TripFinder

Compare multi-day small-group tours from independent operators, then ask a Canadian travel advisor for help.

Explore

Find tripsDestinationsTravel stylesDealsCompare trips

TripFinder

How it worksTalk to an agentAbout usContact

Good to know

Privacy PolicyCookie choicesTerms of UseTravel guides
TripFinder.ca helps you compare small-group trips from independent operators and book with a TripFinder travel advisor. Trips are operated by the tour companies under their own terms. © 2026 HighBar Enterprises Ltd.Made for adventurers in Canada 🍁
TripFinder
Find trips
DealsAsk TheoCompareHow it worksBrowse all trips
Walking on the Greek Islands
Find trips›Greece›Walking on the Greek Islands
EXOperated by Exodus Adventure Travels

Walking on the Greek Islands

From
CAD 3,175
Duration
8 days
Countries
Greece
Activity
easy

The adventure

Discover the most scenic trails on the Cyclades trio of Santorini, Naxos and Paros with a local tour leader When you think of the Greek islands, it’s the Cyclades that spring to mind, with their white-washed houses and blue-domed churches set against the cobalt Aegean Sea. They’re beauty is striking, but even more so with our expert local tour leader guiding you along their most scenic

◆Overview
◆Itinerary
◆Dates & Prices
◆Accommodation
◆Essential Info
◆Reviews
◆All accommodation: 7 Classic nights (hotels)
◆All breakfasts and one dinner
◆Immersive itinerary with all transport (taxis, boat/ferry, and coach) and listed activities
◆Expert tour leader to enhance your adventure
◆Group arrival and departure transfers available
◆Request a single room if required, purchase travel insurance and arrange any visas and vaccinations. On this trip, local tourist taxes are not included.

At a glance

Duration
8 days
Route
→
Countries
Greece
Activity level
easy
Style
Beach & Islands, Cycling, Multi-Country / Grand Tour
Group size
Ask
Flights
Not included
Solo travellers
Ask an agent

Day by day

Charming coastal town with hills and sea under a cloudy sky.
Your journey through

