2-Week Greek Islands Itinerary: The Perfect Mix of Iconic & Underrated

After a literal decade of dreaming up a trip to Greece, I finally made it last October. I’d always told myself I needed to wait to go until I had enough time to dedicate to this country. I was right. This 2-week Greek islands itinerary is a pared down version of my actual trip.

In reality, I was fortunate enough to have 18 days to island hop. But I recognize that’s not for everyone, and there’s a lot you can experience in a couple weeks as well!

Tip: The best way to go Greek island hopping is by ferry! I use and recommend Ferryhopper, make sure you download the app for ease.

14-Day Greek Islands Itinerary for The Cyclades

Whether you have less than, more than or exactly 14 days here’s a guide to help you map out your ultimate Greece itinerary through the cyclades island group: 

Days 1 & 2: Arrive in and Explore Santorini 2 days

I’ve said before how initially, I actively tried to avoid Santorini completely. But I’m actually so glad that those initial plans didn’t work out because otherwise I do feel like I would’ve missed out. 

Especially as a first timer to Greece, I’m glad I got to see Santorini. Sure, it’s very hyped up and an uber popular destination. There’s a reason for that. 

So, I recommend spending a couple days here. Now, I flew in directly to Santorini from Rome early in the morning. This gave me two full days here which felt like plenty for me to get a taste of the island. 

But maybe you’re coming in by flight or ferry from Athens. Adjust the days of this itinerary to best fit your travel plans. For instance, I jumped right into the islands first and then spent a few days in Athens before flying home to Chicago. 

You might prefer to do the opposite. Either way, Santorini in October at least (fewer crowds!) was a nice start to my Greek island hopping adventure. 

Days 3, 4, 5, 6: Travel to and Stay in Sifnos 4 days

Balance out the hubbub of Santorini with a few days relaxing on the quieter Greek island of Sifnos. There’s only one way to get here and that’s by ferry, which takes about three hours from Santorini. 

The moment I stepped off the ferry onto the port in Sifnos I was in awe, as I turned and faced a tall cliffside across the water.

The entire time my taxi driver was taking me to my first hotel in Sifnos, all I could think was people actually live here. Actually grew up here, surrounded by more nature than skyscrapers. 

The beauty on Sifnos island is inspiring, and I very happily spent several days here exploring the island and relaxing.

Maybe you’ve already come across Sifnos in your research, or maybe this is the first you’re hearing about it. In my experience, although the island has some tourism infrastructure in place, it still feels largely untouched. 

If you’re at all intrigued or curious about it, I say you should go for it.

Days 7, 8, 9: Choose Serifos or Paros

Because I had more time to play around with, and had my heart set on a particular destination (I’ll get into this more down below), I did not stay within the Cycladic island group my whole trip. 

However, it does make life a lot easier if you do! So, my next recommendation to you is to go from Sifnos to either Serifos or Paros. While I haven’t been to either of these islands myself, I can give you some guidance on how to decide. 

If you prefer discovering quieter, lesser known islands then make your way to Serifos. As far as I can tell, the vibes here are similar to those on Sifnos. And it’s only a 50 minute direct ferry ride to get to Serifos from Sifnos. 

Alternatively, if you’d like to go somewhere a bit livelier as your next stop after Sifnos then make your way to Paros (about a 3-hour ferry ride). Paros was initially high on my list, until I spoke with a friend who introduced me to Sifnos. 

It’s definitely a better-known island that attracts more tourists than either Sifnos or Serifos, which also means stronger tourism infrastructure.

You’ll find more guided tour options, more shops and eateries, much more in the way of nightlife and more people. 

Weigh your vacation priorities and preferences to help you choose the right fit for your own Greek islands itinerary! 

Days 10, 11, 12, 13: Travel to and stay in Syros 4 days 

Whether you end up in Serifos or Paros, I strongly recommend that you next make your way to Syros. Despite being the actual capital of the Cyclades, Syros does not get enough credit or attention in my opinion. 

Which is a shame (or maybe it’s a good thing…) because it was quite possibly my favorite stop of all. 

I pulled out my phone during my first walk through town to update my sister – “I may need to come back, think I could easily spend a month or more here.” 

To me, Syros strikes a pleasant balance between lively and calm. It feels spacious, yet charming. Due to its history, the island has beautiful Venetian architecture. 

There weren’t many tourists here, at least not ones who stood out, so I felt in among the locals. 

