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Enjoy the Greek sun and sparkling waters of the Aegean as you sail the Cyclades Islands
Take the first step towards a private travel experience, customized just for you.
About this tour:
The shining sapphire waters of the Aegean sea invite you to come and explore on the exciting Cyclades Islands Sailing Adventure. Board the sailing yacht that you’ll call home for the week and discover the freedom of boat life!
During this amazing tour, you’ll visit historic villages and ancient sites while you explore the islands. Sail to hidden coves and secluded beaches to swim, snorkel, and kayak in the turquoise waters. Experience the unique character of each island from lively Mykonos to laid-back Kythnos and Serifos. This island-hopping sailing adventure is the perfect way to experience the incredible Cyclades.
Your tour begins at the dock in Athens where you’ll board the sailboat and get settled in your cabin. The crew will give you a tour of the boat and a safety briefing before you set sail. The destination for your first sail will be Kythnos Island.
When you arrive at the port in Loutra you can visit the natural hot springs and enjoy dinner on this lovely island.
What better than a morning dive from the boat, under the imposing temple of Poseidon, before even taking breakfast?! After breakfast on board, you will set our compasses with direction the island of Serifos, where you can find the Cycladic simplicity you might be looking for.
In case you are in Kythnos, you can go on a morning hike, before setting sails to the unspoiled and charming island of Serifos (≈ 44nm, ≈ 6 hrs sailing).
Once we reach the port, we welcome you to walk with us uphill all the way to Chora, the main town of the island. It is a steep, yet short walk up and the views, especially from the Venetian fortress will captivate your senses! Stroll through the narrow streets and get lost in Chora! Enjoy your dinner in one of the traditional tavernas and why not, some drinks afterwards in one of the fancy bars.
Overnight Location: Sailing yacht at Serifos Island
Today you will sail towards one of the least touristic and most authentic Cycladic islands, Kimolos (≈ 21nm, ≈ 3 hrs sailing). Kimolos is another volcanic island, whose name derives from the Greek word “kimolia”, which is translated into chank. The island is the perfect getaway for those looking to escape the crowds and enjoy peacefulness and tranquility, among some spectacular white sandy beaches and tiny villages.
You will spend the day anchored at one of its pristine beaches (depending on the weather), before reaching the port, from where you can walk to Chora, the main town, explore its narrow, cobbled streets and locally run restaurants and bars.
Overnight Location: Sailing yacht at Kimolos
Right opposite Kimolos lies the small uninhabited island of Polyegos, a secluded paradise with turquoise crystal clear waters that will definitely captivate your senses. This will be your first swimming stop for today. You will have time to enjoy swimming, snorkeling, dives from the boat or simply relax on the deck and sip the sun.
You will then sail along the south coastline of Milos to reach the spectacular coves of Kleftiko, probably the most photographed beach of Milos and for a reason! Kleftiko is a former pirates’ hideout with imposing volcanic rock formations, countless caves and turquoise crystal clear waters, accessible only by boat or on foot via a hiking trail.
There will be time for swimming, exploring the numerous caves and enjoying lunch on board, before sailing towards the port of Milos, where we will spend the night.
Overnight Location: Sailing yacht at Milos
After breakfast on board, you can go on a morning tour around the island to see some more of Milos’ highlights, such as the moonscape-like Sarakiniko beach, the 2nd most well-known landmark after Kleftiko, the catacombs, the place where Venus de Milo was discovered, the ancient theatre and the picturesque fishing village of Klima with its colorful postcard – like houses (tour duration approx. 3hrs, at an extra cost).
You can then say goodbye to Milos and set sails to your next destination, the charming and aristocratic island of Sifnos (≈ 20 – 24 nm, ≈ 3 – 4 hrs sailing). The exact spot/marina where you will spend this evening depends on the weather conditions.
Once in Sifnos, do not miss the chance to visit the traditional and historic settlement of Kastro, a lovely cliff-top village, which literally means Castle. Kastro is built on top of the ruins of the ancient capital of the island, it has a strong medieval character and it offers spectacular panoramic views over the Aegean sea!
Overnight Location: Sailing yacht at Sifnos Island
After breakfast, you’ll set sails to Kythnos island, another hidden gem of the Cyclades that has managed to maintain its authentic character (≈ 38nm, ≈ 5 – 5.5 hrs sailing).
You cannot visit Kythnos, without going to the unique beach of Kolona, one of the island’s landmarks! Kolona is actually a strip of sand joining Kythnos with the islet of Agios Loukas, creating a landscape of unparallel beauty! Once there, you can enjoy swimming and snorkelling, as well as lunch at the only tavern on the beach. You can also walk all the way up on top of Agios Loukas islet and enjoy the panoramic views it offers.
Later you will head to Merichas, the main port of Kythnos, where you will spend the evening (unless you prefer to spend your last night before returning to Athens anchored at a secluded beach, gazing at the stars and enjoying all the tranquillity our sailing yacht can offer.
Overnight Location: Sailing yacht at Kythnos
This morning you’ll start sailing back to Athens. Go for a final swim or snorkel during a stop on the way and enjoy a delicious lunch onboard.
When you arrive at the Lavrio marina you can visit some of the sights in Athens, and then return for your last night on the sailing yacht.
You’ll have to check out of your cabin this morning and begin your journey home or continue on your Greek adventure. Book ahead to spend some extra time in Athens!
Sail to secluded beaches and amazing islands including Kythnos and iconic Mykonos.
Hike to amazing ancient archaeological sites and on beautiful island trails as you explore the Cyclades.
