Sailing and Rock Climbing in Kalymnos

Kalymnos | Greece
Trip Highlights

Top reasons to sail and climb in Kalymnos

  • Trip Highlight

    Greek tradition, Mediterranean weather, and stunning sea views

  • Trip Highlight

    Almost 2500 well equipped sport climbing routes for all climbing levels

  • Trip Highlight

    Mountains plunging into the sea, limestone crags, and turquoise waters all around

As you effortlessly travel from one location to another, climb the best sea cliffs of this rocky island paradise! Kalymnos, one of the most beautiful and well preserved archipelagos in the Mediterranean sea, boasts wonderful scenery, Greek tradition, cozy weather, and stunning sea views. Relatively new on the world climbing scene, Kalymnos is considered to be an incredible addition to sport climbing — easy access, especially by a sailboat, and Aegean Sea surrounding the limestone cliffs make the location arguably one of the best in Europe! The island has almost 4000 well-equipped sport climbing routes ranging from 5.7 to 5.14d! Climb anything from easy slabs, technical wall climbs, wild overhanging, and even climbs between stalactites. With well-bolted crags and a community centered around climbing, it’s the perfect spot for an active vacation, especially when you spend the rest of the time sailing around the island and exploring the best locations it can offer. Find out why you should head to Kalymnos for the best sport climbing in Greece from Emily Cole, avid sport climber and founding member of Crux Crush.


May through October

Nearest city

Kalymnos an hour away by airplane from Athens, Greece


8 days

Skill level

Beginner to advanced


Book This Adventure

Sailing and Rock Climbing in Kalymnos

8 days

Spend eight amazing days of fantastic rock climbing and sailing around the island in the idyllic setting of a Greek holiday! Discover superb rock climbing only accessible by boat, relax with your group under the cozy Greek sun, and make the most of your active vacation. Let your certified guides plan out the perfect days on the rocks and spend the rest of the time exploring the spectacular scenery, traditional cuisine, and amazing locations around Kalymnos including Telendos Island, crags of Eros, Pescatore and Irox, iconic crags of Grande Grotta, Sykati Cave and more! During your week on the sailboat, relax, discover spectacular vistas from the limestone cliffs, and upgrade your skills with an expert guide!

Trip Highlights


Day 1: Kos

Meet your guides in Kos marina in the afternoon hours and embark on your 8-day journey. Organize your equipment, settle into your rooms and get to know the group you will be sailing with for the rest of the week over a welcome dinner in a typical Greek taverna in the old town of Kos.

View on little island Kastri near Kos in Kamari bay, Greece

Day 2: Telendos

Sail out to Telendos and start to climb! You will be among the few lucky climbers that get to climb on Telendos island since it is only accessible by sea, so you can expect a relaxed atmosphere without any crowds. The crag is perfect to get into the climbing mood. There are routes of all grades to warm up for the week and refresh your skills. Enjoy the amazing view of Kalymnos as you climb and spend the evening having fun on the sailboat.

Day 3: Arginonta

Wake-up and dive from the boat before a hearty breakfast! Drop the anchor in Arginonta’s beautiful roadstead where over 900 sport climbing routes await you. This is the ideal place to go to when there’s wind blowing and you want a protected spot in the sun. Plenty of possibilities, wonderful views, and caves waiting to be explored make Arginonta one of the most interesting spots in the area.

Kalymnos Sailing

Day 4: Grande Grotta, Arhi, Sea Breeze, Little Verdon, Pocket Wall and many more…

One day is not enough for Arginonta so spend the morning of day 4 exploring new crags and check-out as many ascents as you can. Sail through the Dolphin’s Bay, also a well-known climbing spot, and move on to the yet unexplored north coast of Telendos where some recently bolted crags will give you the “sharp touch” to wrap up the day.

Kalymnos Rock Climbing

Day 5: Sykati Cave

Put your sailing skills to the test and see what you’ve learned so far from the skipper! Sail towards Sykati Cave, one of the most incredible climbing spots on the island as well as a wonderful natural harbor where you’ll drop the anchor and spend the rest of the day. The crag called “The beach” will be at a swimming distance from the boat, ideal for climbing until the sunset, when you’ll join your group for a BBQ on the beach!

