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
Premium Greece Cyclades Islands
Find trips›Greece›Premium Greece Cyclades Islands
◆Save Deal visible
ITOperated by Intrepid Travel

Premium Greece Cyclades Islands

From
Price on request
Duration
9 days
Countries
Greece
Activity
easy
Group size
Max 12
Rating
★ 4.7 · 30 reviewsvia Intrepid Travel →

The adventure

Let the charm of the Cyclades wash over you on this nine-day Premium island adventure in Greece. Start off in the storied city of Athens, explore the villages of Paros, uncover ancient riches in Naxos and soak up the views in Santorini, where you’ll spend two nights unwinding at your spacious Feature Stay hotel. Hike a caldera, taste local wine as you take in sunset views, sample kitron and take a cooking class with organic ingredients. Travel with a passionate local leader who’s eager to share the magic of their country as you discover fascinating histories, incredible food and welcoming locals.

◆Athens - Welcome Dinner at Local Restaurant
◆Complimentary Arrival Transfer
◆Paros - Highlights of Paros Half Day Island Tour with Local Guide
◆Naxos - Old Town Walk & Portara Guided Tour
◆Naxos - Cooking Class at a Local Farm
◆Naxos - Kaloxylos Olive Oil Press
◆Santorini - Caldera Hike
◆Santorini - Winery visit with tasting and food pairing
◆Santorini - Mythology and Wine experience

At a glance

Duration
9 days
Route
Athens → Santorini
Countries
Greece
Activity level
easy
Style
Beach & Islands, Culture & History, Cycling, Food & Drink, Trekking & Hiking
Group size
Max 12
Ages
15+
Flights
Not included
Solo travellers
Welcome

