Self Guided Walking Holidays & Cycling Holidays

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Naxos and Santorini Walking Holiday


  • The amazing views from the high cliffs of Santorini’s caldera
  • Walking to the summit of Mount Zas
  • Wandering through scented olive groves which date back 1000 years or more
  • Enjoying a chilled glass of local wine as the sea turns from blue to gold
  • Exploring Fira, the iconic whitewashed town perched high on the cliffs of Santorini

Island hop between two of the most beautiful Greek Islands, Naxos and Santorini and discover the best of these island paradises on foot.

After arriving in Santorini, catch the ferry to Naxos, where the walking is sublime. Wander through ancient olive groves, along cobbled paths, past a venetian fortress, and climb the mythical Mount Zas.

Tearing yourself away from Naxos a two hour ferry journey brings you to beautiful Santorini. This sun kissed island conjures up images of whitewashed villages clinging to the cliff top, blue roofed churches in improbably beautiful settings and amazing sun sets. Enjoy a last couple of wonderful days of relaxed island walking before heading home.

DAY 1: Arrive Santorini & Ferry to Naxos

Arrival at Santorini Airport, where a private transfer will take you to the port of Santorini. The ferry for Naxos leaves at 15:30 and takes two hours. You will arrive in Naxos at 17:30 and the hotel shuttle will take you to your hotel.

If your flight arrives too late for the ferry to Naxos we can book you an extra night in Santorini and you catch the ferry to Naxos the next day.

Overnight: Naxos Resort Beach Hotel

The Naxos Resort Beach Hotel is a two minute walk from the golden sandy beach of Ag. Georgios on the edge of Naxos town. The hotel has 88 comfortable and well equipped rooms, all with air conditioning, a huge pool, excellent poolside restaurant and a friendly staff dedicated to ensuring you have a wonderful time on Naxos.

DAY 2: Naxos: Walk from Chalki to Melanes

After breakfast take a bus or taxi to Chalki, located in the center of the Tragea plain. Today you walk through the olive groves and rich vegetation of this fertile hinterland of Naxos. Some of the olive trees are over a thousand years old!

Historical sites also feature as you walk on cobbled paths via the Venetian Fortress Ano Kastro to an ancient marble quarry. Here you will find a 10m high statue of an unfinished Kouros from the 6th century BC!

Walk: 10-19km, 150-450m Ascent, 15-400m Descent

Overnight: Naxos Resort Beach Hotel

DAY 3: Naxos: Walk from Kynidaros to Eggares

After a short transfer to Kynidaros, enjoy a gentle walk to the small village of Eggares. Explore it’s picturesque churches and two restored olive presses one of which dates back to 1885. Enjoy lunch in one of the tavernas on the stone-built main square before returning to your hotel.

Overnight: Naxos Resort Beach Hotel

Day 4: Naxos: Walk to Mt. Zas

Today’s walk is an absolute cracker! Your walk starts from Filoti at the foot of Mount Zas, which is reached by local bus or taxi. From Filoti you begin your ascent to the summit of the legendary Mount Zas. You will pass the cave in which, according to the legend, Zeus, the father of all the gods, was nursed by an eagle. The climb to the summit is rewarded with exceptional views in every direction.

Following your descent there are several options to extend your walk via Apiranthos and Mt. Fanari to Filoti.

Walk: 13-19km, 500-900 Ascent 500-900 Descent

Overnight: Naxos Resort Beach Hotel

Day 5: Ferry from Naxos to Santorini

After a relaxing morning perhaps by the pool, on the beach or visiting the castle in Naxos town you catch the ferry to Santorini at about noon.
A two-hour ferry brings you to the most famous of the Cyclades, Santorini. Entering the flooded caldera of Santorini on the ferry is an unforgettable experience. The steep coloured cliffs crowned by whitewashed villages surround you and you will be filled with anticipation of the delights that lie ahead.
The archipelago of Santorini is essentially all that remains of a giant volcanic eruption that occurred 3600 years ago and is thought to have ended the Minoan Civilization. Or could it be the source of the legend of Atlantis?

Overnight: Hotel Goulielmos

Day 6:
Santorini: Walk from Perissa to Akrotiri

A short transfer after breakfast will take you to Perissa. From here you climb via an old path to an exposed saddle. This is one of the very few points that predates the devastating volcanic eruption in Ancient and Roman times. It enjoys the most fantastic location.

If you suffer from vertigo it may be worth starting the walk slightly further on to avoid some exposed sections—you will find details of how to do this in your route notes.

You then descend via an old path to the quiet interior of the island walking through vineyards (Santorini produces top-class wines!) and picture-perfect villages until you reach Akrotiri village and a refreshing plunge in the pool.

