Santorini Self Guided Walking Holiday


  • Mar - Nov
  • Self Guided
  • 4-7 days
  • Customizable

"Immerse yourself in the dramatic cliffs and stunning panoramic views to the Caldera of Santorini"


Immerse yourself in the dramatic cliffs and stunning panoramic views to the Caldera of Santorini and experience one of the most sought-after holiday destinations! Walk on volcanic islands, through hidden villages, hundred years old hand-tended vineyards, an ancient town buried under volcanic ash… and marvel at the endless views.

The current shape of the island is a result of a series of catastrophic volcanic explosions over the course of thousands of years. The main island, Thira, will blow your mind with its multi-colored cliffs soaring to 300m and its white washed houses lining these cliff tops offering amazing views and glowing sunsets. Along with the smaller islands of Thirasia and Aspronisi they circle the burried under the sea caldera. In the middle you’ll find the volcanic islands of New and Old Kameni… you’ll be rewarded with breathtaking views at every twist and turn!

Ancient paths will introduce you to the intriguing history of the island, the fascinating Minoan site of Akrotiri, Ancient Thera, its picturesque villages such as Oia and Pyrgos, its Venetian castles, its red and black sandy beaches, its excellent wineries and vineyards, pottery and art workshops and the finest food…

Look below at our recommended walks during our Santorini self-guided walking holiday…

Join our Santorini self-guided walking and:

images Absorb the breathtaking panoramic views to the sunken Caldera,

images Soak up the atmosphere and sunsets of chic Oia village,

images Walk along volcanic islands,

images Stroll though hidden villages off the beaten path,

images Explore a preserved ancient town burried for years under volcanic ash,

images Visit 100 years old vineyards and taste amazing volcanic wines,

images Discover the world famous island of Santorini at your own pace!

Our walks during this self-guided walking holiday in Santorini are graded as easy to moderate. You will walk mainly on paths of moderate gradient with ascents of up to 500m in a day. Being predominately limestone some parts of our paths can be quite rough and stoney.

Flexible itineraries, 4-day, 7-day or combined with other Cycladic islands can be arranged for you. 


Please find below our selection of hotels that we have tried and tested for you. We will check for availability upon your request.

Our selection based on value, location and comfort!!

All accommodations offer ensuite bathrooms and most include breakfast:

  • Antonia Hotel
    Best value! Known for their hospitality! Antonia Hotel has luxurious, traditional furnished rooms with private balcony offering amazing views. Unique location also! No breakfast available but kitchen & fridge available in the room.
  • Summer Time Villa
    Family run hotel providing high quality service and authentic Greek hospitality with undiminished care for over 15 years. Minutes walk from the vibrant main square of Fira Town. Breakfast included!

Our selection of superior hotels for those who want extra comfort!

All accommodations offer ensuite bathrooms and include breakfast:

  • Dream island Hotel
    Located within a 3-minute walk from Fira’s centre, Dream Island hotel offers rooms tastefully furnished and decorated in earthy colors. Has a pool overlooking the Aegean Sea. Breakfast included!
  • Villa Ilias
    Quietly situated in Firostefani, only a 15-minute walk from busy Fira, Villa Ilias features a swimming pool with a captivating view over the Caldera, the volcano and the sea. Breakfast included!

Single rooms available

This holiday is suitable for solo walkers. If you travel on your own or require single rooms within your group we would be happy to accommodate you although there is a single room supplement payable.

Contact us for further information and special offers…


This holiday is available from March till November. The best time of year though to walk around Santorini is spring and autumn. April, May and June are absolutely lovely because of the lush vegetation and wild flowers. Autumn is also lovely as it is cooler and you can enjoy the softer colours and golden light as well as the best sunsets of the year. We recommend to visit during March and from September till November.

July and August are the busiest and hottest months and all the prices for flights and accommodation reach their peak. The Greeks also take their holiday in August so if you can only travel during this time of year you need to plan ahead as the hotels and ferries tend to get booked fast. It is also warmer and walking is enjoyable only between 7.00-11.00am and 18.00-21.00pm. For these reasons we recommend that you travel outside this high season period if at all possible.


Santorini is one of the most sought after destinations and it is quite busy between June and mid September. If you wish to travel during the high season we recommend to book as early as possible in order to secure your choice of accommodation. If you book early in the year you can also benefit from special offers. We will do our best to provide suitable alternatives in case you wish to book last moment.

If you have any questions please don’t hesitate to contact us at


Option A: 7-day self-guided walking holiday

All prices are per person for two people sharing a standard double room, staying at a traditional family-run guesthouse:

  • 7 nights – Low Season from EUR 476 High Season from EUR 669

Supplement for single rooms:

  • 7 nights – Low Season from EUR 154 High Season from EUR 346

Option B: 4-day self-guided walking holiday

All prices are per person for two people sharing a standard double room, staying at a traditional family-run guesthouse:

  • 4 nights – Low Season from EUR 410 High Season from EUR 520

Supplement for single rooms:

  • 4 nights – Low Season from EUR 88 High Season from EUR 198

Our Santorini self-guided walking fees include:

  • Our choice of the best 5 self-guided walks at the island of Santorini,
  • Bonus navigation at volcanic Nea Kameni island,
  • Active navigation and step-by-step guidance using digital maps and mobile applications,
  • A detailed info pack on recommended routes, points of interest, photos and a hiking map,
  • Mobile application with active nagivation,
  • Introduction to our unique flora, fauna, history and culture,
  • 4 or 7 nights accommodation & breakfasts at traditional guesthouses (choices available),
  • Suggestions for lunch/supper/excursions/beaches and archeological sites to visit,
  • Local support from our representative 24 hours/day,
  • Transfers from the port or airport to the accommodation and vice versa,
  • Emergency telephone support in the event of a problem,
  • In our island hopping itineraries, ferry transfers between the islands.

