Greek Sailing
Greek Sailing

Greek Sailing Adventure

8 days

Enjoying a sailing holiday in GreecePrivate sailing holiday in GreeceView from the mast on your sailing adventure in the Greek IslandsTheres always time for swimming on this Greek sailboat holidayA hill village you may explore on your Greek Sailing holidayTaking a break at a seaside village in GreeceVisiting undiscovered beaches is a highlight of this sailing adventureLayout of the Hanse 508 SailboatLayout of the Hanse SailboatLayout of the Victoria 46 BeneteauSwimming in the Aegean Sea on this Sailing holidayPrivate Sailboat hire in GreeceSunset from a hill village in GreeceExploring villages in GreeceThis private sailboat hire will provide special memoriesEnjoying sailing in GreeceSunset on the water on this Greek Sailing holidayOn board and sailing around Greece

Experience the best of the Greek islands on this Greek sailing adventure!

Set sail for adventure in the Aegean Sea on this Western Cyclades sailing adventure! Imagine waking up on your sailboat, with the sunshine on the sparkling water greeting you each morning. Best of all, you don’t need any experience, as each boat comes with an experienced skipper, who will also be your tour guide as you explore the best of Greece.

Starting in Athens, you will spend 8 incredible days sailing around Greece. Start each day with breakfast and a refreshing swim. Then spend your days relaxing on beaches, or add some adventure with snorkelling, dinghy tours, and island hikes.

Your group can personalize a tour that best suits your needs and preferences, so this trip is great for families, but can also be customized for groups that want more vigorous adventure.

End each day under the stars and let yourself be lulled to sleep each night by the gentle rocking of the boat and the sound of lapping waves. This sailing adventure in the Cyclades is everything you’ve ever dreamed that island hopping in Greece could be, with the luxury of a chartered sailboat and your own guide and skipper for the week. The dream trip of a lifetime is within your reach, and there’s no time like the present! Book your Western Cyclades sailing adventure today!

Highlights of the Greek Sailing Adventure

Sail between islands in the Cyclades archipelago of Greece and explore them with experienced guides.
View native wildlife, such as wild goats, Mediterranean seals, and dolphins, in their natural habitats.
Swim, snorkel, and explore sandy beaches and rocky coves in the clear waters of the Aegean Sea.
Experience the history and culture of the region, touring archaeological sites, meeting locals, and eating incredible local food.


From $1,495USD
8 days
Partially Guided
  • No Booking or Credit Card Fees
  • Save Money
  • Happiness Guaranteed
Check Availability Group Savings Customize This Trip
Greek Sailing

Western Cyclades Sailing Adventure Sample Itinerary

Please note that this itinerary is a sample and all aspects of this tour can be customized to suit your preferences and goals. Whether you want an easier, family-friendly vacation or one full of epic adventures, this is the trip for you.

Day 1 Athens – Cape Sounion – Kythnos

Depending on your arrival time to Athens, you may have time to explore this historic city or shop for supplies for your sailing adventure. Head to the marina in the afternoon and get settled in on the sailboat that you will call home for this week. After a short orientation, set sail from the marina and head east, with views of some of the suburbs south of Athens. Continue past the Temple of Poseidon, one of the most impressive and iconic landmarks in Greece since ancient times. It sits high on a cliff at Cape Sounion. When you reach the island of Kythnos, spend the night at anchor in Kolona Beach. Here, a natural strip of sand creates a beautiful double bay. Kythnos is considered the gateway to the archipelago, and the island has amazing beaches, a lively town, and many chapels built in the cliffs which boast incredible views of the Aegean Sea.
Overnight Location: Aboard the sailboat
Meals: None

Day 2 Kythnos – Serifos

Start your morning with breakfast and a refreshing swim, then spend the morning exploring Kythnos. On the southern side of Kolona beach, there are sea urchin colonies in the cliffs. Snorkel from the boat over to this amazing area. Then take a short, simple hike to a whitewashed chapel that overlooks the Aegean Sea. Bring your camera to take pictures of the view, and of the wild goats who have made themselves at home in the chapel’s courtyard.

