up to 8 travelers
8 days – 7 nights
April – October




Low Season: 1900€  for

Mid Season: 2200€ for


Upon arrival to the Lavrion Olympic Marina our team will be there to welcome you. Shortly after we’ll be boarding the sailing boat that is going to be our home for the next week. Our skipper and guide will check you in your cabins and introduce you to the itinerary, after a short orientation.

Late afternoon we leave the marina, enjoying views of the southern suburbs of Athens. We head east, towards one of the most iconic landmarks or both the ancient and the modern world. The Temple of Poseidon, built high on a cliff over the dark blue waters at Cape Sounion, is the place where the Aegean archipelagos gets its name from.

Our destination for the night is the island of Kythnos. Gateway to the archipelago Kythnos boasts a lively main town, a world famous beach as well as postcard perfect views of the Aegean from the numerous chapels built high up in the cliffs. Wild goat herds, natural thermal springs and some delicious local dishes served right on the water, make for an excellent introduction to the Cyclades archipelago.

We’ll drop anchor in Kolona beach, a natural double bay separated by a strip of sand and spend the night there.

Alternatively, we’ll spend the night docked at Loutra, a  tiny fishing village famous for its thermal springs and welcoming locals.


Early in the morning, after breakfast and a swim, we will snorkel towards the cliffs on the southern side of Kolona beach. If you’re up for it, there’s a short, easy hike up to a white washed chapel, overlooking the Aegean. The centuries old structure’s courtyard is nowadays home to a small herd of wild goats and photo opportunities are abundant.

Late in the morning we leave Kythnos behind us and sail south towards the island of Serifos. The place that inspired Homer to write the Cyclops section in the Odyssey, Serifos is a true highlight of any visit to Greece.

Well before the island’s marina, we stop for a swim in one of the various tiny bays that dot the island’s eastern side.

Late in the afternoon we dock at the marina and head out to explore the island’s main town, up the mountain. With its tiny alleyways, numerous chapels and windmills, vibrant coffee culture and some insane views of the archipelago to the south, Serifos is as iconic of Greece as anything.

There’s plenty of landmarks to be seen on our hike up the Venetian castle and our guided tour focuses on the ancient and medieval history of the island. And if savoring deliciously fresh seafood right on the beach is your thing, this is the place to do so.

In the morning you have time for a quick swim, while we prepare the sailing boat for yet another amazing sailing experience.

This time our destination is the cosmopolitan island of Milos, a volcanic island boasting unique geological formations and of immense archaeological interest. Some incredible sunset views away from the tourist crowds is reason enough to visit Milos. Add in lunar-like landscapes, a vibrant nightlife and incredible local food and you’ll get why the island is by far our favorite destination for our guests.

If you’re a meat eater we’ll take you to THE place on the island to try lamb or goat stew and if you prefer seafood, the tiny port of Adamas is home to numerous family run tavernas serving freshly caught fish.

In the late afternoon we’ll take the local bus to the main town up in the cliffs. The town, with its traditional cycladic architecture is busy with travelers and locals alike, with boutique cafes, bistros, restaurants and shopping opportunities everywhere. If enjoying a cocktail on a balcony overlooking the Aegean is your thing, Milos delivers.

Milos is a volcanic island, which is evident by the bizarre geological formations one sees around the island. After breakfast we get a chance to sail to two stunningly beautiful swimming spots, starting with the Kleftiko beach, in the southern tip of the island. Kleftiko used to be a pirate’s cove and a visit there is one of the highlights to any trip to the Cyclades. Crystal clear waters, sea caverns and rocks pointing towards the sky, all contribute to an amazing, unique landscape.

We will use the dinghy (the sailboat’s inflatable motorboat) to cruise through the caves, and you can easily spend half a day here, swimming and snorkeling. Hopefully we’ll get a chance to spot some mediterranean dolphins here. Music attracts them so bring your playlists.

In the early afternoon we’ll be continue with our circumnavigation of the island, passing by the Polyaigos straight and heading to our final destination of the night, the tiny island of Kimolos. Home to less than 500 people, Kimolos is the ideal place to experience what the islands were like before the tourist boom.

The short hike to the Venetian castle provides some excellent insight into medieval architecture. The bays around the marina are ideal for snorkeling and paddleboarding and the waters are warm and calm throughout the sailing season.

