SHORTLIST

Greek Island Wanderer

Go island hopping in Greece on this two-week tour of the Cyclades. Land in Athens, Greece's historic and cultural capital, before boarding a ferry to get to grips with island life. From Syros to Paros and Naxos to Santorini, tick off ancient ruins, bustling harbours, and serene beaches on this tour of Greece's island highlights.



Santorini - Discover postcard-perfect Santorini with its volcanic scenery and blue-domed churches.



Syros - Uncover the capital of the Cyclades Islands with coastal walks and pit stops in seafront tavernas.



Paros - Walk an ancient Byzantine road and explore the local sea life with a snorkelling trip on Golden Beach.

Highlights
Island hopping between the Cyclades Islands of Syros, Paros, Santorini and Naxos|Visit gleaming waterfront harbours, rocky coves and sandy beaches|Explore the historic capital city of Athens with the chance to visit the Acropolis

Tour information
Transport: Bus, Ferry, Taxi
Tour staff: Explore Tour Leader, Explore Tour Leader
Meals :Breakfast 13, Lunch 0 & Dinner 0

Tour details
Tour Provider Explore!
Price From
$4,450
Number of Days
13
Start Location
Athens, Greece
End Location
Santorini, Greece
Age Range
Avg. 30+
Group Size
5 to 18
Tour Style
Standard
Tour Themes
Adventure
Physical Rating
Moderate
Itinerary Open all
Day 1 - Join trip in Athens
Our tour starts in Athens, Greece's historic hub. The city is a heady mix of ancient and modern, having been the capital of Greece for less than two centuries, but with a history dating back over 3,000 years. Located on the Plain of Attica, it's also an area of breathtaking scenery, set against a backdrop of mountains and stretching to the blue coast.

For those arriving on time, our tour leader will meet you in the hotel reception at 7.30pm and, for those that wish, there'll be the chance to go out for dinner. Due to a number of flights arriving into Athens later in the evening, our welcome meeting will take place on the morning of day two.

There are no activities planned today, so you're free to arrive in Athens at any time. If you'd like an airport transfer, you'll need to arrive into Athens International Airport (ATH), which is around a one-hour drive from our hotel.

If your flight arrives earlier in the day, you might like to visit one of the cafes in the colourful Psyrri district, which offer traditional Greek cuisine of scrumptious aubergines, tomats and cheese washed down with ouzo or raki. There are traditional rustic tavernas in the well-known Plaka area at the foot of the Acropolis, too.
Day 2 - Walking tour in Athens, chance to visit Acropolis
This morning, we'll have an initial welcome meeting before heading out to explore the Greek capital. Our first stop is the Acropolis, one of the wonders of the ancient world. We'll have a guided tour of the site including the Temple of Athena Nike, Pericles and the Parthenon Tower the Erechtheion.

After the Acropolis we'll head down to Plaka and pass through the Anafiotika district, where the architecture is more in keeping with Cyclades than the Greek capital. The Plaka is one of the oldest neighbourhoods of Athens and the streets here are brimming with atmospheric tavernas, their tables spilling out onto the narrow, cobbled streets, and small traders selling all kinds of specialties. It's a picturesque area and an ideal spot to break for lunch with a wide choice of eating spots offering traditional Greek fare. Why not get a taste for Greek grub and try Tiropita, Kolokithopita or Spanakopita (a delicious spinach and feta-filled snack)

After Plaka, we'll pass the tranquil National Gardens directly behind the Greek parliament. Covering 16 hectares, the gardens were planted between 1838 and 1840 and offer a respite from the busy streets of the city, with tree-lined avenues and over 519 species of plants. Our tour ends at Syntagma Square, which is home to the grand Hellenic Parliament. On the hour, the mesmerising changing of the guard ceremony takes place adjacent to the tomb of the Unknown Soldier.

Please note, depending on our allotted time to visit the Acropolis, we might rearrange our sightseeing itinerary.

Making our way back to our hotel, we'll have the evening free to further explore this great city and our tour leader can make recommendations for eating out tonight.

