Legend

Trip Categories

trip duration
4x4 Guided Self Drive Adventures
trip cultural rating
Multi-Activity Adventures
trip cultural rating
Scuba-Diving
trip cultural rating
Sailing
trip cultural rating
Treasure Hunt

Trip Activities

trip duration
4x4 Driving
trip duration
Hiking
trip duration
Rafting
trip duration
Horseback Riding
trip duration
Scuba-Diving
trip duration
River Trekking
trip duration
Canyoning
trip duration
Rock-Climbing
trip duration
Mountain Biking
trip duration
Cave Walking
trip duration
Cave Walking
trip duration
Camping
trip duration
Swimming
trip duration
Snorkelling
trip duration
Journey by Van
trip duration
Journey by Train
trip duration
Cultural Activity
trip duration
Picnic
trip duration
Restaurant Meal

Trip Info

trip duration
Adventure Duration, 5 days in the example
trip duration
Which months the adventure is available.
From January to April in the example
trip duration
The Level of Difficulty for the Adventure;
1 being Easy 5 being Challenging

Levels of Fitness

Easy : Expect a relaxed pace throughout the whole trip. Activities may include visiting archaeological sites, short walks or hikes, all at a leisurely pace. No previous experience or level of fitness is required.

Easy to Moderate : Expect a relaxed pace throughout the whole trip. Activities may include off road driving, visiting archaeological sites, short walks or hikes, river rafting, horseback riding, cycling and trekking. No previous experience or level of fitness is required.

Moderate: Expect a rather active pace throughout the whole trip. Activities may include off- road driving, visiting archaeological sites, long walks and hikes, river rafting, canyoning, river trekking, camping, rock climbing, horseback riding and mountain biking. No previous experience is needed, but a reasonable level of fitness is required.

Moderate to Challenging : Expect an active pace throughout the whole trip. Activities may include off-road driving, visiting archaeological sites, long walks and hikes, river rafting, canyoning, river trekking, camping, rock climbing, horseback riding and mountain biking. No previous experience is needed (though it could come handy), but a reasonable level of fitness and an adventurous attitude are required. Participants need to be over 18 years old.

Challenging : Expect an intensely active pace throughout the whole trip. Activities may include off road driving, visiting archaeological sites, long walks and hikes, river rafting, canyoning, river trekking, camping, rock climbing, horseback riding, mountaineering and mountain biking. Some previous experience may be needed, as well as a higher level of fitness and an adventurous attitude. Participants need to be over 18 years old.
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SAILING IN THE CYCLADES
Easy : Expect a relaxed pace throughout the whole trip. Activities may include visiting archaeological sites, short walks or hikes, all at a leisurely pace. No previous experience or level of fitness is required.
Easy to Moderate : Expect a relaxed pace throughout the whole trip. Activities may include off road driving, visiting archaeological sites, short walks or hikes, river rafting, horseback riding, cycling and trekking. No previous experience or level of fitness is required.
Moderate: Expect a rather active pace throughout the whole trip. Activities may include off- road driving, visiting archaeological sites, long walks and hikes, river rafting, canyoning, river trekking, camping, rock climbing, horseback riding and mountain biking. No previous experience is needed, but a reasonable level of fitness is required.
Moderate to Challenging : Expect an active pace throughout the whole trip. Activities may include off-road driving, visiting archaeological sites, long walks and hikes, river rafting, canyoning, river trekking, camping, rock climbing, horseback riding and mountain biking. No previous experience is needed (though it could come handy), but a reasonable level of fitness and an adventurous attitude are required. Participants need to be over 18 years old.
Challenging : Expect an intensely active pace throughout the whole trip. Activities may include off road driving, visiting archaeological sites, long walks and hikes, river rafting, canyoning, river trekking, camping, rock climbing, horseback riding, mountaineering and mountain biking. Some previous experience may be needed, as well as a higher level of fitness and an adventurous attitude. Participants need to be over 18 years old.
OVERVIEW DAY TO DAY ITINERARY TOUR INFORMATION DATES & PRICES PRIVATE GROUPS
OVERVIEW

One of the most famous archipelagos in the world, the Cyclades have way more to offer than pristine beaches, crystal clear waters and amazing sailing experiences. They are the cradle of over ten millennia of rich history, boast extreme geographical diversity, abundant marine wildlife and feature the best of traditional Aegean architecture and Mediterranean cuisine. This sailing adventure goes far beyond mere island hopping, giving you a chance to explore way beyond each island's marina, as well as immerse in local culture, savor the local flavors and learn a thing or two about the history of this immensely beautiful part of the world. And did we mention that it provides you with the opportunity to actively engage yourself in sailing, whether you have done it before or not, The Aegean archipelago, with its clear deep blue waters is the ideal place to get acquainted with the basics of sailing and our skippers are always happy to show you the ropes! 