Walk: 13km, 580m ascent, 550m descent, 5.5 Hours

Overnight: Hotel Goulielmos

Day 7: Santorini: Walk from Fira to Oia

Start your day with a short bus to Fira (30m), the iconic whitewashed town perched high on the cliffs, which is the capital of Santorini, taking in views of the Caldera on the way. Take your time to wander through the narrow alleys, hidden squares and quiet corners of this beautiful town, which teases you with glimpses of the blue blue sea at almost every turn.
History buffs will enjoy the Museum of Prehistoric Thira and the Archaeological Museum, whilst others may prefer to just take a little longer over lunch. After lunch, you are in for a treat as you tackle the famous walk from Fira to Oia. This walk will blow you away with fabulous views of the lagoon and the spectacular cliffs with their massive drops. From Oia, you will be picked up and transferred back to your hotel.

Walk: 10km, 300m Ascent, 400m Descent, 3 Hours.

Overnight: Hotel Goulielmos

Day 8:
Depart Santorini

We will transfer you to the airport in plenty of time for your flight home.

Alternate accommodation

During high season, you might be booked into alternative accommodation if our standard accommodation is fully booked. Any alternative accommodation will be of the same or better standard as those described in the itinerary.

Single Rooms

If you require single rooms within your party we would be happy to accommodate you although there is a single room supplement payable.


A delicious breakfast is included each morning. Lunch and dinner are not included but available at your hotel or nearby restaurants.

Time of Year

This walk is available to start any day of the week between April and October. April to June and September and October are the best time for walking as July and August are very hot. Please note that at the very beginning and end of the season (early April and end of October) any swimming pools at accommodations may be closed and restaurant offerings may be more limited during this time.

Grade & Fitness

This walking holiday is graded moderate overall. Daily walks range between 2 and 7 hours but average 3-5 hours. Most days have an option of an easier or tougher walk. The walk to the summit of Mount Zas would be graded more as moderate-strenuous. The walk on Santorini from Perissa to Akrotiri does have a couple of quite exposed sections and therefore would not be suitable for vertigo sufferers. However it is possible to skip the first section of this day to avoid the worst parts. The walks follow a mixture of gravel roads, footpaths and minor roads. A few ascents and descents are steep.

Navigation, Route Notes & Maps

The walks are mostly waymarked but we provide detailed route notes and maps so you will have no problem following the route.

Single Rooms & Solo Walkers

If you require single rooms within your party we would be happy to accommodate you although there is a single room supplement payable. This holiday is available for solo walkers but we would recommend that you are experienced in walking and navigating alone. If you are travelling solo the holiday there is an additional supplement as some costs are not shared.


Most transfers are included in your trip including; roundtrip transfers on Naxos and Santorini, taxi transfer Akrotiri-Perissa and Oia-Akrotiri on Santorini and Santorini-Naxos-Santorini ferry tickets in tourist class. The bus and taxi transfers to and from the start/end of the walks not mentioned above are not included and will be paid locally.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

General Information

The distances and ascent are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.

Getting to and from Santorini

Direct flights to Santorini Airport from the UK are available from easyJet, flythomascook, Thomson Flights and Meridian Flights. Direct flights from other European destinations are also available.

Once you arrive a private transfer will take you to the port of Santorini to catch your onward ferry to Naxos. It takes approximately two hours and upon arrival in Naxos you will be transferred from the port to the accommodation by a taxi or a minibus (owned by the accommodation).

Upon departure a transfer is included from your last night’s accommodation to Santorini Aiport for your onward journeys.

It is also possible to travel by ferry between Athens and Naxos or there are some flights with Olympic Airlines from Athens to Naxos too. If you wish to travel this way please let us know so that we can co-ordinate your transfers accordingly.

As transfers at the beginning and the end of the tour are included please provide us withy your flight arrival and departure information as soon as possible.


  • 4 Nights in a 3* hotel in Naxos and 3 Nights in a 4* hotel in Santorini in garden-view rooms
  • 7 Breakfasts
  • Transfers from Santorini Airport to the port and from Naxos port to the first nights accommodation on Day 1
  • A transfer from the last nights accommodation to Santorini Airport on Day 8
  • Taxi transfers Akrotiri-Perissa and Oia-Akrotiri on Santorini
  • Santorini-Naxos-Santorini ferry tickets in tourist class
  • 24-hour telephone assistance from our local representative
  • Detailed pre departure information pack, route description and maps


  • Flights to/from Santorini
  • Dinners
  • Lunches
  • Travel Insurance
  • Personal expenses such as drinks, phone calls, extra transfers, tips, etc.
  • Any items not specifically mentioned in the program


  • Single room supplement(s) if applicable
  • Solo walker supplement if applicable
  • Additional nights during the holiday and extensions.
  • Upgrade to sea view rooms

How fit do I need to be?

