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Highlights
Experience the best of the Greek islands on this 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.
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!
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!
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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
Greek Sailing Adventure Price and Dates
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:
- Hanse 418 42’: from EUR12350 per boat (from EUR2060 per person)
- Hanse 508 51’: from EUR15175 per boat (from EUR1895 per person)
- Hanse 548 55’: from EUR16870 per boat (from EUR2110 per person)
Boat Details for Greek Sailing Tours
Beneteau Oceanis Sailboat– 46 feet
She sports 2 double cabins (2 in the stern) and 1 bathroom/shower for the guests. There is also one extra double cabin in the bow and 1 bathroom/shower for the crew. She also boasts a fully equipped kitchen and a very large dining room area in her galley, as well as an impressively large sundeck. She has a 57 hp motor engine that we use when there's not enough wind to power the sails. She comes equipped with snorkeling gear. br> Total price for a group of up to 6 guests: from EUR12350Hanse 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 8 guests: from EUR15175
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 8 guests: from EUR16870
Accommodation on the Western Cyclades Sailing Adventure
What’s included in the Western Cyclades Sailing Adventure?
Meals
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
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
- How hard is this tour?
- Is this trip appropriate for families?
- Will the tour company help me prepare for my trip?
- What can I expect the tour company to provide prior to my tour?
- What add-ons or additional services are available?
- Do I need a Visa?
- Are meals included?
- Do I need insurance?
- Can you accommodate guests with disabilities?
- How do I get to Athens to start this tour?
- When and where should I arrive to begin my sailing adventure?
- Where does the tour end?
- What can I expect from a typical day of sailing?
- Do you sail at night?
- What if there’s bad weather?
- Are the tours in English?
- How much should I plan for food and personal expenses?
- Can I rent any water-sport equipment?
- What is the weather like in Greece?
- What should I pack?
- Do I need vaccines?
- Are there any travel restrictions for this country?
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.
Yes! The sample itinerary is fine for families with children ages 4 and up. Arrangements can be made to accommodate families with children ages 3 and younger. Please make a note of this when booking your tour.
Yes! The tour company will arrange 3 different video chats in preparation for your trip. By the time you arrive in Athens, you and your guide will have gotten to know each other, customized your tour to your preferences, and talked through everything you need to know to have a great trip!
The tour company offers access to online resources such as packing lists and interactive sightseeing maps. They can also offer advice and help booking extra hotel nights or transportation. If you would like to extend your trip to visit other parts of Greece, they can organize that as well.
For an additional fee, guests can rent a paddleboard or SUP, arrange for a private cultural and culinary walking tour of Athens, take a private archaeological tour of Athens with a professional archaeologist, or extend their trip in other parts of Greece.
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
7 breakfasts are included. Other meals and snacks are at your own expense. A shopping tour can be arranged to purchase supplies. Dinner will often be in a restaurant (at your expense).
Yes, it is mandatory to have Health and Medical insurance to join this trip. Get your Travel Insurance.
Generally, it is expected that guests be able to get on and off of the sailboat unassisted by walking over a gangway. They should also be able to climb the 4 steps between the deck and the galley. However, arrangements can sometimes be made to accommodate guests with mobility challenges, so please reach out so we can learn more about your individual needs.
Make your own way to Athens, flying to Athens International Airport (ATH). The tour begins at the Lavrion Marina, which can be reached from the airport via public transportation or by arranging a private transfer.
Please meet at the Lavrion Marina in Athens on the Saturday that your trip begins between 1-3 PM. If your travel plans require this time to be adjusted, please contact your tour guide. In the case of needing to change marinas, you will be contacted directly.
The tour ends in Athens where it began. Checkout on the last day of your trip (Saturday) is at 9:00AM, which allows time to travel to the airport in time for most departing flights.
Your day begins with breakfast and time for a refreshing swim or a stroll on the island. By late morning, set sail toward the next destination. In the early afternoon, stop at point of interest along the way, or simply take a break to swim or snorkel in an uninhabited bay. Early in the evening, you’ll reach the place where you’ll spend the night, either dropping anchor in a bay or pulling into a marina. Spend the evening on the island sightseeing and end with an authentic Greek dinner in a local restaurant.
Rarely. We only sail at night if the need arises, such as an unfavorable weather forecast or a guest’s need to leave later for a specific reason.
Your guide and your skipper will monitor weather conditions and forecasts and choose an alternative itinerary if necessary.
Yes, the tour guide is English speaking.
Compared with North America, Greece is relatively inexpensive. A budget of $40-60 USD per day will allow for a nice dinner (including alcohol) and personal snacks throughout the day.
Yes, you can rent a paddleboard or SUP for an additional charge.
Expect summers in Greece to be hot and humid. In May and October, there is higher likelihood of cooler temperatures and occasional rain, but in July and August, temperatures range between 25-40°C. While open seas are always unpredictable, typically the seas are calm and ideal for sailing in the summer.
Remember that space is limited on a sailboat, so please try to pack light. You’ll need clothes appropriate for the weather, and a water/windproof jacket in case of wet or cool weather. Bring sun protection such as a hat and sunscreen, swimwear, snorkelling gear and good walking shoes for hikes. Remember that wearing shorts is not permitted in monasteries and churches, so have at least one pair of long trousers or a long skirt. A flashlight and an umbrella may prove useful, and you can also consider bringing a camping mat and sleeping bag if you choose to sleep on deck.
Check with your family doctor.
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview on the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provides advice on foreign travel. Note that the travel advice may change depending on your nationality.
Customer Ratings
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.
