The Perfect 2-Week Greece Itinerary: Athens, Milos, Paros & Santorini

Greece is often imagined as a land of white-washed buildings, blue-domed churches, and endless island sunsets—and honestly, it lives up to the hype. But beyond the Instagram-perfect views, this country offers a rich blend of ancient history, warm hospitality, and some of the best food we’ve ever eaten. From wandering the vibrant streets of Athens to jumping off cliffs in Milos and sipping wine by the sea in Santorini, this two-week itinerary gives you a taste of it all.

Athens: 2 nights

Day 1: Arrive to Greece!

Athens can either go at the end or beginning of your Greece trip, but we went first so we could meet up with our friends Eline & Roel, and experience our first tastes (literally) of Greece altogether! We arrived early in the morning and thankfully our friends were already there so we were able to drop off our luggage and head out for breakfast! Beyond the city centre with the Acropolis and the Plaka area, Athens in an enormous city. We stayed close to the Metaxourgeio Metro Station which connected us to Monastriki in the centre of Athens. If you’re arriving in time for dinner, we recommend heading to the Monastriki metro station and then wander around the square and adjacent laneways, you’re bound to find an incredible Greek eat straight away!

Breakfast suggestion: The Brunch Factory
Dinner suggestion: Delicious Souvlaki (for a quick simple eat if you arrive late)

Day 2: Athens Ancient Centre

Again, Athens is huge. But there are definitely a few spots you need to see in this ancient city! We knew we wanted to watch the sunset from the Filopappou Hill just southwest of the Acropolis, so we spent the day walking around the areas between Monastriki square, Plaka and the hills that look onto the Acropolis! We had a busy morning at the camera store and a late breakfast which meant we didn’t have time to queue up and actually enter the acropolis, but for us this was fine as we spent a few hours at sunset admiring the incredible, ancient structure amongst Athens other incredible sites from the Filopappou Hill with our friends.

Next time we visit Athens we’ll definitely visit the Acropolis itself, along with the new Acropolis Museum just to its southeast! Athens has a bustling nightlife, so hang around after dark to enjoy it or get back to your hotel and prepare for the next step of the journey, heading to the islands!

Milos: 4 nights

Day 3: Head to Milos

Despite travelling in late June, the price of flying from Athens to Milos was marginally more than the ferry, which would’ve involved more than ten times the amount of time spent transferring to the port of Athens, Piraeus, boarding and sailing to Milos. Ferry time will come later, but for getting to the Aegean islands, we opted to fly.

Regardless of which mode of transport you choose, you’ll arrive to Milos the same day, travel from the port or airport to your hotel and get ready to experience our favourite Greek island! We opted to rent a car for our stay in Milos (and on everyone island we visited) and were picked up at the airport and taken to the rental agency to complete the documentation. Once sorted, we headed just around the corner from the office to our accommodation in Adamantas. There are many places you might choose to stay in Milos, with Adamantas (the primary port area), Pollonia in the north west or the hilltop town of Plaka the most common options. Adamantas provided us the most dining options and proximity to the sights we wanted to visit in the south and plenty of space for car parking so that was our choice!

For your first lunch or dinner, head down to the port area and get a selection of goods from the many bakeries or enjoy some of our favourite gyros in Greece!

Best ice cream: Aggeliki Ice Cream Shop

Best Gyros: Gyros of Milos

Best Bakery (in Adamantas): Artemis Bakery

Day 4: Hit the road!

Your first day of Greek island freedom! Jump in the car, hit shuffle on ‘All of ABBA’ and cruise to the closest bakery for breakfast on the go as you head to your first incredible piece of coastline. We’ll start the first day with a short drive, heading north out of Adamantas to the now very popular, Sarakiniko Beach! This place was definitely top 3 of our Greek trips highlights, the stark white cliffs and that iconic deep blue water meet at one of the most beautiful, fun spots we’ve ever visited. It’s important to get here early in the peak season as the carpark isn’t very big and will fill up quickly, meaning you’ll either need to shift your plans for the day or park up along the main road and take a fair walk to get down to the cliffs. Once down, you’ll find a shallow, walk-able beach entrance in a long thin cove and further along the track the popular jumping cliffs that by now you’ve certainly seen on social media.

