Greek Island Explorer

8 days from €1,499
Explore Greece on foot
Challenging and rewarding itinerary
Experienced Hiking Guides
Boutique small hotels
Like-minded travellers
Enquire Now View all pricing
HIKE THROUGH ANCIENT GREECE

Hike to new heights as you explore the best of the Greek islands on our Greek Island Explorer!

Our small group tours take like-minded travellers off the beaten track, allowing you to explore a hidden side of the Greek islands on foot. Led by experienced hiking Guides, this tour showcases the rich history, nature and culture Greece has to offer those who wander off the well-trodden path.

Marvel at the Acropolis, hike the historic Byzantine Path, take in the Temple of Apollo and hike along Santorini's caldera on the Greek Island Explorer!

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Reviews

A fabulous Experience

The organisation of the island hopping/hiking holiday was excellent. The hikes were an ideal mix of interest and challenge - we are both reasonably fit 70 year olds and we didn’t have any problems. We enjoyed the mix of abilities and nationalities in our group of eight. Our guide, Amalia, was very professional as well as being knowledgeable, caring and helpful - nothing was too much trouble. The choice of restaurants and coffee stops was 5*, we particularly enjoyed the wine tasting and food at the winery in Santorini. I can’t recommend this holiday highly enough.

Kath, September 2025
Glorious Greek Tour

I had a wonderful time exploring Athens and the Greek Islands. The trip was well organised, very interesting and informative as well as friendly and fun. We saw some wonderful sights did some fabulous walks and ate at a wide range of delicious restaurants. It felt like we were away longer as we saw so much. It was an absolute delight and I would recommend it to anyone who loves to explore and meet new people.

Kate, May 2025
Island Hopping

I arrived at the hotel on day 1 and we did a brief meeting with Dimitri our team leader and with the group, then we did a short tour and had dinner. Next thing I knew, it’s our last day on our trip - everything happened so fast! The hiking was great, it’s for all ages. The hotel is very clean and comfy, and lastly our team leader, Dimitri, is knowledgeable and so good! I will definitely recommend this to everyone.

Lesly, May 2025

Itinerary

SUMMARY

The Athens to Santorini itinerary kicks off in the historic heart of Athens and takes you on an unforgettable 8-day journey through the stunning Cyclades Islands, including Paros, Naxos, and Santorini. Packed with incredible destinations, scenic trails, and breathtaking views, this trip showcases the very best of the Greek islands.

Wander ancient pathways, and immerse yourself in the rich history and culture of charming island towns on this diverse and exciting adventure.

Perfect for travellers flying into Athens from Europe or beyond, this route ends in Santorini, offering the flexibility to depart from its airport or extend your Greek island explorations at your own pace.

Daily Hike Overview:

  • Average Daily Distance: 5.6km
  • Average Daily Hike Time: 2.5hrs

Itinerary Highlights:

  • Hike the 1,000-year-old Byzantine Path
  • Explore the whitewashed charm of Parikia
  • Stroll through the historic Chalki Village
  • Hike between three picturesque mountain villages in Naxos
  • Visit ancient marble quarries dating back to the 6th Century BC
  • Take in the breathtaking view from the ‘Great Door’ at the Temple of Apollo
  • Witness the world-famous Santorini sunset
  • Walk along a volcanic crater to the iconic village of Oia
  • Savour local wines at a Santorini vineyard

SUMMARY

Welcome to Athens!

Check in to your hotel and join your fellow travellers and Guide for a Welcome Meeting at 3.30pm.

This afternoon we'll explore Europe's oldest capital city, taking in some of the most famous monuments of historical and modern-day Athens on an orientation walk.

After you've worked up an appetite, get to know your fellow travellers over dinner at a local Greek taverna.

Day 1 Hike Overview

  • Distance: 6km
  • Time: 2hrs
  • Ascent: 80m

Inclusions

  • Athens Orientation Walk

Accommodation

SUMMARY

Rise and shine! This morning we'll depart Athens and take a ferry to Paros, where we’ll begin our Greek island adventure.

