Santorini Cycling Trip

7 days / 6 nights / 4 rides




Difficulty: 4 out of 5

Total Distance: 200km

Total Elevation: 3900m

Bike Types: Road, Fitness, E-bike & Gravel


Cycling on the island of Santorini has a lot more to offer than just spectacular sunset views and iconic churches. A great cycling landscape unfolds at every corner making a bike tour here a truly fascinating experience. The rich, almost untouched, authentic cultural side of the island welcomes all cyclists to discover it with no compromises.

Self Guided
from €1750/person
Fully Guided
from €2200/person
from €6700/person
Prices are valid for January, February, March, April, May, November and December for groups of 8 with double occupancy (double or twin room)
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Day 1

Arrival in Santorini

Shuttle to the hotel

Day 2

Towards Oia, Santorini's true gem

Distance: 61km Elevation: 1100m

Day 3

Lighthouse, Red Beach and a Great BIO-Meal

Distance: 35km Elevation: 600m

Day 4

Santorini's Summit and Wine roads

Distance: 35km Elevation: 700m

Day 5

Ancient Thera & Sunset Sailing

Rest day - Activities for all

Day 6

Circling the Island - The last ride

Distance: 71km Elevation: 1550m

Day 7

Dapture from Santorini

Shuttle to the airport / port

Hotel list

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Prices are indicative for groups of 8 persons *

Self Guided

Bikes, Shuttle, Accommodation & Support

€1750 / person

Fully Guided

Bikes, Shuttle, Accommodation, Support & Guides

€2200 / person


Bikes, Shuttle, Accommodation, Meals, Support, Guides & Luxury treatments

€6700 / person

* for January, February, March, April, May, November and December. For other months, the price will be adjusted accordingly.


Cycling in Santorini


The Island of Santorini is famous for its spectacular sunset views, the iconic churches, the narrow alleys and its rich cosmopolitan way of life. Visiting the island and examining the landscape through a cyclist’s eyes, we could hide our awe for this secret gem we have discovered.

With multicoloured cliffs soaring above a sea-drowned caldera, Santorini looks like a giant slab of layered cake. The main island of Thira will take your breath away with its snow-drift of white Cycladic houses lining the cliff tops and, in places, spilling like icy cornices down the terraced rock. When the sun sets, the reflection on the buildings and the glow of the orange and red in the cliffs can be truly spectacular. Santorini is no secret and draws crowds for much of the year, yet it wears its tourism crown well. The island's intrigue reaches deep into the past, with the fascinating Minoan site of Akrotiri and the gorgeous traditional hilltop village of Oia. It also glides effortlessly into the future with accomplished artists, excellent wineries, a unique microbrewery and some of the Cyclades' finest accommodation and dining experiences. The multicoloured beaches are simply the icing on the cake.

Despite the influence of mass tourism, the authentic side of Santorini, the very thing a cyclist set out to explore, has remained, to a high degree, untouched and fascinating. On this dry, volcanic landscape the main source of income for many families, has always been agriculture. It is very difficult for someone to grasp how that was even possible, for example there are no water reserves on the island. However, this adverse soil, the steep hills and the weather conditions have shaped an enchanting history and culture in Santorini; using a bike is probably the best way to explore all. 

Cycling through Santorini’s history

It is totally mind blowing that an island with the dimensions of 11x17km can offer so many things that a week of stay is barely enough to enough all it can offer. Minor volcanic eruptions have been the norm in Greece’s earthquake-prone history, but the phenomena in Santorini were truly earth moving, which explains why its shape has changed several times.

Although many have occupied Santorini ( Venetians, Ottomans), the island's culture was most influenced by the Minoans, who came from Crete some time between 2000 BC and 1600 BC. Back then the island’s shape was circular and according to cited it was called Strongili (Round One). According to the latest theories and based on the carbon footprint found on olive-oil samples, a tremendous volcanic eruption caused the centre of Strongili to sink. That left the caldera with its towering cliffs to put together a truly dramatic sight.

Quite recently, in 1956, a major earthquake lest the villages of Oia and Fira completely devastated. However, by the late 1970s the islanders embraced tourism, and today Santorini is a destination of truly spectacular global appeal.

What type of bike should be used in Santorini?

Road cyclists: the road network in the Island of Santorini is very small and the tarmac conditions are not grade. Quite frequently the road surface is full of potholes or very corroded, which results in an intense vibration level especially when going downhill. Cycling here would require at least 28mm tyres or a gravel bike. In the case you select GrCycling to be your bike provider, we will equip you with one on 28mm tyres.

Recreational cyclists on fitness bikes: a bike with wide enough tyres or a short front suspension will be enough to the the best out of your time in Santorini

When to visit Santorini?

We believe that the best months for someone to visit the island for a week is October to mid December and February to the beginning of May. The island of Santorini tends to get really busy during the summer months making the whole experience of discovering a small island not straightforward with a lot of hassle (traffic on the roads, having reservations in place for pretty much everything and long queues is what someone should expect during summer months)

Why do the cycling routes begin from Perissa - Santorini?

There are two reasons for that. The first is that traditionally the cycling activity starts early in the morning. We also believe that it is much better catching the first sun rays and the feel the morning breeze. The second, is the easy access to the beach side; Perissa is Santorini’s longest beach and by selecting the accommodation here jumping into the water is just a few minutes of walking.