After breakfast we leave Kimolos behind us and head east.  A short sail away is Polyaigos, a tiny, barren, uninhabited island that is home to a dwindling population of Mediterranean seals, usually hunting for fish near the sea caverns they call home. The highlight of any visit to Polyaigos island, besides marine wildlife lucky viewings, is swimming. The island’s south side boasts some of Europe’s most terrific beaches, ideal for swimming and snorkeling.

You can also hike on the island, frequently coming across wild goats grazing by the sea.

In the early afternoon we set sail north towards the island of Sifnos. Our head skipper’s favorite place in the world is the bay of Vathy on the southern part of the island.

We always try to spend a night there, as there’s a great sandy beach and two family run taverns serving what is considered by many of our guests as their best meal in Greece. Think of fresh vegetables and salads straight from the garden, goat or beef stews, grilled lobster or mullets fresh from the sea and you get the idea.

After breakfast, it’s time to leave Sifnos behind us, as the island of Kythnos awaits once again. This time we head to the island’s eastern side, after a stop for a midday swim in a remote bay south of the island. Our destination of the day is the tiny fishing village of Loutra.

Once there our suggestion is to unwind in the hot springs or opt for another swim on the sandy beach right next to the marina. Early evening our guide will take you on a guided tour of the island’s main town, which is a ten minute drive away.

The main town is stunningly beautiful, full of traditional whitewashed ancient houses, cobblestone streets and alleyways, and boasts some of the best meat based food in the archipelago. Think of grandmas observing passersby from their tiny, well kept courtyards, delicious homemade baklava and chocolate pies, friendly locals and the ever present sense that time here truly slows down, and you get the idea.

After dark feel free to enjoy a bottle of cold, locally brewed beer right on the water, or put on a bathing suit and observe the Milky Way, while relaxing in the natural pools where the hot springs meet the sea.

After a cup of traditionally brewed coffee in the fishing village of Loutra, we leave Kythnos behind us and set sails towards the mainland and Cape Sounion, home to the temple of Poseidon.

We drop anchor in one of the numerous bays close to the cliffs where the temple is built on and use the dinghy to get to shore. Once there, we’ll hike to the temple and visit one of the most important archeological sites this side of the world.

In the early evening we’ll set sails north towards the Olympic marina, our destination for the night. Our crew will be there to have one last dinner with you before we settle in our cabins for the night.

Early in the morning we pack our bags and bid farewell to the sailing boat that’s been our home for the past week and our adventure ends.


     1. What are accommodations like on your tours?

In order to guarantee a memorable overall experience throughout your adventure with Bearing True South, we have carefully handpicked a mix of family-run, boutique hotels for your accommodation. On your sailing adventures with Bearing True South, we operate a fleet of 4 or 5 cabin sailing yachts with a large sundeck and a comfortable indoor galley for meals and relaxing. There are three/four double bed cabins available for our guests, depending on the sailboat you choose, under the main deck of the yacht and separate crew quarters.
In all our trips, land or sailing, accommodation is operated on a twin share basis. This means that traveling as an individual, you will be sharing accommodation and room facilities with another person of the same sex or your partner, spouse, family, friend etc. 


    2. What are meals like on your tours?

When traveling with Bearing True south, you’ll experience a great variety of delicious food, based on traditional Greek cuisine. Emphasizing on the regional cuisine of our destinations, we have carefully selected local, family run, restaurants for our groups.
On our land trips, breakfasts are always included in the total price and are provided at the hotels. On an outdoor activity day, when a picnic lunch is mentioned in the day to day itinerary, we usually buy local cheeses, vegetables, cured meat, bread, local pies from local markets so you don’t miss out on the specialities of the region. Picnic lunches are always included in the price of the tour.
On our sailing trips, all breakfasts and “light lunches” are provided by us on board on a self-serving basis.  “Light lunch” and “breakfast” usually refers to fresh Mediterranean salads, pasta, milk, coffee, tea, juice, cereal, bread, sandwiches, omelets or fresh fruit, local cheeses and cold cuts. You have access to a fully equipped kitchen to prepare your meals on your own or together with the crew.
Dinners are usually in local restaurants and are not included in the tour price. This gives our groups the flexibility to either eat together or explore the destination on their own and enjoy a larger variety of local dishes after a long day. When a meal is not included feel free to ask your tour leader to suggest a local restaurant in the village or town you are staying.
For the meal plan of the tour please refer to the day to day itinerary and the extra info of the tour. If you are a vegan or vegetarian, have any food allergies or any special requests when it comes to food, please let us know at the time of booking.



