Sailing & Climbing in The Greek Islands

A unique 8-day experience of sailing and climbing through Greece’s idyllic Dodecanese islands.

8 Days (land only)

from Kos to Kos


from $2,352


Activity Level

An 8-day adventure exploring Greece’s legendary Dodecanese islands, by land and sea. You’ll hike, climb and explore mountains and coastlines by day and sleep at sea by night in the most excitingly diverse combination of adventure styles we’re running this year.

Welcome to Greece’s Dodecanese islands - and your journey starts in Kos, first mentioned in Homer’s Iliad and visited by the legendary Heracles (Hercules). We’ll arrange for your transfers from the airport to the marina, where your floating home for the next week is currently moored - and after introductions and a little free time to go exploring, you’ll turn in for the night, since you’re setting sail in the morning.

Exciting times. Best of luck sleeping!

Night: Onboard sailing boat.

Today we’ll set off early, leaving Kos to follow the underwater mountain range that forms these islands. Our next destination is Pserimos, a beautiful island of little more than a hundred inhabitants, and we’ll sail along the coast and walk around the island enjoying the hot sun and cooling turquoise water that will be our constant companions for the next week. From here we’ll move on to the dramatic mountains of neighbouring Kalymnos, where we’ll be rock-climbing for the next few days. We’ll moor the boat at Kalymnos for the night.

Night: Onboard sailing boat.

Kalymnos has been described as ““the epitome of sport climbing”, and with 80 scalable crags and more than 2,000 different routes on offer, it’s not hard to see why. For the next two days, you’ll be shown the best in Aegean rock climbing, and be given the chance to explore routes according to your level of skill, under the expert guidance of our instructors. If you are a beginner, training can be provided. You’ll enjoy incredible views and stretch your muscles nicely - before collapsing back on the boat at night for the best sleep you’ve had all year.

Climbing: 6 - 8 hours / day.
Nights: Onboard sailing boat.

Now to explore properly! For the next 3 days,you’ll set off on a circular sailing adventure round the nearby islands, combining sailing around spectacular coastlines and into stunning bays and inlets for some rest & relaxation time, and hiking along beaches and across mountainsides.

You’ll get a feel for what life is like in the Dodecanese, you’ll meet the people, try the local food, and explore landscapes essentially unchanged since Classical times. This is the Greece you came to see - and you’ll be exploring it up close, and experiencing a world you’ll never forget. Weather permitting, your route will be Kalymnos to Astypalaia (the most beautiful place we’ll visit on the whole trip), to Nisyros and finally back to Kalymnos - with an alternate route available from Kalymnos to Leros, Lipsi, Kampos/Patmos and back to Kalymnos. On the seventh day, you’ll sail back to Kos, ready for departure the next day - and everyone will toast their farewells during your last night on the boat.

Trekking: decided in group.
Sailing: depending on weather and route.
Nights: Onboard sailing boat.

Once you’re packed, it’s sadly time to depart. Depending on your flight time you might have a chance to enjoy a little more of Kos - and we’ll arrange for transfers to the airport when it’s time for you to hit the road home.

  • Two days climbing the limestone rock faces of the island of Kalymnos, one of the best rock climbing locations in the world, training provided if needed.
  • Hiking and exploring the rugged mountains and warm, pristine beaches of the islands of the Dodecanese, including Kalymnos, Pserimos, Leros, Lipsi and Kampos and/or the cycladic Astypalaia if weather allows.
  • Learning how to sail in some of the most stunningly beautiful seascapes in Europe.
  • Enjoy swimming and snorkeling in the paradisiac water of the Greek Islands, discovering an entire world of life under the water.
  • Sleeping onboard a boat at night, and learning the rhythms of life at sea while you’re exploring an island chain in the company of experts and enthusiasts.
  • Get a unique perspective of an exciting and beautiful country and its people.
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What's Included

  • 7 breakfasts, 1 dinner.
  • Sailing boat with professional skipper and accommodation onboard for 7 nights
  • Port taxes, fuel, electricity and water port costs and cleaning fees
  • Bed linens and towels.
  • Snorkeling equipment.
  • 2 Full days of guided and instructed climbing (including transfer from port to crags and all the necessary gear)
  • Transfers between marinas and from/to airport.
  • Financial protection in accordance with The Package Travel regulation

What's Not Included

  • Flights
  • Meals other than stated
  • Travel insurance
  • Allow £10-15 for each meal not included.


07 Sep - 14 Sep
...or check with us for any other dates and tell us about your group size - most of our departures are bespoke!

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