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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.

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  • 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

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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 and embark the boat from 6pm onwards. Organize your equipment, settle into your rooms and get to know the group you will be sailing with for the rest of the week.

    View on little island Kastri near Kos in Kamari bay, Greece
  • Set sail towards Kalymnos Island and enjoy stunning views of the Dodecanese islands. Upon reaching Vathy’s inlet, anchor the boat in a secluded bay with emerald waters and an inviting beach. From here, you’ll have access to a newly bolted climbing crag, located just 100 meters from your boat! Rest assured, you’ll likely be the sole occupants spending the night in this enchanting spot.

    Vathis, Greece
  • Sail around Kalymnos and head towards the smaller island of Telendos. You are fortunate enough to be among the few climbers who have the chance to ascend Telendos Island, as it’s accessible only by sea. The plan is to explore a couple of crags, each offering routes of varying difficulty levels and distinct climbing styles. Continue climbing until the sun sets, casting a warm orange glow over Kalymnos before you.

    Telendos island in Greece
  • Wake-up and dive from the boat before a hearty breakfast! Drop the anchor in Arginonta’s beautiful roadstead where over 1,000 sport climbing routes from grade 4 up to 9 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 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 arrive at Palionisos in the evening, a serene and charming village with a stunning beach, a small pier, and an exception seafood taverna that promises an unforgettable dinner!

    Rock climber at Scenic Rocks in beautiful golden light on a sunny day. Destination Greece, Europe
  • Set sail towards Sikati Cave, a truly unique wonder in the world, perfect for those with extraordinary skills—it just might become the most incredible climbing spot you’ve ever experience. The secluded white beach nestled at the cave’s base forms a perfect natural harbor where you’ll anchor. Additionally, there’s a crag known as “The Beach”, conveniently located just a short swim from the boat, providing an ideal setting for climbing until sunset.

    Kalymnos Rock Climbing
  • The crags are easily reachable from the boat and you’ll enjoy climbing there until lunchtime. It’s your final opportunity to savor the island’s exceptional homemade cuisine at your guides’ friend’s taverna. Take one last refreshing swim in Palionisos’ azure waters before hoisting the sails and setting the course for Kos.

    Kalymnos Rock Climbing
  • 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 by 9 am.

    Typical Greek monastery in Kalymnos
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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!
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

  • 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
      • Skipper 
      • 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
      • Pantry-ready service (shopping for food and beverages will be done by the VST staff prior to your arrival)

    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
      • 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 for any extra nights spent in the harbor (if the skipper decides to stay due to adverse weather or sea conditions)
      • Boat fuel (to be divided equally among participants, estimated to be €25 per person)
      • Alcoholic beverages on board
      • Personal items and equipment
      • Climbing gear
  • Good physical shape is important but don’t worry — regardless of your climbing grade, 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!

    Still, health and physical fitness are crucial to actively engage in daily activities of hiking and rock climbing. Participants are strongly encouraged to have proficient swimming skills, especially if they plan to engage in the challenging deep water soloing during the tour.

    Please keep in mind that there’s no multi-pitch climbing, no slack-lining, no deep water soloing, and no water skiing available on this trip.

  • 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.

    You will spend your week on a 45 to 55-foot Monohull or Catamaran sailing boat. This magnificent boat has 4-5 two-people cabins, a spacious living room, well-equipped kitchen, and a deck perfect for late night hang-outs. With her, you’ll sail countless coves and experience the island the way it was meant to be experienced! If this is your first time on a sailing boat and you don’t know what to expect, here is what you can expect from life on board:

      • 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.
      • When at sea, it’s important to use water and electricity conservatively. 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!
  • Personal climbing gear:

      • Helmet
      • Single rope 60/80 m
      • Climbing hardware (quickdraws)
      • Sport climbing single rope
      • Belay device
      • Chalk bag
      • Harness with a locking carabiner
      • Spare carabiners
      • Climbing shoes shoes 

    If you need to rent any gear, contact us prior to booking to make arrangements.

    Personal items:

      • 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 (35/45L)
      • Hiking shoes (no sandals, the terrain is rough)
      • 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.
      • The crew typically consists of the skipper, the mountain guide, and occasionally a third staff member, along with 7 to 10 guests.

    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.

  • 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.

    You can board the boat in Kos Marina from 6 pm onwards on Day 1.

  • 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!

  • Secure your place on this year’s adventure with a $550 deposit due upon booking. The remaining amount is paid 2 months (60 days) prior to departure.

    Secure your spot for 2025 with a 10% deposit! This tour gets sold out very quickly, but with early-bird booking, you’ll be the first one to know. Pick the month that suits you best and we’ll let you know once the dates are live—don’t risk missing out on your bucket list adventure!

      • 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 in case the dates don’t suit you by the end of the year.
      • Once the set dates for the following season are live, you can confirm your booking by the end of this year by paying another 20% of the total amount.
      • The final balance is due 2 months (60 days) prior to departure.

    Once the trip is confirmed by the guide, the cancellation policy stated below applies. If the Client does not pay the remaining balance at the latest 2 months prior to the tour, the Guide reserves the right to cancel the Booking and retain the Client’s deposit. If the Client cancels…

      • More than 45 (forty-five) calendar days prior to the start of the tour, the balance payment will be fully refunded.
      • 45-30 (forty-five to thirty) calendar days prior to the start of the tour, Client is entitled to a 50% (fifty percent) refund of the balance payment.
      • After that deadline, Client is not entitled to any refund.

    Cancellation requests must be made in writing. Payment for boat extras has to be paid in cash at boarding. If the Guide cancels a tour, Client who has booked the tour will receive a full refund of the amount paid to the Guide at the time of booking. The Guide will not refund any additional expenses incurred by the Client related to the tour (such as transportation tickets, hotels, etc.). Client will also have the option to apply the amount paid towards joining another tour. In the unfortunate event of tour cancellation caused by a force majeure event, including but not limited to natural calamities (e.g., storm, earthquake), political tensions, national disasters, medical emergencies, or any other cases beyond the Guide’s control, no refunds will be provided.

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