Greece & Hidden Cyclades Sailing Adventure

Greece & Hidden Cyclades Sailing Adventure

From $ 4,226 AUD


Get lost in colourful cities filled with natural and ancient treasures on this whirlwind tour of mainland Greece. See where democracy began and how life was lived when Zeus called all the shots. Explore ancient ruins and rituals of the past. Unwind in the evening after a big day with a sip of ouzo over a banquet of culinary treats. Yamas!

Trip Name
Greece & Hidden Cyclades Sailing Adventure
Last Updated
  • Uncover thousands of years of civilisation in Athens with a visit to the world-famous Acropolis and the ancient Agora
  • Like endless pilgrims before you, visit the home of the Oracle of Delphi in the Sanctuary of Apollo, one of Greece's most important archaeological sites
  • Be mesmerised by the magical monasteries of Meteora, an extraordinary site precariously perched on a series of ancient rock pinnacles
  • Discover the many flavours of Greek cuisine. There's nothing quite like dining on rich and hearty moussaka or grilled lamb and tzatziki in a traditional taverna as Rembetika music floats around you


ITINERARY CHANGES: Our itineraries are updated regularly throughout the year based on customer feedback and to reflect the current situation in each destination. The information included in this Essential Trip Information may therefore differ from when you first booked your trip. It is important that you print and review a final copy prior to travel so that you have the latest updates. Due to weather, local conditions, transport schedules, public holidays or other factors, further changes may be necessary to your itinerary once in country. The order and timing of included activities in each location may also vary seasonally to ensure our travellers have the best experience. Your tour leader will keep you up to date with any changes once on tour. OPTIONAL ACTIVITIES: A selection of optional activities that have been popular with past travellers are listed in the day-to-day itinerary. This isn't an exhaustive list and should be used as a guide only for some of what might be available. Prices are approximate, are for entrance only, and don’t include transport to and from the sites or local guides unless indicated. All activities are subject to availability. It may not be possible to do all the activities listed in the time available at each destination, so some pre-planning for what you are most interested in is advised. When it's recommended that travellers pre-book these activities, look for a note in the Special Information section of the day-to-day itinerary. For most, they can either be organised independently on the day, or let your leader know you are interested and they can assist. Where activities are considered medium or high risk, we work with operators whose safety and credentials we have sighted and assessed. Although it is possible that you may find the same activity cheaper with another operator on the ground, we cannot vouch for the safety or quality of that operator. Medium and high risk activities not listed above have not been assessed by us and as such our staff and leaders are unable to assist you with organising these activities. Activities that contravene our Responsible Travel policies are also not listed. Please remember that the decision to partake in any activity not listed is at your own discretion and risk.