Kalymnos Rock Climbing

Day 6: Palionisos

After a nice breakfast, continue on to a nice climbing crag characterized by long pitches on red limestone. Climb until dark with breaks for lunch and swimming, and end the day at the local taverna. Taste the typical Greek cuisine served at the terrace right on the sea.

Rock climbing and sailing in Sardinia

Day 7: Vathis

Today you’ll get the chance to climb right from the sea. In Vathis’ roadstead you’ll find two gorgeous spots: one cave perfect to do some deep water solo and a cliff with bolted pitches where the belayer will have to do his job while floating on the dingy! In the afternoon, sail back to Kos by 18:00.

Kalymnos Sailing

Day 8: Disembark

Pack up and take a few last photos of this wonderful location, exchange contacts with your new friends, and say farewell to Kalymnos! Disembark in the morning before 9.00 a.m.

Kalymnos Scenery

Reviews (5)

Camilla from Switzerland about Vertical Sailing Tour

I would totally recommend the Vertical Sailing Tour experience to any climbers, from the most passionate and advanced to the beginners and the ones that are curious to discover this amazing sport in the best way possible, on a sailing boat ! The team is very professional but above all fun, the best mix to have an incredible climbing experience in the best corners of Europe !

Jim from USA about Vertical Sailing Tour

This Vertical Sailing Tour is the best thing since sliced bread and cheese ! A true dream come true!! Well thought out, organized and truly Awesome. From start to finish, professional, easy to work with, Tony and Lorenzo went out of their way to accommodate my needs.
And seriously what better group of people could you want to hangout with?
Great Time, Great People, Great Tour! Lifetime friends are just waiting to meet you on this adventure!

Elisa from Italy about Vertical Sailing Tour

The idea of combining sailing and climbing together is brilliant…the nature always surrounds you, a real trip among nature and poetry! The staff is very competent, great food and lots of prosecco! A must do experience with the risk of not being able to live without it!

Flavio from Italy about Vertical Sailing Tour

To me the Vertical Sailing Tour was the best way to experience Greece and the Amalfi Coast…two unforgettable experiences!

Jonathan from Germany about Vertical Sailing Tour

Awesome crew, vertical sailing is an incredible way to explore new cracks and having the full experience of the outdoors & bay surrounding. I had an inspiring and joyful time. Always again, thanks crew!

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Things to know

Things to know

Covid measures in Kalymnos, Greece

57hours is committed to providing safe outdoor adventure experiences. We require all guides using our platform to have a COVID-19 safety plan and to make the details of that plan accessible to travelers. In most cases, group sizes will be reduced, guides will avoid overcrowded locations, and other safety measures will be met depending on the location and activity.

We also expect clients to respect local regulations and take measures to protect themselves, guides and the communities they’re travelling to. For more information on COVID-19 measures in Greece, please refer to the Discover Greece website.

Please contact us if you have any questions or require further information. We are happy to provide you with the most up-to-date information!

What’s included?

What you get in this adventure:

    • An experienced rock-climbing guide with extensive knowledge of the area
    • Skipper
    • Accommodation on a sailing boat — double size bed or bunk beds sorted and arranged by and among guests
    • Food and beverages
    • Boat fuel
    • Harbor fees
    • Final cleaning
    • Insurance covering the crew and the group during sailing and climbing

If you have any dietary restrictions, contact us prior to booking to make arrangements.

What’s not included:

    • Transportation to the harbor of departure
    • Meals on land
    • Alcoholic beverages on board
    • Climbing gear

How fit do I need to be?

Good physical shape is important but don’t worry — it doesn’t matter the grade you can climb on, you’ll always find a partner matching your level, and if that’s not the case, your guide will be there for you. Rock climbing is more about using good movement technique rather than muscling up a cliff using brute strength. To ensure you have a fun retreat, your guide will be there to supervise the climbing and to help all the climbers to improve their skills, and to choose routes that best suit your skill and fitness level. You don’t need any knowledge of sailing — the skipper will take care of everything!

