What you need to know!
Join us onboard as we sail our way around the world to exciting and stunning locations. Experience what living on an OYSTER 56 is truly like. We like to do things in comfort and at a steady pace, we are not racing through life.
Have you ever wondered what its like to live onboard a boat? Experience first hand the enjoyment and fun that everyday life can bring. From sailing each day to a new harbour, that amazing feeling as a new location opens up before your eyes or maybe sailing overnight with no land in sight. Swim off the back of the boat, snorkel new locations. Take part in every aspect of the adventure from passage planning, provisioning, sail handling, steering, systems management, cooking, daily repairs and maintenance and a whole raft of challenges not usually found on land.
Stunning Destinations
Complex challenges
Sailing Tips


What you need to know
What Is the Right Experience for Me?
Onboard Osprey, we welcome everyone – from seasoned sailors to absolute beginners. Our oldest crew member so far has been 85, and the youngest was just 8 months old, so there’s no age limit for adventure! While sailing experience isn’t required, we’ll discuss the sailing area, your crew’s skills, and how it may align with your desires. The only thing you’ll need is a sense of adventure.
Who is this experience for?
- Planning your own sailing journey? If you want to know if you and your family will enjoy living on a boat, this is the perfect opportunity to get a feel for it.
- Considering buying a used Oyster? Want to try before you buy? This is a great way to test the waters.
- Never sailed before? Looking for a new challenge? No problem! We’ll guide you through everything.
- A seasoned sailor? If you can’t leave shore life permanently but still want to enjoy some time at sea, this experience is ideal for you.
- Adventure-seeker? If you love visiting remote, hard-to-reach locations, we can take you there.
- Mile-building? If you need more sailing experience to meet your goals, this is a great way to accumulate miles.
Bring Your Own Crew:
Want to bring your own crew? Let’s plan a trip together that’s inspiring and exciting, with dates and locations to match your vision. We have room for up to 4 friends and family, or you can come solo, knowing you won’t have to share a cabin with strangers.
- Maximum 4 berths (a 5th adult or child can sleep in the workshop cabin).
- Private cabin – No sharing with strangers.
- You have the boat exclusively for your crew.
- Customized itinerary – Sail a specific area that suits your needs.
Benefits:
- Sail with your own people – Only your group on board.
- Private cabin – No need to share with strangers.
- Exclusive use of the yacht – Perfect for family or close friends.
- Tailored itinerary – You choose the dates, locations, and experiences.
- Maximum 5 berths – Ideal for families or small groups.
- Best for 2 couples – Share the cost while enjoying the journey together.
- Minimum 7-day stay – We work with you to maximize your time onboard.
Individual Berth:
Prefer to join an existing crew? Individual berths are available whenever we don’t have a group booking. The minimum stay is 4 days and the cost is per berth in a shared cabin.
Benefits:
- Meet like-minded people – Share the experience with other solo travelers.
- Affordable – Cabin-sharing keeps costs lower.
- Maximum 4 crew members – We keep things intimate and comfortable.
- 4-day minimum stay – Subject to location.
- Bring your partner – Or come solo and meet new people!
How Do I Join the Crew?
Joining the crew is easy! Simply send us a text, email, or contact us on social media. We aim to respond within 2-3 days to start planning your trip.
If possible, we will invite you to a WhatsApp call to chat further and finalize your booking.
Meals Onboard:
Osprey boasts plenty of storage space for food, and all meals are prepared from fresh, local produce. With guidance from Chef Sally if required, every crew member takes a turn cooking meals. We guarantee that there are no freeze-dried meals or canned beans with sausages here!
If you’re not keen on cooking, you’re welcome to offer to wash up and swap duties with others. We strive to accommodate all diets, but if you’re vegan or have very specific dietary needs, we ask that you take a more hands-on role in meal prep. We’re always open to trying new recipes and dishes!
Boat Locations:
Our yacht’s location is based on the agreed plan at the time of booking. As we’re constantly on the move, we don’t typically post specific dates for locations. However, we do have a basic itinerary with a few events on the calendar that we plan to attend (check out the details below).