For those wishing to see more of Athens, it's well worth visiting the highly acclaimed Acropolis Museum to see the layers of history painstakingly excavated right beneath your feet. It's now possible to see the ruins of the ancient Athenian neighbourhood that stood on this very site millennium ago. The museum closes at 5pm on a Monday, we recommend pre-booking a ticket online to avoid a long queue. As there's not much time today, you might consider going on day 1 before our tour starts.
Day 3 - Ferry to Syros Island, afternoon coastal walk
This morning, we'll drive from our hotel to Piraeus Harbour where we'll board the ferry to Syros (which departs at around 7.30am and takes just under four hours). We'll have reserved seating on the ferry but you're also free to take in the sea air and views from the deck. We'll disembark at Ermoupouli Harbour and drive to our hotel in Galissas. Syros is the capital of the Cyclades and covers an area of about 56 square kilometres.

This afternoon, we'll drive along the coast to Kini. From here, we'll take an easy coastal walk back to Galissas (covering approximately 4.7 kilometres with 100 metres of ascent and 100 metres of descent and taking around two hours). This peaceful walk takes us through typical Mediterranean scenery with cypress and olive groves and serene sea views. If you don't want to walk, you can visit Kini and then take the public bus back to the hotel.

If you don't want to take part in the walk or visit Kini, then this afternoon is free for you to relax on the long beach near our hotel; with shallow waters, it's an ideal spot for swimming. Alternatively, you can explore the tranquil village of Galissas, which is set around a small harbour in a scenic agricultural area.
Day 4 - Free day, chance to take coastal walk around the island
Today is free for you to relax in Galissas or to explore more of the island at your own pace.

This morning, you might like to join a coastal walk with our tour leader. We'll hop on a public bus to Azolimnos where the walk begins. The trail to Vari takes around one and a half hours (covering approximately 4 kilometres) and gives you a flavour of the island's beautiful scenery. Once you arrive in Vari, you can enjoy a swim, relax on the beach, and have lunch in a nearby tavern before taking the public bus back to Galissas.

This afternoon, you might choose to join a bus tour of the island to see more of the surroundings. The island produces loukoumi, a Greek sweet that's similar to Turkish Delight, and you'll have the chance to visit a small factory to purchase the local speciality. As part of our tour, we'll take a walk to Ano Syros, which oozes medieval charm. Its long history can be seen in its many landmarks, including the old castle gates that lead into the old town area. The town is built onto a hill with tiered white and sand-coloured buildings rising up to the Capuchin Church at the very top.

Tonight, if you participate in the optional tour, there'll be the opportunity to join our tour leader for dinner in the island's capital, Ermoupolis.
Day 5 - Free day in Syros, evening ferry to Paros
There'll be the opportunity to go on a coastal walk this morning (or to relax in Galissas if you don't feel up to it). On the walk, we'll head to the small coastal village of Fonikas and visit the Church of Agios Panteleimonas or the lovely Kokkina beach located nearby. It's an easy three-and-a-half-kilometre route and should take around 45 minutes each way.

Later this afternoon, we'll drive to Ermoupoli, where you can store your main luggage on the bus. You'll have free time to discover the island's capital and to have dinner before boarding the ferry to Paros. There's only one ferry between the islands each day and it departs at around 9pm, taking around one and half hours. Note, as this is a shorter crossing, there's no reserved seating. On arrival we'll drive to our hotel in Drios, arriving at our hotel around midnight.

Paros is one of the most attractive of all the Cycladic Islands. Its capital is Paroikia, on the west coast. Dominating the interior is Mount Profitis Ilias (770 metres) on the slopes of which are the famous marble quarries.
Day 6 - Walk along the Byzantine road
Paros was the birthplace of the pt Archilochus, the inventor of iambic verse. Among the many places of interest are the marble quarries, the picturesque fishing villages, and a Venetian fortress. Especially interesting is the Ekatontapiliani Church of 100 Doors - legend says that when the 100th door is discovered, the Greeks will take back Constantinople (Istanbul).

Today, you might choose to take a walk along one of the well-preserved Byzantine roads that cross the island. This is an easy walk that takes around two hours. We'll use the public bus to reach the trailhead at the traditional mountain village of Lefkes. This is a very popular walk and the path is lined with wild herbs such as thyme, sage and oregano, so the walk is both fragrant and beautiful. We'll stop in Piso Livadi for lunch, in the side streets you'll usually find the locals playing a game of chess or backgammon. From here, you can either walk back to Drios or take the local bus.

Once back in Drios, you\ re free to relax on the Golden Beach or you might like to join a cooking lesson in the Hotel Anezina, to learn about traditional Greek cuisine.
Day 7 - Free day with optional caique boat cruise
Today is free to explore Drios a little more at your own pace. There's the opportunity (weather permitting) to explore the island's coast from a different perspective by joining a half-day boat trip aboard a traditional Greek caique. During the boat cruise, there'll be the opportunity to go swimming in the clear blue waters.