Greece

Showing Days 1-7

8-day itinerary

Day 1Adventure starts in RafinaOur adventure begins in Rafina, a port town around 25 minutes’ drive from Athens, the history-soaked capital of Greece. Around 6pm, say yassou (hello) to your tour leader and fellow travellers, when we gather as a group to get to know each other and learn more about the adventures ahead. Your tour leader then ensures a big welcome by arranging a group dinner. Rest well tonight, tomorrow we wake early to catch a ferry. If you’d like to explore the many ancient wonders of Athens, we highly recommend adding extra days to the beginning or end of the main itinerary. Speak to your sales representative to book.
Aerial view of a coastal town with buildings and beach at sunset.Rafina
Our adventure begins in Rafina, a port town around 25 minutes’ drive from Athens, the history-soaked capital of Greece. Around 6pm, say yassou (hello) to your tour leader and fellow travellers, when we gather as a group to get to know each other and learn more about the adventures ahead. Your tour leader then ensures a big welcome by arranging a group dinner. Rest well tonight, tomorrow we wake early to catch a ferry. If you’d like to explore the many ancient wonders of Athens, we highly recommend adding extra days to the beginning or end of the main itinerary. Speak to your sales representative to book.
Map showing Rafina
Day 2To Santorini; explore Fira townCross the water to Santorini this morning. There’s a selection of restaurants and cafes on board, serving throughout the journey. Santorini (known locally as Thira) is a remnant of a volcanic cone whose top was blown off and many speculate it was the location of the legendary lost Atlantis. This beautiful island has a lot to offer to hikers, including excellent beaches and magnificent views of the Aegean Sea. Walk around the town of Fira in the late afternoon, taking a paved path to enjoy stunning views of the caldera. From April to October, we take the five-hour catamaran to Santorini. From November to March, we use the eight-hour ferry.
A breathtaking sunset view of a cruise ship near the island of Santorini, Greece.Santorini
Cross the water to Santorini this morning. There’s a selection of restaurants and cafes on board, serving throughout the journey. Santorini (known locally as Thira) is a remnant of a volcanic cone whose top was blown off and many speculate it was the location of the legendary lost Atlantis. This beautiful island has a lot to offer to hikers, including excellent beaches and magnificent views of the Aegean Sea. Walk around the town of Fira in the late afternoon, taking a paved path to enjoy stunning views of the caldera. From April to October, we take the five-hour catamaran to Santorini. From November to March, we use the eight-hour ferry.
Map showing Santorini
Day 3Hike the caldera from Fira to OiaSantoriniThe 6mi (10km) Cliff Trail is a spectacular walk, 1,310ft (400m) high above the volcanic caldera, a photographer’s delight and not too challenging. Half the path is pathed, while the other is a mix of volcanic soil, pumice and lava. Halfway along the trail, we stop for a picnic lunch in a small canteen with amazing views, where we enjoy fresh orange juice and freshly prepared Santorinian walnut and honey cake. Views of the Aegean are virtually ever present as we wind gently up and down to the pretty village of Oia, home to artists, galleries, boutiques and cafes. There’s time to explore, relax and soak up the culture before a transfer back to Fira.
Iconic blue dome church in Santorini with a stunning view of the Aegean Sea.Santorini
The 6mi (10km) Cliff Trail is a spectacular walk, 1,310ft (400m) high above the volcanic caldera, a photographer’s delight and not too challenging. Half the path is pathed, while the other is a mix of volcanic soil, pumice and lava. Halfway along the trail, we stop for a picnic lunch in a small canteen with amazing views, where we enjoy fresh orange juice and freshly prepared Santorinian walnut and honey cake. Views of the Aegean are virtually ever present as we wind gently up and down to the pretty village of Oia, home to artists, galleries, boutiques and cafes. There’s time to explore, relax and soak up the culture before a transfer back to Fira.
Map showing Santorini
Day 4Free time in Santorini; afternoon ferry to NaxosEnjoy free time in Santorini this morning. Optional excursions include a visit by bus to the buried city of Acrotiri, time at the black beaches of Kamari and/or a visit to the prehistoric museum of Thero in town. Leaving Santorini in the afternoon, we board the approximately two-hour ferry to Naxos.
Breathtaking view of Santorini's blue-domed church overlooking the Aegean Sea, capturing Greek architecture.Santorini
Enjoy free time in Santorini this morning. Optional excursions include a visit by bus to the buried city of Acrotiri, time at the black beaches of Kamari and/or a visit to the prehistoric museum of Thero in town. Leaving Santorini in the afternoon, we board the approximately two-hour ferry to Naxos.
Map showing Santorini
Day 5Hike through the lush Tragea ValleyTransfer (one hour) to hike in the lush Tragea Valley, best known for ancient olive and citrus groves. It is a great opportunity to discover the most authentic part of Naxos, where picturesque villages and churches punctuate our walk. Wander along the ancient stoney path in the middle of the Naxian marble quarries until we reach Kouros, a gigantic statue from the fifth century BCE, which was damaged during transportation and then abandoned ever since, lying under trees in the Melanes Valley. Our transfer back is approximately one hour. There is time in the afternoon to swim from St George’s sandy beach, just five minutes from our hotel.
Transfer (one hour) to hike in the lush Tragea Valley, best known for ancient olive and citrus groves. It is a great opportunity to discover the most authentic part of Naxos, where picturesque villages and churches punctuate our walk. Wander along the ancient stoney path in the middle of the Naxian marble quarries until we reach Kouros, a gigantic statue from the fifth century BCE, which was damaged during transportation and then abandoned ever since, lying under trees in the Melanes Valley. Our transfer back is approximately one hour. There is time in the afternoon to swim from St George’s sandy beach, just five minutes from our hotel.
Day 6Ferry to Paros; hike the Byzantine path from Lefkes; return to NaxosTake a 45-minute ferry to Paros in the morning, then a 20-minute bus to the heart of the island and Lefkes village, where we join an Old Byzantine path that runs all the way to the east coast of Paros, passing through beautiful Cycladic and medieval villages. The route, which is on paved path and over small hills, is believed to be about 1,000 years old and used to traverse the entire island. We explore the town of Parikia, the castle and fourth-century Byzantine Cathedral before our ferry back to Naxos in the evening.
Take a 45-minute ferry to Paros in the morning, then a 20-minute bus to the heart of the island and Lefkes village, where we join an Old Byzantine path that runs all the way to the east coast of Paros, passing through beautiful Cycladic and medieval villages. The route, which is on paved path and over small hills, is believed to be about 1,000 years old and used to traverse the entire island. We explore the town of Parikia, the castle and fourth-century Byzantine Cathedral before our ferry back to Naxos in the evening.
Day 7Explore Hora town; visit the Temple of ApolloTake a walk to explore the main town, Hora, a Venetian Castello town. The market area is a delight to wander through, with craft shops, chapels and quaint restaurants. A visit to the famous cheese shop of Naxos and a century-old olive wood-burning bakery is a must – our tour leader treats us to warm bread and Naxian cheeses. After lunch in one of the seaside cafes in town, we visit a family-run pottery workshop to watch them make their creations and, if you'd like, purchase one of their pieces. On the islet of Palatia stands the impressive Portara, an ancient marble gateway and the entrance to the remains of the Temple of Apollo.
Take a walk to explore the main town, Hora, a Venetian Castello town. The market area is a delight to wander through, with craft shops, chapels and quaint restaurants. A visit to the famous cheese shop of Naxos and a century-old olive wood-burning bakery is a must – our tour leader treats us to warm bread and Naxian cheeses. After lunch in one of the seaside cafes in town, we visit a family-run pottery workshop to watch them make their creations and, if you'd like, purchase one of their pieces. On the islet of Palatia stands the impressive Portara, an ancient marble gateway and the entrance to the remains of the Temple of Apollo.
1 / 2

