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

Last updated: May 2026
This is not a sponsored post and I am not affiliated with any of the businesses or organisations mentioned.

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 are coming from. However, have you ever 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 of a kind experiences. All of them are a short boat ride from Santorini, yet 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 go solo! Let’s hop on a ferry, and explore some of the best corners of Greece.

PLANNING YOUR ISLAND HOPPING ROUTE: START OR END IN SANTORINI?

While all of the itineraries included in this post can be done in reverse, I have specifically presented them with Santorini being the final stop, or some may say the grand finale! There are two reasons for this.

Firstly, a practical one. Most travellers, start their Greek Odyssey in Athens, and rightly so. So, whether you are taking the boat from Athens to the islands closest to the mainland or flying to one of the islands further away, finishing your trip in Santorini makes logistical sense. It enables you to fly back to Athens, (or Thessaloniki, Greece’s second largest city) or fly straight to one of the many European destinations that are directly connected to Santorini. Naturally, there’s nothing stopping you from taking the boat back to Athens, but that takes about 5.5h on the fastest catamaran -just so that you know.

Secondly, arriving in Santorini by boat is an experience in itself (and it’s far quicker to catch the boat from an island nearby). The island’s port lies inside the caldera, and seeing its cliff-hanging villages rise high above the sea for the first time is simply unforgettable.

Ultimately, the choice is yours, and there’s no right or wrong here. If it makes sense with the rest of your itinerary or hotel bookings, go with whatever suits your budget and plans. As for those iconic caldera views from the sea, you can also enjoy them on one of the many day or half-day boat trips around Santorini.

Let’s start! Oh, don’t miss the last section of this post where I provide practical info and links about booking tickets, best time to go to Greece, etc.

TOP 5 SANTORINI ISLAND HOPPING:
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 villages, whitewashed cobblestone alleys, beaches with turquoise water and dramatic landscapes with jaw dropping views.

From the iconic architecture and cosmopolitan haunts of Mykonos and the turquoise waters of Koufonisi, to the jagged windswept peaks and slow pace of Amorgos and the dramatic caldera of Santorini, these are the Cyclades’ and Greece’s greatest hits.

This is a trip filled with one of a kind experiences.


PS. In case you are wondering, I named this itinerary ‘Seafarer’s’ because it covers the greatest distance compared to the rest. However, due to the popularity of Mykonos and Santorini, the fastest boats operate these routes daily, so you won’t be able to tell!

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Alternative route option:
Check out ‘the Cycladic Explorer’s itinerary’ where you can swap glitzy Mykonos for perennial crowd pleaser Paros (similar landscape / architecture, less designer bags) -you can find it on my Paros island hopping itineraries (head to No 5).

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TOP 5 SANTORINI ISLAND HOPPING:
NO2. THE PHOTOGRAPHER’S ITINERARY

The Photographer’s Itinerary:
Astypalaia – Amorgos – Santorini

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 take you from Santorini’s red cliffs and dramatic caldera to the wild ruggedness of Amorgos‘ jagged peaks and the serene beauty of Astypalaia‘s soft hills and sheltered coves. All while being surrounded by the deep nautical blue of the Aegean Sea.

But there is more. When you are done with landscape photography, have a stroll around the whitewashed streets of some of the most beautiful traditional villages in Greece, and probably the world.

The village of Oia in Santorini and the capital towns of Amorgos and Astypalaia 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 super star that everyone knows, 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 but if you love coastal landscapes and traditional architecture, you will not want to leave.

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Extending the itinerary:
Eager to see more rugged landscapes? Romantic Folegandros is just 1h away from Santorini, to the west. From there, you will need to take the boat back to Athens though. Alternatively, if you wish to mix it up with some relaxing beach time and flat terrain, Koufonisi makes for a great detour from Amorgos before the grand finale in Santorini.

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TOP 5 SANTORINI ISLAND HOPPING:
NO3. THE HONEYMOONERS’ ITINERARY

The Honeymooners’ 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 on neighbouring Kimolos with its cute little village and uncrowded beaches. 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 a bit of an Indiana Jones mentality 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 charming capital town 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 you are on your honeymoon or not.