Perhaps you'd prefer to take a local bus to nearby Naoussa or Parikia. Naoussa is a coastal, white village that's buildings glimmer in the sunshine. The area is famous for its wine and jam, made in the surrounding vineyards, which you can try in the village cafes. The Old Port area is the perfect spot to sample the cuisine alongside a glass of wine in one of the traditional tavernas that line the harbour.

It's in Parikia where you can visit the Church of 100 Doors and other historical places found here including the Byzantine site of Panagia Ekatontapyliani, an old Venetian fortress on the hilltop above the town, an 8th century BC waterfront cemetery and the Paros Archaeological Museum.
Day 8 - Ferry to Naxos, afternoon orientation tour of old town
This morning, we'll drive to Parikia to catch the ferry to the island of Naxos. Our ferry normally departs just after midday, so we'll have a little time to look around Parikia before we board the boat. The crossing takes around one hour and there's no reserved seating as it's a short journey.

The island of Naxos is the largest (and some would argue the most beautiful) of the Cyclades. The god Dionysus is believed to have lived here and taught the inhabitants to cultivate wine, which still has an excellent reputation today.

At the entrance to the harbour sits the grand Portara Stone that has greeted visitors for over 2500 years. The town itself is a mix of whitewashed houses and medieval Venetian mansions, with the fortified 'kastro' (castle) occupying a prominent position overlooking the bay. Our luggage will be taken directly to our hotel, meanwhile our tour leader will make recommendations for lunch after which, we'll be introduced to the town with a wander through the network of alleyways and courtyards, as well as the kastro before returning to our hotel later in the afternoon.
Day 9 - Full day exploring Naxos
Today we have a full-day trip to explore the islands' interior. Heading inland, we'll leave the beaches of the west coast and head into the Tragea region, a vast highland valley dotted with olive trees, citrus plantations, and sleepy villages.

We'll make a number of stops this morning including Bazeos Tower, a Venetian monastery built in the 17th century, and Halki (also known as Chalkio), which has a number of fine Byzantine-era churches. Once the capital of Naxos, Halki has had somewhat of a renaissance with several new tavernas and shops opening to cater to the tourist trade, as well as a delightful town square where we'll stop for a morning coffee.

Continuing further inland, we'll reach Moni. The village itself offers outstanding views of the surrounding mountains and a good choice of tavernas. There's a particularly excellent viewpoint at Stavros Keramotis, just outside of Moni, where it's possible to admire 360 views across the whole island. Depending on timing, we'll break for lunch in Moni or Kinidaros, the starting point for our afternoon walk to Eggares.

After lunch, we'll set off for a moderate walk which will take us around three hours and covers approximately seven kilometres. This walk is different to many of the others we'll have taken whilst in the Cyclades as it takes us inland. Kinidaros is located close to the mountainous centre of the island and is nestled into the rocky hillside, nearby the island's marble quarry. Eggares is a small farming village surrounded by fields and fertile farmland. Whilst there, you might like to visit the Olive Press Museum to learn about the process of making olive oil, alternatively, there are a number of pretty churches to take a look at.

For those who\ d prefer not to walk, there is the option to travel to Eggares by bus and catch up with the group after the walk. We'll return to Naxos late afternoon.
Day 10 - Free day in Naxos with optional visit to Delos and Mykonos
Today, you might like to join a full-day boat trip to Delos and Mykonos islands. We'll depart first to Delos, which takes approximately one and a half hours. Delos is covered with ancient ruins, amongst the highlights are the Temple of Apollo, Terrace of Lions, a third-century BC theatre, an ancient town and Mount Kynthos (113 metres). We'll have a bit of time to explore these historic delights before we take the boat on to Mykonos (a journey of around 30 minutes).

A world away from Delos, Mykonos is frequented by the rich and famous. Whilst here you can explore its winding streets lined with boutique shops and the famous windmills, which are one of the most photographed places in the Cyclades. Later in the day, we'll return to Naxos by boat (a crossing of around one and a half hours).
Day 11 - Ferry to Santorini and wine tasting
This morning, we'll walk the short distance from our hotel to the port and hop on the ferry to the island of Santorini.

