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Island Hopping in the South Aegean: Naxos & Santorini (Self-Guided)

Experience the beauty of two Cyclades gems in one trip: Santorini and Naxos. Santorini, shaped by ancient volcanic activity, captivates with its dazzling whitewashed houses, vivid sea, and stunning sunset-lit caldera.

  • Greece

  • 7 nights
  • Bed and Breakfast
  • Coast & Islands


  • June - October


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Walking grade

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.  

Usual daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

The above statistics are generalisations of a day’s key walk, it does not include distance covered during general sightseeing or daily activity. Detailed information of the daily walking requirements are specified in the specific holidays ‘Daily Itinerary".


Self-Guided Collection

Expertly planned, flexible walking itineraries, led by you, with accommodation, route plans, and luggage transfers all taken care of by us.


Holiday Highlights

  • Explore the picturesque cliff-top villages of Santorini, perched high above the stunning caldera.
  • Take in the sweeping vistas of the Cyclades from the summit of Mt. Zas (999 m).
  • Admire the ancient Kouros statues on Naxos, dating back 2800 years.
  • Navigate distinctive cobblestone paths along ancient trails across the islands.
  • Explore the historical sites of Thira and Akrotiri in Santorini.

Embark on a journey to two enchanting Cycladic islands, Santorini and Naxos. Santorini, shaped by an ancient volcanic eruption, boasts a unique brilliance: from whitewashed cube-shaped houses to the lapis lazuli sea and captivating sunset-lit caldera.

On Naxos, you'll ascend the highest local peak, Mount Zas, with its summit offering breath-taking views of olive orchards contrasting against the deep blue Aegean Sea. Naxos presents a blend of lively town and beaches in Naxos town with traditional countryside life. Santorini's steep cliffs, adorned with layers of vibrant colours, tell the tale of the Thira volcano's eruption millennia ago. The submerged caldera still displays volcanic activity, evident when visiting the Kammeni Islands. Immerse yourself in this extraordinary landscape on foot and discover its unique beauty.

  • Seven nights accommodation on a bed and breakfast basis.
  • Transfers from Airport to the port in Santorini on day one and five.
  • Transfers from port to hotel on Naxos on day one and five.
  • Walks transport on day six and seven.
  • Detailed maps and route descriptions in English.
  • 24-hour telephone assistance.
  • Routes in digital format (.gpx) for GPS or mobile devices.
  • Lunches and dinners not mentioned in the programme.
  • Flights.
  • Local Tourist Taxes.
  • Transfers by public transportation.
  • Personal expenses such as drinks, phone calls, extra transfers, tips, etc.
  • Any items not specifically mentioned in the program.

Holiday Information

Click the button below for a detailed Holiday Information Sheet containing all the particulars about this trip.

NOTE: Itineraries and Holiday Information Sheets can vary by a specific date chosen

View Holiday Information Sheet

Tour Codes


Itinerary & Travel

Itinerary Details

Whilst every effort will be made to adhere to the outlined itinerary and advertised programme, local conditions can change due to weather or other unforeseen circumstances. This may mean that routes and timings need to be amended or the order of days may change, sometimes at short notice.

Your Itinerary

Day 1

Naxos Town


Your journey commences at Santorini airport, where a taxi will greet you and transport you to the port for your ferry to Naxos. The ferry voyage between the islands lasts approximately 2.5 hours. Upon arrival in Naxos, you will be received at the port and escorted to your hotel. If the daytime permits, consider embarking on a 1.5-hour stroll to Chrisostomos from the port. This allows you to familiarize yourself with the town, appreciate scenic views over Chora, and enjoy a leisurely stretch of your legs. Flights must arrive at Santorini airport before 13:00. Transfer from the airport to the port are included today. 

