Santorini island hopping: 5 amazing itineraries to easily do on your own

last updated: February 2024

Santorini’s jaw-dropping landscapes, spectacular architecture, incredible food and wine culture, unique beaches and hard to believe history are more than enough to merit a trip to Greece, no matter how far you come from. However, I bet that many of you have wondered what lies further away from the deep blue waters of the island’s caldera.

Allow me to introduce you to the Cycladic and Dodecanese islands. Will one of them be the ‘next Santorini’? No. There is only one Santorini. But, these gems, don’t need to be. They all have their own distinct character and stunning sights able to provide you with one a kind experiences. All of them are a short boat ride from Santorini yet some of them feel worlds apart.

So, without further ado, here are the 5 best island hopping itineraries starting from or ending in Santorini. You can do all of these, completely on your own. No guides or ‘experts’ required. You don’t even need to speak a word of Greek (though you will get big smiles if you try!). Grab your friends, partner, family or no one, hop on a ferry and let’s explore some of the best corners of Greece.

TOP 5 SANTORINI ITINERARIES:
NO1. THE SEAFARER’S ITINERARY

The Seafarer’s Itinerary | Mykonos – (Ano) Koufonisi – Amorgos – Santorini

There are so many Greek islands worth exploring, each one offering something unique. One of the main goals of this blog is to cover as many as possible! However, I am fully aware that many people will not be able to visit Greece multiple times. For that once in a lifetime trip to Greece, the Seafarer’s itinerary might the best one to take.

The Seafarer’s itinerary will take you through some of the most photogenic islands in Greece. It also achieves a nice balance between super popular and off the beaten track destinations, ensuring you get the best of both worlds. You can live it up in Mykonos and Santorini and experience authentic, low-key island life in Koufonisi and Amorgos.

This is an itinerary filled with sun-drenched Cycladic whitewashed villages, cobblestone alleys, beaches with turquoise water and dramatic landscapes with jaw dropping views. This is a trip filled with one of a kind experiences.

CHECK OUT THE TRAVEL GUIDES:

Koufonisia: Beach bumming in the most exotic Greek islands
Amorgos: Wild beauty in the bluest of the Greek seas
Santorini: Bold, beautiful & absolutely worth it – Trip planning guide

TOP 5 SANTORINI ITINERARIES:
NO2. THE PHOTOGRAPHER’S ITINERARY

The Photographer’s Itinerary | Santorini – Amorgos – Astypalaia

A trip bursting with endless views of the horizon. Clear skies in the morning, hazy at midday, bathed in colour during sunset, star-studded at night. The Photographer’s itinerary will quench a thirst for dramatic jagged cliffs dropping into the sparkling blue sea you never knew you had.

But there is more. When you are done with landscape photography, have a stroll around the cute streets of some of the most beautiful traditional villages in Greece, and thus, the world. The villages of Oia in Santorini, Amorgos’ Chora and Astypalaia’s Chora* are some of the best examples of stunning Cycladic architecture perfected to withstand pirate attacks, protect from ferocious winds and living life -literally- on the edge of a cliff…

While Santorini is the star of the show, I guarantee that you will absolutely fall in love with both Amorgos and Astypalaia and wonder why you have never heard of these islands before. This is one of my Santorini itineraries that I recommend to just about everyone.

*the term Chora is used by many Greek islands as a name for their capital town.

CHECK OUT THE TRAVEL GUIDES:

Santorini: Bold, beautiful & absolutely worth it – Trip planning guide
Amorgos: Wild beauty in the bluest of the Greek seas
Astypalaia: The butterfly of the Greek seas

TOP 5 SANTORINI ITINERARIES:
NO3. THE HONEYMOONER’S ITINERARY

The Honeymooner’s Itinerary | Milos – Kimolos – Folegandros – Santorini

Don’t take the name of this itinerary too literally; replace honeymooners with couples. Honeymooner sounds more romantic though, no? After all, this is the most romantic of my Santorini itineraries.