What if I’ve never climbed or sailed before?

Kalymnos has plenty of options for beginner climbers. Whether you’ve never climbed before or are transitioning from the gym to outdoor climbing, your guide will customize the day to suit your skill level and objectives. With a guide by your side, you’ll learn something new, stay safe on the rocks, and most importantly, have fun!

For intermediate to advanced climbers, Kalymnos has loads of routes to spend the day on. Your guide will discuss your objectives and customize the day to your goals. Let your guide plan the day so you can focus on developing your skills while climbing the classic routes or best hidden gems the area has to offer.

If this is your first time on a sailing boat and you don’t know what to expect, here is what you can expect:

    • On board , everyone is responsible to clean up after themselves.
    • Teamwork makes the dreamwork! Be ready to participate in cooking, prepping food, washing the dishes, etc. Don’t worry if you don’t know how to cook or if you hate to wash the dishes, you can always swap the job with another crew member.
    • You may be asked to use water and electricity with moderation while out at the sea
    • Don’t worry about any sailing knowledge. The skipper will be there to ensure your safety and will give you precious tips on how to live on board.
    • If you wish to learn how to sail or if you are an experienced sailor and want to help your skipper, they will be glad to operate the sails with you and teach you anything you want to know!

What about required equipment?

Here’s what you’ll need:

    • Helmet
    • Ropes
    • Climbing hardware (quickdraws, cam devices, stoppers, etc.)
    • Belay device
    • Chalk bag
    • Harness with a locking carabiner
    • Rock shoes

Here’s a list of the equipment we suggest you bring:

    • Pack large enough to carry all the items listed (no rigid suitcases — make sure your suitcase is foldable to save space on board)
    • Backpack for daily tours, climbs and hikes
    • Hiking shoes
    • Clothes for a week of sailing and climbing
    • A warm pullover and a waterproof jacket
    • A pair of long pants and a pair of shorts
    • Bathing suit
    • Bathing towel
    • Water bottle
    • Toiletries (sunscreen, bug spray, toilet paper, etc.)
    • Sunglasses
    • Camera — optional

Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

Group sizes and age requirements

Group sizes and prices:

    • For this group adventure, the max client to guide ratio is 9:1, and cost is per person.
    • Costs per person doesn’t decrease as the group grows.
    • It takes a minimum of 5 people for the tour to operate.

Climbing days can be arranged for bigger groups. Contact us prior to booking.

Min. age requirements:

    • If you are older than 18, you’re good to go.
    • Minors younger than 18 may be permitted to climb on a case-by-case basis, but must be in the presence of a parent or legal guardian.

If your group has climbers under the age of 18, contact us prior to booking to make arrangements.


There is a $600 deposit for reserving your place onboard. Once the tour is confirmed, your guide will notify you via email. The remaining amount of the trip cost will have to be paid within 90 days prior the departure.

If the minimum number of 6 participants is not ensured, you’ll have the option to either receive a full refund of the deposit or to switch to another tour with Vertical Sailing Tours.

A deposit fee of $360 (300 euros) in cash per person will be collected by the skipper when boarding. The deposit serves as a guarantee fund which will be returned at the end of the trip if no damages had been made.

Cancellation policy

All policies regarding cancellation will be clearly laid out by your guide after booking your adventure.

If the tour is cancelled by the guide due to the lack of participants, the down payment will be fully refunded. Please note the trips for 2022 are expected to reach the minimum number of people soon, and the likelihood of trip not happening is very low. Once the tour is confirmed, the down payment cannot be refunded anymore.

If Client cancels the Booking forty (40) calendar days or less in advance of the trip contemplated by the booking, Client is not entitled to any refund.  

Getting there and meeting location

To get to Kalymnos, most people fly into Kos International Airport, about 30 minutes away from the marina. You can also fly to Athens International Airport, Greece, and then fly to the island of Kalymnos just an hour away. Once you get there, you can rent a car or motorbikes to get to the Kos marina.

Once you and your guide agree on the details of your itinerary, your guide will suggest the best place to meet. You should be at the Kos marina at 4 PM on the first day.

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