This beautiful Cycladic island offers white-washed towns and quintessential Greek beaches, easily recognisable by their turquoise blue water. Once on Paros, check in to your accommodation and join your Guide for an orientation walk around the picturesque main town, Parikia.

Meander the twisting alleyways filled with boutique shops and explore the town at your leisure.

This afternoon we'll catch a short ferry to the neighbouring island of Antiparos, where we'll enjoy a short walk before indulging in a traditional Greek dinner.

Day 2 Orientation Walk Overview

  • Distance: 4km
  • Time: 1.5hrs
  • Ascent: 30m

Accommodation

SUMMARY

Paros is well-known to hiking enthusiasts for its marble-paved Byzantine Path that dates back over 1,000 years!

Start the day with a hearty breakfast, before being transferred to the scenic Lefkes Village, where we’ll begin today's hike.

Step back in time as you hike the ancient rock-lined trail, taking in views of Lefkes Village and the Aegean Sea along the loop.

After the hike, explore the picturesque village of Lefkes and enjoy your first Greek coffee! Greek coffee is a cultural icon and a must-try when visiting the country. We’ll guide you through its origins and preparation before savouring this local delicacy for ourselves.

Afterwards, you’ll be transferred back to Parikia for an optional seaside lunch, with the afternoon free to relax on the beach, swim in the hotel pool, or explore the local area.

This evening, explore Parikia Town or head into nearby Naoussa Village by public bus.

Day 3 Hike Overview

  • Distance: 6km
  • Time: 2hrs
  • Ascent: 270m

Inclusion

  • Greek Coffee Experience

Accommodation

SUMMARY

Enjoy breakfast and a relaxing morning at the hotel before we take a midday ferry to our next destination; the island of Naxos!

Today's hike begins in the picturesque Chalki village. This beautiful hike takes us out of the cobbled lanes and whitewashed paths of the village, and through idyllic olive groves with mountainous views, toward the impressive church of Agios Georgios Diasoritis. This Byzantine church dates back to the 11th Century and boasts impressive stone arches and enchanting interior frescos.

This afternoon a transfer will take you to Damala Village where we will visit a pottery workshop and olive oil press, learning more about these artisan crafts.

Before dinner, we’ll visit a local distillery to sample their renowned citrus-flavoured liqueurs. Afterwards, we continue to Chora, where guests can enjoy dinner at one of the charming local tavernas.

Day 4 Orientation Walk Overview

  • Distance: 3km
  • Time: 1hrs
  • Ascent: 43m

Inclusion

  • Local Distillery Tasting

Accommodation

SUMMARY

After breakfast, a private transfer will transport you to the middle of Naxos for today's hike. Starting at Melanes Village, we'll begin our hike between three mountainous and picturesque Greek villages, taking in varied scenery and terrain.

Halfway through the hike, we'll take a short break to marvel at the ancient quarries and sculpted marble statues of Kouroi, which date back to the 6th Century BC.

We'll continue through the lush valley, taking in the traditional village of Ano Potamia before finishing our hike in Melanes Village, where we’ll enjoy lunch at a local taverna.

This afternoon, you have the option to join a local cheese tasting, sampling a variety of cheeses, cold cuts, fruits, and chutneys, all made right on the island of Naxos.

Tonight, we’ll take a walk to the Temple of Apollo to admire the spectacular view through the ‘Great Door’ before enjoying dinner in Chora Naxos.

Day 5 Hike Overview

  • Distance: 10.5km
  • Time: 3.5hrs
  • Ascent: 302m

Optional Excursion

  • Local Cheese Tasting (€25)

Accommodation

SUMMARY

This morning we take a short ferry to one of Europe's most famous and most visited islands; Santorini!

Get ready to experience magic moments and breathtaking views in this picturesque destination!

