up to 8 travelers
7 days – 6 nights
April, May, September, October





Our skipper and guide will meet you at the marina at 10am on the day of departure, check you in your cabins and introduce you to the itinerary, after a short orientation.
Shortly after we leave the marina behind us, enjoying views of the southeastern 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.
We’ll drop anchor in Kolona beach, a natural double bay separated by a strip of sand and you’ll have plenty of time to swim in the bay’s turquoise waters and do the short hike to St. Luke’s medieval chapel. The centuries old structure’s courtyard is nowadays home to a small herd of wild goats and photo opportunities are abundant.
From there we’ll continue on to the nearby marina of Merihas and dock for the night.
Early evening our guide will take you on a guided tour of the island’s main town.
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. 

In the morning we leave Kythnos behind us and sail south towards the island of Serifos. Well before the island’s marina, we stop for a swim in one of the various tiny bays that dot the island’s southern side. We’ll drop anchor in either Koutalas, Ganema or Kalo Ampeli, all boasting crystal clear green blue waters and on occasion sea turtle sightings.
Early evening we dock at the marina and head out to explore the island’s main town, up the mountain. Our guide will take you on a private walking tour, hiking up to the Venetian castle on the very top of the island’s main town. 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. 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 to the north and the turquoise waters of Psili ammos beach, a protected bay on the eastern part of Serifos island, ideal for swimming and snorkeling.
In the late afternoon we’ll continue sailing north towards the eastern side of Kythnos island and the fishing village of Loutra, our destination for the night.
The tiny village is unaffected by mass tourism and a great place to observe islanders going about their daily life. The few restaurants by the water all serve excellent freshly caught seafood and the local meat dishes are unexpectedly affordable and downright delicious.
Once there our suggestion is to unwind in the hot springs or opt for an insanely relaxing spa treatment.
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. 

Early in the morning, after a hearty breakfast and some proper Kythnaian coffee, we’ll leave the village of Loutra behind us and sail north towards the island of Kea.
On our way there, we’ll stop at the southern side of the island at the ancient Greek town of Karthaia. Weather permitting, we drop anchor in the bay and swim to shore. Karthea is a proper archaeological site complete with a Greek theater, a temple to Athena and another one to Apollo. We’ll have plenty of time to explore the site and swim in the bay before we continue our sail north.
This time we’ll circumnavigate the island and dock in the port of Korresia. In the evening your guide will take you on a private walking tour of the island’s main town Ioulida, nestled deep in the mountains in the central part of the island. 

After breakfast we set sails west towards Athens. Our return to the marina is followed by bidding farewell to our skipper and boarding the minibus that is going to help you explore the mainland.
Driving along the national highway we’ll drive west through the central Greek highlands towards the mountain settlement of Arachova. You’ll arrive there in the early evening and have plenty of time to check in your hotel, have an evening stroll in the village and unwind before dinner. 

After breakfast, it’s time to drive to the archaeological site of Delphi located a short distance from our hotel in Arachova.
The archeological site, complete with the Temple of Apollo, awaits us next for a walking tour of the premises. Being the most important religious site of the ancient world, Delphi is responsible for many of the important decisions Ancient Greeks would take, under the guidance of the Oracle that lived there. It’s also a very photogenic place, nestled in a small valley between two mountainsides.
You’ll have plenty of time to explore the rather extensive archeological site.
In the late afternoon we’ll board the minivan again and drive north this time, through the plains of central Greece, towards the UNESCO protected geological marvel that is Meteora.The six surviving monasteries date back to the 14th century when monks built on top of limestone cliffs. The views are insane throughout the day, with spectacular sunsets in the summer months.
In the afternoon you’ll get settled in your hotel and have plenty of time to unwind. Just before sunset, should you wish to, your driver can take you up the cliffs to film/capture the sunset views with the Monasteries in the background.
When it’s time for dinner there are plenty of excellent options in the area, but one that truly stands out with amazing views of the cliffs. If dry aged steaks, cured local meats, farm to table fresh salads and delicious traditional desserts are of interest to you, you’re in for a real treat.

On this day, after a relaxed breakfast, you’ll have a private guided tour of the area around Monasteries with a local guide, stopping at viewpoints along the way with plenty of time to capture the atmosphere. You’ll also get to visit one of the Monasteries on your own, and learn about its history and traditions.
Please keep in mind that these Monasteries are  still inhabited by monks and nuns, so discretion and a modest dress code (i.e. no shorts or mini skirts) is expected.
In the afternoon we’ll arrive back to Athens and we’ll drop you off at the airport or your hotel anywhere in the center and wish you farewell.


 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 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 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