better time to be bougie on *splurge* budget.

I found Ambrosia on a list of most romantic restaurants in the world. It’s a very small restaurant with only a handful of tables. We really enjoyed the view and the food. I’d recommend booking this restaurant for after sunset because it doesn’t have a sunset view but the view of the lights in the dark is quite beautiful.

Hart mentioned to me after dinner that we were actually sitting next to a famous soccer player, Thibaut Courtois, who plays for Real Madrid. I don’t know who that is, but it seems like it gave our dinner a few extra points from Hart so that’s great.

Tips & Tricks for Exploring Santorini

• Be prepared for steps! There are so many steps throughout Santorini and no matter where you stay, you’ll be getting your workout’s worth.
• Oia is the most crowded village in Santorini. It only gets more crowded at sunset.
• Make reservations in advance for restaurants if you want a good sunset view. If you don’t make a reservation, restaurants will sit you before 6pm and after 9pm but not during that window.
• Buy your ferry tickets in advance and if you want it printed out, do that yourself. You’ll be charged a fee. You can print a digital copy on your phone though.

Well, this is how we spent our 3 full days in Santorini. I hope you enjoyed reading about it! You can check out my quick recap reel on my Instagram if you’re looking for more! If you’ve been to Santorini, let me know in the comments what other things you had on your list of things to do. If you haven’t been, what are you most excited to do?