Trip Highlights



  • Immerse in the rich culture, delicious cuisine and millennia spanning history of Athens

  • Explore over a dozen different beautiful sailing destinations, visiting six islands in the process

  • Swim then hike to the Temple of Poseidon at Cape Sounion

  • Enjoy the laid back atmosphere on the quiet island of Kythnos

  • Relax in a hot spring while looking at the Milky Way at the tiny fishing village of Loutra

  • Savor amazing Aegean seafood on the island of Sifnos

  • See unique geological formations and swim in turquoise waters on the volcanic island of Milos

  • Swim in turquoise waters by the uninhabited tiny island of Polyaigos and, if you are lucky, spot a Mediterranean seal hunting for fish

  • Hike to the main town of Serifos and experience the "Iron island's" coffee culture  


 

DAY TO DAY ITINERARY
01
ATHENS, CAPE SOUNION & KYTHNOS

In the afternoon we meet at the marina and board the sailing boat that is going to be our home for the next week. Our guide will check you in your cabins and introduce you to the itinerary, after a short orientation on the sailing boat. Late afternoon we leave the marina, enjoying views of the southern suburbs of Athens. We head southeast, 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 Sea from the numerous chapels built high up in the cliffs. We drop anchor in Kolona beach, a natural double bay separated by a strip of sand and spend the night there.


Overnight: Cabin aboard the sailing boat

02
KYTHNOS & SERIFOS

Early in the morning, we have breakfast and a swim at both sides of Kolona beach. If you are up for it, there is a short, easy hike up to a white washed chapel, overlooking the Aegean Sea. The centuries old structure's courtyard is nowadays home to a small herd of wild goats and photo opportunities are abundant. Early afternoon 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 eastern side. Early evening 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. And if savoring deliciously fresh seafood right on the beach is your thing, this is the place to do so.


Overnight: Cabin aboard the sailing boat
Meals Included: Breakfast, light lunch on board

03
SERIFOS & MILOS

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. Some incredible sunset views is reason enough to visit Milos. Add in lunar like landscapes, a vibrant nightlife and incredible local food and you will get why the island is by far our favorite destination for our guests. If you are a meat eater we will take you to THE place on the island to try lamb or goat stew and if you prefer seafood, the tiny fishing village of Pollonia is home to numerous family run restaurants serving fresh fish right on the water. In the evening we will 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 that.


Overnight: Cabin aboard the sailing boat
Meals Included: Breakfast

04
MILOS

Milos is a volcanic island, which is evident by the bizarre geological formations seen around the island. After breakfast we get a chance to sail to a couple of 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 a half a day here, swimming and snorkeling. Hopefully we will get a chance to spot some mediterranean dolphins here. Music attracts them so bring your playlists. In the evening, we will head back to the marina in Milos and you will have the evening to yourselves to explore the island some more. Our guide will be there for you, to suggest things to do, places to visit and of course direct you to the most authentic of restaurants on the island.


Overnight: Cabin aboard the sailing boat
Meals Included: Breakfast, Light Lunch on board

05
POLYAIGOS & SIFNOS

After breakfast we leave Milos behind us head northeast passing by the straights of Kimolos. 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 evening 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 is a great sandy beach and two family run tavernas serving what is considered by many of our guests as their best meal in Greece.


Overnight: Cabin aboard the sailing boat
Meals Included: Breakfast, Light Lunch on board

06
KYTHNOS

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 on the southern part 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 an insanely relaxing spa treatment. Early evening our guide will take you on a guided tour of the island's main town, which is a 20 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 Aegean Archipelago. 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 Aegean sky, while relaxing in the natural pools where the hot springs meet the sea.


Overnight: Cabin aboard the sailing boat
Meals Included: Breakfast

07
TEMPLE OF POSEIDON & ATHENS

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 will hike to the temple and visit on of the most important archaeological sites on this side of the world. Late afternoon we will head back towards the marina in Athens, stopping along the way for a swim. Once at the marina your guide will be there to accompany you for a proper farewell dinner.