    3. What are some extra services you provide?

Upon request we can arrange for taxi or minivan transfers from and to the airport and the marina, paddleboard and SUP rental on our sailing tours, shopping for personal supplies from guests prior to their arrival. Should you require a private guided tour of the Acropolis and the historical center of Athens we work with government registered archaeologists and can arrange half or full day tours. Should you require a private full or half day sightseeing tour of Athens with one of our guides we can also arrange that. 



    4. What equipment is provided while sailing?

On all our sailing tours there’s enough snorkeling gear for everyone onboard. That includes masks, breathers and fins. There’s also an inflatable dinghy available to take guests to shore or on short rides when we’re anchored in various bays. 

Upon request we can also arrange the rental of paddle boards (SUPs) at an extra charge per week.  



    5. How physically demanding are your tours? 

Our tours are catered to all ages and the level of physical excretion can be adjusted to reflect each group’s specific dynamics. We expect our guests to be able to walk on their own, as, unfortunately, sightseeing in the mainland and sailing on the islands isn’t ideal for wheelchair dependent guests. We also expect our guests to have a reasonable level of fitness, i.e. to be able to walk unassisted for a couple of hours on a daily basis during our tours. 



    6. Are the itineraries set? 

The style of travel in our adventures provides us a great deal of excitement, however it is dependent on several factors, such as weather, terrain conditions and technical problems with transportation. These may create unexpected circumstances throughout our tours that we have to deal with by making minor changes to the tour itinerary or the activities included in a particular day. For that reason the described day to day itinerary is used as a guideline which gives us the flexibility to make changes when needed.


    7. What does a typical sailing day look like? 

After a self serving breakfast on the sailboat the crew informs you of our first destination of the day. This could be another island or a different part of the same island. We sail there, drop anchor and have plenty of time to explore the bay, snorkel, swim, paddleboard or relax on the deck. In the early afternoon, after a light lunch is served onboard we set sails once again for our next destination of the day. That’s usually an island’s marina, where we dock and have time to relax and unwind until the early evening. Your tour leader will then take you on a private walking tour of the local sights. These tours focus on culture, history, architecture and of course food. We hike or use public transportation or on occasion private taxis. The tours, depending on the place, last between 1 and 3 hours and usually end just before it’s time for dinner. Dinner options are aplenty and our tour leader is always there 


    8. What is the tipping culture in Greece? 

Tips are welcome and ideally presented in cash. It is customary to tip your tour leader and skipper for their services throughout the trip. 


    9. Do you offer post tour extensions / add-ons?

We do offer tour extensions and add-ons for our guests. We realize that your time here is limited and some people want to see as much as possible without the hassle of figuring things out as they come.

If you feel like exploring more of the mainland we offer 2-3 day tours of the Monasteries of Meteora and the Delphi archaeological site. We also offer tours to the Peloponnese and Ancient Olympia as well as Kalamata, Nafplion and the Mani Peninsula. We operate those tours ourselves and have had nothing but great feedback over the years. 


    10. What is the weather usually like?

Greece in general has warm and humid summers lasting from May till October. In May and October weather can be less predictable with some rain and chilly temperatures being possible especially in the Greek mainland. Greek summers are generally hot, with temperatures rarely getting lower than 25 degrees Celsius in most of our destinations, while temperatures of over 40 degrees Celsius during the day are not unheard of in July and August. In the open sea, weather can be tough to predict all year round, but in the summer the seas are generally calm and ideal for sailing. Generally, cool temperatures and occasional rainfalls occur often at night, especially in the mountains, a fact that you have to take into account when packing for your adventure. 


    11. What should I pack for my tour?

Being as light as possible is always important on an adventure tour plus space is limited on board a sailboat so our travelers are expected to bring with them a backpack or suitcase as well as a daypack for personal items and valuables. A sample packing list will be provided by us upon booking your adventure with us. Feel free to use it as a general guideline on how to pack sensibly for that specific tour at that specific time of year. 



up to 8 travelers

7 days - 6 nights

starting from

2200 EUROS

up to 10 travelers

3 days - 2 nights

starting from


up to 8 travelers

8 days - 7 nights

starting from

1900 EUROS

up to 8 travelers

8 days - 7 nights

starting from

1900 EUROS

up to 14 travelers

7 days - 6 nights

starting from

2200 EUROS



+30 698 416 99 94

+30 697 743 33 91