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Cultural Sailing Holidays

Explore the beauties of the Aegean Sea

Join us on this sailing adventure holiday in Cyclades.

A truly unique and full sailing experience. We create and deploy cultural sailing cruises, taking you hand-by-hand across the most beautiful corners of the Aegean Sea and around breathtaking coastlines without forgetting that our main purpose is to enjoy happy miles of sailing while experiencing the local culture.

Combine sailing & cultural experiences in Kea, Kythnos, and Serifos Islands.

Sail with our professional experienced skippers, off the beaten path, away from the tourist traps, in a unique journey you will remember forever.
Let our local guides introduce you to the secrets of the islands. 
Here is a sample of what you will experience while sailing and exploring with us for a week…

Day 1 : KEA

Meeting in the morning at Lavrio port. Then we depart for the island of Kea. Briefing, arrangement of provisions, and supper at one of our favourite taverns in Korissia or on board. 

Day 2: Kea

In the morning and after breakfast we will visit Ioulida, Kea’s Main Town. A short guided walk through the village and onto its outskirts to pay homage to the island’s mascot: Leon, the lion of Kea. Back to the boat and sail to Karthea Beach and its archeological site.

Overnight on board – Karthea Beach.


Sailing and exploring the east side of Kea and the coastline. Free time to swim and relax and why not try a Qigong Session on board.

Optional Scuba dive. * 

Evening sail to Kythnos Island


Sail around Kythnos. Day of leisure, swimming, and relaxing on board at one of the most beautiful beaches of the island, the Kolona beach. In the evening we will go deep into Kythnos culture and get a pottery workshop in the heart of Chora village, conducted by the oldest potter on the island! Step by step you will be guided through its intriguing secrets, and of course, at the end of the day, you will depart with your own handmade souvenirs!
Overnight on board.


In the morning and after breakfast we will head to picturesque Dryopidae village and then we will explore, with a light hike the Katafiki Cave. We will have lunch at the village and in the evening we will head to Loutra beach, in the homonymous bay which took its name from the hot springs located there. Time to rejuvenate at the first spa/therapy hotel in Greece, built during the time of King Othon and Queen Amalia in the mid-19th century.
Overnight on board.


Sail to Serifos. Depending on the wind, Platis Gialos, Skala, and Avessalos are just a few of the top beaches to visit and enjoy swimming. In the evening we will explore the capital town From Kastro, the peak, you’ll be treated to views of other Cycladic islands, like Sifnos, Milos and Kimolos, and in cute little squares like Pano Piazza you’ll experience authentic tastes such as rakomelo (raki infused with honey and spices).


Serifos is often dubbed the Iron Island of Greece, as it has been known for its ores since ancient times. The island’s mining activity carried on throughout the centuries until it stopped in the 16th century when the Ottomans occupied Serifos, today we will explore on foot the mines with a short hike. Evening free of activities, time to relax and swim. Dinner on board.

Day 8: End of Program

Last day, the last dip in the sea, and time to go back to Lavrio Port.

Kea Cyclades Greece
Kea Island Walking Tours
Kea Walking Tours Cyclades
Kea Island Walking Tours
Kythnos Cyclades Greece

  • Duration

    8 days / 7 nights

  • Persons

    6 (min – max)

  • Next Departure

    From April to October

  • Departure Dates

    Any time between April to November

    Private Basis
  • Highlights

    • 7 days of sailing
    • Sightseeing Tour at Ioulida Town in Kea(*+Archeological Museum) with a light hike to “Leon” statue
    • Karthea Archeological Site visit in Kea
    • Pottery Lessons in Kythnos
    • Sightseeing Tour in Dryopidae Town in Kythnos
    • Hike to the cave in Kythnos
    • Thermal Springs in Kythnos
    • Sightseeing Tour in Serifos
    • Local Products tasting with rakomelo in Serifos
    • Serifos mines short hike
  • Included services

    • 7-night on board (The boat – The Skipper – Fuel – port fees – end cleaning)
    • Group Leader, Cultural Guide, Walking guide
    • Outboard and tender
    • All experiences and activities as described
    • All necessary local transfers.
    • 24-hour support.
    • English-French – Italian-speaking skippers and guides with local knowledge.
  • Not included

    Boat Services :

    • Hostess/Light Cooking 
    • Chef on board
    • Provisions (breakfast, lunch & supper)
    • Crew’s meals 

    Other Services :

    • Flight Tickets
    • Airport Transfer to /from Lavrio Port (upon request)
    • Travel insurance (please arrange your own)

Trip Details

Insurance: Participants should be covered by their own personal travel-health insurance prior to the trip. The personal insurance must at least cover medical expenses.
One Foot Forward is not responsible for any accidents or mishaps directly or indirectly related to the tour. 
(See Terms & Conditions)

On land Transportation: We travel by taxi, private cars or minivan 

The above itinerary is an example of what you will experience on our Culture Sail Program around the islands of the Cyclades. We don’t follow the same route every week and the itinerary may slightly change due to the weather and other factors beyond our control. Remember that we cannot go against the weather

Group Size: 6 participants in 3 double cabins.

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