Overnight: Cabin aboard the sailing boat
Meals Included: Breakfast

08
ATHENS

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.

TOUR INFORMATION
1.
Accommodation/Meals
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Accommodation/Single Room Booking

In order to guarantee a memorable overall experience throughout your sailing adventure with Bearing True South, we have carefully handpicked a fleet of 4 - cabin sailing yachts with a large sundeck and a comfortable indoor galley for meals and relaxing. There are four double bed cabins on the main deck of the yacht. There is also an extra inflatable boat and a boat ladder that facilitate our swimming and snorkelling activities.
In all our sailing trips, accommodation is operated on a twin share basis. This means that travelling 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. There is also the option of booking a single cabin for an additional cost depending on availability at the time of booking.

Meals

When sailing with Bearing True South, you will experience a great variety of delicious food,  based on traditional Greek cuisine. Emphasizing on the regional cuisine of our destinations, we can recommend carefully selected local, family run, restaurants for our groups.
On a day when a barbeque dinner is included in our itinerary, we usually buy local cheeses, vegetables, meat or fish and bread from local markets so you don't miss out on the specialities of the region. We always choose a quiet, beautiful island beach for our BBQs and you can either help with the grilling and marinating or, alternatively, you can opt to have a swim under the stars while we cook for you.
Generally meals on board the sailing yacht are included in the standard price of our tours. "Light lunch" and "breakfast" usually refers to fresh Mediterranean salads, sandwiches, omelets or fresh fruit and local cheeses. 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.

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Tour Activities
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The style of travel in our adventures provides us a great deal of excitement, however is dependent on several factors, such as weather, terrain conditions and technical problems of our 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.
Some of the activities listed in the day to day itinerary are included in the standard tour price, while there are also optional activities at your own expense. When a guided tour at a historical/cultural site is mentioned, the costs of a professional guide is included in the standard tour price. In every outdoor activity we work with fully qualified operators whose safety track has been extensively assessed personally by us. The necessary equipment needed for every outdoor activity is always provided by the local activity operators. For your personal gear please refer to the "prepare for your trip" section below.
Please note that all activities are subject to availability, while due to the time limit in each destination, it may not be possible to do all the optional activities listed in the itinerary.

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Tour Budgeting
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Please refer to What's included/What's not included section for the services that are included or not in the standard price of your tour. For the optional activities of our tour, outdoor activities and cultural sites? entrance fees, take a look at the Tour Activities.

Tipping Your Tour Leader/Local Guides
In appreciation to the outstanding quality of services provided throughout your adventure, you may also consider tipping your Tour Leader and Local guides. Although tipping is not compulsory and it may not be customary to you, it works as a kind voluntary gesture to the people who will guide you throughout your adventure.

Spending Money
Each traveller is different when it comes to spending money while travelling. Take your spending habits and requirements into account and prepare your tour budget allowing for food, drinks, souvenirs and participation in activities not included in the tour price.
The Euro (EUR) is the official currency in Greece. You can exchange your currency for Euros at the airports or in major towns. Cash may also be drawn for ATMs available in most of our destinations. Credit cards are widely accepted in Greece. However, you should always have some cash on you, as in some remote villages no ATMs may be available.

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Joining Your Tour
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At Bearing True South, we operate "Land Only" based adventures. This means that flights to Greece are not included in the tour price. Travellers are responsible to make their own travel arrangements and make sure that they will be able to join the group at the joining point and time announced when booking, as described at the overview of the tour. Please note that the finishing point of the tour is always the same as the joining point

Our "Land Only" adventures provide you the flexibility to join one of our tours as part of longer holiday in Greece. You may spend a couple of days before or after your tour in Athens or even visit another Greek region, combining adventure, leisure and rest.

In Athens, you may also consider joining one of our day activities. Take a dive at one of Greece's numerous wreck sites, easily accessible from downtown Athens, or participate in our Historical Athens Treasure Hunt, a 'walk-through-history' game around Athens.

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Visa/Travel Insurance Information
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Health Information/ Travel Insurance

Bearing true South travellers are required to be in good physical health in order to be able to participate in one of our adventures. Please read through the day to day itinerary carefully and take into account the "Level of Difficulty" icon that appears on each one of our adventures, before booking your place.