You can stay updated with our current location by following our blog page, as well as through regular updates on Facebook and Instagram.
If you’re joining us last minute, we can usually arrange to meet you at the nearest town with short notice, so don’t hesitate to reach out!
Crew Register and Special Events:
Interested in last-minute trips or special events? Join our Crew Register for discounts and priority booking on any upcoming opportunities. Just send us an email via the contact form below to get on the list.
If you know of any great events you’d like to attend, we’d love to hear about them! Share your ideas for an itinerary, and we’ll see how best we can fit them in. Group experiences typically range from 7-10 days, but we are open to longer trips depending on the request
Arrival and Departure Dates:
All crew members are welcome to arrive after lunch on the day prior to departure. This allows time for the safety briefing and for everyone to settle in comfortably before setting sail.
- Departure Day: Typically, the departure will be on the following day after the arrival, subject to the weather forecast.
What’s Included?
- All meals onboard – Dinner on the first night, 3 meals a day, snacks, and breakfast on your last morning
- Lifejacket and Safety Tether for your peace of mind
- All safety equipment onboard to ensure your safety at all times
- First Aid kit for emergencies
- Bedding – Quilts, pillows, sheets, and towels
- Wifi when onboard to stay connected
- TV & DVD collection for your entertainment
- Use of the RIB Dinghy and outboard for exploring the coastline
- Marina fees when anchoring is not an option and up to a maximum of €100 for standard ports
- Fuel for the yacht’s journey
- Log book endorsement (if required)
What’s Not Included?
- Travel and visa costs to and from the yacht (Osprey)
- PLB, AIS, or personal responders for additional safety equipment
- Travel and medical insurance costs for your protection
- Foul weather clothing (recommended for your comfort)
- Alcohol onboard – We maintain a dry ship while sailing, but a small amount of alcohol is permitted once the anchor is down. BYO onboard.
- Crew member shore fees – Most ports don’t charge for the crew.
- Satellite telephone for email and phone calls – Must be pre-booked.
- Marina fees in locations of choice and or exceeding 100e per night.
- Meals and drinks ashore – Not included in the package
- Race fees or special event charges – Additional costs for specific races or events
Crew Happiness
We believe crew happiness is key to a fantastic sailing experience. If you or anyone in your group needs something to make your trip perfect, please don’t hesitate to let us know. We’re happy to tailor your trip to meet your needs as best we can.
Passage planning is a big part of the crew involvement. If you have a bucket-list destination or request that fits within the budget (or for a small additional charge), we’ll do our utmost to accommodate it.
Safety Procedures:
- MOB (Man Overboard) procedures will be practiced shortly after departure, ensuring everyone is familiar with emergency protocols as appropriate
Last Minute Cancellations Sailing Guarantee
We understand that life can be unpredictable, and sometimes you may need to rebook or cancel your time onboard at short notice. To accommodate this, we allow you the opportunity to make one new booking to be taken up to 12 months from your original boarding date, without penalty, up to 7 days prior to arrival, provided the following conditions are met:
- The trip is fully paid.
- All crew on the same invoice must rebook together.
- A time and location can be agreed upon by all parties involved.
While we may not be able to guarantee the same location, we will do our best to get you back onboard. We strongly recommend you take out holiday travel insurance to cover any unforeseen changes.
Please note: Deposits are non-refundable.
Vessel Guarantee
In the event of any breakage or safety-related issue that makes the vessel unavailable on the first day of your booking, we will provide a full refund.
Occasionally, we may need to adjust pickup and drop-off locations. While we do not guarantee specific locations, we will always set realistic goals and do our best to get you as close as possible to your preferred pickup/drop-off point. This may include transferring via dinghy or water taxi.
Paperwork Required
To ensure a smooth boarding process, every crew member must provide the following documentation by email 7 days prior to boarding:
- Passport with relevant visas
- Travel/Health Insurance to include medical repatriation coverage
- Airline Ticket or onward travel booking
- Next of Kin contact details
Please note: We cannot take crew onboard without all required paperwork in place. Ensure all documents are submitted on time.