Santorini (or Thira, as the island is also known) is the most southerly of the Cycladic Islands. It's one of the most picturesque areas in the Aegean and the familiar images of whitewashed churches with blue-domed roofs adorn this beautiful landscape. It's also an area of particular interest to those keen on the Lost Atlantis legend. Formerly a huge volcano, its centre disappeared in an enormous explosion in around 1450 BC and the area now forms a lagoon where some believe Atlantis sites beneath the waters. Records show that the eruption overwhelmed the Minoan settlements at Akrotiri as well as those on Crete.

This evening, we'll sample local wines at Aroma winery in Exogonia or another winery in the area.
Day 12 - Free day on Santorini Island, optional volcano excursion
Today you\ re free to relax, explore the island or join a cruise to an active volcano.

During the boat trip to the volcano, there'll be the opportunity to take the dramatic path to the peak and stand in the centre of the Caldera. The climb takes around 30 minutes each way, and the ascent is steep in places. There'll also be the chance to enjoy a swim in the sea to the warm springs.

The last stop on the cruise is the tiny island of Thirassia. You'll have a couple of hours to relax in the bay with views of the volcano and out to sea. There'll be time for lunch here or you can climb up through the hillside village and walk around the surrounding vineyards.

Alternatively, you might like to take the local bus to the ancient site of Akrotiri to see the remains of a Bronze Age settlement. Note, if you choose to visit the site, we recommend hiring a local to help explain the remains, excavation, and preservation process.
Day 13 - Exploring Santorini Island, including Caldera walk to Oia and free afternoon
This morning, we'll have the opportunity to go on a coastal walk from our hotel to Fira and then on to Oia. This is a moderate walk and should take approximately four hours, covering 16 kilometres. The path gs along the lip of a caldera and offers views along the way out to sea and of the surrounding countryside. Halfway through the walk, there's the option to stop at a coffee shop for refreshments.

The village of Oia is built along a rocky stretch of coastline and is one of the most photogenic places on Santorini. It has a seafaring culture and there are two types of houses here - cave houses that are dug into the volcanic rock in the cliffside and the captain houses above ground where the upper-class ship owners once lived. Many of the churches here are also dedicated to sailors.

After exploring Oia, you can take a local bus back to Fira and then walk the short distance to our hotel (around 20 minutes). Whilst in Fira this afternoon, you might like to visit the Museum of Ancient Thira, which explains the island's ancient heritage, or the Pre-historic Museum of Thera.

From the halfway point of the walk, it's possible to take a public bus back to Fira or to Oia to enjoy more free time in either place. Oia has a host of taverns and cafes; it's well worth spending time here after our walk and getting the bus back to hotel later in the day, it's also a great place to witness the magnificent Santorini sunset.

Note, in the busy summer months, this walk might be done in the reverse direction to avoid overcrowded busses, in this case sunset can be enjoyed from Fira.
Day 14 - Trip ends in Santorini
Our tour ends after breakfast at our hotel in Santorini.

There are no activities planned today, so you\ re free to depart at any time. If your flight is departing later in the day, luggage storage facilities are available at our hotel. If you\ d like an airport transfer today, you need to depart from Santorini Airport (JTR), which is about 15-minute drive from our hotel.
Departure dates
All pp pricing is based on twin share occupancy. Single supplements will apply
Start End Availability Price NZD
20 Apr 2025 03 May 2025 13 - Guaranteed $4,450
04 May 2025 17 May 2025 12 - Guaranteed $4,450
11 May 2025 24 May 2025 15 - Guaranteed $4,450
18 May 2025 31 May 2025 10 - Guaranteed $4,450
25 May 2025 07 Jun 2025 15 - Guaranteed $4,450
01 Jun 2025 14 Jun 2025 15 - Guaranteed $4,560
15 Jun 2025 28 Jun 2025 15 - Guaranteed $4,560
22 Jun 2025 05 Jul 2025 12 - Guaranteed $4,560
20 Jul 2025 02 Aug 2025 15 - Guaranteed $4,980
03 Sep 2025 16 Sep 2025 16 - Guaranteed $4,560
07 Sep 2025 20 Sep 2025 14 - Guaranteed $4,560
10 Sep 2025 23 Sep 2025 16 - Guaranteed $4,560
14 Sep 2025 27 Sep 2025 16 - Guaranteed $4,560
17 Sep 2025 30 Sep 2025 14 - Guaranteed $4,560
28 Sep 2025 11 Oct 2025 16 - Guaranteed $4,450
05 Oct 2025 18 Oct 2025 14 - Guaranteed $4,450