The Greek Islands, specifically the Cyclades, really have it all - incredible food, beautiful beaches, and the most picturesque villages filled with white washed houses. But planning a trip to the Greek Islands can be daunting! There’s so many different islands to choose from and the travel logistics of island hopping can be a pain. We put together the perfect itinerary that mixes relaxation with adventure, allowing you to really get a feel for the local culture of the islands, eat incredible food, and not feel like you're being funneled into tourist traps.
Top 3 Must-Do’s for a Greek Island Itinerary
Boat day around Milos
Walking from Apollonia to Artemonas on Sifnos
Lunch on Vathi Beach in Sifnos at Restaurant Symposio
Duration: 9 nights
Typical Daily Cost for two people: $362 (excludes airfare to/from Athens)
Best Time to Go: Late May, June, September, Early October
Table of Contents
The Art of Picking the Right Greek Islands
Planning our trip to the Greek Islands was one of the most labor intensive trip planning experiences we’ve had - there’s just so many options to choose from! We spent countless hours scouring travel blogs looking for the perfect mixture of islands to explore, and honestly, we think the three we picked are pretty great! For this trip, we specifically focused our research on the Cyclades islands.
What we looked for: We wanted a trip that mixed relaxation with adventure and that allowed us to see the local culture of the islands, eat incredible food, and not feel like we were being funneled into tourist traps. It was also very important to us to find islands that had amazing towns to explore (not just beaches) - we wanted the quintessential white washed houses that Greece is so famous for!
What we avoided: We wanted to avoid over touristed areas with crowds and crazy parties - this very quickly removed Santorini and Mykonos. We also wanted to avoid long ferry rides from one island to the next.
The three islands we chose in the Cyclades were Milos, Sifnos, and Naxos. They each had their own distinct personality that resulted in the perfect balance of relaxation and adventure we were looking for!
Sifnos: Sifnos was by far our favorite island of the trip! It was the most authentic of the three islands and had the most amazingly beautiful hilltop towns to explore. The photo opps are literally endless. This is what we hoped for when we pictured the most perfect Greek island.
Milos: Milos is a very relaxing and low-key island. It's relatively flat compared to the other islands in the Cyclades but it has some seriously dramatic landscapes that make you feel like you're on another planet. In our opinion, the best way to see Milos is by taking a day trip on a sailboat.
Naxos: Naxos was the most touristy island of the trip (which was ironic because everyone we met while in Naxos said it was the least touristy island they visited - most of those people had come from Santorini or Mykonos). It's still very enjoyable and the food was incredible.
Quick Tips for the Greek Islands
Ferries: Book your ferry tickets in advance on FerryHopper using the Island Hopping option
Arrive at least at hour early for your ferry from Piraeus port in Athens. Once you're on the islands, you only need to arrive maximum 30 mins early.
Download the FerryHopper app on your phone to keep track of all your tickets, track in realtime where your ferry is, and locate the correct departure gate.
If you get motion sickness easily then definitely bring some meds! The waves are no joke, and there is no outdoor area on these ferries to get fresh air. We also recommend having only a very light breakfast and bring some snacks/drinks.
Bring bug spray for the islands (or pick some up at the pharmacy once you get to Athens)
Bring a warm jacket for nights if you're visiting in the shoulder seasons (Sept/October or May/early June). I made the mistake of only bringing a jean jacket in the end of May and I was freezing!
Greek Islands Itinerary at a Glance
Day | Activities | Night |
Day 1 | Arrive in Athens late afternoon. Short walk around town and dinner in Athens. | Athens |
Day 2 | Morning ferry to Milos. Have a relaxing traditional Greek lunch by the beach and explore the main port town of Adamantas. | Milos |
Day 3 | Boat trip day around Milos! | Milos |
Day 4 | Quick ferry to Sifnos. Pick up rental car at the port. Explore the hilltop towns walking from Apollonia to Artemonas. | Sifnos |
Day 5 | Explore the tiny village of Kastro and walk down to the Church of the Seven Martyrs in the morning. In the afternoon, head over to Faros, explore the beaches, and stop by the Chrisopigi Monastery. | Sifnos |
Day 6 | Drive down to Vathi beach for an easy hike and lunch on the beach at Symposio (our favorite meal of the trip!). In the afternoon, relax at the hotel pool and enjoy your final sunset in Sifnos. | Sifnos |
Day 7 | Morning ferry to Naxos. Explore the main town during the day and head to the Temple of Apollo (with a bottle of wine!) for sunset. | Naxos |
Day 8 | Relaxing beach day at Naxaki Beach Bar. | Naxos |
Day 9 | Afternoon ferry to Athens. Enjoy sunset overlooking the Acropolis at Areopagus Hill. | Athens |
Day 10 | See all the historic sites of Athens in one day (trust us, it’s 100% reasonable to pack it into a single day) - Hadrian’s Library, Ancient Agora, Roman Agora, and the Acropolis. **Depending on where you are flying next, you can either take a late flight today, or stay 1 more night in Athens (we took a 9pm flight back to Lisbon). |
Just the Facts
Athens
Stay
Eat
Krasopoulio tou Kokkora: Traditional Greek restaurant
Bandiera: Another traditional Greek restaurant
Η Στοά του Ψυρρή: Lunch spot and the best food we had in Athens. This place looks like nothing, and we actually almost bailed because it looked like a hole in the wall coffee shop, but we're SO glad we went! Incredibly well done Greek tapas and super friendly service.
