A unique sailing experience tailored for you

No 2 trips are the same

Off The Beaten Tack is not just about sailing, it’s about using the wind to take us to places most other tours don't go.

We have extensive knowledge of the Greek Islands and waters with its hidden bays, idyllic beaches and beautiful destinations and use this knowledge to take our guests to the places that suit them – as the wind takes us.


sailing between Mykonos and Santorini

For the 2020 season we will be starting and finishing our sailing trips in either Mykonos,Santorini or Naxos and exploring the Lesser Cyclades Islands. Naxos is midway between Mykonos and Santorini, both of which have international airports and very good ferry links to Naxos (2 hours). 

Santorini (Thira) is well known for its stunning views over the old Volcano and its white washed Cycladic arcitecture. A romantic destination for many travellers.

Naxos is the largest of the Cyclades Islands, a dramatic patchwork of rich gardens, vineyards and orchards backed by wild mountain crags and a wealth of historical sites.

Mykonos is more of a boutique cosmopolitan island where the old meets the new with a big contrast from one side of the island to the other. an island for everyone.

After setting sail we have no fixed itinerary - we literally sail where the wind takes us.  Each day your skipper will assess the weather forecasts and depending on wind conditions will suggest a plan for the next day. This means every day can be different from the last, with that sense of adventure in the air, anticipating what is going to happen next.

How does a day with OTBT look?

Start of the day
  • Breakfast aboard our Yacht, provided by OTBT

  • There may be time for a morning swim or activity of you choice

  • Based on the weather conditions and what you'd like to do, Your Skipper will recommend a plan for the day

  • Sail for usually 2-5 hours to the next destination

  • Lunch aboard provided by OTBT

  • Now arrived in the new destination there will be opportunity to swim, snorkel, walk, explore the island/beach/town and many other activities

  • In the evening all guests have the option of eating together with OTBT crew at one of there recommended local restaurants or you can go and do your own thing

  • They can also guide or accompany you to some of the best local bars if you'd like a longer night out

  • You will then sleep aboard and prepare for a new adventure the next day

  • Please note that due to the nature of using the weather to determine the days plan, each and every day looks different. We may take you on tours of the islands by vehicle (additional fee's for car hire may be applicable), have BBQ's on beaches, visit places of heritage and culture, sometimes we'll do a night sail to view a beautiful sunset or arrive in a new destination ahead of weather systems. We have a very flexible approach, whilst providing the very best experience.

What will we do aboard...

  • You can learn to sail

  • Relax on deck soaking in the sun and scenery

  • Read a captivating novel

  • Chill out to the tunes of your choice

  • Swim and snorkel over ship wrecks in the Cyclades crystal clear waters

  • Explore Stunning beaches

  • BBQ fresh fish on uninhabited islands

  • Paddle boarding

  • Cliff jumping

  • Fishing

  • Sleep under the stars in hammocks on the deck or the beach if you choose!

The Cyclades Overview
The Cyclades comprise 200 islands south of Athens - explore them with a Greek sailing island adventure from Off The Beaten Tack

The Cyclades

The Cyclades comprise a cluster of 56 main islands some 120 miles south east of Athens. 24 of the islands are inhabited with the most well-known being Naxos, Mykonos and Santoríni, whilst others are tiny and undisturbed by tourism. Cyclades derives its name from Kyklos meaning ‘circle’ as the islands surround the sacred island of Delos which was the cradle of Greek civilisation 3000 - 1000 BC. 

The islands are the peaks of a submerged mountainous terrain rising from deep waters, with the exception of two volcanic islands, Milos and Santorini which has a spectacular caldera. If you had a bird's eye view the Cyclades, they would look like an intriguing mosaic of tufts of verdant earth floating on the turquoise waters of the Aegean sea. It's an incredible formation created by the geological changes that took place millions of years ago. 

According to the Greek mythology, Poseidon, God of the sea, was so furious at the behaviour of the Cyclades nymphs that he turned them into islands. 

Skipper Jimmy’s favourite islands are the Lesser Cyclades, a group of tiny, unspoilt islands south of Naxos, some of which remain uninhabited and hide the relics of an ancient past. 

These stunning islands are surrounded by crystal clear turquoise waters with a mixture of rugged coastline with impressive cliffs and gorgeous sandy beaches offering safe anchorages and opportunity to explore on land as well as at sea. The architecture is very traditional with whitewashed buildings in contrast to the bright blue shutters. There are hidden gems everywhere you visit.

The main islands of Naxos, Ios and Santorini offer interesting culture and history, good places to eat and a vibrant night life with shops open late and charming tavernas.

There are plenty of uninhabited islands to explore and enjoy complete isolation, BBQ’s on the beach and the option to sleep under the stars onshore.


The best ways to join the yacht is to either fly direct to Santorini or Mykonos, or fly to Athens then use the excellent ferry service from Pireaus (Athens) to the islands. We recommend you set aside a couple of extra days at either end of the trip to spend more time in Santorini and Mykonos which are destinations in their own right.

If you had a bird's eye view the Greek Cyclades, they would look like an intriguing mosaic of 20 tufts of verdant earth floating on the turquoise waters of the Aegean sea. It's an incredible formation created by the geological changes that took place millions of years ago.

According to the Greek mythology, Poseidon, God of the sea, was so furious at the behaviour of the Cyclades nymphs that he turned them into islands.

However they were formed, The Cyclades — which means the Sacred islands around Delos — their beauty and dazzling light can lend itself to a spot of spirituality.