This afternoon we'll get a private transfer to the volcanic sands of Kamari Beach, where we'll spend the afternoon having lunch, swimming and relaxing.

Afterwards, get to know Santorini on an orientation walk around Fira Town, where we'll take in the quirks of this town perched atop a cliff.

Enjoy a free evening and indulge in Greek cuisine at one of the many restaurants with a view that Santorini is so famous for.

Day 6 Orientation Walk Overview

  • Distance: 1.5km
  • Time: 40min
  • Ascent: 40m

Accommodation

SUMMARY

Rise and shine! This morning, we will hike along the famous Santorini Caldera, ending in the iconic village of Oia. We will pass historic churches, whitewashed buildings, and even donkeys as we take in the azure sea views.

In Oia, you’ll have the opportunity to explore the many shops, boutiques, restaurants, viewpoints and photo opportunities this village has to offer.

We'll be transferred back to the hotel to freshen up for tonight's included wine tasting.

Taste wines crafted from unique local grape varieties and enjoy your wine tasting with new friends on the final evening of your Greek Island Explorer Tour.

Day 7 Hike Overview

  • Distance: 8.2km
  • Time: 3hrs
  • Ascent: 200m

Inclusion

  • Wine Tasting

Accommodation

Enjoy breakfast and a relaxing morning at the hotel before it's time to check-out.

Explore more of Santorini independently, or if you're booking onward travel, ask your Guide for assistance with ferry tickets.

Inclusions

Experienced Hike Guide
Experienced Hike Guide

Explore Greece with a local, experienced guide who leads each days hiking itinerary

7 Nights Accommodation
7 Nights Accommodation

7 nights accommodation in boutique hotels (twin-share)

Daily Hikes
Daily Hikes

Explore Greece on foot with daily guided hikes

Ferry Tickets & Port Transfers
Ferry Tickets & Port Transfers

We’ll organise your ferries & port transfers for you

Greek Coffee Experience
Greek Coffee Experience

Experience the cultural icon that is Greek coffee!

Breakfast Daily
Breakfast Daily

Continental breakfast is included daily

Wine Tasting
Wine Tasting

Taste Greek wines at a local winery. Return transfers are also included

Hike Transfers
Hike Transfers

Selected transfers to/from the start/end hiking locations

Who Are Your Guides?

Passionate Hikers

Your experienced Guide has hiked these trails many times before and works closely with us to curate the perfect itinerary for our guests! Our Guides are passionate about Greek mountains and the local flora and fauna of Greece, showing travellers the best trails, peaks and views this incredible country has to offer.

Health & Safety Experts

Guides are Health and Safety trained, following guidelines from the British Safety Council. Your Guide is well versed on how to look after guests during their tour!

Greek Experts

Your Guide is local to Greece and knowledgeable in the flora, fauna, culture and history of Greece!

First Aid Trained

Your Guide is First Aid trained and able to respond in the unlikely event of a medical situation arising whilst hiking.

Your Accommodation

Poolside - Paros Accommodation
Poolside - Paros Accommodation
Bedroom - Paros Accommodation
Bedroom - Paros Accommodation
Foyer - Naxos Accommodation
Foyer - Naxos Accommodation
Bedroom - Naxos Accommodation
Bedroom - Naxos Accommodation
Bathroom - Naxos Accommodation
Bathroom - Naxos Accommodation
Bedroom - Santorini Accommodation
Bedroom - Santorini Accommodation
Poolside - Santorini Accommodation
Poolside - Santorini Accommodation
Bedroom - Athens Acommodation
Bedroom - Athens Acommodation
Bathroom - Athens Accommodation
Bathroom - Athens Accommodation
Boutique Hotels

Twin-share rooms are included on all Greek Island Explorer tours, providing a relaxing and welcoming space to retreat to after an invigorating day of exploring! Rooms are air-conditioned and include a private ensuite.

Each unique hotel is family-run, offering Greek hospitality and a relaxing atmosphere. There are various spaces to relax and unwind at each hotel - with some locations also featuring a pool.