Day 2

Round walk from Chalki via Melanes




  • Time

    3.5/4.5/7 hours

  • Distance

    6.2/8.6/11 miles

  • Ascent/Descent


Today, you'll commence your journey by opting for either a local bus or a local taxi to Chalki, situated in the heart of the Tragea plain. Here, you'll traverse the fertile countryside of central Naxos, characterized by olive groves and lush vegetation, some of which includes olive trees that have stood for over a thousand years! Following cobbled paths through the Venetian Fortress, Ano Kastro, you'll reach an ancient marble quarry housing a 10-meter high statue dating back to the 6th century BC. Consider concluding your walk in the nearby village of Melanes, from where you can conveniently return to the hotel via either a taxi or a local bus. Should you choose to extend your journey, you'll pass through the villages of Potamia, named after the Greek word for river. As you traverse lush valleys, you'll loop back via Ano Kastro to Chalki.

Day 3

Walk from Kynidaros to Eggares





  • Time

    2.5 hours

  • Distance

    4.3 miles

  • Ascent/Descent


Following a brief transfer to Kynidaros, savour a leisurely stroll to the quaint village of Eggares. Take in the charm of its picturesque churches and discover two meticulously restored olive presses, one of which boasts a heritage dating back to 1885. Indulge in a delightful lunch at one of the tavernas situated on the stone-built main square before making your way back to the hotel. Don't forget to explore the olive press in Eggares during your visit.

Day 4

Mount Zas




  • Time

    3/2/2 hours

  • Distance

    4.2/3.3/3 miles

  • Ascent/Descent


Today, you'll opt for either another public bus or a taxi to reach the village of Filoti, where your walk begins. Nestled at the foothills of Mt. Zas, also known as Mount Zeus, the village serves as your starting point for ascending to the summit of this legendary mountain. Upon reaching the pinnacle, you'll be treated to breathtaking panoramic views of Naxos and the surrounding islands. Upon descent, your route winds through agricultural fields and along a monastery, leading you to Apiranthos, one of the largest villages on Naxos. Following a leisurely break in a local café, you have the option to return to Naxos Chora via taxi or public bus.

For the more adventurous, utilizing the app and GPS track, you have the challenging option to trek back from Apiranthos to Filoti. This route is demanding and recommended only for the most seasoned hikers.

Day 5

Naxos to Santorini




The ferry from Naxos to Santorini is included today as well as transfers from hotel to port and port to hotel. 

  • Time

    2.5/1 hours

  • Distance

    4.5/1.5 miles

  • Ascent/Descent


Today, your journey takes you from Naxos to Santorini. In the morning, you have the option to explore the Castle in Naxos town (Chora) and visit the museum, allowing for a leisurely morning.

The hotel bus will transport you to the port of Naxos. Typically, the ferry departs around one o'clock, and approximately 2.5 hours later, you'll arrive on Santorini. As the ferry approaches through the submerged volcano crater, you'll be captivated by the striking views of the steep, colorful cliffs of this ancient volcanic island and the whitewashed villages perched on top. It's noteworthy that the eruption that occurred here 3,600 years ago is believed to have brought an end to the Minoan Civilization and might be the inspiration behind the legend of Atlantis.

Upon arrival, you have the option to take a short round walk from Akrotiri along the caldera or visit the Akrotiri Ancient Site, conveniently located within walking distance from your hotel.

Day 6

Perissa to Akrotiri




Transfer from your hotel to Perissa is included today.

  • Time

    5.5 hours

  • Distance

    8 miles

  • Ascent/Descent


Today, a transfer will bring you to Perissa, marking the starting point for your ascent along an ancient path to a prominent saddle. This particular area of the island stands as one of the rare remnants predating the catastrophic volcanic eruption. Your journey begins by ascending to Ancient Thira, the erstwhile capital of the island during both Ancient and Roman periods. Following this, you descend via an old path into the tranquil heart of the island, passing through vineyards and idyllic villages. As you proceed through the volcanic terrain, your walk concludes in Akrotiri village.

Day 7

Fira to Oia




Transfer from Oia back to your hotel is included today.

