• Captain or pirate?

    Captain or pirate?

    Decide and explore the ocean!

Sailing & climbing

09.09.2017 - 16.09.2017

16.09.2017 - 23.09.2017

23.09.2017 - 30.09.2017


Enjoy the ocean!

Enjoy the ocean!

Now it is all about sailing and conquering peaks. Reach for your highest highs!

We chose one of the most extraordinary spots in the world for climbing.

Kalymnos and Telendos are awaiting you to explore their geophysical beauty. Bring your climbing equipment and don´t forget your towel – there is nothing better than a refreshing bath in the sea after exploring the rocks.

Start sailing!

Start sailing!

Discover beautiful greek islands and hidden splendours most landlubbers couldn’t get to! Explore new climbing routes and the view on top will be your greatest reward.

Entering the yacht at the port of Kos, you start heading to Arginonta bay in Kalymnos for a sunset climbing session. The following day is dedicated to the beauty of Telendos where you can spend the entire day climbing, swimming and relaxing. For the rest of the week you will explore Kalymnos to its full extent with stops at Emporios bay, Sykati, Palionisos and Vathi before returning back to Kos.

This week is a perfect mixture between activity and tranquility – so sail like a captain and play like a pirate.

  • Vertikal week

    Vertikal week

    09.09.2017 - 16.09.2017
    16.09.2017 - 23.09.2017
    23.09.2017 - 30.09.2017
    Where: Kos Marina Greece
    Duration: 7 days
    Activity: Climbing
    Price: 890€

    Yacht & Skipper
    Climbing 6 days
    Climbing equipment
    Breakfast and lunch
    Mooring fees
    Mountain guide
    Towels and linen

    Not included:
    Dinner and beverages

    CAVE: There is no climbing coach. It aims towards experienced climbers who are expected to bring their own gear.

    Contact us!

  • Your Yacht

    Your Yacht

    We will place you on the perfect yacht along with other people who have booked cabins. If you want to stick with your friends, notify us at the time of booking or just email us. We will send you the details of your yacht, arrival instructions and invite you to a Facebook group to meet the rest of your crew at least 2 weeks prior to departure.

    Contact us!

  • Itinerary



    Welcome aboard

    Check in and bags drop-off at Kos Marina at 5:00 pm. Meet your captain, crew and boat.


    Open your Sails

    Departure at 09:00 am towards Arginonta bay at Kalymnos. Arrival time at about 1:00 pm. Climbing, swimming and relaxing for the rest of the day.


    Exploring Telendos

    Departure at 11:00 am towards the north coast of Telendos. Arrival time at about 12:00 pm. Climbing, swimming and exploring the nature until sailing to Telendos port in the evening – Arrival time at about 07:00 pm.


    Emporios Bay

    Departure at 10:00 am. Arrival time at about 11:00 am. Explore new routes and conquer new peaks. The view on top might be your greatest reward.


    Sykati Bay

    Departure at 10:00 am. Sailing north and crossing the straight of Leros before heading back south towards Sykati Bai. Arrival time at about 12:00 pm. Enjoy a great variety of possible routes on the rocks and jump into the refreshing sea.


    Palionisos Bay

    Departure at 10:00 am. Cruising south to Palionisos bay – Arrival time at about 12:00 pm. Improve your climbing skills and get ready for a late night swim.


    Vathis Bay

    Departure at 10:00 am. Completing the island tour around Kalymnos and anchoring at Vathis Bay. Arrival time about 11:00 am. Last chance today to sleep under the amazing starry sky on deck of the yacht surrounded by the light ripples of the waves.



    Time to say good bye...

    Departure at 08:00 am sailing back to Kos Marina. Arrival time about 10:00 am. Now it is time to say goodbye and keep all the great moments in mind. Check-out at 11:00 am.


    The itinerary is a suggestion based on our experience and planned events. The winds and the sea have the ultimate saying for the final and exact schedule! We take daily meetings to decide on the best and safest routes.

    Contact us!


Sailing & Climbing routes are shaped depending on the type(s) of climbing you prefer and the level of the crew. Our accredited (HFMC or IFMGA) mountain guides will recommend the optimal options and we will customize your trip.

Take a look in our suggested route and please This email address is being protected from spambots. You need JavaScript enabled to view it. for taylor-made sailing & climbing weeks.






More impressions - click here to open!

For more information get in touch with us! You can reach us via mail, whatsapp or use our easy booking request form.

  Booking request


Our partner & tour operator is:

Jack & Jenny Ltd., 16 Beaufort Court, Admirals Way, Docklands, London E14 9XL, United Kingdom - Click here to download & read the terms and conditions.


 Booking & Payment

How do I reserve a spot or cabin?

Booking can be easily done completely online via our step-by-step booking section. You are always most welcome to contact us directly by email at This email address is being protected from spambots. You need JavaScript enabled to view it. or call us if you have questions or need assistance with booking.