View Accommodation

Greek Island Explorer Specials

20% Off Greek Island Explorer
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Tours On Sale 20% Off Greek Island Explorer

Book your Greek Island Explorer adventure and take 20% off selected departures when you book by the 31st of January, 2026.

Secure your spot with a €60 deposit, then sit back and relax knowing that you will be marvelling at the Acropolis, hiking the historic Byzantine Path, and wandering along Santorini's caldera in 2026!

Hike FAQ's

The Greek Island Explorer is a small-group tour, covering the Greek Islands of Paros, Naxos and Santorini on an 8 day hiking adventure. This tour is made for travellers who are looking to relax, explore and socialise on their vacation.

The tour officially starts at 3.30pm in Athens, with the welcome meeting taking place on the rooftop of your hotel. You can check in from 2pm. The tour ends on day 8 in Santorini when you check out of your accommodation.

We recommend you have a reasonable level of fitness to participate in our Greek Island Explorer Tour. Each day’s itinerary brings a different challenge, and your guide will cater to your group’s interests and abilities. If you don’t feel up to hiking, or feel a particular day may be too strenuous, you’re welcome to spend the day relaxing at the hotel or exploring a nearby town.

You will stay in twin-share ensuite rooms on the Greek Island Explorer Tour. Each boutique, family run hotel offers unique facilities, with some hotels providing pools, on-site bars and gardens.

View more information on the accommodation on this tour here .

Please note: images are representative of the acommodation provided at each destination. Accommodation of equal standard will be provided at each location.

Rooms are based on two people sharing, however if you're travelling solo or in an odd-numbered group, a single supplement fee is applicable. Single supplements are an additional 30% of the per person price.

Athens has an international airport that many low-cost European and International carriers service. Flights are not included in our tours.

A basic continental breakfast is included every morning on your Greek Island Explorer. On days when you depart the hotel early, a breakfast box will be provided so that you can have breakfast on the go! All other lunches, dinners and snacks are not included. This is another way we save on costs by allowing you to try authentic local cuisine and spend as much or as little as you like on food and drinks. Your friendly Guide can recommend places to eat and drink throughout the tour!

This tour is suited to young professionals and young-at-heart travellers. The Greek Island Explorer is an 18+ tour and attracts travellers between the ages of 20 and 60.

Our Greek Island Explorer is not a cruise. You will travel between the islands via public ferries and stay in boutique hotels on each island and in Athens.

The Athens Orientation Walk will take travellers through the iconic Monastiraki and Syntagma squares, providing glimpses of the Acropolis along the way. Unfortunately entry to the Acropolis is not included in the orientation walk, and we recommend buying tickets in advance to visit this very popular monument prior to your tour, or after your orientation walk.

Using a combination of ferries and high-speed catamarans we book the most convenient ferries as close to departure as possible. This ensures you have as much time as possible to explore each destination. Once you arrive at your destination we arrange all transfers between the ports and hotels

The length of the ferry will vary depending on availability and the destination, ranging from 1 - 4.5 hours. We recommend bringing a good book or utilising the onboard wi-fi on some of the longer journeys.

We recommend a starting budget of €60 per person, per day to cover meals. If you would like to participate in additional excursions or dine at higher-end restaurants, we suggest allowing additional budget. Greece is a part of the European Union and uses the Euro. There are plenty of ATM’s in Greece where you can get cash out.

Yes! You'll have time to explore local culture, take a stroll, or get up to whatever you desire to make the most out of your experience. Your tour guide will advise you each day as to when free time is available.

Yes, we are! Sail Croatia owns and operates Island Hopping. Sail Croatia has been operating since 2003 and today is one of the biggest and most respected tour operators in Europe.

Yes, the itinerary may change due to a variety of factors beyond our control, including weather conditions. In the event of an itinerary change, we will make every effort to offer a suitable alternative that ensures an enjoyable and safe experience for all guests.

Inspiration For Your Next Hike