For most of the year the wild rugged volcanic scenery remains whitewashed with sugar cubed Cycladic architecture that looks superb against the dark or vegetal backdrop with the deep blue sea lapping at their shores. Here are six suggestions.




Some say the most beguiling and popular island of this Aegean archipelago is Santorini. Everyone will have seen that iconic image — you know, the one with the cliff-top blue-domed church standing out amid shimmering white architecture that looks dazzling against the blue skies and seas. 

The island of Santorini is famous for breathtaking views, beautiful sunsets and its very own active volcano. Putting natural beauty aside, Santorini is also teeming with cultural attractions and architectural splendours. 

There are beaches, a pebbly one at Kamari and a black sand ones at Perissa and Karterados and these are overlooked by jagged cliffs and a brilliant light that seems peculiar to the cyclades — it can be mesmerising.

The hillside towns of Fira and Oia are quaint with sometimes steep steps and knotted alleyways and make for idyllic afternoon exploration. And in the evenings the roof terraces of restaurants are light and alive with diners enjoying libations and alfresco dinner in the warm night air. This island is all about relaxing sophistication.



With its pristine sandy beaches, crystal blue waters and cosmopolitan nightlife, it's no wonder that holidays in Mykonos are among the most popular in Greece. Mykonos seamlessly blends its whitewashed cube-shaped houses with its picturesque fishing village environment, ensuring that all visitors on holiday in Mykonos are embraced by its tranquil surroundings. For such a small island - just 16 kms (10 miles) long - it offers a uniquely varied selection of clubs, bars and great shops, so you can be sure that holidays in Mykonos will never get boring.

Mykonos Town, with its picture perfect white washed houses and cobbled streets is quite simply one of the most attractive towns in the Greek islands. With an array of excellent bars and restaurants to rival anywhere in the Mediterranean and its opportunities for designer shopping in the narrow streets behind the harbour, Mykonos Town is the place to be seen as many a celebrity will testify.



This is the largest of the Greek Islands in the Aegean Sea and when you arrive by boat you will be met with its most famous archaelogical site — the Portara, the doorway to the ancient temple of Apollo built in 522 BC. The island is home to the highest mountain in the Cyclades — Mount Zeus — which is the source of much mythology. They say that this was the nuptial isle of the Dionysus, the God of wine. That's why there is a sanctuary dedicated to him. It's coastline is a doily of sensational beaches, some secluded. Mikri and Vila in the west are beloved by windsurfers. 

Inland its incredibly mountainous and villages seem to appear out of the fertile valleys and there are plenty of fields and olive groves. Its harbour is in the capital where several alleys lead steeply to the citadel, a landmark that can be seen for miles and elsewhere there are old churches, monasteries and Venetian castles and homes.





There are two completely contrasting areas to Ios. One offers peace and tranquillity with 365 churches and the other offering  great nightlife and beach parties that start early and last throughout the night. Near to Chora there is a kilometre stretch of beach peppered with bars and restaurants and myriad of water sports but there are more sedate options in the south of the island at Valmas beach or Kolitsani beach. The island also has the tranquil hillside village of Chora, probably the most picturesque in all the Cyclades. The views from its highest point are simply breathtaking. OTBT have a good relationship with a local spa which offers amazing quality food and a variety of treatments.



Paros, a ferry hub and a beautiful Venetian port, is considered as one of the most beautiful islands defined by its beaches and quaint villages. Parikia, the island’s main town and port is filled with narrow, winding streets which were originally intended to confuse any invaders, giving the locals time to escape! The town now boasts an atmospheric and intriguing mix of the old and new, with its white-washed buildings and an excellent selection of restaurants, bars and shops.

The most popular town is Naoussa. It was once an old fishing village but who would know? Today it is a popular cosmopolitan holiday destination. For a little culture visit the blue domed Byzantine Museum.



This world heritage site, located in the centre of the archipelago, is the birth place of Apollo and Artemis and in ancient times was the religious centre for the whole of Greece. The remarkable monuments, such as the Minoan Fountain and Temple of the Delians, and the impressive mosaics are certainly worthy of a visit.





Flights are not included in our prices. Once you have confirmed when you will be sailing with us, we would recommend you book your flights as it’s often cheaper to book well in advance. There are regular flights into Mykonos and Santorini direct with some airlines and via Athens with others. For flights you could use:

You may choose to take a ferry from Athens to Naxos, Mykonos or Santorini to join us. The ferry service is regular and reliable throughout the Cyclades and it’s a great way start your Off The Beaten Tack adventure. There are ‘Fast Ferries’ which are futuristic looking catamarans, or the more traditional ‘bone cruncher’ type ferries which are slower and typically cheaper.. You could use the following companies to book your ferry tickets:


If you're flying in or out of to Mykonos, we recommend staying at Makis Place, beside the ferry port. The hotel has a nice pool, great views, comfortable double and family rooms, friendly staff and there’s a convenient water taxi direct to Old Mykonos  (3€) . Book direct and save! Don't forget to mention OTBT.

Getting there

The best ways to join the yacht is to either fly direct to Santorini or Mykonos and if meeting in Naxos take the according ferry, or fly to Athens then use the excellent ferry service from Pireaus or Rafina (Athens) to join our yacht. We recommend you set aside a couple of extra days at either end of the trip to spend more time in Santorini or Mykonos which are holiday destinations in their own right.


JOIN US in Greece, April to October 

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