This walking holiday is graded moderate overall. Daily walks range between 2 and 7 hours but average 3-5 hours. Most days have an option of an easier or tougher walk. The walk to the summit of Mount Zas would be graded more as moderate-strenuous. The walk on Santorini from Perissa to Akrotiri does have a couple of quite exposed sections and therefore would not be suitable for vertigo sufferers. However it is possible to skip the first section of this day to avoid the worst parts. The walks follow a mixture of gravel roads, footpaths and minor roads. A few ascents and descents are steep.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as both Naxos and Santorini are very popular.  

What equipment do I need?

You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack, warm clothing in the early/late part of the year and hats etc during the summer. We supply a detailed packing list with your information pack.  

When is the best time of year?

April to June and September and October are the best time to walk in the Greek Islands as July and August are too hot for most people. 

What happens if I can’t walk a stage?

You can use public transport or local taxis to continue to your next overnight stop.



What better way to get to know a country than to hike through it's villages where the real local people live. We LOVED Greece because we got close to it's soil and it's people. We feel like we really got a taste of this culture. It's different than just checking into a hotel and spending time by the pool. Trekking through the countryside was amazing! The directions for each hike look impossible when we received them ... but they actually were very detailed and accurate. Well Done Mac's!


Olympia, WA


Island hopping


I couldn't understand the route notes, so ended up working hikes out myself with just the idea of where to go from the plan. The accomodations were great though and the pre-organised transfers were reliable.




Two very different, yet interesting islands to visit.


Santorini is a beautiful island, with unbelievable views and colours. Old Naxos, with its narrow, twisting labyrinth of streets and villages in the hills.Both fantastic places to walk and explore.

Happy Aussie



Great trip! we went in June, had amazing weather!


Great trip, had a mishap and missed out on one day of hikes. This mishap could have been avoided by the company so this was a bite disappointing--they responded quickly but never truly rectified the problem. The hikes were in general really nice, would recommend going early in the morning if in June. The towns we stayed in were great and the hotels were good for relaxing by the pool. overall, we had a blast!




Excellent holiday


We had a wonderful holiday and were blessed with great weather. Just 2 things that need to be addressed: on Naxos we had real problems getting bus tickets. The places that sold them were inevitably closed, and you can't buy them on the bus. Once we were turned away by the driver and had to get an expensive cab, and once we only managed to get on because another group had 2 spare tickets. You really should include these with the pack.

Walking friends



Ideal way to see some Greek Islands


I had long dreamed of visiting the Greek Islands but never got much beyond the vision of the white houses overlooking the Sea on Santorini. For my husband's 50th it seemed ideal to book a walking tour of the area I had put on my bucket list. And this was the ideal way of seeing an area I had no idea about without me having to do a lot of research or arranging. We learned early that you really do need to pay attention to the directions/instructions! Being from North America, there were a couple of discoveries along the way that we hadn't anticipated. Such as all the glorious outdoor pools at the hotels being unheated. And while we were there in early October, it was still quite warm but the pools were absolutely icy! And the advertised spa/hot tub in the one hotel was only available for $10 euros per person, per hour. I would also think that it is better to do the tour with 3 nights in Santorini and 4 in Naxos as the beaches/restaurants/accommodations are generally better on the larger island but the tour has more night in Santorini

The anniversary couple

Manitoba, Canada


Some amazing scenery some not so much


I think this must have been a challenging hike for MAC to put together. Parts of the trails were scenic and interesting but other parts were not pleasant at all. The food was just OK. There were too many transfers. We took a taxi or bus to the start and ending of all the hikes. The hotel on Santorini was a gem. We loved the rooms and the owners were very nice.


New York


Exceeded expectations, enjoyed the walks & the views


Naxos walks marginally better than Santorini.

Wilbur the Greek



Fantastic Honeymoon


We went on the Island Hopping trip in Naxos and Santorini as the first part of our honeymoon. Rachel from Macs Adventures arranged everything for us, going above and beyond to get us quotes for slightly fancier hotels and to make sure we had all the information we needed. The walks were well marked and (apart from one marker) the guide notes were accurate and easy to follow. Our hotel rooms were absolutely beautiful, and we couldn't have asked for a better trip for our honeymoon.

Josh & Kathryn



Great Holiday


This was a very well organised and thought through holiday. The information provided by Macs Adventures was very detailed and comprehensive. Every walk has different length options so there should be something for everybody. Even in October we got to all the walks just using local buses. The weather was consistently sunny and about 23C although it was so windy one day we swapped walks to ensure we weren't too exposed, (it was well forecast so it all went smoothly). The Greek people were very friendly and even the food was unexpectedly excellent. Naxos was lovely and the west coast of Santorini is jaw-droppingly beautiful.




Island Hopping: Naxos & Santorini

4.4 14


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