How many people are required to book a whole yacht?

A group of 6-10 is ideal for a full yacht booking.
We can also be able to customize options for as few or many people as you desire, just 
contact us to design your trip.

I am a solo traveler. Can I book a spot?

Yes, you can! We do encourage solo travelers, those sailing weeks offer a great balance of making great new connections and same time isolating yourself when you desire.

Would a spot/cabin or yacht booking be best for my group?

If you are a group of 6 or more, booking your own yacht seems your best option. You can guarantee that you will be travelling with your friends and the price per person is slightly lower.

Spot and cabin bookings are great for friends, solo travelers, and couples. We will form your sailing crew of like-minded people accompanied with an awesome skipper and possibly a hostess.

If you are certain about your trip and do not wish to deal with chasing and organizing all of your friends, just book your spot(s) and they can join you when they are ready. We will always make sure to match you on the same yacht, as long as we are notified at the time of booking.


When are payments due for booking?

You can chose if you wish to pay the full amount straight away or break it down into 2 instalments.

Your first payment is due within 48 hours from booking either you choose to proceed with the full amount or the 1st instalment (50% of the cost).

If you choose to break down the payment, the 2nd instalment of the rest 50% of the cost is due 10 weeks before your departure. And the balance of the costs must be received no later than 6 weeks prior to departure.

Feel tranquil about the due dates, we will send you friendly email reminders with payment details for easy processing.

What is your cancellation policy?

We have a moderate cancellation policy. If you cancel 2 months in advance prior to the trip, your payment is fully refundable. Minor charges may apply only for transactional cost.

Less than 2 months notice cancellation charges (as a percentage of the total booking cost) and will be determined by the date we receive your notice.
They apply for both Yacht and Spot/Cabin Bookings:

  1. From booking date to 61 days before the departure date – 0%
  2. From 60 to 31 days of the departure date – 50%
  3. Within 30 days of the departure date – 100%

The cancellation charges account mainly for charges imposed by suppliers that confirm the yachts booked for your trip. You will only be refunded the money for cancelled booking if we can find alternative customers who will take your booking.

How much does it cost to do a private tour?

Please contact us to get the latest information on your desired trip.



Do I need to be an experienced sailor to join?

Not really. Most of our travelers were first time sailors and they loved it. Jack & Jenny Sailing Weeks are led by friendly and professional captains, so you can relax on board while your captain or crew take care of the rest.

It is a great opportunity though to pick up some nautical skills. Pulling ropes, setting sails or steering the wheel?  Engage your self in sailing as much as you desire.


How many yachts will be part of our group?

The number of yachts will vary depending on the week. We usually sail out 2-3 yachts on the White & Blue Week and at least 5 (flotilla) on the Red Week.
We all sail out and moor together, there is though independent flexibility for each yacht.

Do we have to follow the Sailing Week's itinerary?

The winds and the sea have the initial saying into that. Then, it is solely up to you and your crew about what you want to do and where you want to go. The itinerary is a just a suggestion based on our experience. You can choose to go to different locations and are free to plan how many nights you want to spend in a marina or anchor in a gulf by the beach.

What should I bring with me?

First of all, travel light! Think like a traveler and not like a tourist.
Moreover as sailors, we share a limited amount of space for a week, so be practical and keep in mind that most of the day we only wear our swimwear.

Sailing boat essentials:
– Swimsuit
– Flip Flops
– Hat
– Sunglasses
– Sunscreen & after sun cream
– Towel / scarf or pareo
– Light jacket (windproof type) or a hoodie
– Books
– Cash (euros)

Beddings and towels are provided, consider only bringing a sleeping bag if you want to sleep on the deck or beach.
Feel free to bring music in any kind of forms.


I am a solo traveler. What should I expect?

Only encouragement on Jack & Jenny’s behalf!
We can put you on a yacht that has a single bed (bedroom or bed in the saloon) or you can be grouped with someone of the same sex.

What is the average age of the other guests?

Most of our guests are between 20-35 years.

Do you follow a male/female ratio of guests?

We do not impose any ratios for our sailors, however we aim for a balanced crew and usually we average about 50/50.

Are there any health requirements for joining a Sailing Week?

For the White and Blue Week you should be fit enough to join the chosen activities.

Any medical conditions that might constrain you traveling for a week with Jack & Jenny must be avoided. All crew members are asked to fulfill a questionnaire sent by us, where you notify us about any allergies and health concerns that we should be aware of.

If you have any doubts or questions regarding health requirements, please feel free to contact us.


Can I book a yacht only for few days?

We only do sailing weeks, which are typically Saturday to Saturday.

If you wish for a shorter period of time, might be possible only off-season and you are welcome to contact us for a customization.


What happens if I cannot make it on the yacht departure?

You can arrive a couple of hours or days later, but then you need to make your way to the yacht yourself. Send us an email and we will facilitate you with detailed information closer to your arrival.
Please keep in mind that your payment remains the same.