Depending on how long you spend at Sarakiniko, it might be time for lunch and a power nap after all that time in the sun, so head back to the village your staying in or continue along the main road to Pollonia for lunch. The road to Pollonia will take you along more and more of that incredible Greek coastline straight out of your imagination.

There are plenty of places to stop just in this small section of road like the Papafragas caves and blowhole, as well as Alogomandra beach, and Pollonia itself is great for a walk around or beach swim!

In the afternoon you can head back to relax and enjoy a chill evening before more adventures tomorrow morning! Or if you’ve got plenty of energy we’d recommend checking out Firopotamos, another small beach side village perfect for some more pontoon jumping & exploring.

If you’re looking for a great dinner and some amazing local wine, head to ‘O! Hamos! Tavern’ in Adamantas for an amazing, local Greek taverna style feast complete with hand painted wine carafes and handwritten menus!

Day 5: More beach time!

Get ready for another insane day of Greek beach hopping! Start your day with a good feed at your favourite bakery before heading out on todays adventures to the south coast to visit Fyriplaka beach and nearby Tsigrado beach!

These two are right next to each other and both are perfect for a lazy day by the water! You could spend the morning at one and then go check out the other before heading for lunch or vice versa.

Milos is quite a rural island, so from here lunch can be harder to come across. In the afternoon you’ll be heading to Mandrakia in the north so you could either return to the village you’re staying in or stop along the northern coast on the way back at a place like ‘O! Hamos! Tavern’ again to try some different dishes and enjoy a proper lunch at the beach.

After some food and time to relax, you’ll be heading to the tiny fishing port of Mandrakia to soak up the golden light on this Greek isle before dinner at the popular seafood restaurant, Medusa! The tiny harbour is lined with colourful houses, some functioning in the modern day as AirBnB holiday rentals, but still perfectly preserved and maintained in that classic Greek style. The water is perfect both inside the little harbour and in the small cove on the north side of it, so go for a swim, lay in the sun and enjoy Mediterranean paradise before dinner!

Day 6: Kleftiko Boat Day!

Today is a perfect day to get a little sleep in. Take it easy and wander around the village where you’re staying and rest up in preparation for this afternoons trip to Kleftiko! Enjoy breakfast and a slow morning, making sure you’ve booked how you’ll be visiting the most impressive cliffs on Milos. There are two popular methods, you can book onto a group trip, a boat that departs from either Provotas Beach, Pollonia or Adamantas or rent your own small boat to take from Provotas beach around to Kleftiko. We booked a private boat for the four of us with ‘Aegean Rent a Boat’, who don’t require a boating license but recommend some prior experience, for a half day visiting the cove.

The drive out takes about 45 minutes and when you arrive into the beautiful, shallow waters of Kleftiko with its towering pitch white cliffs, you’ll know you’re in paradise! We took some snacks and relaxed on the boat surrounded by the cliffs for hours here. We watched as the packed group-tour boats came in and out to enjoy their 20 minutes in the cove before moving on, while mega yachts anchored in the deeper water and tendered towards the cliffs for some time in the crystal clear water.

This was another absolute highlight of our time in Greece, and we cannot recommend hiring a boat for a half day and taking yourself to Kleftiko as opposed to the group tour options - the marginal increase in price is more than worth the extra time you get to spend there, and the freedom to visit other coves as you please!

Paros: 3 nights

Day 7: On to Paros!

That’s a whole lot of adventure for your time in Milos, so depending on the time your ferry takes you to Paros you could also enjoy one more visit to Sarakiniko early in the morning, alongside another nice breakfast.

The ferry from Milos to Paros took us about four hours in June, as the Aegean gets some pretty strong winds in Summer. The duration of the ferry can vary depending on the route the ship takes and if there’s any traffic at the ports as ships come and go! Generally, we’d suggest going for the larger ferries from ‘Blue Star Ferries’ over the fast boats as the time you save isn’t really worth the relatively large price increase.