My absolute favorite experience on Syros was swimming off of a concrete city “beach,” if you can even call it that, with gorgeous views of the Church of Agios Nikolaos.

Day 14 – depart

There is SO much to see in Greece, on trip will hardly cover it. But this 14-day itinerary for Greece will give you a great first experience. 

You might be tempted to cram even more stops into this 2-week plan, and hey, to each their own! All I ask is that you bear in mind how taxing travel days can be. 

Spending 3 or 4 full days per island and seeing a handful can be a lot more enjoyable than hurriedly scraping the surface of a bunch of different islands.

Based on the logistics of your overall travel plans – when you’re set to be flying in and out of Greece – this day 14 may be your day to fly back to Athens. 

If you have a flight from Athen back home on this day, then you should make your way from Syros to Athens the night prior. The good news is that Syros also has a domestic airport, if you’d prefer that over taking another ferry. 

If you have more time…

I mentioned above that I had my heart absolutely set on a non-Cycladic destination. Where?

Crete. For some reason, I just had to get to Chania. So my Greece solo travel itinerary looked different from what you see above. I went from Sifnos to Syros (not an ideal route) then flew from Syros to Chania. 

If you have more time in your Greece travel itinerary then you might consider a visit to Crete as well. But, I recommend seeing more of Crete than Chania which felt a bit disappointing in the end. Only to me – most people love Chania! And folks, even locals, really love Crete. 

Go to Crete if you can spend 4-5 days there and consider renting a car so you can see as much of the island as possible. 

Or, take an overnight ferry from the Cyclades to Rhodes. This was another option I was considering. 

The reality is that there is so much more to Greece than the Cycladic island group we seem to hear about the most.

As a first timer, I’m glad I started with the Cyclades because it closely resembles the Greece I’d envisioned. But in the future, I want to expand beyond this group. 

Of course, you should also spend some time in Athens. I spent 4 full days in Athens after Greek island hopping. I would’ve been okay with just a couple days there though. 

If you have less time…

Don’t have 14 days? That’s okay! Simply make cuts to the above itinerary based on your own travel priorities, preferences and logistics. 

If you want to make some swaps, you could plan to stick closer to Athens. Consider visiting Hydra or Nafplio in the Peloponnese region – all are within a couple hours of Athens by car or ferry (and all are on my own destination wish list for future trips to Greece!). 

How to get to and around for Greek island hopping

Let’s talk a bit about how to get from island to island, and how to get around on the actual islands themselves: 

Ferryhopper

A friend who frequents Greece told me about Ferryhopper, and it’s what I used to plan and book all my ferries. I found it easy to navigate and figure out BUT I did make one mistake. 

I accidentally booked one of my ferries for the WRONG date – oops. I managed to get a refund credit that has to be used within a year. I’ll probably lose out on that… Be sure to check your dates carefully before booking. 

Aside from my user error, I had a great experience with Ferryhopper. Their customer service was helpful as well to help me get that refunded credit after my mistake. 

Be sure to download the Ferryhopper app. This made my life so much easier as all ferry tickets and details were right on my phone. 

I also don’t recommend spontaneity when it comes to booking your ferries. Especially not if you’re visiting in peak season. 

⛴️ Book your ferries in advance

Something to be mindful of and prepared for is that sometimes, ferries can experience last minute schedule changes or even cancellations.

I was lucky enough not to run into this and you will probably be fine, too. But it’s always good to be mentally prepared for things not going according to plan when traveling. 

Finally, don’t get on a ferry without #33 on this list. Add some salty snacks and a ginger ale or sprite to that mix to complete your ferry survival kit. 

Car or ATV rentals

Most people rent cars or ATVs to get around effectively on the islands themselves. If this is something you’re comfortable with then it’s the ideal mode of transportation. 

Unfortunately, I really dislike driving and have not yet built up my driving-alone-in-a-foreign-country muscle. I relied on walking, buses and the occasional taxi. 

Flights 

Although ferries are the most popular way to get from island to island in Greece, flights are also available. This can be a convenient option when you’re shorter on time and traveling longer distances. 

Of course, not every island has an airport but some of the major ones do so it’s worth checking for domestic flights here.

Final thoughts on planning a Greek islands itinerary 

Planning your Greek islands itinerary may take some time upfront, but it will be well worth it in the end. Greek island hopping is a bucket list travel experience and the reality of it is, overall, just as dreamy as the visions you’re likely having!

While there are different island groups to choose from in Greece – Ionian, Saronic, Dodecanese, etc – the Cyclades is a fantastic starting point.