Drink
Milos
Stay
Hotel Rigas: Cute family owned hotel, about a 10 min walk from town. The rooms are basic but nice, and the breakfast here is INCREDIBLE!
Eat
O! Hamos! Tavern: Open air restaurant with traditional Greek food - we highly recommend getting as much Greek salad with the famous Milos cheese as you can while you're on this island! Also, the grilled meats were very good here.
Nostos: Slightly upscale grilled seafood spot right on the water.
Mikros Apoplous: Right next door to Nostos, and basically the same menu, so take your pick!
Zygos: Super casual and delicious grill spot - we had the grilled lamb chops which were amazing.
Drink
Akri Bar: Cute cocktail spot overlooking the harbor
Do
Sifnos
Stay
Nival Boutique Hotel: The views, the vibes, the pool, this place is it! We felt so relaxed at Nival and both agreed this was our favorite hotel of the trip.
Eat
Agianemi: Cute little restaurant right by the ferry. Come here for lunch before heading up to your hotel
Kafeneio Drakakis: Traditional taverna with Greek small plates
Captain Sifakis: Fresh grilled seafood, view of the ocean
Cafe Mosaic: Greek tapas spot with nice outdoor seating. Be sure to bring bug spray here!
Γιάντα;: Greek tapas spot
Restaurant cafe Symposio: Winner for best meal of the trip! This place is so unassuming, but trust us and just go there. It's owned by an old Greek couple, we sat at a table right on the beach that was literally partially in the water. The food is traditional Greek and OMG, it's delicious. Order everything, but don't forget to order the octopus skewer.
Drink
Doloma Bar: We came here most nights - it has good cocktails and darts!
Naxos
Stay
Hotel Grotta: We loved this hotel! We were originally hesitant to stay here because there was no pool and it seemed a little far from town, but we have no regrets! This was some of the best service we've ever experienced at a hotel and the breakfast was incredible. They also have a great roof deck to enjoy a drink and the sunset overlooking the main town, and the location was actually perfect - it was only about a 5 minute walk to town.
Eat
All the restaurants we ate at in Naxos were very similar - traditional Greek food with amazingly flavorful grilled meats and of course so much greek salad!
Drink
Belman: Great craft cocktails
The Rum Bar: Grab a table upstairs by the balcony overlooking to harbor. Nice rum-based cocktails and tiki drinks
Avaton 1739: Daytime spot, come for a coffee in the morning or a drink in the afternoon. Great views over Naxos
Do
Naxaki Beach Lounge Bar: We loved this beach bar so much, we stayed here the whole day. Very reasonably priced sunbeds, the cocktails are perfectly balanced, and the food is fresh. If you're looking for a relaxing beach day, this is the spot.
Map
Detailed Greek Islands Itinerary
Day 1: Arrive in Athens
Arrive at the Athens Airport in the mid-afternoon and take the Metro Line 3 to downtown Athens (about 40 minutes). If you prefer, you can also call an Uber from the airport, but honestly, the metro is so direct and straightforward, we preferred it over an Uber.
For your first night in Athens, we recommend you chose an Airbnb or hotel close to the Monastiraki Metro stop since it's super easy to grab the metro in the morning for your ferry (BED in Athens is a great option for a hotel).
Note: Even if you have an early ferry, we still recommend staying near Monastiraki and not booking a hotel at the Piraeus port.
Depending on when you arrive, you may have a bit of time to explore the city before dinner. We recommend walking past the outside of Hadrian's Library and then taking a stroll down Adrianou Street (directly opposite Hadrian's Library). Feel free to stop at any of the bars/restaurants for a drink and some people watching (Tip: we don't recommend eating dinner at any of the restaurants on Adrianou Street - these are very touristy and don't have high quality food in our opinion).
For dinner, head over to Krasopoulio tou Kokkora in the Psyri neighborhood for some traditional Greek food. Psyri is a great area that's a bit away from the most touristy areas of town and has lots of amazing restaurants and bars. Most of our Athens food & drink recommendations center on this area. If you're up for it after dinner, walk just down the block to Little Kook and snap a few photos - this is an Alice in Wonderland themed bar/restaurant that is so over the top - you need to see it for yourself (no need to go inside or buy anything, you can see it all from the street).
