Discovering Greece: hiking or sailing?

To cut straight to it, take the test: in two minutes it tells you which way your heart leans.

Greece on foot: stepping into the landscape

Walking in Greece means stepping into the landscape rather than skirting it. The trail takes you under the olive trees, over a pass where a white chapel clings to the rock, out onto a plane-shaded square where a cold frappé is waiting. It is travel at human scale, paced by villages and encounters: the shepherd who greets you, the taverna owner proud of her recipe.

It is also the most accessible way to discover Greece in depth, with no need to be an athlete. On our self-guided trips, you move at your own pace, route notes in hand and luggage transferred from stage to stage. On our guided trips, an English-speaking guide opens up the history of each place and the addresses worth knowing. The gentle Cyclades of Serifos, Sifnos and Milos, the gorges and villages of Crete, the ancient sites and turquoise coves of the Peloponnese, or the luminous green of the Ionian Islands: every region has its trails, and all of them lead to a table. Here, culture makes the journey as much as the scenery does.

That is precisely the journey Kelifos has been composing season after season: the trails and the village tables, minus the logistics. There remains a quite different way to travel the country, and it has its devotees: heading out to sea.

Greece under sail: the freedom of the open sea

Taking to the sea means trading the trail for the wake. Under sail, Greece reads differently: you link the islands without a ferry timetable, drop anchor in a cove no road reaches, dine on deck facing the sunset, dive off the hull at first light. The Cyclades, the Saronic Gulf, the Sporades and the Ionian Sea lend themselves beautifully to this island-hopping. It is a full week of travel, far more than a day out: the boat becomes your floating home.

You still have to pick your formula, and the parallel with travel on foot is uncanny. Chartering a sailboat with a skipper (and why not a cook or a hostess on board) is the maritime equivalent of a guided trip: someone steers, knows the anchorages and watches over everything, you simply enjoy the ride. A charter without a skipper is the counterpart of a self-guided trip: the helm and the logbook are yours, provided you hold a license and have some experience. Between the two, the cabin cruise is the friendliest formula of all: you book a cabin with a private bathroom aboard a boat shared with other travelers, most often a catamaran. Professional crew, itinerary already mapped out, all-inclusive: it is the seagoing counterpart of a small group on the trails.

This is not something you improvise on your own. If it tempts you, a specialist agency like GlobeSailor lets you charter a sailboat or a catamaran, with or without a skipper, or book a Greece catamaran cruise almost anywhere in the country: a dedicated expert advises you from the choice of boat to the day you cast off, and every boat comes from a professional owner or charter company.

The cruising area then matters as much as the boat. The Saronic Gulf and the Ionian Sea, more sheltered, suit beginners and families. In the Cyclades, the meltemi can blow at the height of summer and make sailing more demanding: better then to have a few miles under your belt, or a skipper at the helm.

Walking or sailing: the comparison at a glance

Here, without varnish, is what really sets the two ways of traveling apart.

On foot or under sail: what should really guide your choice

In the end, the right trip is simply the one that matches how you like to be on holiday. All that is left is to work out which way you lean.

Walking is made for you if…

• What makes you travel is the encounter, the village taverna, the old stones and the stories that come with them.
• You want to discover Greece in depth without needing sea legs or any technical background.
• You like everything arranged (charming addresses, transfers, luggage carried) so that you only have to walk and savor.
• A predictable budget and a turnkey trip matter to you.

If that sounds like you, our bias is out in the open: to taste the Greek soul and its village tables, nothing replaces the trail.

Sailing will call to you if…

• The sea is your horizon: you dream of empty anchorages, swims straight off the hull and nights rocked by the waves.
• The freedom to change course with the wind appeals to you more than exploring inland.
• You already sail and feel up to taking the helm, or you would rather hand it to a skipper and think about nothing at all.
• Sharing one boat with family or friends tempts you.

In that case, chartering a sailboat or a catamaran, with or without a skipper, will be your gateway to Greece seen from the water.

Take the test: walker or sailor?

Seven answers, and you will know which way your heart leans. Play along, without overthinking it.

If you travel for the culture of a place and the taste of its tables, Greece is discovered first on foot, and that is our whole craft. If it is the call of the open sea that stirs you, sailing will open up coves the land knows nothing about. Either way, what matters is taking your time.

Frequently asked questions

Hiking or sailing: which costs less for a week in Greece?

Travel on foot has the advantage of a clear, predictable budget: charming accommodation, transfers and luggage are included, and you know the price in advance. Sailing varies more: the rate depends on the boat, the season, the fuel, the home port and whether or not there is a crew. With a group, chartering a sailboat can become competitive per person. For a couple, travel on foot is often still the more economical.

Do you need a boat license to sail in Greece?

Yes for a charter without a skipper: Greece asks for a license and sailing experience, often evidenced by a sailing résumé. But you can absolutely take to the water without knowing a thing about handling a boat by choosing a sailboat with a skipper, or a cabin cruise: a professional steers, and you enjoy the trip.

Can you discover Greece by boat without knowing how to sail?

Yes. It is even the most relaxed option for a novice: on a sailboat with a skipper, or a cabin cruise, a professional knows the anchorages, reads the weather and handles every maneuver. You only have to enjoy the trip and choose your coves. A charter without a skipper, on the other hand, calls for a license and real experience at the helm.

What is the best season, for walking as much as for sailing?

For walking, spring (May-June) and early autumn (September-October) are ideal: the heat is gentle, the light superb and the crowds thin. In July and August the trails call for an early start, but sailing is fully in its season. The meltemi, that northerly wind, only concerns the Cyclades and only at the height of summer: elsewhere, from the Saronic Gulf to the Ionian Islands by way of the Sporades and the Dodecanese, summer sailing is trouble-free.

Do people get seasick on a sailboat in the Cyclades?

It depends on the person and on the weather. At anchor and in a calm sea, you barely feel a thing. Sailing in a strong wind, the more sensitive among us can be affected. If seasickness worries you, a sheltered route (Saronic Gulf, Ionian Islands) and a skipper who adapts the program make a real difference. And if the doubt lingers, travel on foot spares you the question.

Hiking or sailing with family or friends?

Both lend themselves well to traveling as a group. Sailing has the charm of a shared adventure on one boat, with swimming and life aboard, popular with teenagers and groups of friends. Travel on foot suits every age, with no prerequisites, and lets each person move at their own pace. A matter of temperament more than of age.

Can you combine hiking and sailing on the same trip?

It is possible, but the two formulas each have their own logistics, and mixing them into a single week often calls for a tailor-made trip. The simplest approach is to live one experience fully at a time: one year on foot, from village to village, another on the water. On our side, we guarantee the first, with the slow-living touch that is our signature.