  • Time

    3 hours

  • Distance

    6.5 miles

  • Ascent/Descent


This morning, you'll take a public bus to Fira, the capital of Santorini. In Fira, immerse yourself in the charm of the narrow alleyways of this whitewashed town perched atop volcanic cliffs. Consider visiting the museum of prehistoric Thira and the Archaeological Museum for a glimpse into the island's rich history. In the afternoon, embark on the renowned walk from Fira to Oia. Your route follows a well-maintained mule path, offering breath taking views of the lagoon and the dramatic, sheer cliffs. Upon reaching the small town of Oia, you'll be picked up and transported back to your hotel.

Day 8

Final day



Depending on your flight departure time, consider taking a brief stroll to the nearby archaeological site of Akrotiri, often referred to as the Greek Pompeii. Optionally, you can extend your walk from Ancient Akrotiri to the red beach. If the conditions permit, you may continue to the black beach after passing a certain point with the waves. From there, follow an unpaved road inland, traversing one of the most authentic parts of Santorini known as Loumarades. Proceed along paths through vineyards and terraces, eventually making your way back to Akrotiri. Along the route, you'll pass by the Venetian Fortress in the village before returning to your hotel. Your trip ends at Santorini Airport. Airport transfers are included today.

Travel Details

The best arrival and departure airport is Santorini Airport. Airport and port transfers are included. 


Accommodation information

Below is an example of the type of accommodation you will be allocated on this holiday. Your final accommodation list will be confirmed on your travel documents, these will usually be with you around two weeks prior to departure.

Anixis Hotel or similar

In Naxos Old Town, Anixis is situated 400 meters from Agios Georgios Beach. The air-conditioned rooms at Hotel Anixis, designed in the Cycladic style, and feature dark wood furnishings . Each room is equipped with a satellite TV, radio, ensuite facilities and fridge. Guests can indulge in a breakfast buffet or enjoy a drink at the rooftop bar with sea views. The traditionally decorated living room houses a small library. Numerous Greek tavernas and bars are located just 50 meters from the hotel. Naxos Port is conveniently located 200 meters away.

Kalimera Hotel or similar

Nestled in a prime location just a short distance from the Red Beach and the White Beach, this family-operated hotel boasts views of the caldera, the volcano, or the Aegean Sea.

Positioned in proximity to the archaeological site of Akrotiri, Kalimera Hotel presents Cycladic-style rooms, suites, and maisonettes that provide contemporary amenities.

Kalimera Santorini showcases an outdoor swimming pool, and complimentary wireless internet is accessible in the hotel's public areas. Rooms are equipped with ensuite facilities satellite TV, free Wi-Fi, a fridge, a direct dial phone, a hair dryer, air-condition, bath amenities and a balcony or veranda. 

Trip Information

All the details you need

Holiday Grade

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.  

Usual daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

The above statistics are generalisations of a day’s key walk, it does not include distance covered during general sightseeing or daily activity. Detailed information of the daily walking requirements are specified in the specific holidays ‘Daily Itinerary".

Spending Money

Holiday Budgeting

As you plan your holiday budget, it's essential to account for expenses such as drinks, meals not covered in the holiday price, entrance fees not included, optional local excursions, and any souvenirs or additional services like laundry. For a rough estimate, budgeting around £10-£20 per person per day for lunches and drinks is a helpful guideline.

If your holiday does not include dinners (see itinerary) we recommend budgeting an additional £25-30 per day.

The currency in Greece is the euro.


Tips are not included in the holiday price. Although entirely at your own discretion, tipping is an important aspect of tourism and hospitality life and expectations are fairly high.  We strongly recommend when receiving good service you make a tip to the local supplier.

Your Travel Details

Your arrival and departure airport should be Santorini Airport where airport transfers are included from. Port transfers to and from the hotels are also included. Your flight must arrive into Santorini Airport before 13:00 hours in order to catch the ferry across to Naxos. 

