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About


It's Your holiday, you're the boss

This really is your sailing adventure, and can be tailored to be as energetic or as relaxing as you want it to be

Book Now

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About


It's Your holiday, you're the boss

This really is your sailing adventure, and can be tailored to be as energetic or as relaxing as you want it to be

Book Now

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 and flotillas 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.

You can join as a group of

  • Up to 10 friends or family
  • As a solo traveller
  • or any combination!
  • All of our sailing adventure weeks our open to anyone between the ages of 5 and 80... We are family friendly!
 

start from Santorini or Mykonos

You must join the yacht at one of our start and finish ports (Santorini or Mykonos). From then on, apart from our final destination, 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
Daytime
  • 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
Evening
  • 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! 

Specialised weeks...

We have run specialised yoga and meditation weeks with qualified instructors as well as art weeks with local qualified art teachers. If you'd like to curate a specialist week, from yoga, art, a corporate getaway, sailing school, water sports or anything else, just let us know and we'll do everything we can to accommodate for your needs!

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Story


Find Your Escape

Between May & October we explore the Islands of Delos, Rhinia, Koufonsia, Iraklia, Milos, Sikonos, Amorgos, Naxos, Santorini, Ios, Mykonos by land-and-sea and many hidden coves, shipwrecks, and secret beaches in-between! 

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Story


Find Your Escape

Between May & October we explore the Islands of Delos, Rhinia, Koufonsia, Iraklia, Milos, Sikonos, Amorgos, Naxos, Santorini, Ios, Mykonos by land-and-sea and many hidden coves, shipwrecks, and secret beaches in-between! 

Book Now

Pic credit: Nick Filmalter

We are here to do what you want to do 

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

A typical day on your weeks holiday will include breakfast aboard our Yacht, followed by 1-5 hours sailing to a new destination. We'll stop for lunch on the Yacht and then you'll have an opportunity to explore the destination or stay close to the Yacht and enjoy swimming, snorkelling, fishing or just relax in the sun. In the evening we'll either take harbour on a new island and enjoy the local cuisine or have a BBQ on a secluded beach. 

Other than start and finish ports of Santorini or Mykonos, we have no fixed itinerary – we literally sail where the wind takes us. The night before, your Skipper will assess the weather and depending on wind conditions will discuss options and make recommendations that, with his local knowledge, will enable you to have a holiday to remember! 

Every day is different from the last, with that sense of adventure in the air, anticipating what is going to happen next!

You can join as a group of up to 10 friends or family, as couples, as a solo traveller or any combination! It’s an awesome way to meet new people, make new connections and for old friendships to flourish.

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Cyclades Destinations


Explore

The Cyclades Islands are quintessentially Greek and sailing between them is an awesome way to see all they have to offer

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Cyclades Destinations


Explore

The Cyclades Islands are quintessentially Greek and sailing between them is an awesome way to see all they have to offer

Book Now

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 of about 220 islands south of Athens, the most well known being Mykonos and Santoríni which is where our tours will start and finish. We visit popular islands such as Ios, Paros, Milos, Naxos and Amorgos.

Other islands include Andros, Antíparos, Delos, Ios, Kea, kilimons, Kithnos, Folegandros, Serifos, Sífnos, Síkinos, Syros and Tinos. That leaves 100’s of islands for us to explore alone!

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

All of the 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 islands are peaks of a submerged mountainous terrain, with the exception of two volcanic islands, Milos and Santorini. The climate is generally dry and mild and local agricultural produce includes wine, fruit, wheat, olive oil, and tobacco.

The main islands 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.

 
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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.

 

Santorini
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Santorini

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.

Mykonos
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Mykonos

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.

Naxos
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Naxos

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.

 

 

Ios
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Ios

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
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Paros

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.

Delos
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Delos

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.

 

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Prices


Step into a Perfect Dream

Sunset sailing, hidden coves, crystal clear waters and great food

Book Now

Prices


Step into a Perfect Dream

Sunset sailing, hidden coves, crystal clear waters and great food

Book Now

£749 per person, per week

Group discounts available from £549 per week

Included in the price:

  • 6  Nights accommodation aboard our Yacht
  • Locally sourced fresh breakfast and lunch
  • Drinks on board
  • Use of paddle board, canoe, fishing and snorkelling gear
  • All safety equipment
  • All port and fuel costs
  • An RYA-qualified Yachtmaster skipper
  • Daily swim stops

Flights:

Ferries:

Flights are not included in our prices. Once you have confirmed when you will be sailing with us, and your start and finish Port (Santorini or Mykonos) we would recommend you book your flights. 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 Mykonos or Santorini. There is a regular and reliable ferry service throughout the Cyclades and it can be a great way start to your Off The Beaten Tack adventure. You could use the following companies to book your ferry tickets:

Accommodation

If you're joining us in MyKonos, we recommend staying at Makis Place, beside our departure Port before sailing with us. Book direct and save! Don't forget to mention OTBT.

 

JOIN US in greece, june to october