Return to the boat and sail to Serifos, stopping for a swim on the eastern side of the island. Dock at a marina for the night and leave the boat to explore the main town on the island. The town of Serifos is everything you picture in an iconic Greek town: narrow alleys, abundant chapels, windmills, plenty of great coffee, and stunning archipelago views. If you enjoy eating fresh, delicious seafood on the beach, here is a great place to do so. Return to the marina and spend the night on the boat.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 3 Serifos – Milos

Once again, begin your day with a leisurely breakfast and swim as the boat is prepared for a new day of sailing adventures around the Greek islands. Today, set sail for the island of Milos. This volcanic island is very cosmopolitan, but also boasts fascinating and unique geological formations. Milos offers all the attractions of Santorini without the crowds. Take in the traditional architecture, cafes, restaurants and bistros, and plenty of shopping opportunities. Breathtaking sunsets are guaranteed, and the moon-like landscape of Milos gives your visit a very exotic feel. There is also a vibrant nightlight. Your guide will help you find a restaurant to suit your tastes, whether it’s the best lamb or goat stew on the island or a family-run taverna right on the water that serves incredible fresh fish. End the day on a balcony overlooking the sea, sipping a cocktail.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 4 Milos – Kleftiko Bay

Continue exploring Milos today. You’ll often be reminded that this is a volcanic island, due to the unusual geological formations that can be seen all around the island. After breakfast, sail to two different swimming areas, including the incredible Kleftiko beach on the far southern point of the island. The amazing landscape and sparkling clear waters will enchant you. Discover why Kleftiko cove was previously used by pirates as you take a dinghy tour through the sea caverns and caves. Swim, snorkel, and watch for dolphins, which are often attracted to the sound of music so come prepared! Return by boat to the marina in the evening for more opportunities to explore the things you missed the night before, or repeat your favorites. Your skipper can help you find something fun to do or a great restaurant for dinner.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 5 Milos – Polyaigos – Sifnos

Leaving Milos today, you’ll sail to the northeast past the Strait of Kimolos. Visit the small, uninhabited island of Polyaigos where you can see Mediterranean seals as they hunt for fish. Spend the day swimming and snorkelling on some of Europe’s most amazing beaches on the southern side of the island. You can also choose to go for a hike, where you’re almost certain to find a herd of wild goats grazing. Leave Polyaigos in the evening and sail to Sifnos. On the southern side of this island is the Bay of Vathy, where you’ll find yet another fantastic beach and two family-run tavernas. Many guests consider this meal to be their favorite in Greece, full of fresh, local ingredients.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 6 Sifnos – Kythnos

After breakfast, leave the island of Sifnos and return to Kythnos. This time, visit the eastern side of the island, stopping along the way in a remote southern bay for a midday swim. Today’s destination is Loutra, a small fishing village where you’ll have the opportunity to soak in the hot springs or relax with an inexpensive spa treatment. Early in the evening, follow your guide for a tour of the main town on Kythnos, which is full of the traditional Greek-island atmosphere. The ancient buildings are whitewashed, the narrow streets and alleys are cobblestone, and they offer some of the best meat in the Cyclades. It is everything you ever imagined the Greek islands to be, and you’ll feel as though time truly moves more slowly here. Continue relaxing long into the evening, sitting under the stars with a bottle of cold local beer by the water or relaxing in a natural pool where water from the hot springs meets the sea. Feel your cares washed away into the Aegean Sea and sleep well on the gently rocking boat.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 7 Kythnos – Temple of Poseidon – Athens

Start the day today with a traditional cup of coffee in the village of Loutra, then sail toward the mainland. Your first stop will be the Temple of Poseidon at Cape Sounion. The sailboat will sit at anchor as we take the dinghy to shore and hike up to the temple. The Temple of Poseidon archaeological site is considered to be one of the most important in the world and you’ll be able to experience it up close. Later in the afternoon it will be time to set sail back to Athens, but not without one more swimming stop on the way. From the marina in Athens, your guide will escort you to historic central Athens where you’ll enjoy a farewell dinner. Return to the boat for one last night onboard.
Overnight Location: Aboard the sailboat
Meals: Breakfast

Day 8 Departure

Sadly, your Western Cyclades sailing adventure has come to an end. Pack your bags after breakfast and say farewell to your boat and skipper. Pleasant travels home or on continued adventures!
Overnight Location: Aboard the sailboat
Meals: Breakfast

Book Now

Greek Sailing Adventure Price and Dates

Pricing for this sailing tour in the Cyclades is the same regardless of the number of guests in your group (up to 6 people). The best time to travel to the Cyclades for this tour is from May until early October.

