Here's all you need to know

Top 5 asked questions

  • 1. 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.

    Nevertheless, it is a great opportunity to pick up some nautical skills. Whether it's pulling ropes, setting sails or steering the wheel, you can engage yourself in sailing as much as you desire.

  • 2. Who will I share my cabin with?

    If you book with a friend, you will share one cabin together.

    If you’re traveling solo, we will do our best to pair people of the same gender in cabins but we cannot guarantee it.

    A cabin of two single bunk beds might be available depending on yacht availability.

  • 3. How many people are required to book a whole yacht?

    A group of maximum 6 or 8 persons is the optimal number to book a yacht to full capacity.

    Thus, a group of 6 persons can book a 3 double-cabin yacht, and a group of 8 can book a 4 double-cabin yacht.

    Nevertheless you can be a group of 1 to 6 (or 1 to 8) persons and still book a whole yacht. The final price will be adapted according to specific costs that can be reduced.

  • 4. 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.

  • 5. Can I meow on board?

    Meow, despite general misconception, is not restricted to adorable felines. It expresses sensitive and thoughtful humans as well.

    With the exception of any objection by the skipper or any other member of the crew, meowing is allowed at all times - not to say encouraged!

    Please meow with consideration during the short hours of the night.


    - Captain Meow

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  • 1. How many yachts will be part of our group?

    The number of yachts will vary depending on the week. We usually sail out 1-3 yachts and at least 5 on the flotilla Week. We all sail out and moor together although there is  independent flexibility for each yacht.

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

    Trip planning is a big part of what we do. We want to make sure you have the best experience while sailing and enjoying the activities we have planned for you. This is why we design our trips with a theme in mind and an itinerary tailored accordingly.

    For destinations where activities are booked it is not possible to change the itinerary.

    Nevertheless, minor or urgent changes may be discussed with your skipper who will take the final decision.

    Since all trips are influenced by the weather, the winds and the sea have the ultimate saying for the final and exact schedule!

  • 3. 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.

  • 4. What is the average age of the other guests?

    Most of our guests are between 25-40 years old.

  • 5. 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 aim for a 50/50 ratio on average .

  • 6. Can I book a yacht only for a few days?

    We normally book trips for entire weeks, which are typically Saturday to Saturday.

    Shorter period bookings may be possible only off-season. You are welcome to contact us for customized trips.

  • 7. Are there any health requirements for joining a sailing week?

    For the active weeks you should be fit enough to join the chosen activities.

    Any medical conditions that might constrain you from 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.

  • 8. What happens if I cannot make it for the yacht departure?

    If you arrive a couple of hours or days after the trip departure, you will 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.

  • 9. 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.

  • 10. I am a certified diver and i wish to partake in advanced dives during the Scuba diving activities. How do i prove it?

    After your booking in any trip that includes a scuba diving activity stated as "Advanced" you are required to send us an email at [email protected] with a scan of your Diving ID and the last page of your Diving Log Book. You are also required to bring those documents with you on the trip. Upon doing so you will receive an online copy of the necessary form which will contain several health related questions in order for us to prepare better and offer you the best possible experience. You dont have to fill this form and submit it online but instead you will fill it up on the day of your dive. 

Booking & Payment

  • 1. 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 do our best to form a sailing crew of like-minded people accompanied by a qualified 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 make sure to match you on the same yacht, as long as we are notified at the time of booking.

  • 2. What is your cancellation policy?

    We have a moderate cancellation policy.

    If you cancel 2 months prior to the trip, your payment is fully refundable. Minor charges may apply only for the transaction cost.

    If you cancel less than 2 months prior to the trip, cancellation charges are applied as a percentage of the total booking cost, and will be determined by the date we receive your notice.

    Charges apply as follows:

    1. From the booking date to 61 days before the departure date – 0%
    2. From 60 to 31 days before 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.

    A refund may apply on a cancelled booking if alternative customers take your booking.

    Cancellation charges apply for both Yacht and Spot/Cabin Bookings.

  • 3. 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 along with the booking of your trip, whether 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 remaining 50% of the cost is due no later than 30 days prior to departure.


    We will send you email reminders with payment details for easy processing.

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

    Yes, you can!

    If you’re traveling solo, book one spot and we will do our best to pair people of the same gender in cabins but we cannot guarantee it.

  • 5. How do I reserve a spot or yacht?

    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 [email protected] or call us if you have questions or need assistance with your booking.

  • 6. Is it possible to organize a customized trip?

    Please contact us to see what we can do for you.

Skipper & Hostess

  • 1. 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 he is the responsible person for your safety and comfort, it's important to listen to him while on board.

    Our skippers are not considered as employees, but as companions ready to help you out when you need.

  • 2. Can I be the skipper of the yacht?

    Trip planning is a big part of what we do. We want to make sure you have the best experience while sailing and enjoying the activities we have planned for you. This is why we design our trips with a theme in mind and an itinerary tailored accordingly.

    All of our trips are accompanied by an experienced skipper who has been involved in (or briefed with) the planning.

    In case you have the appropriate experience and qualifications (RYA Day Skipper/VHF or equivalent offshore sailing licence) we can point you to trusted bare-boat chartering companies.

  • 3. 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.


  • 1. 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.

  • 2. How much time do we spend on the yacht daily?

    This depends on which sailing week you choose, its planned destinations and activities.

    Some trips are spent almost entirely on the yacht with full days of sailing and spending the night under anchor in selected safe anchorages. Other trips include mooring in harbors and more time off the boat according to the planned activities.

  • 3. What about cooking and cleaning?

    1) When the hostess is already included: Special menus are pre-designed and cooked on board, while everything else is looked after. The hostess/host will clean after cooking and dinner, and keep the kitchen and saloon clean. Your cabins are up to you.

    2)Hostess "add-on": To avoid the hassle of preparing meals and cleaning, you may hire a host or hostess. They will cook the arranged menu and clean up after dinner.They will also clean after cooking and dinner, and keep the kitchen and saloon clean. Your cabins are up to you. 

    3) When no hostess is included: 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.

    In all cases the bathroom's hygiene is a subject common to everybody's responsibility, so it's up to the whole'crews' effort to keep it clean.

  • 4. What's the deal with food on board?

    We have three types of menu arrangements:

    1) When the hostess is already included:

    a- For "Dash" weeks:

    All food is included in the price. Menus are designed beforehand and all groceries are delivered and arranged onboard before your arrival for your comfort.

    During the week, the hostess will prepare breakfasts, lunches and dinners which are all served on board. Contact us to get more information on the Dash menus.

    b- For Yoga Week:

    A special menu is designed in collaboration with the yoga teacher

    2) When the hostess is added as "add-on":

    Depending on cost arrangements, Jack & Jenny may provide you with breakfast and lunch on board. Provisions are made by the hostess along the week in the different ports you will visit.

    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.

    3) When no hostess is added:

    There are no food arrangements. You will have to supply the groceries you may need for your trip.

    We can also arrange groceries to be delivered to your yacht beforehand (subject to charge).

  • 5. 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.

  • 6. Will I be safe on board?

    Safety on sea is our priority. Every boat is equipped with life-jackets, a pharmacy box and all the precautions for your safety.

    Your qualified captain will brief you extensively about the necessary precautions to keep you safe while he will make sure you are in good hands and feel secure.

  • 7. 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.