Is it possible to leave the Sailing Week earlier?

You just need to organize transport back to the mainland yourself. Your skipper will drop you off at the most convenient spot and the rest of your crew will continue the trip normally. Transport connections vary depending on your sailing week’s route, so speak to your skipper or contact us and we will advise you about how to get back.

Please keep in mind that your payment remains the same.



What are our obligations to the skipper?

The Captain’s Rules:

#1 The Captain is always right. #2 If the Captain is wrong, see rule #1.

Your captain will brief you on safety and everything around the yacht. As the most experienced and responsible one for your safety and comfort, you shall listen to your skipper while on board.
Our skippers are not considered as employees, but as companions ready to help you out when you are needed.


Can I be the skipper of the yacht?

Only available for full yacht bookings. You are required the appropriate experience and qualifications (RYA Day Skipper/VHF or equivalent offshore sailing licence). If you are willing to take on the responsibility, you can skipper the yacht. The price will be of course adjusted to account for not needing to pay for a skipper.

Does the crew speak English?

Both our skippers and hostesses are fluent in English. Most of them even in a second and third language as well. They have really high hospitality standards and they will ride any wave to make sure you have an unforgettable experience.



Do I need to pay a deposit? What is it for?“ open=

Yacht deposit varies between 1.500 – 3.000 eur. and it is necessary to cover damages and loses generated by crew members up to that amount.

Deposit is charged before boarding. As long as there are no damages, nor loses, full deposit will be returned upon check-out. Of course, in case of accident generated from third party fault or exclusively from skipper’s fault, deposit is not affected.

Is there WiFi on board?

We do supply a wifi device for your group to use while on the yacht. Please keep in mind there is a data limit for the week of 5GB. Additional data can be purchased.

Coffee shops and restaurants in most Greek islands have free internet access for customers and are easily accessible any time we are ashore.

What’s the deal with the food on board?

Jack & Jenny provide you with breakfast and lunch aboard. The dishes are simple, healthy and easy to prepare.
Breakfast typically includes cereal, bread with ham and cheese or nutella, eggs, yogurt with honey or marmalade. And last but not least coffee!
For lunch we usually prepare salads and “mezedes”. Ouzo and tsipouro are perfectly accompanied with some octopus by the seaside. Meanwhile sailing fruit salads are very popular to keep the vitamins up.

You can always bring your own extra food and drink on board. There are local shops and supermarkets at most shore stops to re-supply if needed.

Do not hesitate to ask if you would like us to organize something for you.

What about cooking and cleaning?

There’s always a kitchen and fridge available for you on the yacht. Most commonly prepared dinners on board are oven and pasta dishes.

You will be required to prepare your own food and clean up after yourself. Don’t worry – you are not alone on the yacht and everyone may choose to rotate duties. Keep in mind that the skipper is also a part of the crew. Do prepare a meal for him as well if you wanna keep him going.
If you don’t want the hassle of preparing meals and cleaning, you may hire a host or hostess.


Who will be on my yacht?

Most of the yachts have 3-5 cabins, which accommodate 6-10 sailors plus skipper and/or hostess. “Sailing is all about people” and we put a great deal of attention in matching the crew. We aim to bring together a mix of like-minded people and keep a gender balance. The allocation is finalized closer to the departure date.

Who will I share my cabin with?

If you book with a friend, you are most welcome to stick together.
If you’re traveling solo, we will do our best to accommodate you comfortably. We pair people of the same gender in cabins. There are also some single bed options available or the saloon if needed. Moreover, despite having their own cabin, we experience a number of romantic sailors preferring to sleep on the deck under the stars.
We always find a solution that satisfies everyone.

How much time do we spend on the yacht daily?

Depends on the sailing week & destinations, but on average we sail 3-4 hours per day. Due to the plethora of islands on the Greek Pelagos, you always keep sight of at least one land spot.

When we moor, you are free to do as you desire! You can stay aboard, explore the islands or choose one of the numerous activities.

Will I be safe aboard?

Safety on sea is our priority. Of course, every boat is equipped with lifejackets, pharmacy and all the precautions for your safety. Your skilled captain though is the one that will make you feel that you are in good hands.

Can I be the skipper of the yacht?

Only available for full yacht bookings. You are required the appropriate experience and qualifications (RYA Day Skipper/VHF or equivalent offshore sailing licence). If you are willing to take on the responsibility, you can skipper the yacht. The price will be of course adjusted to account for not needing to pay for a skipper.

Does the crew speak English?

Both our skippers and hostesses are fluent in English. Most of them even in a second and third language as well. They have really high hospitality standards and they will ride any wave to make sure you have an unforgettable experience.

What about my electrical appliances?

You can always charge phones, tablets, cameras and any other similar devices via a 12V to USB converter on the boat.

For the rest of electrical appliances like hair dryer, shaver and equipment that requires 240V, it is only possible to use when the boat is docked in a marina.



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