Prices and dates for Guided Western Cyclades Sailing Adventure

Tours begin and end on Saturdays. Tours are typically available each Saturday between May and October, though custom bookings are available outside those months.

Pricing varies depending on the standard of boat you choose:

  • Beneteau Oceanis 46’: $8,895 USD per boat (from $1,495 USD per person)
  • Hanse 508 51’: $14,075 USD per boat (from $2,350 USD per person)
  • Hanse 548 55’: $15,695 USD per boat (from $2,625 USD per person)

Boat Details for Greek Sailing Tours

Beneteau Oceanis Sailboat– 46 feet

Built in 2011 but fully renovated in 2017, this sailboat includes 3 double-bed cabins plus a bunk bed cabin for the crew. There are 2 electric toilets and 2 showers, a fully-equipped kitchen with 2 refrigerators and a microwave, and a large dining room. There are multiple fans to keep you cool (but no AC). Solar panels keep everything running smoothly and high powered dinghy engines ensure smooth and fast sailing.
Total price for a group of up to 6 guests: $8,895 USD

Hanse 508 – 51 feet

Brand new 2020 model luxurious sailboat that includes 4 spacious double-bed cabins, one of which is reserved for the crew, all with en-suite toilets and showers. There is a fully-equipped kitchen and a large dining room. High-powered solar panels keep everything running smoothly and air conditioning will keep you cool even on the hottest day. This boat is larger, wider and has foldable water platform to make sunbathing and swimming in an open sea more entertaining.
Total price for a group of up to 6 guests: $14,075 USD

Hanse 548 – 55 feet

Brand new 2020 model luxurious sailboat that includes 4 spacious double-bed cabins, one of which is reserved for the crew, all with en-suite toilets and showers. All cabins have air conditioning thanks to a generator. There is a fully-equipped kitchen and a large dining room. High-powered solar panels keep everything running smoothly. This boat is larger, wider and has foldable water platform to make sunbathing and swimming in an open sea more entertaining.
Total price for a group of up to 6 guests: $15,695 USD

Book Now

Accommodation on the Western Cyclades Sailing Adventure

Hotels on Standard Tour

Night 1-7

Onboard your private sailboat

Yes, you and your party will have private use of your own sailboat! All boats include 3 spacious, double-bed cabins as well as at least 2 toilets and 2 showers. There is a fully-equipped kitchen and a spacious dining area.

What’s included in the Western Cyclades Sailing Adventure?


7 breakfasts on board are included typically consisting of seasonal fruit, peanut butter and jam, local bread, cheese, bacon, orange juice, coffee and tea.


Accommodations for 7 nights on the sailboat are included.

Transportation during the Tour

Sailboat charter and all related expenses (fuel, marina fees, etc.) are included in the price of the tour.

Also Included

  • Services of a skipper for a week
  • Services of a bilingual tour guide for a week
  • Guided hiking, walking and sightseeing tours of all the places visited by a professional guide
  • All taxes (including VAT)

Not included

  • Airfare to/from Athens, Greece
  • Transfers where needed (can be arranged for an extra fee)
  • Meals not listed in inclusions (a shopping trip for supplies can be arranged free of charge in Athens). Dinners are typically in Greek tavernas in villages each night, and are not included.
  • Personal expenses
  • Gratuities to your guide and skipper
  • Travel insurance (required)

Optional Extras

  • Extra night in a hotel in Athens
  • SUP or Paddleboard Rental
  • Private cultural and culinary walking tour of Athens
  • Private archaeological tour of Athens with a professional archaeologist
  • Trip extensions to other parts of Greece

Frequently Asked Questions about Greek Sailing Adventure

Bearing True South is dedicated to showing the best of Greece, creating authentic, memorable and unique experiences. Their flagship sailing adventures allow guests to customize their holiday, making these adventures suitable from family holidays to epic adventures in the Aegean Sea.

Learn More

Is this tour for me?

We rate this tour as a 1 / 5, though it can be customized to more difficulty depending on your group. All activities and destinations can be customized to your interests and abilities. Guests should be able to swim.

Ask a Question

Got any questions regarding the tour? Interested in promotions for groups or want to customize this tour to fit your needs? We are here to help you!
Ask a question

Related Tours

    Greek Sailing Adventure

      Greek Sailing Adventure

        Greek Sailing Adventure

          Greek Sailing Adventure