The fee excludes:

  • Flights to Greece and ferries to the starting and ending islands (if needed),
  • Lunches, dinners, snacks and drinks,
  • Entrance fees to museums and archeological sites,
  • Travel insurance and personal equipment,
  • Taxi transfers or public transport not mentioned above (estimate per week will be provided),
  • Anything not included above.


  • Upgrade to 3* or 4* hotels,
  • Athens Extension (3 Days & 2 Nights),
  • Extra nights at your chosen destination,
  • Private transfers to and from the airport of Athens,
  • All transfers by taxi or public transport pre-booked (EUR 20 – EUR 97,5 pp)

Book your Santorini self guided walking holiday…


Fira is the capital of Santorini and its cultural and commercial centre, based on the caldera cliffs opposite the volcano. It’s the ideal base for exploring the island. After you settle at your guesthouse, take the time to stroll around the narrow alleys of this charming town and enjoy the sunset, the only hour of the day when literally everything and everyone stops to admire the view!
If you had to choose one hike not to be missed at the island of Santorini, this is it! Starting from the captivating main village of Fira, you follow a scenic path along the rim of the caldera towards the picturesque villages of Firostefani and Imerovigli till you reach Oia to watch Santorini’s famous sunset! As you walk along you will enjoy astonishing views of the caldera, the volcanic islands Nea & Old Kameni as well as Thirasia from different perspectives. Words cannot describe the beauty! On the way you must stop at Skaros rock, once a a fortified castle and capital of Santorini, and walk through the ruins. End the day with a supper at our favourite tavern at chic Oia where you can try Santorini’s delicious dishes prepared with local anhydrous ingredients.

Distance: 10 km Time: 4 hours (actual walking time can reach 5-6 hours)
You start today’s walk from the beautiful village of Emborio, once a fortified Venetian castle settlement. The path resembles a mini gorge as it follows a trail in between two hills and underneath two arches. As you admire the beautiful nature and vineyards on the slopes you will reach the 567m summit of Profitis Ilias, the highest point in the island offering stunning views and an ideal place to stop for a snack and a rest. Descend from Profitis Ilias through a magnificent mountainous path offering panoramic views of the island towards ancient Thera! Walk through time as you explore the excavations of remnant houses, market, theatre, Roman baths, cisterns, a holy road dated from the 9th century AD. Take the short path which leads to the black beach of Perissa where you can plunge into its crystal clear waters and enjoy a delicious supper!

Distance: 9.4 km Time: 4 hours (actual walking time can reach 5-6 hours)
A very interesting trail that combines the two diametrically opposed sides of Santorini; on one hand, a wild landscape depicted with vineyards and isolated churches and on the other hand, the welcoming, scenic but unexplored villages of Santorini.

You will start from the beautiful Cycladic village of Pyrgos, wonder around its narrow alleys and explore its ruined Kasteli (castle), traditional architecture, remains of neoclassical mansions and breathtaking views of the whole island. You’ll follow the old path leading to the traditional farming villages of Exo and Mesa Gonia. On the way you will have the chance to visit 2 of the most acclaimed wineries of the island. Time to explore Santorini’s “hidden” villages, get a glimpse into the island’s agricultural life and taste the island’s awarded volcanic wines!

Distance: 3.7 km, Time: 1h30 (actual walking time with visits to wineries can reach 3-4 hours)
Today it is an opportunity to rest from hiking. We recommend to take a boat trip to the volcanic island “Nea Kameni” and walk the short, dusty path to the active crater. You will also visit the hot springs where you can enjoy swimming in the sulphurous springs of the volcano as well as the small island of Thirasia which, although so close to Thira, remains totally uspoilt from tourism. Admire the magnificent views towards the caldera and Thira from a different perspective!

Distance: 2.6 km, Time: 1h-1h30
Today we have a special hiking route for you starting from the outskirts of the village of Megalochori. We’ll guide you through a path that runs parallel to the volcanic rock so you’ll have the chance to admire the strange shapes and scenery of white volcanic ash mixed with black lava rocks. You’ll descend the steep cliffs of the caldera towards Agios Nikolaos Palou chapel. Stop to absorb the tranquility and beautiful contrast of the landscape with the deep blue of the Aegean sea.

Your next stop will be Akrotiri village, another fortified Venetian settlement. Take the old path and reach the Akrotiri excavation which has uncovered one of the most important Aegean prehistoric settlements. The three storey sophisticated buildings, the elaborate drainage system, magnificent wall-paintings, furniture and vessels of this ancient city buried under volcanic ash will fascinate you. End the day with a coastal walk to the incredible Vlychada beach.

Distance: 6.8km, Time 3 hours (actual walking time can reach 6 hours)
Join us for a scenic tour from one of Santorini’s most beautiful village, Foinikia, and admire its unique island architecture of cave houses dug into rocks. Walk through a valley full of vineyards and dozens of chapels scatered around, adorned with beautiful objects collected by sailors from around the world. Stop at the small church of Kyra Panagia (Lady of the Virgin) to admire the surrounding natural beauty and rest. On the way back have a break at one of the most famous wine estates, sit in the courtyard under the vines and sample high quality volcanic wines.

Distance: 8.9 km, 3h-3.3h (actual walking time can reach 5-6 hours)


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