Luggage Allowance & Travel Documents

Should you have decided to book any overseas flight arrangements through us, details of your travel arrangements and baggage allowance will be clearly outlined in your 'Final Travel Documents'. These will be sent to you approximately 10 days before your departure, ensuring you have all the necessary information for a smooth and well-prepared journey.

Personal Details Check

To ensure the accurate administration of your holiday arrangements, kindly verify that the personal details we have for you are current and correct. Confirm that you've given us all the necessary information for securing your travel and accommodation. Please review your passport details, date of birth, and any other pertinent information crucial for the management of your holiday.

Additionally, please make us aware of any dietary allergies or intolerances you may have. Your well-being is important to us, and this information will help us make appropriate arrangements for your meals during the trip.

You can access and update the provided information or add missing details through the "Manage My Booking" feature on our website at www.rambleworldwide.co.uk. Alternatively, reach out to our Sales and Reservations team at +44 (0)1707 331133. Upon receiving your booking confirmation, promptly check the details. Your cooperation ensures a seamless and enjoyable holiday experience.


After booking your holiday, expect to receive a confirmation and holiday information sheet soon after.

Once you've settled your balance, about 2 weeks before your holiday, you'll get instructions on how to log into your ActiveNav App. Grab your Apple or Android smartphone and head to the app store for a quick download. Once installed, the app grants you access to all route information and provides guidance on how to navigate it.

Around 2 weeks prior to your departure, you'll also get a destination manual & road book. This comprehensive guide includes detailed information on your walking route and interesting facts about the areas you'll stay in. Alongside, a trip voucher will confirm all the services booked for you, complete with the names and addresses of your hotels and other service providers. Be prepared to present this voucher as confirmation at your accommodations, and don't forget to bring along a valid form of ID.

Passports and Visas

European Passport Advice

If you are planning to travel to an EU country (except Ireland), or Switzerland, Norway, Iceland, Liechtenstein, Andorra, Monaco, San Marino or Vatican City, you must meet the Schengen area rules.

Your passport must meet 2 requirements. It must be:

  • less than 10 years old on the day you enter (check the ‘date of issue’)
  • valid for at least 3 months after the day you plan to leave (check the ‘expiry date’)

For some Schengen countries your passport may need to be less than 10 years old during your whole visit, and the 3 months at the end of your visit may need to be within 10 years of your passport’s issue date.

Check both the issue date and the expiry date in your passport. If you renewed your passport early, extra months may have been added to its expiry date. This could affect the requirement for your passport to be less than 10 years old.

Non British Passport holders should consult the host country’s embassy for applicable passport and visa entry requirements.


Seven breakfasts are included in the holiday. Items for lunches are available from local shops and it is recommended you take a picnic lunch with you each day. There are plenty of choices of tavernas close by to eat hotel for evening meals.

Footwear & Kit List


Footwear is a walker’s personal choice; however, we suggest lightweight waterproof walking boots with a good, moulded sole (such as Vibram or similar) and a deep tread and which provide ankle support and may be essential for some walks.

Luggage Transfers

On a self guided holiday, the days you walk from one property to another, your main luggage will be transferred for you as part of your holiday arrangements. This leaves you free to just carry what you need for the day. Please refer to your individual itinerary for which days your luggage will be transferred. Before you leave your accommodation in the morning, please speak with your host for where the luggage should be left and by what time. 

General Kit List

Outdoor activities are always safer and more enjoyable if you are prepared.

If you have not travelled with us before the following list might be of use:

  • Day sack (this should be able to carry all you would need for the day's activity)
  • Day sack liner
  • Waterproof jacket (Goretex or similar) and trousers
  • Compass
  • Map case
  • Whistle
  • Lightweight quick-drying trousers
  • Walking T-shirt/shirts
  • Walking socks
  • Fleece or jumper
  • Sun hat, sunglasses, lip salve and sun block
  • Warm hat and gloves (if appropriate)
  • Water bottle - at least 2 litre capacity (more may be required)
  • Basic first aid kit
  • Lunchbox
  • Walking poles (should you find them useful)
  • Sit mat
  • Mobile
  • Power Bank for charging mobile if needed.
  • Phone charging lead

This list is not exhaustive, and every walker is different and may have their own preference.

