Sailing and Hiking cruise

Combine sailing with an amazing hiking cruise through the Greek Cyclades islands, with breath-taking views of the Aegean; follow mountain trails through traditional villages, ancient settlements and sail to virgin beaches where you can rest and have a refreshing swim.

Why go on a Sailing and Hiking Cruise?

You can charter the whole boat (up to 6 guests) or by the cabin on our sailing and hiking cruises. On board will be a skipper and a hiking guide. Each day you will sail to a new island in the Cyclades, away from the crowds and the tourist hotspots, to lesser known, more traditional islands with wonderful landscapes. You will stop in a beautiful bay or small fishing port for lunch and a swim and sail a bit more in the afternoon to the next destination. If there`s time, you`ll go for an evening hike, often following a mountain trail to the hilltop village with magnificent views, or around the surrounding countryside. Then dinner at a taverna and a well earned sleep on board the yacht. Sometimes you`ll hike in the morning before you set sail. Hikes are adjusted to accommodate all levels of walkers and a comfortable pace is set.

Hiking season is usually from May to mid July and from September to October as it`s too hot to hike in August. Cruises are from Saturday (embark 5pm) to Saturday (disembark 9 am) and usually begin from the island of Paros or Syros in the heart of the Cyclades islands.

Sailing and Hiking Cruises


  • Discover off-the-beaten track traditional Greek trails
  • Experience local Greek culture, cuisine and traditions
  • Visit remote mountain villages
  • Sail to a new Cyclades island every day
  • Meet like-minded explorers
  • Keep fit and healthy breathing in the fresh Aegean air

We’re as flexible as the weather!

The below itinerary is an example of what you will experience on our Sailing & Hiking Cruise around the Cyclades islands. 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! We will do our best.

Please note itineraries vary week by week, with embarkation / disembarkation also from Syros, Paros, Naxos, Milos – all of which are well connected by ferry from Athens.

Charters run from Saturday (check in: 17:00) to Saturday (check out: 09:00)



  • s/y Tahita, Sun Kiss 45 Classic (Click to view photos)

    On our sailing yacht “Tahita” (Jeanneau Sun Kiss 45) we can accommodate up to 6 guests in 3 double cabins. Your crew: Skipper and hiking guide will occupy a separate crew cabin. The Sun Kiss 45 is one of the most exceptional and elegant classical models created by Jeanneau, known and recognised for its strength and sailing capabilities, for sailing as well as cruising the world over. There are 2 toilets/showers and a stern shower on the diving platform. In order to guarantee the maximum space and comfort for our guests, we take up to 6 people each time, while keeping the cost at a minimum.

Further details...


“Finished up our holiday with time in Greece including a week onboard the yacht “Tahita” on a sailing & walking tour of the Small Cyclades Islands. Beautiful weather and great sailing with our skipper Sotiris and his first mate Annie. We visited many small islands and walked in the afternoons with Annie who has great local knowledge. This usually ended up in a local taverna with delicious local cuisine, lots of wine and singing, so much fun!! Angels, William, Patrick, Deborah and Lara, Australia!

“Tahita sailing for our family around the Cyclades was a memorable experience. Sotiris and Annie were fantastic and gave us a truly full on sailing time. The afternoon walks with Annie topped off our days on the water perfectly. I personally would love to do another adventure on Tahita and will be recommending you to my friends back in Australia. Thanks for the great time!” Pat, Australia 

2023 prices

Prices start at €850 per person in a shared cabin. Please contact us for a specific quote for your requirements.

Price includes:

  • skipper and walking guide
  • accommodation on sailing boat (up to 6 guests)
  • sailing around the Greek islands
  • local VAT & taxes
  • breakfast provisions (self-service)
  • water supplies
  • port fees
  • outboard and tender
  • final cleaning
  • bed linen & towels


The fee doesn’t include*:

  • fuel
  • private marina fees (if any)
  • crew meals
  • lunch or supper
  • optional crew gratuity

* You should allow around €100 per week per person, payable on embarkation in cash, (for 6 guests) for fuel, crew meals and cruise expenses. How much fuel is used will depend on how much wind there is and how often the engine is used. Marina fees are only charged in a few locations. You will usually moor at small fishing ports and remote bays but once or twice per week it is necessary to go to marinas to refill the water tanks and so on.

Regarding lunches, guests usually buy provisions for a light lunch i.e. salads, snacks on board, and in the evening you would go out together to the main villages for supper at local tavernas. Supper at a local taverna with local wine costs around 10-15 Euro per adult. Tasting local food, products and wine is an important aspect of your holiday and you`ll find that most taverna owners grow their own vegetables, raise their own animals & make their own wine.

Are you interested? Fill in the form below...

Personal Information

Booking Information

ESPA Banner