Day 2: Ferry to Milos & Explore Town
Time to go island hopping - your first island will be Milos. We recommend booking tickets for the 9AM ferry from Piraeus port. To get to Piraeus Port, simply take the Metro Line 3 from Monastiraki to Piraeus (about 30 mins). We recommend getting to Piraeus Port by 8am so you can find your ferry - if you booked SeaJets, you will likely be leaving from Gate E9 (there are TONS of ferries, so just remain calm, follow the signs, and ask any of the port workers if you need help).
The ferry to Milos takes 3.5 hours (this is the longest ferry ride of the trip) so you'll arrive just in time for lunch. Once you arrive at the Milos port, walk to Hotel Rigas (10 min walk), check-in, drop your bags off, and head to lunch at O! Hamos! Tavern.
If you're in need of some chill time after the long ferry ride, head across the street from O! Hamos! Tavern and relax on the beach chairs, otherwise, you can walk into town and explore a bit.
Dinner tonight is at either Nostos or Mikros Apoplous for some fresh grilled seafood. Both restaurants are next door to each other, located right on the water, and have very similar menus, so just take your pick!
Day 3: Boat trip in Milos
It's boat trip day! This was one of our favorite days in Greece and we highly recommend you splurge a bit for this one. The trip will circumnavigate the entire island, giving you the opportunity to see Milos' dramatic landscapes that are best seen from the water!
For dinner, we recommend you head over to Zygos. It's only a few minutes walk from town and has some great grilled meats and of course, our favorite Greek salad with Milos cheese.
Day 4: Ferry to Sifnos & Explore Hilltop Villages
Onto the island of Sifnos today, and get excited, because Sifnos was hand-down our favorite island of the trip! It's only a 40 minute ferry ride from Milos to Sifnos, so pick the ferry time that works best for you - we recommend taking one that gets you into Sifnos around lunchtime.
Once you get off the ferry in Sifnos, head just 2 minutes down the road to grab lunch at Agianemi before picking up your rental car (also 2 minutes away).
Note: You can technically do Sifnos without a car, but we highly recommend you get a car for this island. There's so many cool off the beaten path places to explore that you can really only access with a car. The roads here are super easy to navigate and there's virtually no traffic since Sifnos is not a commonly touristed island.
Pick up your rental car from the pier and drive about 5 mins up the hill to Nival Boutique Hotel - we LOVED this hotel! You'll be tempted to just relax at the pool, but trust us, there's things to see! Explore the hilltop towns walking from Apollonia to Artemonas following the walking paths. We both agreed that Sifnos had by far the cutest towns and we loved just getting lost in the small pedestrian streets.
For dinner, walk back down to Apollonia and pick from one of the many tavernas - we liked Kafeneio Drakakis. After dinner, grab a cocktail and play a few rounds of darts at Doloma Bar.
Day 5: Explore Sifnos
Today is a day of exploring! In the morning, we recommend grabbing your car and heading down to the town of Kastro - this town is CUTE, and we mean really, really cute! After you've snapped hundreds of photos of Kastro, walk down to the Church of Seven Martyrs. The views here are spectacular - you may also be tempted to come back here one of the days for sunset to snap some more epic photos!
For lunch, stay in Kastro and stop by Captain Sifakis for some amazing fresh grilled fish and of course more Greek salad with another amazing view.
In the afternoon, drive over to the tiny fishing village of Faros and explore for a bit - there's a few small beaches you can walk to and some nice hiking trails. Then drive over to the Chrisopigi Monastery for, you guessed it, more epic views!
Head back to the hotel for sunset (or you can go back to Kastro for sunset). For dinner, we recommend walking over to Artemonas and going to either Cafe Mosaic or Perivoli Restaurant.
Day 6: Vathi Beach in Sifnos
It’s your final day in Sifnos so why not relax a bit and spend the day at the beach! In the late morning, drive over to Vathi Beach. You can either chill on the beach for a bit or take an easy hike to get an incredible view of the harbor. For the hike (and honestly, we would barely call it a hike - we did it in sandals), walk all the way to the far end of the beach (past Symposio Restaurant) and pass through a small gate. Follow the trail up the hill for maybe 5-10 minutes and you’re there! If you want to go further, feel free - the trail continues up the hill along the coast.
For lunch, head back down to Vathi Beach and grab a table right on the beach at Symposio Restaurant. This was our favorite meal of the entire trip! This place is so unassuming, but trust us and just go there. It's owned by an old Greek couple, we sat at a table right on the beach that was literally partially in the water. The food is traditional Greek and OMG, it's delicious. Order everything, but don’t forget to order the octopus skewer. Spend the rest of the afternoon relaxing on the beach, or head back to the hotel and chill at the pool.