Day 1 - Athens
Kalimera! Welcome to Greece. Named after the goddess of wisdom, the birthplace of Western civilisation, Athens has an amazing array of historic sites to explore; a weighty history that spills out over the modern city, represented most dramatically by the ancient Acropolis. There's much to be seen in the ancient capital of Greece, vibrant and refreshed following the 2004 Olympics, yet still retaining so much visible history. After the welcome meeting, perhaps head out for some gyros and ouzo with your new travel companions.
Day 2 - Athens / Thessaloniki
This morning head out to visit the famous Acropolis, one of the Western world's most important historical structures. Start with an ascent to the top of this sacred rock via the towering entrance, the Propylaia. Once inside, encounter the Parthenon – the greatest Doric temple in the ancient world. In the afternoon board a train to cosmopolitan Thessaloniki, the second largest city in Greece. This city especially comes alive in the evening, thanks in part to its large student population, so make sure you hunt down the perfect gyros or some live music.
Day 3 - Thessaloniki
Relax in the splendour of what is regarded as the cultural capital of the country. Walk along the waterfront to the White Tower, take in the Byzantine churches (like the beautifully frescoed Church of Saint Nicholas the Orphan), Ottoman sites and Roman ruins, and appreciate the wonderful views over the gulf. On a clear day you might even catch a glimpse of the home of the gods, Mount Olympus. If you’d like someone to show you the way, perhaps join an Urban Adventure for a local view. The city is undoubtedly the gastronomic capital of the Greece and its flavours are unique. For 2,000 years it’s been a melting pot of cultures, with eastern spices, French, Balkan and Mediterranean tastes. Seek out the eateries in the area around the agora, where age-old columns and arches brush up against modern apartments and the ancient Rotunda.
Day 4 - Kalambaka
Travel by public bus or train to Kalambaka (approximately 3 hours). Upon arrival embark on on a short orientation walk of town, where your leader will point out amenities and help you get your bearings. The rest of the afternoon is free for you to explore the scenic area around Kalambaka and Meteora, where the views are stunning whichever way you look. Having two days here allows you to explore at your own pace, discover the history and legends, witness the incredible views of one of the few World Heritage sites listed under both nature and art at different times of the day, and avoid the crowds. Your leader will have suggestions on hand. In the evening, maybe head to a taverna for dinner and stroll the main square for a taste of Thessalian life.
Day 5 - Meteora / Kalambaka
Climb into the heavens, just like monks have done for centuries, towards ancient monasteries precariously placed atop 400-metre-high rock formations. Meteora is home to 24 14th century monasteries that sit at the top of karst pinnacles, though only six are still occupied. They were once only accessed by rope ladders, but thankfully there are now steps. The cliff faces also feature caves where hermits lived an even simpler life than those in the teetering monasteries. The monasteries, which used to be supplied by rope and pulley systems, house woodcarvings, frescoes, paintings, and one even features the skulls of the first founders. You’ll enjoy some great views back over the town. The area makes for incredibly dramatic photos – multi-colour streaked rock, bright green forest, and the pale terracotta of the monastery roofs against the Grecian sky. The mists that can surround the pinnacles make the constructions seem like they’re floating in the air. Hawks drift on the valley thermals looking for prey, and black-frocked priests shuffle silently around.
Day 6 - Delphi
Travel by public bus to Delphi (approximately 4,5 hours). Located on the slopes of Mt Parnassos, by a valley of cypress and olives trees, this modern town and ancient ruins overlooks the Gulf of Corinth. The ancient Greeks regarded Delphi as the centre of the world (legend says that Zeus sent two eagles flying from opposite ends of the world and they crossed paths over Delphi), and today it’s one of the country's most inspiring and memorable archaeological sites. On arrival, your leader will take you on an orientation walk of the cliffside town of Delphi. Then, make the most of your afternoon by visiting the ancient site of Delphi. Here you’ll find the famous sanctuaries of Apollo and Athena, which contain numerous monuments, temples, a well-preserved theatre, and the impressive reconstructed Athenian Treasury. The site was also home to the Delphic oracle, said to have spoken for Apollo himself – she sat on a chasm, inhaling vapours from the Earth and entering a trance-like state, her cryptic answers to questions translated by priests. There’s also a mountain-top stadium, which were used for the Pythian Games (an Olympic Games precursor), held every four years as early as 586 BC.
Day 7 - Athens
Travel back to Athens today by bus, arriving in the late afternoon (approximately 3,5 hours). Shop for the perfect souvenir at the Monastiraki flea market or take a relaxing stroll through the Greek national gardens. If you haven’t already, check out the Temple of Olympian Zeus or the Tomb of the Unknown Soldier to watch the changing of the guard. While in the neighbourhood explore the excellent Museum of Athens, Syntagma square with the Parliament building, and the Panathinaiko Stadium which housed the first Olympic games in 1896.
Day 8 - Athens - Kythnos
Your sailing adventure commences at 11am at Alimos Marina in southern Athens. To ensure you are not delayed in morning traffic we have booked in your transfer at 10.15. If all going well you should arrive at the marina by 10.40am. Your transfer driver will be waiting for you in the hotel foyer. If you have a large suitcase you can leave your bag at the hotel for a small fee. Please ask at reception on arrival for this service and do not leave any items of value in your bags. Board your boat for a safety briefing with your Skipper before sailing out towards Kythnos, an island in the Western Cyclades. Feel the spray of salt and the wind in your hair during a six-hour sail while getting to know your group, and spend the evening anchored offshore, waking up the following morning next to a beautiful beach. 
