The best itinerary for the 'underrated' Greek Islands

Looking to experience a different side to the Greek Islands? This is your itinerary for the ‘underrated’ Greek Islands. We love the Greek Islands and have visited quite a few. The ones we love the best are those that are a little underrated by most travellers. Maybe because they feel more undiscovered, or you meet the locals, or they just aren’t as busy. Either way this is the best itinerary for the most underrated Greek Islands.

Table of Contents

How many days for this underrated Greek Island itinerary?

Ok you could definitely add or take away some days to this, I am doing a 20 day itinerary because these islands deserve a little more time. Either for you to really appreciate them or to get around them as they can be big! This is a guide for the minimum amount of days in each island.

What do you need to pack for the Greek Islands?

Check out my Greek Island packing list to make sure you have the essentials for your trip. The best advice I can give is not to overpack. We usually travel as lightly as possible. It makes getting on and off ferries, scooters, hiring cars and in general just moving around easier. The Greek Islands are hot. You do not want to be lugging masses of luggage around all the time. With this best itinerary for the ‘underrated’ Greek Islands you will be moving each 2 to 3 days, that can start to be annoying if you have to much luggage.

How to get around the Greek Islands.

You can fly into Athens from anywhere in the world and then get to the ferry port. The ferry takes between 3-6 hours from Athens depending on which you choose. We always book with Ferry Hopper. They show all the options for boats and times. You can purchase your tickets and have them on your phone to show when getting on board. It really makes it so much easier than having to print out tickets. On each Greek Island you can take a ferry to the next. It is such a comfortable and easy way to get around.

I will add these details in to the itinerary below. Naxos and Milos both have domestic airports. You could fly into them from Athens to start and finish your trip if you prefer. We found great prices for flights from Milos to Athens when we were there.

What is the best time to go to the Greek Islands?

The Greek Islands all but shut down in winter. The high season is June to August and is the best time of year for the weather. It is also the most expensive and busiest. The islands I recommend here are definitely not as busy as the more well known islands of Santorini and Mykonos.

The months of May and September are the shoulder season and the cheapest and quieter times to travel the Greek Islands.

The best itinerary for the ‘underrated’ Greek Islands!

Our itinerary starts in Naxos and goes through to Milos. For me these are the best islands we have been to yet! They have so much diversity and opportunity to really experience the Greek Islands.

Day 1-3 – Naxos

Naxos is full of authentic Greece vibes. It is sleepy and not overrun at all. The ferry port is so simple, just walk forward and you are in the Chora and bus stop to anywhere in the island. Naxos has so much to offer from excellent hiking, beaches, historical sites, beautiful mountain villages and more. Check out our Naxos blog for all the best things to do and how we spent 3 days here. Tip – this island has the cheapest souvenirs and shops selling unique jewellery so save some time to shop!

Day 4-7 – Paros

Paros is one of our favourite Greek Islands. The ferry from Naxos to Paros takes between half an hour and 1 hour depending on which boat and time you choose. It is incredibly beautiful across the whole island. Want to spend time in the white washed Chora, it is full of churches, history and cute shops. Prefer to explore some of the best beaches in the Greek Islands? Or maybe you want to spend some time in one of the loveliest villages in all of the Greek Islands? The choice is yours they are all here. Check out my favourite things to do on Paros!

The View from the Church of 100 Doors, Paros

Day 8-10 – Antiparos

Antiparos is a very tiny and quiet little island right off the shore of Paros. You can actually take a little ferry over for a day trip or book one of many tours there from Paros. This one is really popular, it is with Get Your Guide who we always use and recommend.

We took the ferry from Pounta in Paros to Antiparos and stayed there for two nights and it was exactly enough time for us to stop and soak it up. When I say it is tiny, I mean it has one main street where everything is really located. It is completely low key and I think that is the appeal. It feels local. Check out how we spent two days on Antiparos to see if you would prefer to do the day trip or to stay there. If you choose to do a day trip then add one day to Paros for this and stay there. Add the other day to any of the islands on this itinerary you will easily be able to fill the day and enjoy taking the pace a little slower! Another option is to pop over to Antiparos for drinks in the afternoon. Many people just drive to Pounta, leave their car at the port there and take the ferry over and back for a few hours. The main street of Antiparos is right near the port, it is all really walkable.

Antiparos in such an underrated Greek Island

Day 11-13 – Sifnos

Sifnos is a nature lovers dream. It is full of hikes, rugged mountains and stunning views. It feels authentic and rural. There are some stunning hotels and resorts here our top pick for a splurge is Verina Astra. This is the most beautiful, earthy, tranquil place, a true dream destination hotel. Otherwise staying in Apollonia is great for a central location. You must visit this excellent authentic Greek taverna on the beach in Sifnos which should not be missed! The Kastro and church is beyond perfect and the coolest bar in Greece is right here in our Sifnos Island blog. It takes between 50 minutes to 3 hours for the ferry from Paros to Sifnos.

Day 14-16 – Kimolos

Kimolos is the idylic getaway from it all Greek Island. It is not only small but it barely gets visited by tourists. You will find locals that are interested in why you are there and stop for a chat if you allow the time. You should they are so sweet. We loved our time here. It is such a creative community of people. There are so many creative decorations throughout the streets, stores selling unique decor and jewellery. The cafes and bars are all so beautifully crammed in near the Kastro at the centre. It is a place you could get lost in and spend your time living simply and enjoying life. It takes about two and a half hours for the ferry between Sifnos and Kimolos. You can find out what we did on this beautiful island in our Kimolos blog, this Greek Island is seriously underrated!

Day 17-20 – Milos

Our final Greek Island on this underrated Greek Island itinerary is Milos! I have put four days for Milos but you could easily spend more. Milos is big, and there is a lot to discover. It has such beautiful fishing villages, incredible unique beaches and great food. I could spend a week here and not be bored of it. Milos is an absolute must do! Check out what we got up to on our Milos blogs. We have covered our favourite beaches must dos and how to spend you time. The ferry from Kimolos to Milos only takes about an hour.

Alternatively you can take a tour around Milos, this one will show you all the best places and is well run: Best of Milos Private Land Tour

These are our favourite Greek Islands! They offer so much and you really get to taste and experience the real Greece. Meet the locals, visit the historical sites, and eat the food. I can’t wait to go back and would gladly visit any of these again. If you need any help at all in your planning feel free to reach out in comments or via email, we are happy to help. Check out all our Greek Island blogs!