There was an error with your log in

With over 4,000 well-equipped routes, the rocky paradise of Kalymnos is unlike anything else in the Mediterranean. Spending a week on a sailboat is easily the best way to explore the ruggedness of this Greek island, allowing you to spend the rest of the time sailing and exploring. Relatively new on the world climbing scene, Kalymnos is regarded a treasured source of routes—ranging from 5.7 to 5.14d—accompanied with a light breeze, crystal-clear Aegean Sea, and delicious food. 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. 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.

Book a call
  • Greek tradition, Mediterranean weather, and stunning sea views

  • Almost 2500 well equipped sport climbing routes for all climbing levels

  • Mountains plunging into the sea, limestone crags, and turquoise waters


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!

  • 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
  • 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.

  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
Get free trip brochure
The brochure contains:
Adventure and location overview, itinerary, available dates, what's included, how to prepare, and much more.
Brochure sent, check your inbox
Talk with us and let one of our adventure experts help you plan your perfect adventure.

Meet your guides

Lorenzo Pernigotti
Lorenzo Pernigotti
Skipper and Passionate Climber
Passionate about outdoor sports since a young age, Lorenzo chose to pursue his passions and share his enthusiasm. In the winter he teaches them how to ski by working as a ski instructor, while in the summer he makes them experience his favorite combo: sail and climb! Head of the Vertical Sailing Tour, onboard he becomes the skipper. As soon as the boat anchors, you might find him making cocktails, cooking Italian risotto, spearfishing for dinner, climbing a crag, flying down a mountain on his paraglider…
Alberto Trombetta
Alberto Trombetta
IFMGA Mountain Guide
Alberto is an experienced UIAGM/IFMGA Mountain guide and the chief guide at the Vertical Sailing Tour. From the point of Cerro Torre to the wall of El Capitan, from the desert of Saudi Arabia to the picks of Mt. Blanc, he has travelled the world to climb in the most remote places. Since the beginning, he has been on board with the VST and his kind personality combined with his great expertise are the things that make the clients love him.
Vertical Sailing Tour
Vertical Sailing Tour
Vertical Sailing Tour
Since 2013, Vertical Sailing Tour have been sailing the Mediterranean sea and climbing in the best locations in the area. Being able to access the wildest places by boat gave them the opportunity to expand the list of magical climbing spots and combine the best of sailing, climbing and other outdoor activities. Explore with them the most beautiful destinations around the world!

Watch our webinar

5.00 (5 reviews)
Camilla from Switzerland

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

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

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

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

Jonathan from Germany

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!

Things to know

  • 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 you get in this adventure:

      • VST well-proven organization (world-leading Sail & Climb guided tours since 2013)
      • An experienced, U.I.A.G.M. certified mountain guide with extensive knowledge of the area
      • Accommodation on a sailing boat — double size bed or bunk beds sorted and arranged by and among guests
      • VTS T-shirt
      • 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.
    Due to the nature of this adventure, the guide requires that a part of the cost of the trip, 300 euros, is paid upon boarding in cash. This will cover the costs of:

      • Food and pantry service
      • Bedsheets and towels
      • Boat fuel
      • Final cleaning of the boat
      • Other incurred costs during the trip.

    If you have any questions about this, contact us and we will get back to you as soon as possible!
    What’s not included:

      • Travel expenses to reach/leave the harbor of departure
      • Meals on land (skipper’s and guide’s cost of the meal on land divided among all guests)
      • Harbor fees (one or two stops at the harbor during the week)
      • Alcoholic beverages on board
      • Personal items and equipment
      • Climbing gear
  • 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!

  • 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!
  • 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 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 7 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.

  • Secure your spot for next year with a 10% deposit!
    This tour gets sold out very quickly, but with early-bird booking, you will be the first one to know about any new upcoming dates. Pick your preferred dates without the risk of your bucket list adventure selling out!
    • Only 10% of the total amount should be paid as a deposit upon booking. This deposit is non-refundable, but can be transferred to another 57hours adventure any time in case the dates don’t suit you.
    • Once the dates for 2024 are set, you can confirm your booking by the end of this year by paying another 20% of the total amount.
    • The final balance is due 3 months (90 days) prior to departure.
    • Once the trip has been confirmed, the regular cancellation policy applies.


    For regular dates, 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 7 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.

    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 2023/2024 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.  

  • 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.

Have more questions? Read our FAQ, or Talk with us
From $2,670 ()
/ 8 days
Saved to bucket list!
View list
Removed from bucket list
View list

Choose a currency

  • USD - $
    US Dollar
  • EUR - €
  • AUD - AU$
    Australian Dollar
  • CAD - CA$
    Canadian Dollar
  • GBP - £
    British Pound Sterling
  • CHF - CHF
    Swiss Franc
  • JPY - ¥
    Japanese Yen
  • SGD - S$
    Singapore Dollar
  • HKD - HK$
    Hong Kong Dollar
  • DKK - Dkr
    Danish Krone
  • NOK - Nkr
    Norwegian Krone
  • SEK - Skr
    Swedish Krona