For your final dinner in Sifnos, walk over to either To Liotrivi or Γιάντα; for traditional Greek small plates. This is also give you one last chance to wander through the walking paths between towns and get some last minute pictures in along the way.
Day 7: Ferry to Naxos & Explore Old Town
Off to Naxos today - drop your rental car off at the pier around 8:15am and take the 9am ferry to Naxos. This is a 3 hour ferry so you’ll arrive right around lunch time. If you stay at Hotel Grotta (which we highly recommend), they will be waiting for you at the ferry terminal to drive you over to the hotel. Naxos Town is by far the largest town of the 3 islands but it is still very walkable and there’s plenty to explore.
For lunch, walk over to Oasis Restaurant on the other side of Naxos Town and for some grilled meats and Greek salad. In the afternoon, we recommend just exploring all the pedestrian streets of Naxos Town. Walk up to the Venetian Castle of Naxos and stop for a coffee or glass of wine at Avaton 1739 - they have the best deck in the town overlooking the town and the harbor.
At sunset, walk over to the Temple of Apollo (with a bottle of wine!) and then head to Doukato Restaurant for dinner. If you want to grab a cocktail after dinner, we loved Belman and The Rum Bar.
Day 8: Beach Day in Naxos
We recommend making your final day in the Greek Islands your most relaxing one by spending the day at Naxaki Beach Lounge Bar. We absolutely loved this beach bar - it has very reasonably priced sun beds, the cocktails are perfectly balanced, service is friendly, and the food is fresh. We got there before lunch and had no problem getting a great spot on the beach, but you can also call ahead to reserve sun beds for the day.
For dinner, head to either To Elliniko Restaurant or Nostimon Hellas - both restaurants have outdoor seating and great traditional Greek food.
Day 9: Ferry to Athens
It's time to head back to Athens, but don't fret because there's still tons of cool things to see and do in Athens (and of course, more Greek salad!). We decided to take the early afternoon ferry from Naxos (1:30pm departure) which allowed us to have a leisurely morning to stroll around Naxos for a bit and then arrive in Athens around 5pm.
Once you check-in to your hotel, walk over to Areopagus Hill for what we think is the best sunset spot in all of Athens - it's on top of a big rock and has the most perfect view overlooking the Acropolis. For dinner, we recommend going to Bandiera and then wandering around the Psyri neighborhood for drinks (we liked Tettix Cocktail Bar).
Day 10: Explore Athens
We decided to pack all the historic sites of Athens into one day, and honestly, it worked out perfectly. We never felt rushed, and we even had some extra time to wander a bit between sites. To make the most of the day, we recommend leaving your hotel no later that 9am. Start at Hadrian's Library - we found it super easy to buy the 1-day pass here that gets you into all the historic sites. The ticket counter is located just below street level so many tourists don't even realize you can buy the 1-day pass here. After Hadrian's Library, we finished off the morning by going to the Ancient Agora. If you have some extra time before lunch, you can walk over to Kerameikos Archaeological Site and see the turtles - we'll be honest, this was not that exciting so don't feel bad about skipping it.
For lunch, we HIGHLY recommend going to Η Στοά του Ψυρρή. This is a total hole-in-the-wall restaurant that doesn't even look like it serves food, but let us tell you, the food here is incredible! It's all Greek tapas and the flavors are some of the best we had on the entire trip.
The afternoon is the main event. Start by exploring the Roman Agora and then make your way into to the Acropolis. We arrived at the Acropolis around 3:30pm and found that it was crowded, but not unmanageable - you can easily get through the Acropolis in 1 to 1.5 hours. It is absolutely worth seeing up close!
We opted to take a late flight out of Athens at 9pm, but you can also choose to spend a final night in Athens and fly out the next morning. Overall, we felt this 9 night trip was the perfect amount of time to explore 3 islands and Athens!
Cost Breakdown (2 people for 9 nights)
Note: Flights to/from Athens are not included in this cost breakdown.
Roundtrip metro tickets to/from Athens airport | $34 |
Sifnos Rental car | $150 |
Hotel- Athens (2 nights) | $275 |
Hotel - Milos (2 nights) | $195 |
Hotel - Sifnos (3 nights) | $482 |
Hotel - Naxos (2 nights) | $257 |
Ferries | $612 |
Breakfast | $0 |
Lunch | $320 |
Dinner (2 entrees, 1 app, bottle of wine) | $540 |
Cocktails | $180 |
Milos Boat trip | $258 |
Naxaki Beach Club | $60 |
Athens Site Ticket | $80 |
Total | $3,443 |
Daily Cost for 2 people | $362 |
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