Travel Documents Checklist

Documents and Information to take with you:

  • Passport (make sure it's yours and valid)
  • Your travel tickets or e-ticket itinerary
  • Any visa or electronic travel authorisation (if required)
  • Holiday money
  • Credit or debit cards (and separate details of who to call if lost)
  • Car parking ticket and car park directions (if prebooked)
  • Coach or rail travel tickets (if prebooked)
  • Your holiday Booking Confirmation document
  • Your travel insurance details
  • Alternative form of identification (such as a driving licence)
  • Photocopy of the personal details pages of your passport
  • A valid European Health Insurance Card (EHIC) if relevant
  • Details of any medical condition or allergy your holiday leader should know about

Electricity in Greece

Electricity in Greece is supplied at 220 Volts. If you wish to use electrical equipment you will need a European two pin adaptor with round pins. More information can be found at  https://www.power-plugs-sockets.com/

Water To Go

Opting for filtered water from a reusable bottle with its built-in water filter, like the Water-to-go bottle available at www.watertogo.eu, is a sustainable alternative to single-use sealed water bottles. Simply refill it from any water source and contribute to saving the environment from disposable plastic bottles.

Exciting news: Water-to-go has introduced two new bottles to their collection. The Active bottle is designed to fit bike water bottle holders, and the Sugarcane bottle is an even more planet-friendly option. Crafted from fibrous cane, a by-product of liquid extraction, it undergoes a process to create plant-based plastic. Explore the details on the Water-to-Go website for this innovative new range.

As a token of appreciation for your commitment to the environment, we've secured an exclusive 15% discount with Water-to-Go for you. Visit www.watertogo.eu and use the code RWH17 during your order.                        

Note: If you're booked on a long-haul holiday departing after November 1, 2023, you'll receive a complimentary Water to Go bottle, sent to your home address 2 or 3 weeks before your holiday. Thank you for being a part of our sustainable journey!

Maps, Guidebooks & Other Information


Visit the following websites for an idea of the climate in your destination:

Staying Healthy On Holiday

Health requirements in destination can change, and it's crucial for you to take responsibility in staying informed. Ensure that you consult a professionally qualified source and comply with any health requirements at least 6 to 8 weeks before your departure. Your GP can provide advice on vaccinations. Stay proactive about your health preparations to ensure a safe and enjoyable travel experience.

Health Advice for Greece

No compulsory immunisations are required for visits to Greece. 

You should be up to date with the usual immunisations recommended in the UK. 

You may also wish to consider immunisations against Tetanus and Tick-borne Encephalitis.

There is a low to no risk of malaria in Greece. Malaria risk is from May to October and is very limited; confined to the villages of the Evrotas delta area in Lakonia district. Please seek advice from your doctor or travel clinic.

Further Travel Advice

For further advice please visit:

You might wish to take a small bottle of antibacterial hand gel with you for times when you're unable to wash your hands.

Travel Insurance

It’s a condition of booking that you obtain adequate travel insurance, from a reputable provider, to undertake the holiday, including UK trips chiefly due to the cancellation element of cover.

The policy must cover the period from the date of booking to the last day of your trip and should include, as a minimum, cover for: medical expenses (including the consequences of a Covid positive test result), mountain rescue including helicopter rescue, death, repatriation, cancellation and curtailment and shall not have exclusion clauses limiting cover for the activities you will partake in on your trip, including altitudes reached in the holiday arrangement. It is your responsibility to check that your policy is adequate for the nature and destination of the holiday booked.

Once you have obtained your travel insurance, please provide us with the name of your travel insurer, the policy number and the insurer’s 24 hour emergency assistance number.

In the event that you fail to obtain suitable Travel Insurance we shall not be liable for any costs incurred or claims made against us due to your failure to comply with this term.