Young couples have been flocking to Milos years before it became the new ‘it’ island of the Cyclades. And while in Milos, don’t you dare miss out neighbouring Kimolos. Then, there is Folegandros, a small, rocky outpost that charms everyone who wonders its thousand year old paths. Lastly, I guess I should mention that on a three day visit to Santorini, I witnessed two wedding proposals. I rest my case.

Frankly, I don’t think that anyone really knows why these islands attract couples more than other places. Maybe it’s the weird and wonderful beaches that require being in an Indiana Jone’s mood to access. The larger than life vistas or the glorious sunsets. The romantic restaurants and lack of intense nightlife.

Whatever it is, you will utterly and unequivocally fall in love with the jaw-dropping beaches in Milos, the crystal waters of Kimolos, the cute Chora of Folegandros and the one of a kind caldera view of Santorini. More than that, each island, in their own unique way, creates a heady atmosphere that is bound to seduce you, whether on a honeymoon or not.

CHECK OUT THE TRAVEL GUIDES:

Folegandros: Rugged beauty in the most romantic Greek island
Santorini: Bold, beautiful & absolutely worth it – Trip planning guide

TOP 5 SANTORINI ITINERARIES:
NO4. THE REVELLER’S ITINERARY

The Reveller’s Itinerary | Mykonos – Paros – Antiparos – Ios – Santorini

Let’s get loud.

But first, I need to clarify. The islands included in this itinerary are by no means only intended for partying. Personally, I have visited most of them with friends and my fiancé and you can definitely have a relaxing / romantic time in all of them. However, if you are looking for beach parties or exciting nightlife, you will definitely find that here too.

Mykonos will give you plenty of opportunities to revel in luxury amongst the international jetset, whether on the beach or in Chora. On the other hand, chic Paros will get you hanging out with a young, energetic crowd and so will hippy Ios. Last but not least, Antiparos is quite the dark horse. It is generally considered as an undiscovered, laid-back kind of a place, and it is. Nevertheless, you can easily find yourself seeing the sunrise with your shoes and a drink in hand!

Where does Santorini fit in all of this? Well, it is the outlier here, even though you will find some clubs in Fira. However, if you actually follow the whole itinerary through, I think you’ll very much welcome the change of scenery!

Best for? The young and young at heart.

CHECK OUT THE TRAVEL GUIDES:

Paros: Planning your trip to the most ‘marblellous’ Greek isle
Paros: Exploring Naousa & the north of the most ‘marblellous’ Greek island
Santorini: Bold, beautiful & absolutely worth it – Trip planning guide

TOP 5 SANTORINI ITINERARIES:
NO5. THE ESCAPE ARTIST’S ITINERARY

The Escape Artist’s Itinerary | Santorini – Thirasia – Anafi

Last but certainly not least, the only itinerary I have not done yet (not even partially) but really want to. A combination of super popular Santorini (with all the good and less good things about that) and TRULY off the beaten track Thirasia and Anafi.

I often write in this blog about Greek islands that are off the beaten track. But most of them are not really that, at least for Greek people such as yours truly. Similarly, plenty of French and Italian travellers have been visiting these islands for years.

While this was not the case a decade ago, today, the list of actually off the beaten track Greek islands is getting smaller every summer. However, Thirasia and Anafi are still on that list, despite their close proximity to Santorini which brings me to another great thing about this itinerary. It is perfect for travelling slow but also for a fairly short trip.

Given the unique landscapes, Cycladic architecture and intrinsic small island charm of Thirasia and Anafi, I do expect that they are bound to become quite popular very soon. Escape artists, bohemian souls and those of you who have perfected the art of travel, don’t wait around, go now!

CHECK OUT THE TRAVEL GUIDES:

Santorini: Bold, beautiful & absolutely worth it – Trip planning guide

PLANNING YOUR ISLAND HOPPING TRIP -PRACTICAL INFO

FINAL THOUGHTS

I hope my suggested itineraries starting from or ending in Santorini gave you lots of ideas about combining your trip to Santorini with other Greek islands. Remember that the above mentioned itineraries can also be done partially which I’d strongly recommend if you are planning a short trip or just want to relax and travel slow.

If you have any questions, feel free to let me know in the comments section below, I will gladly help out. Now, let’s get the map out and start charting that course!