Where you'll stay & how you'll travel

Accommodation
  • Overview
  • Itinerary
  • Dates & Prices
  • Accommodation
  • Essential Info
  • Reviews
  • All accommodation: 7 Classic nights (hotels)
  • All breakfasts and one dinner
  • Immersive itinerary with all transport (taxis, boat/ferry, and coach) and listed activities
  • Expert tour leader to enhance your adventure
  • Group arrival and departure transfers available
  • Request a single room if required, purchase travel insurance and arrange any visas and vaccinations. On this trip, local tourist taxes are not included.
Meals
  • Overview
  • Itinerary
  • Dates & Prices
  • Accommodation
  • Essential Info
  • Reviews
  • All accommodation: 7 Classic nights (hotels)
  • All breakfasts and one dinner
  • Immersive itinerary with all transport (taxis, boat/ferry, and coach) and listed activities
  • Expert tour leader to enhance your adventure
  • Group arrival and departure transfers available
  • Request a single room if required, purchase travel insurance and arrange any visas and vaccinations. On this trip, local tourist taxes are not included.
Transport
  • Overview
  • Itinerary
  • Dates & Prices
  • Accommodation
  • Essential Info
  • Reviews
  • All accommodation: 7 Classic nights (hotels)
  • All breakfasts and one dinner
  • Immersive itinerary with all transport (taxis, boat/ferry, and coach) and listed activities
  • Expert tour leader to enhance your adventure
  • Group arrival and departure transfers available
  • Request a single room if required, purchase travel insurance and arrange any visas and vaccinations. On this trip, local tourist taxes are not included.

Discover Greece

A glimpse of the destination you'll explore.

Breathtaking aerial view of Kerkyra's lush landscape with hills, valleys, and ancient structures under a clear sky.
Breathtaking coastal landscape of Agios Stefanos, Greece featuring rocky hills and a tranquil sea.
Breathtaking view of a Greek island coastline with clear blue waters and vibrant nature.
Scenic view of Athens cityscape from a hilltop with clear skies.
Picturesque coastal scene with clear skies, azure waters, and distant mountains.

Upcoming departures

DatesPrice / personAvailability
27 Sep – 4 Oct 2026(price may vary)
CAD 3,175Available
Book my trip
EX
Operated by Exodus Adventure Travels

TripFinder compares the available catalog facts and can help with the booking. You travel under the operator's terms; final price and availability are confirmed before purchase.

Book my trip →
Ask Theo about this trip
From
CAD 3,175 CAD / person
Twin share · prices may vary by departure
Next departures
Sep 27, 2026CAD 3,175 · available
Oct 11, 2026CAD 3,270 · available
Mar 21, 2027CAD 3,420 · available
See all 9 departures →
Book my trip
No payment now — tell us a few details and an expert confirms everything & finishes your booking.
✓No payment & no obligation to send a request
✓An expert confirms by email or phone — your choice
Prefer to talk first? Send a request and choose phone as your contact preference.
Operated by Exodus Adventure Travels · view on operator site ↗

More Europe adventures

OpeningZagreb to Santorini: 35 Unforgettable Days image
GG Adventures
Save 20%

Zagreb to Santorini: 35 Unforgettable Days

Bosnia and Herzegovina, Albania, Greece, Montenegro, Croatia · 35 days · Easy

fromCAD 8,639
Next: 09 Aug
OpeningUltimate Europe: Berlin, Tuscany & Greek Temples image
GG Adventures
Save 35%

Ultimate Europe: Berlin, Tuscany & Greek Temples

Albania, Austria, Czechia, Greece, Netherlands, Montenegro, Germany, Italy, Croatia · 34 days · Easy

fromCAD 5,960
Next: 09 Aug
OpeningOne Month in Europe: Germany, Italy & Croatia image
GG Adventures
Save 25%

One Month in Europe: Germany, Italy & Croatia

Albania, Austria, Czechia, Greece, Netherlands, Montenegro, Germany, Italy, Croatia · 30 days · Easy

fromCAD 5,310
Next: 09 Aug
From
CAD 3,175/ person
Book my trip