The Best Of Greece – The Perfect Greek Island Hopping Itinerary

The Best Of Greece – The Perfect Greek Island Hopping Itinerary

Published On: March 1, 2021Last Updated: April 5, 20246 min readBy

☞ Table of Contents:

When planning a Greek holiday, you want to create an experience for yourself that embodies the authenticity of Greece. Then, who better than an expert local to give you advice? We imagine that one of the first things you’d love to do is explore the islands. So, we have crafted the perfect Greek island hopping itinerary. Ideal for first-time travellers, this will give you an idea of where to stay and what to do on four of the most beautiful and must-see islands in the Cyclades.

☞ Related: Greek Island Groups – Greek Island Complexes

Travelling by ferry?

Embark on a delightful water adventure by booking your ferry tickets effortlessly using the form below.

Travel Tips

Before you begin Greek island hopping there is some important things to know. When planning we suggest that you stay a minimum of two nights on each island. The Greek island hopping dream is not as dreamy if you miss out on a ferry, or spend the whole day on one. So, take the time to rest and relax into the rhythm of each island.

The timing of the ferry schedules means that often you need to rise early to catch it first thing, or wait until later in the evening. In the meantime you don’t want to be held back by carrying around your luggage. There is a solution however! You can store your bags using RadicalStorage.

☞ Related: What is the Ideal Greek Island For You According To Your Type Of Vacation

First Destination – Paros!

First on the Greek island hopping itinerary is Paros, which is fondly thought of as a relaxed version of the famous island, Mykonos. Paros has amazing beaches, delicious food and equally vibrant energy. But here there are also quiet villages and that you can escape to that lie just out of the main town and can be reached within a few minutes by car or ATV. You can also delve into the party scene in Paros, just as much as Mykonos if you stay in Naoussa.

As always, we like to show you the lesser-known side of Greece, the insight that only local knowledge can give you. If you are spending a few days on Paros we recommend you take a boat tour for the day. Because of the size of the island, there are many hidden coves that are waiting to be explored. Take a journey by boat and you’ll find shipwrecks and secluded bays of crystal clear spectacular turquoise water!

☞ Related: 10 Of The Most Amazing Things To Do In Paros


Naxos is often underrated compared to other islands, but this very reason makes it unmissable. This quiet and rugged destination is second on your Greek island hopping itinerary. If you are only staying a few days, get accommodation in the main capital of the island so that you can explore easily.

Due to the size and fertility of the land on the island, it has some delicious local produce available such as olives, cheese, honey and seafood. So be sure to check out these on the menu! Don’t forget to try the local delicacy – Graviera of Naxos, which is a special type of cheese! All you need to do is walk along the waterfront and take your pick from a plethora of restaurants and tavernas. The islands have the most wonderful seafood dishes that will enchant your tastebuds.

While there are a number of things to do in Naxos, one of the best things for nature lovers is climbing Mount Zeus. This is the highest point in the Cyclades and at just over 1,000m it offers incredible 360 views of the Aegean Sea and beyond.

In Naxos, there are some beautiful little mountainous villages to explore. Hiring a car is the easiest way to take a tour of the highlands! Go for a wander and have a late lunch at a traditional Greek taverna, pick some fresh figs and, admire the quaint whitewashed houses.

☞ Related: The Best Beaches You Need To Visit When In Naxos


Located in the westernmost part of Cyclades, Milos is known for the discovery of the statue of Venus de Milo, one of the most important pieces of Ancient Greek art. This piece is now exhibited in the Louvre Museum.

Milos is arguably one of the most romantic Greek islands! When you are Greek island hopping we recommend staying close to the main port of Adamas. This makes for a great central location! There is nothing better than savouring a seaside dinner here, watching the sun go down, and enjoying the twinkling lights of the village dance on the surface of the Aegean.

Milos is like Santorini in that it is a volcanic island. This means its geography is incredibly unique. You have probably heard of the most famous beach in Milos, Sarakiniko. Large white volcanic rocks surround the clear blue water and form natural caves. If you are there late at night you will see the light of the moon reflect on the rocks and it is like a lunar landscape.

☞ Related: Your Master Guide to All Greek Islands and How to Pick One


A Greek island hopping trip is not complete without visiting Santorini. Every idyllic story you have heard about this majestic island is true. So, let’s start with where to stay! Oia is the more bespoke side of the island. Here is where people flock from all over to catch a glimpse of one of the most impressive sunsets in the world. Having a private pool overlooking the Aegean will be something you’ll remember forever.

If you prefer to be in the action, Fira, Firostefani, and Imerovigli are all connected, so you can roam around from one to the other! And if your budget is a little more restrictive – have a look at hotels further south. You may still have an incredible view of the caldera but you will just need to hire a car to explore.

A great Greek island hopping addition is a sunset cruise. This will give you the chance to explore some of the beaches and amazing snorkeling spots around the island, all while you experience a stunning sunset in the water. Sunset Oia (who we recommend) have private options available for those looking for a more luxurious experience!

Last but not least we couldn’t forget the White Door theatre! Grab your ticket for an interactive Greek musical! Based at the centre of Fira, you will be part of a Greek wedding. It is one of the most highly recommended shows on the island so book your tickets in advance!

☞ Related: 2 Sunsets In Santorini: How To Make The Most Out Of Two Days in Santorini

*Disclaimer: This page includes affiliate links. If you decide to book something through one of them, I might get a little bonus, but it won't cost you anything extra.*

Discover the Athenian Riviera

Don't forget to use the discount code "DefinitelyGreece" and get 5% OFF

Related Articles