If travelling outside the UK you must carry proof of insurance with you and produce it if reasonably requested to do so by RWH Travel staff, tour leaders or suppliers. No refunds will be made should you be excluded from the walking programme through being uninsured or you being unable to demonstrate that you are insured.

Our house broker MPI should be considered for whom we are an affiliate and contact information is on our website and will be referred to in your booking confirmation.

If you are travelling to an EU country or Switzerland please also ensure that you have either an existing valid EU EHIC card (European Health Insurance Card) or a valid UK GHIC (Global Health Insurance Card). You can apply for a UK GHIC free of charge on the NHS website at https://services.nhsbsa.nhs.uk/cra/start.


Starting January 1st, 2021, you, as a UK traveller, can continue using your European Health Insurance Card (EHIC) throughout its valid five-year period, granting you access to medical assistance during your holiday until its expiry date. Be aware, though, that this coverage will no longer extend to Iceland, Liechtenstein, Norway, or Switzerland. In case you don't have a valid EHIC, you can apply for a new UK Global Health Insurance Card (GHIC), which will replace the EHIC as it gets phased out.

It's essential to emphasize that the EHIC/GHIC, while valuable, should not be regarded as a substitute for comprehensive medical or travel insurance. For your peace of mind and comprehensive coverage, considering additional insurance is highly recommended.

For more information, please visit www.nhs.uk/ehic

Personal Safety

The UK Foreign, Commonwealth & Development Office is your go-to for the latest info on security, local laws, and the nitty-gritty of passports and visas at www.gov.uk/travelaware. Make sure to take a quick peek at the current advice for your upcoming destination—it'll only take a few minutes.

When you're out and about, stay aware of your surroundings. Take smart precautions with your credit cards and passport, and maybe tone down the flashy accessories. Less is more, especially when it comes to carrying cash—just enough for the day will do. Consider using a money belt for that extra layer of security. Stay alert, stay safe, and make the most of your travels!

Cultural Awareness

The Ramble Worldwide Outdoor Trust

Unlike many other tour operators, we take pride in our unique approach. Ramble Worldwide channels its surplus profits back into various outdoor, walking-related, or environmental conservation projects in the UK through our own trust. When you choose us, you contribute to this impactful initiative.

The primary focus of our Trust's financial support is directed towards Britain's premier walking charity, The Ramblers. They play a crucial role in advocating the benefits and significance of walking to the British public. Additionally, our Trust invites applications for small grants from local organizations in the UK that require support for walking-oriented activities. This encompasses initiatives such as establishing footpaths and bridleways, funding for the reconstruction of bridges and refurbishing huts, and bursary funding for organisations that support individuals to enjoy the beauty of the great outdoors..

For more comprehensive details, please visit the 'About' section on our website and click on the Charitable Trust link. Your choice to travel with us goes beyond a memorable vacation; it contributes to meaningful projects that have a positive impact on our community and environment.

Heart and Sole

We appreciate that we are in a fortunate position to be able to use our profits to help make a difference to people's lives. Heart & Sole is a venture managed by our office staff, whose aim is to reach the heart of the communities in the countries we visit. Through Heart & Sole, we hope to make more of a long term, direct impact to these communities, particularly in less developed countries where even a small amount goes a long way. See our website for more information and details of some of the projects we support.


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  • Currency


  • Language


  • Time Difference

    UTC +03:00

  • Flight duration

    4hrs from UK

Visas and Passports

No Visa Required

Average weather

  • January


    Avg. Rain: 91mm

  • February


    Avg. Rain: 78mm

  • March


    Avg. Rain: 65mm

  • April


    Avg. Rain: 43mm

  • May


    Avg. Rain: 29mm

  • June


    Avg. Rain: 15mm

  • July


    Avg. Rain: 10mm

  • August


    Avg. Rain: 11mm

  • September


    Avg. Rain: 28mm

  • October


    Avg. Rain: 71mm

  • November


    Avg. Rain: 94mm

  • December


    Avg. Rain: 106mm

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