Swim in the turquoise waters of the Aegean and sail to secluded beaches.
Enjoy delicious local cuisine as you explore authentic restaurants and tavernas at your island ports.
6 breakfasts and 3 lunches are included. Dinners, drinks, and alcoholic beverages are not included.
Accommodations for 7 nights are included. Accommodations before and after the tour in Athens are not included but can be added as a supplement.
Transportation for you and your luggage are included throughout the tour on the sailing yacht. Transfers from the airport or central Athens to the marina are not included.
Pricing for this sailing tour of the Cyclades depends on whether you choose to join an existing group on a specific date or if you prefer a custom tour for your group only, as well as the kind of cabin and dates of travel you choose. Note that for fixed-departure dates, a minimum of 4 travellers is required to run the tour.
Have your own private tour with just your group! There are various boat rentals available for groups from 4 to 8 (with some catamaran models that can fit up to 12). The price depends on the group size, chosen yacht category and your travelling dates. Please contact us with your preferred dates and group size to learn about all the options available. Please note that the departures are on every Saturday.
Make new friends and join a group sailing in Greece. Prices below are per person:
| Start | Finish | Duration | Places Left | Price | ||
|---|---|---|---|---|---|---|
2024-06-08 Athens, Greece 8 days / 5+ Spaces Left | 2024-06-15 Athens, Greece | 8 | 5+ | $2,325USDBook Now | Book Now | |
2024-07-06 Athens, Greece 8 days / 5+ Spaces Left | 2024-07-13 Athens, Greece | 8 | 5+ | $2,325USDBook Now | Book Now | |
2024-09-07 Athens, Greece 8 days / 5+ Spaces Left | 2024-09-14 Athens, Greece | 8 | 5+ | $2,325USDBook Now | Book Now | |
2024-09-21 Athens, Greece 8 days / 5+ Spaces Left | 2024-09-28 Athens, Greece | 8 | 5+ | $2,225USDBook Now | Book Now |
Your accommodations on this tour will be on a crewed sailing yacht. The boat can accommodate 8 to 10 guests. You’ll be able to swim and relax on the boat, or lend the skipper a hand and help with the sailing.
In some cases, the accommodation listed below may need to be substituted for other comparable accommodations.
Single Rooms and Solo Travellers
Rooms are double occupancy. You can pay a supplement of $675USD-$725USD (depending on the departure date) to have a private cabin on scheduled departure tours. Solo travellers may be required to pay a supplement.
The size of the boat depends on the numbers of guests, but you can expect to sail in a yacht from 43 to 51ft long that has 3-6 cabins with 2-5 wc’s. The examples of yacht model are Bavaria 49 and Oceanis 43.
This type of yacht offers 4-6 cabins with 2-5 WC’s (depending on your group size) and ranges from 38 to 52ft. The examples of models are Bavaria Cruiser 48, Bavaria Cruiser 51 and Bavaria Cruiser 46.
The size of the boat depends on the numbers of guests, but you can expect to sail in a catamaran yacht from 28 to 52ft long that has 3-6 cabins with 2-5 wc’s. The examples of yacht model are Lagoon 39 and Lagoon 380.
The size of boat starts from 42ft and some models meant for bigger groups offer en suite facilities. Also, these yachts are newer (build between 2015 and 2021). Some examples are Lagoon 42 and Lagoon 50.
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How hard is the Cyclades Islands Sailing Adventure?
We rate this tour as a 1/5. This tour has a flexible itinerary that allows you to choose how much you want to hike, swim, and explore. Accommodations are on a sailboat, so it is most suitable for people who are comfortable on a small boat and confident in their swimming abilities.
Do I need a visa to travel to Greece?
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
Are meals included on the Cyclades Islands Sailing Adventure?
6 breakfasts and 3 lunches are included. Dinners, drinks, and alcoholic beverages are not included.
What does partially-guided mean?
Booking a partially-guided tour is a perfect choice for those who like to be in charge of some of their time while travelling, but also don’t want to be on their own during activities. In most cases, a partially- guided tour doesn’t have a tour leader assigned to a group, but some or most of the activities, such as hikes, city walks, or historic site visits, are led by different guides. Also, in most cases, booking a partially-guided tour is way cheaper than booking a fully-guided tour!
Do I need insurance?
Yes, it is mandatory to have health and medical insurance to join this trip, and your insurance should cover all included activities. Get your Travel Insurance.
How do I get to Athens to start this tour?
You’ll meet the tour group in central Athens. Fly into Athens International Airport (ATH). If you would prefer to fly to another airport please request this at the time of booking.
Is the Cyclades Islands Sailing Adventure in English?
Yes, the tour guide and boat staff are English-speaking.
Where does the Cyclades Islands Sailing Adventure end?
This tour ends in Athens. You can depart from Athens International Airport (ATH).
What are the accommodations like on the sailboat?
You will have a private cabin based on double occupancy. There is a communal kitchen and sitting area and shared washroom facilities. You can upgrade your cabin to have more privacy and separate facilities.
Do I need special vaccines to travel to Greece?
Check with your family doctor.
Are there any travel restrictions for Greece?
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 of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.
Very Easy
We rate this tour as a 1/5. This tour has a flexible itinerary that allows you to choose how much you want to hike, swim, and explore. Accommodations are on a sailboat, so it is most suitable for people who are comfortable on a small boat and confident in their swimming abilities.
Read about our scale for Tour Difficulty Ratings.
This tour was made for you!
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