If for any reason you are not able to participate in activities included in the tour itinerary, please inform us before booking. For any other important health issue please don't hesitate to contact your tour leader.

Travellers with Bearing True South are required to hold valid travel insurance, covering a minimum medical expenses due to accident or sickness and 3rd party liability. We strongly advise you to ensure that your insurance covers you for all outdoor activities you intend to participate in during your adventure. There might be an additional charge for certain ones. Your travel insurance needs to be evident when you join our tours.

Visa Information

Holding a valid passport and visa in order to visit Greece is your responsibility. Generally EU citizens or citizens of Member-States of the Schengen Agreement do not need to display a visa in order to travel to Greece.

Visas are not required by holders of valid passports from the following non-E.U. countries if they want to visit Greece and remain in the country for up to 3 months (90 days): Argentina, Brazil, Chile, Uruguay,  Malaysia, Singapore, Japan, South Korea, Australia, New Zealand, USA, Canada, Israel, Monaco, Switzerland, Norway, Iceland, Lichtenstein

For travellers not coming from the above countries, please contact your local Greek embassy/consulate for visa information. Please also note that most countries expect you to have at least 6 months validity on your passport in order to be issued a visa.

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Preparing for your Trip
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Before you travel, we encourage you to learn about the region you'll explore while on a tour. From local weather conditions to information on geography, local history and culture, all are essential in order to make the most out of you tour, while minimizing the possibility to face unexpected, unpleasant circumstances.

Weather Information

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 especially at night, a fact that you have to take into account when packing for your adventure.    

Packing for your tour

Space is limited on board so, while on one of our sailing trips, you are expected to bring with you a backpack or suitcase that you should keep as light as possible, as well as a daypack for your personal items and valuables.

Travel documents: Passport, visa if required, valid travel insurance

Personal health care items: personal medication, sunscreen, insect repellent, travel sickness tablets, sunglasses, insect bite gel

Clothing/walking/swimming gear (depending on the season and tour): waterproof & windproof jacket, sun hat, long trousers (wearing shorts is not permitted in monasteries and churches), shorts, swimming costume,extra towel for swimming, t-shirts, hooded tops, trainers/walking shoes, personal mattress or a sleeping bag (should you choose to sleep on the yacht's sundeck), torch, snorkelling mask and fins.

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DATES & PRICES

Contact info@bearingtruesouth.com for information and pricing on our 2020 departures.

PRIVATE GROUPS

If our dates don't suit your plans, or if you want to experience one of our adventures with your family or group of friends, we can arrange a private tour just for you on the dates that suit you, based on one of our existing itineraries.
Furthermore, with a minimum number of 4 participants, all of our tours can be customised as far as date of departure, activities and itinerary are concerned, according to your group's requirements. For groups of less than 4 travellers, standard tour prices are subject to change. In that case, please contact us in order to get a new quote.
For more information don't hesitate to contact us with your ideas at : sales@bearingtruesouth.com and we'll get back to you shortly with detailed information and pricing.

CONTACT
If you want to arrange a private group tour based on this itinerary, please contact us with your ideas and we'll get back to you shortly with detailed information and pricing.

sales@bearingtruesouth.com

TRIP ACTIVITIES
Swimming Snorkelling Sailing Hiking Cultural activity Restaurant Meal
EXTRA INFO

Duration: 7 days

Level of Difficulty: 2/5

Group Size: minimum 2 persons - maximum 8 persons per yacht

Ages: 4 years and older, younger kids travel at their parents' discretion and responsibility


INCLUDED IN THE STANDARD TOUR PRICE

Accommodation: Sailboat charter for a week, Accommodation for up to 6 guests in double cabins

Meals : 7 breakfasts & 3 light lunches on board

Transport:  Sailing boat rental costs, all electricity and water port costs, fuel costs, port authorities and marina fees

Tour Staff:  Bearing True South tour leader, Bearing True South skipper, local guides when needed

All taxes including VAT

NOT INCLUDED IN THE STANDARD TOUR PRICE

Airline tickets to/from Athens

Transfers to/from the marina arranged if needed at an extra fee

Meals not listed in the inclusions

Personal expenses

Travel insurance

Optional activities as listed in 'tour activities'

Local transport (such as taxis or buses on the islands)

Tips and Gratuities