Where you'll go

Premium Greece Cyclades Islands route map

Day by day

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

Greece

Showing Days 1-7

9-day itinerary

Day 1AthensKalimera! Welcome to Greece. Your adventure begins in Athens, Greece’s capital. There’s a lot to experience in this ancient city, so arriving a few days early is highly recommended. When you arrive at the airport, you’ll be met by a local representative and transferred to your hotel, where you’ll have a welcome meeting at 6 pm. If you arrive early, you might like to visit Athens’ iconic Acropolis or walk around the National Garden. After your meeting, get a taste of Greece’s celebrated cuisine during dinner with your group at a local restaurant and perhaps toast the beginning of the adventure with a glass of ouzo.
View of the ancient Erechtheion Temple with its iconic Caryatids, located at the Acropolis in Athens, Greece.Athens
Kalimera! Welcome to Greece. Your adventure begins in Athens, Greece’s capital. There’s a lot to experience in this ancient city, so arriving a few days early is highly recommended. When you arrive at the airport, you’ll be met by a local representative and transferred to your hotel, where you’ll have a welcome meeting at 6 pm. If you arrive early, you might like to visit Athens’ iconic Acropolis or walk around the National Garden. After your meeting, get a taste of Greece’s celebrated cuisine during dinner with your group at a local restaurant and perhaps toast the beginning of the adventure with a glass of ouzo.
Map showing Athens
Day 2ParosThis morning, you’ll be transported to Athens' port at Piraeus, where you’ll board a ferry to Paros – a beautiful and relaxed island with a layered history. Ferries are a great way to travel between the islands and are essential to reach many remote islands in Greece's archipelagos. In the afternoon, get to know Paros during an island tour with a local guide. Start off in Parikia, the island’s main town, where you’ll visit the Ekatontapiliani church, also known as the Church of a Hundred Doors. Drive across the island, passing ancient marble quarries and verdant hills, to Marpissa for a visit to a cultural centre to learn about island life from a group of local women. Carry on to Naoussa – a village known for its whitewashed alleys, Venetian castle and scenic port. Then, join your trip leader for a taste of Greece’s favourite street food — the iconic souvlaki wrap, or gyros, with freshly grilled meat tucked into soft pita bread. Delicious vegan options are also available.
A surfboard with stickers on Paros beach with cloudy skies and a tranquil sea.Paros
This morning, you’ll be transported to Athens' port at Piraeus, where you’ll board a ferry to Paros – a beautiful and relaxed island with a layered history. Ferries are a great way to travel between the islands and are essential to reach many remote islands in Greece's archipelagos. In the afternoon, get to know Paros during an island tour with a local guide. Start off in Parikia, the island’s main town, where you’ll visit the Ekatontapiliani church, also known as the Church of a Hundred Doors. Drive across the island, passing ancient marble quarries and verdant hills, to Marpissa for a visit to a cultural centre to learn about island life from a group of local women. Carry on to Naoussa – a village known for its whitewashed alleys, Venetian castle and scenic port. Then, join your trip leader for a taste of Greece’s favourite street food — the iconic souvlaki wrap, or gyros, with freshly grilled meat tucked into soft pita bread. Delicious vegan options are also available.
Map showing Paros
Day 3ParosThe day is yours to uncover more of Paros’ charms. There’s no shortage of things to see and do on the island. You might like to take a guided morning hike along the coast – starting off at a fishing village and weaving through some of the island’s best beaches. In the afternoon, you’ll have the option to visit the nearby island of Antiparos – a favourite secret holiday spot for royals and celebrities. Or maybe you’d like to spend the day relaxing on one of Paros’ many beaches, cooling off with dips in Aegean Sea. Speak to your leader for more information about the activities on offer today and for tips on how to make the most of this island.
Picturesque Greek island landscape with hills, sea, and sailboats under a summer sky.Paros
The day is yours to uncover more of Paros’ charms. There’s no shortage of things to see and do on the island. You might like to take a guided morning hike along the coast – starting off at a fishing village and weaving through some of the island’s best beaches. In the afternoon, you’ll have the option to visit the nearby island of Antiparos – a favourite secret holiday spot for royals and celebrities. Or maybe you’d like to spend the day relaxing on one of Paros’ many beaches, cooling off with dips in Aegean Sea. Speak to your leader for more information about the activities on offer today and for tips on how to make the most of this island.
Map showing Paros
Day 4NaxosSay goodbye to Paros this morning and catch a short ferry to Naxos. The largest of the Cyclades islands, Naxos has something for everyone – from beaches to an Old Town and hundreds of years of Venetian history. Take some time to settle in, then regroup in the late afternoon to learn about the town. Visit the Portara with a local guide – this giant marble doorway is the only remaining part of an unfinished temple of Apollo from 530 BC. Naxos is unique in the fact that it is the Cyclades’ only self-sufficient island, meaning all produce is grown and available on the island without imports. Because of this, the cuisine is hyperlocal and differs from the rest of the country. Try it for yourself this evening during a group dinner, where you’ll learn all about the regional specialties.
Captivating coastal view of Naxos Town with bright blue waters under a clear summer sky.Naxos
Say goodbye to Paros this morning and catch a short ferry to Naxos. The largest of the Cyclades islands, Naxos has something for everyone – from beaches to an Old Town and hundreds of years of Venetian history. Take some time to settle in, then regroup in the late afternoon to learn about the town. Visit the Portara with a local guide – this giant marble doorway is the only remaining part of an unfinished temple of Apollo from 530 BC. Naxos is unique in the fact that it is the Cyclades’ only self-sufficient island, meaning all produce is grown and available on the island without imports. Because of this, the cuisine is hyperlocal and differs from the rest of the country. Try it for yourself this evening during a group dinner, where you’ll learn all about the regional specialties.