Day 9 - Kythnos - Serifos
Enjoy a relaxed morning swimming, stand-up paddleboarding and exploring Kythnos' gorgeous beach. Eat lunch on board before heaving up anchor sailing towards Serifos, stopping in Livadi Bay. Serifos was a place of exile during Roman times but the only exile these days is willingly self-imposed. With small blue and white houses built into the hill, countless beaches and a strong presence in Greek mythology, Serifos is a destination that'll lodge itself deep in your heart. Or maybe it won't, but it's still a phenomenal place to spend an evening. Anchor in the bay and take a dinghy to shore to eat at one of the traditional tavernas at Livadi's harbour and enjoy the sunset, then pick up supplies and an ice-cream before returning to the boat.
Day 10 - Serifos - Vathi
Take an optional morning walk (approx. one hour) to the hora (town) of Serifos, for beautiful views of the island and the Aegean Sea. Enjoy a coffee in the town square before making your way back down the Livadi's harbour and taking the dinghy back to the boat where you'll have lunch. After lunch, sail the town of Vathi, on Sifnos, and arrive in time for an early evening swim. Don't worry, it doesn't matter what time you swim in these waters, it's always warm. Take a dinghy to shore and eat at a beautiful, beachfront taverna, perhaps with raising a glass of ouzo with the group, then spend another night anchored offshore in the bay.
Day 11 - Kimolos
Spend the day sailing south to Kimolos and swimming in the ridiculously clear water until evening. Kick back on deck with a good book, or a bad one, and get to know the people in your group with some quality bonding time soaking up the sun. Fun fact: Kimolos may be small, but approximately eighty churches have been built by the townsfolk and once you visit the island, you'll find yourself worshipping its very existence. Visit the main village for dinner and enjoy fresh seafood and, of course, some more ice cream because you are on holiday, right?
Day 12 - Polyaigos
Spend a day sailing around Milos and exploring its coastline. Milos is one of the bigger islands in the area and your first stop is Sarakiniko, known as Moon Beach thanks to its lunar-like landscape. The dazzling white rock formations are twisted into incredible shapes as a result of erosion from the wind and sun, juxtaposed with the deep turquois waters of the sea. This is THE spot to get that holiday happy snap and make your friends back home unbelievably jealous. Continue sailing around the island to Kleftiko, a crazy-beautiful cove accessible only by boat. Revel in the rock formations and caves that are purported to hide pirate treasure, then sail to Polyaigos where you'll spend the evening. Polyaigos is an unihabited island, unless you count the goats on land and the rare Mediterranean monk seals that call the sea caves home. Tonight you'll be protected by Polyaigos' cliffs with dinner prepared by the group, so enjoy an evening together under the stars.
Day 13 - Sifnos - Platys Gialos
Sail to the Platis Gialos Marina on the southern end of Sifnos and spend the day relaxing and swimming at its sandy beach. Here, you'll have lunch (maybe a cold Mythos beer too) and pick up supplies for the rest of the journey. In the evening, take a bus up to the village of Artemonas then enjoy a short stroll to Apollonia, where the group will have dinner. There's also an option to take a short taxi to Kastro, the ancient capital of the island. Apollonia is the modern capital of Sifnos and the centre of the island's nightlife, which resembles an earlier version of Mykonos – think unpretentious bars and restaurants found in paved, winding alleyways. Return later in the evening to the marina and overnight on the boat. 
Day 14 - Serifos - Koutalas Bay
Prepare for a super relaxed day. Sail to  Koutalas Bay or north to the far side of Serifos to Psili Ammos, which was voted Europe's Best Beach in 2003 by the Sunday Times. It translates as 'soft fine sand', and nothing much has really changed in the past 15 or so years – it's still a stellar stretch of sand. Wherever the boats end up, you'll enjoy swimming, mucking around on stand-up paddleboards and taking dinghy rides to explore the coastline. The boat will remain anchored in the evening and the group will prepare dinner as the sun sets. It's not a hard life, is it?
Day 15 - Kythnos - Agios Ioannis
Today you'll return to the island of Kythnos, north of Serifos. But before you arrive, there's a swim stop at Agios Ioannis Beach and time for you to really work on those stand-up paddleboard skills. Maybe combine it with a bit of yoga practice and flip into a nautical headstand, because hey, the worst case scenario is falling into the warm embrace of the glittering water. Continue sailing to Loutra, a small port at the northern end of Kythnos where you can grab dinner and some drinks in a local taverna. 
Day 16 - Kea
Wake up to another day in paradise, this time sailing north to the island of Kea. Hit the beach at Mikres Poles on Kea's southside and check out the ancient Karthaia ruins. Karthaia was one of the four ancient cities of Kea, and these days you can see the remnants of two temples, dedicated to Athena and Apollo, as well as the theatre. Continue up to Vourkari, a small village with a buzzing atmosphere thanks to its proximity to Athens and popularity with travellers, both Greek and foreign. Enjoy a farewell dinner at a beautiful taverna in town and, if you haven't already, raise a glass of ouzo to your new nautical friends.
Day 17 - Athens
Depart early from Kea on your final morning, at around 7 am. Sail back to your starting point, a marina on Athen's southern coastline, approximately six hours from Kea. Arrive and disembark the boat around 1 pm, at which point this sailing adventure comes to an end.

Trip Dates

StartEndPrice FromRoom Type
04-05-201920-05-2019AUD $ 4,226-
21-09-201907-10-2019AUD $ 4,226-


Hotel (7 nights)


Train,Public bus,Private vehicle,Taxi