It’s likely you’ll arrive to Paros in the evening if your ferry is after lunch, so when we arrived, Roel & I headed straight to the car hire office that we’d pre-booked, picked up our ride for our time in Paros while Eline & Erin got some takeaway dinner. Then we set off on the drive to our accommodation in Santa Maria, about a 20-minute drive from the port town of Paros, just past the popular nightlife area of Naoussa.

Day 8: Picture perfect Greek villages.

Paros has something for everyone, it’s well developed, full of cute villages & relaxed beaches and has some of Greece’s most famous nightlife after Mykonos and Santorini! While Santa Maria is quite sleepy, nearby Naoussa has plenty of breakfast options as well as a large supermarket which is perfect for picking up some extras to snack on during the day or for an easy mezze platter to enjoy for breakfast or afternoon tea.

If you’re looking for a rest from all the beach time over the past few days, Paros is an awesome place to explore some quintessential Greek villages. Our favourites to visit were Lefkes and Marpissa. These two were the most beautiful and quiet Greek villages we visited in the entire country, but we’d recommend getting off to an early start to beat the tour buses. For parking, be careful driving up some streets as they can be very tight or one way. Generally, the best rule is, take the first park you find, the walks aren’t too far. You’ll also be able to find some local restaurants at both which are perfect for lunch. In Marpissa, Mylos was a great place for an affordable gyros!

In the evening, you could stop in at Naoussa for dinner. There is a single main street in Naoussa for car-parking so it can take a while to find a park. There are also paid parking lots that run off this street but we always managed to find a free spot before 8pm.

Some of our favourite food spots in Naoussa were,

For gyros: Souvlakia KARGAS or Pita Frank

For a nice dinner: Open Garden or Kapari Restaurant

For brunch: Almond in Paros

For Italian food: Piatsa Estiatorio

For ice cream: Nonna Crema

Day 9: Naoussa and Kolimpithres

Drive in to Naoussa for breakfast, this time spending some time wandering the narrow streets and boutique stores. Make sure you sit down for coffee or a drink at the small harbour where restaurants and bars spill out onto the streets and watch the boats moored in the harbour! You’ll find countless beautiful streets with their famous painted crazy pavers and those iconic bougainvillea trees!

Once you’ve spent enough time in the village of Naoussa, head up to Kolimpethres, one of the most idyllic swimming beaches we visited in Greece - seriously we could’ve spent many days at this beach alone! There’s a nearby beach club if that’s more your fancy, but we were more than happy to lay our towels out on the smooth rocks at Kolimpithres and enjoy the beaches sandy bottom and clear, shallow water!

Day 10: Road trip around the island and head to Santorini!

Paros is a relatively big island, so jump in the car and explore it! We drove down to Aliki in the far south and stopped by the side of the road to admire the south coast of Paros as the main road follows the top of a hill with the most incredible views! You could head down to Tripiti beach or stop in Dryos for lunch on the last day. If you’ve got a full day before your ferry to Santorini, you could also visit Antiparos today, which is just a short boat from the Paros main port. Once you’re all done, return to the port, drop off the car and get ready for the final ferry of the trip to Greece’s most famous island!

Santorini: 3 nights

Santorini is considerably busier than both of the first islands we visited, just getting off the ferry felt like we were heading into Disneyland. Once you arrive to the new ferry port, you can either jump in the car with a taxi driver or prearranged transfer, or find the local bus that takes you up to the Fira bus interchange for just a few euros. Once there, we transferred again to the airport to pickup our rental car before finally making our way to our accommodation! We stayed just outside Kamari on the islands west coast. Santorini is very well developed so no matter where you stay it won’t take long to get around to the islands most popular destinations. If you’re looking for a luxury visit and plan to wander only around Oia/Fira and enjoy food, wine & sunsets from the comfort of your hotel or restaurant/bars, Oia or Fira are great places to stay. They will be considerably more expensive than other parts of the island, but you’re paying for the view and the convenience. We prefer something a little quieter and wanted to get out and explore everyday, so the high costs of accommodation in these areas weren’t worth it for us.

Day 11: The famous Oia!