Map showing Naxos
Day 5NaxosDrive to Kaloxylos in the heart of the island’s biggest olive grove (which is also one of the oldest in the world!). Here, you’ll tour an olive oil press museum to learn about the importance of olive oil in Greek culture and traditional extraction methods. After your visit, you’ll put your new knowledge to good use as you travel to the nearby village of Galini for a hands-on cooking class. Meet with a local who will share her culinary knowledge with the group, leaving you with recipes you can cook up at home. First, collect fresh ingredients from your host’s organic garden and learn about cultivation and farming on Naxos. Then put the ingredients together to create a Naxian dish from scratch, enjoying the fruits of your labour for lunch. The evening is free for you to explore Naxos at your leisure. Your trip leader will be on hand to provide recommendations. For a taste of the island’s culture, perhaps sample the beloved local kitron liqueur which has a history stretching back to the 19th century and is produced exclusively on Naxos.
Idyllic beach scene in Naxos, Greece with charming white buildings and blue shutters.Naxos
Drive to Kaloxylos in the heart of the island’s biggest olive grove (which is also one of the oldest in the world!). Here, you’ll tour an olive oil press museum to learn about the importance of olive oil in Greek culture and traditional extraction methods. After your visit, you’ll put your new knowledge to good use as you travel to the nearby village of Galini for a hands-on cooking class. Meet with a local who will share her culinary knowledge with the group, leaving you with recipes you can cook up at home. First, collect fresh ingredients from your host’s organic garden and learn about cultivation and farming on Naxos. Then put the ingredients together to create a Naxian dish from scratch, enjoying the fruits of your labour for lunch. The evening is free for you to explore Naxos at your leisure. Your trip leader will be on hand to provide recommendations. For a taste of the island’s culture, perhaps sample the beloved local kitron liqueur which has a history stretching back to the 19th century and is produced exclusively on Naxos.
Map showing Naxos
Day 6NaxosToday is free for you to explore more of Naxos as you wish. You may like to head to one of the island’s beaches or discover more of its history at a local museum. The Archaeological Museum of Naxos in Chora Naxos dates back to the 17th century and houses artefacts from the Neolithic to the early Christian periods, and the Geological Museum of Apeiranthos digs up the natural history of the island. If you’re after a sweet treat, walnut cake flavoured with local kitron is an excellent regional specialty. Your leader will be on hand to help tailor a day that suits your interests.
Whitewashed buildings with blue accents reflect classic Cycladic style on a Greek island.Naxos
Today is free for you to explore more of Naxos as you wish. You may like to head to one of the island’s beaches or discover more of its history at a local museum. The Archaeological Museum of Naxos in Chora Naxos dates back to the 17th century and houses artefacts from the Neolithic to the early Christian periods, and the Geological Museum of Apeiranthos digs up the natural history of the island. If you’re after a sweet treat, walnut cake flavoured with local kitron is an excellent regional specialty. Your leader will be on hand to help tailor a day that suits your interests.
Map showing Naxos
Day 7SantoriniDepart Naxos in the morning and catch a ferry to Santorini. When you arrive in Santorini's capital, Fira, you’ll be met and transferred to your Feature Stay hotel – Majestic Hotel and Spa. With views of the Santorini caldera or Aegean Sea from your private balcony, elegant marble bathrooms, plus a swimming pool, sauna and champagne lounge, this is an excellent base for soaking up the whitewashed island scenery or heading out to explore the city centre. Tonight, make sure you catch Santorini's world-famous sunset.
A breathtaking sunset view of a cruise ship near the island of Santorini, Greece.Santorini
Depart Naxos in the morning and catch a ferry to Santorini. When you arrive in Santorini's capital, Fira, you’ll be met and transferred to your Feature Stay hotel – Majestic Hotel and Spa. With views of the Santorini caldera or Aegean Sea from your private balcony, elegant marble bathrooms, plus a swimming pool, sauna and champagne lounge, this is an excellent base for soaking up the whitewashed island scenery or heading out to explore the city centre. Tonight, make sure you catch Santorini's world-famous sunset.
Map showing Santorini
1 / 2

What's included

Included
  • ✓Soak up the beauty of Santorini from your Feature Stay hotel, offering volcano or sea views from your private balcony, a swimming pool, spacious rooms and a prime location.
  • ✓Taste a variety of Greek foods throughout the trip, including a visit to an olive oil press museum in Naxos, a cooking class complete with local kitron tasting and a sunset wine tasting with views of the caldera in Santorini.
  • ✓Learn the tricks of the trade in Naxos during an in-depth cooking class with a local, using organic ingredients from her garden to create regional specialties which you’ll then enjoy for lunch.
  • ✓Hike along Santorini’s caldera, passing steep cliff faces and impressive views as you learn about the geological history of the island along the way.
  • ✓Explore Paros with an expert guide who will share insider knowledge of the island’s history and villages.

Traveller reviews

4.7
★★★★☆

Based on 30 reviews · via Intrepid Travel →

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.
IT
Operated by Intrepid Travel

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
Price on request
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 Intrepid Travel · 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
Price on request
Book my trip