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Alternative island hopping itinerary with Santorini and Milos:
Looking for something a little more cosmopolitan? If you’d like to combine the romance of Santorini and the dramatic landscapes of Milos with stylish beach clubs, refined dining and some of the Cyclades’ most luxurious hotels, consider the extended ‘Luxury Traveller’s Itinerary’ starting from Mykonos and making its grand finale in Santorini. Including Paros and Antiparos, it offers a more glamorous take on island hopping while still featuring two of Greece’s most memorable destinations. Read all about it in my top 5 spectacular itineraries from Mykonos (it’s right in the beginning, itinerary No 1).

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TOP 5 SANTORINI ISLAND HOPPING:
NO4. THE FOODIE’S ITINERARY

The Foodie’s Itinerary:
Sifnos – Naxos – Schinousa – Santorini

Is there a better way to experience Greece than through food?

This itinerary is a journey through the flavours of the Cyclades. While not the most efficient logistically, it will make sense to those who love good food, as each stop offers a different expression of Aegean food culture, lots of local produce and some finger licking meals.

We start from Sifnos, birthplace of Greece’s most famous cook. Here, slow-cooked chickpea stew, handmade ceramics and elegant village tavernas are part of everyday life. Don’t miss Omega3, a most sophisticated fish shack.

In Naxos, fertile valleys and mountain villages unveil a more agricultural side of the Cyclades. My friends there tell me that their island is, in fact, self-sustained. Naxos is indeed famous throughout Greece for the local cheeses, citron liqueur, potatoes, homegrown vegetables and long lunches in shaded village squares.

From Naxos, pop to tiny Schinousa. Due to the arid conditions, home grown produce is limited, but you have to try local grown fava (head to the cute courtyard of Bizeli) and freshly caught fish (go to Nikolas of Schinousa).

Lastly, the volcanic soil of Santorini has shaped the island’s world famous white wines and sweet cherry tomatoes. Don’t leave Santorini without trying tomato balls in a local taverna (the furthest from the caldera, the better, though we did love our meal in Skala in Oia), and visiting a local winery. For an elevated experience, skip Nobu and head to award winning Selene for Santorinian fine dining.

This is an itinerary for travellers who experience Greece through long meals, local ingredients and the atmosphere of places where food still feels deeply connected to the landscape and the rhythm of island life.

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TOP 5 SANTORINI ISLAND HOPPING:
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 fully at least) but really want to.

A combination of superstar Santorini (with all the good and less good things about that) and TRULY off the beaten track Thirasia and Anafi. The Escape Artist’s itinerary is a tale of two worlds. Only a short boat ride away, but million miles apart.

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. This brings me to another great thing about this itinerary. It is perfect for travelling slow, but also for a fairly short trip.

Thirasia and Anafi reveal a quieter, more untouched side of the Cyclades shaped by simplicity, isolation and dramatic natural beauty. Given their unique landscapes, Cycladic architecture and intrinsic small island charm, I do expect that they are bound to become more popular soon.

Escape artists, bohemian souls and those of you who have perfected the art of travel, don’t wait around, go now!

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Alternative itinerary option:
For those who love to explore off the beaten track destinations (but still wish to visit Santorini), ‘the Globetrotter’s itinerary’ might be perfect if you have time on your hands. I discuss all about it in my Paros island hopping itineraries (head for No 3).

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HOW TO PLAN YOUR GREEK ISLAND HOPPING TRIP FROM SANTORINI

FINAL THOUGHTS

I hope my suggested itineraries ending in (or starting from) 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 reach out. I will gladly help out. Now, let’s get the map out and start charting that course!

SEARCHING FOR OTHER GREEK ISLAND HOPPING IDEAS?

Mykonos Island Hopping: 5 spectacular itineraries to easily do on your own
Paros Island Hoping: 5 extraordinary itineraries to easily do on your own