We woke up before sunrise and drove to Oia to enjoy those postcard views without the crowds that come in from the cruise ships each morning. The nature of just how famous this place is means its almost impossible to have it to yourself as the viewpoints can be cramped and theire are always more than a handful of commercial photographers taking travel photos for tourists, newlyweds and honeymooners, so get in, take the photos you need then just chill and wander the iconic cliff-top town in the morning light!

If you want to treat yourself to a boujee breakfast, you can hang around the top of the cliffs in Oia and find a cafe or restaurant. From the menus we saw, you can expect to pay over 20 euros per plate here. If you’re just ready for food and the view isn’t so important for you, we’d recommend KooKoo Bar for a delicious under 10 euro breakfast, just need the main Oia parking lot.

Once you’ve had your share of Oia, jump back in the car and head to a few of the other cute towns like Pyrgos and Megalochori. Grab a scoop of ice cream at Mr Scoop in Megalochori for a snack as you wander around. From both towns, its a short 10 minute drive to Fira where we’d recommend going for lunch and an afternoon stroll. We loved Lucky’s Souvlakis for a quick, cheap lunch, but there is a tonne of restaurants and cafes to choose from if you want something more substantial. The cliff front walk here is beautiful, but can get hot in summer so make sure to bring a hat & sunglasses (the white wash buildings are super bright on your eyes). If you’re book lovers like us, there’s also a beautiful and well-renowned bookstore in Fira that is quite famous and worth a look, Atlantis Books.

This evening we’d recommend the walk down (and back up) to Skaros Rock in nearby Imovigli. In Imovigli, you’ll also find a huge range of more upscale restaurants and bars perfect to enjoy the night after watching the sunset from Skaros Rock.

If you’re after something a little less fancy, some restaurants we loved were:

Kantina ‘O MINAS’: this is over in Kamari which was close to where we stayed however definitely not central or convenient if you’re staying in Oia/Fira
Jaipur Palace: obviously not authentic Greek food, but it was delicious Indian food!
Los Tres Amigos: good for burritos, we got them to takeaway and perched up along the cliff front to watch the sunset another evening
Τα Ποστάλια του Αιγαίου: a delicious local Greek find with cheap plates, great for sharing

Day 12: Our favourite spot in Santorini

While the beaches in Santorini aren’t as nice as those from Milos and Paros, the Red Beach is worth a look. After brekkie, jump in the car and head there for the morning, enjoying another swim and the incredible red Earth and volcanic rocks. You can rent umbrellas, sunbeds and snorkels here. Afterwards spend the rest of the day how you like! There’s just one stop you need to make before leaving Santorini.

A few hours before sunset, head back up to the north of the island to Ammoudi Bay, this (besides those famous Oia views), was definitely the highlight of Santorini for us! In fact, it was so nice, we took no photos, just soaking in our last Greek summer hours. The path through the bay lined with restaurants gives out to a more rural path leading to a great spot for some time in the sun and more beautiful swimming. It was quite busy so the later you go the more likely you’ll be able to find a place to lay out your towel on the rocks in this small spot. There’s a tiny rocky island about a 30m swim from where we set our things down that you can climb for some pretty fun jumping. Make the most of the cliff jumping and perfect blue water while you soak in your last Greek sunset!

Day 13: Ya sas Greece!

It’s flight day! Depending on where you stayed in Santorini, you might have time for one last quick beach dip or time to enjoy your hotel pool before you head out. For us, we enjoyed a swim at Kamari’s pebble beach, watching the flights land and takeoff over the airport.

This is a slightly condensed version of our itinerary in Greece from June 2024, we spent a couple extra days in Milos and Paros to revisit a few locations at different times of day and spend some more time chilling out between shooting photo and video and getting some other work done, and let us tell you that besides Santorini, no amount of time would be too long on these islands! The vibe is on point, the food is amazing and the water is just right, we can’t wait to be back in Greece.

One suggestion we’d have is swapping Santorini to the beginning of the trip as for us personally it was a bit lacklustre and much too touristy for the type of travel we enjoy, but of course it is a bucket list destination for a lot of people and the clifftop villages are definitely worth the visit!

That’s It!

If you’ve made it down here, thank you so much for reading!

That covers everything you need to know for a beautiful two weeks soaking in Greek summer!