Sailor's bucket list: 12 must-try experiences

Sailor's bucket list: 12 must-try experiences

A list of experiences and things a captain and crew member should do at least once in their lifetime.

We have compiled a list of what we think every sailor should experience during their voyages, including some that are more of a challenge. Do you feel like your career as a skipper is going nowhere? Get a bit bored on the boat sometimes? Take some inspiration from our top 12 tips.

1. Sail 2 or more weeks in a row

The feeling you get when you sail on a boat for more than 2 weeks is unique. Break away from the traditional Saturday-to-Saturday charter routine and embark on a unique week-long journey, sailing in one direction for three days and returning for another three days. Alternatively, consider chartering a boat for two or more weeks, allowing you to sail to your heart's content without the pressure of meticulously planning your daily itinerary. This liberating experience grants you a genuine sense of freedom as you gradually adapt to the boat's intricacies and characteristics. For further insights on why a 14-day sailing adventure is highly recommended, check out our 10 reasons to go on a 14-day charter.

2. Take the mother-in-law on the boat

You might find this situation amusing, and it does have its comical elements. However, it presents a socially intricate scenario, especially when aboard a boat. As the captain, you aim to make a positive impression while dealing with the high expectations and occasional critical remarks or comments from the mother-in-law. It can certainly be a challenging dynamic to navigate.

3. Dive under the boat

For many sailors, a remarkable experience is diving beneath the boat's surface to witness its underwater appearance and perhaps even perch on the iconic "bomb" keel. Plus, it offers an opportunity to observe schools of fish that tend to gather around the boat, creating a captivating sight.

sinking under the boat

Sinking to the keel is an experience.

4. Getting pulled up the mast

Similar to the fascinating world beneath the boat, the experience above it is equally so. Allowing yourself to be hoisted up the mast provides a unique perspective of the boat. From the top, the view is exceptionally picturesque, offering opportunities to capture stunning photographs of the bay or even take memorable selfies against the backdrop of the sea.

YACHTING.COM TIP: If you don't know how, watch our video on how to hoist someone up the mast.

at the mast

If you are not afraid of heights, get hoisted up the mast.

5. Head into cold waters

Is the Mediterranean your sole sailing destination? A skilled sailor should also seek the experience of navigating the cold waters of the Baltic. It offers a wholly distinctive adventure, as the conditions are frequently more demanding, requiring adept handling of various situations unlike those encountered during a laid-back vacation in warmer regions. We highly recommend exploring sailing opportunities in captivating destinations such as Scotland, Poland, northern Germany, or Sweden.

YACHTING.COM TIP: Considering a Baltic cruise? We've prepared a complete guide to the wonders of sailing the Baltic Sea and a list of the 10 best Baltic harbours. Set course and embark on an exhilarating voyage! 

6. Night sailing

Sailing at night presents a distinct and incomparable experience compared to sailing during the day. The surroundings take on a different perspective, distances seem altered, and navigation becomes more intricate, demanding heightened attention to safety. Even if you aren't particularly fond of lengthy night crossings, embarking on a night voyage is highly recommended. You could opt for sailing into the night and returning to port around midnight, or setting sail at night and reaching your destination by morning.

sailing at night

Sailing at night will test your navigational skills and your knowledge of signals at sea.

7. Participate in a regatta

Regardless of whether you possess a competitive spirit, participating in a regatta, a sailing race, is an experience worth undertaking at least once in your lifetime. Of course, we are referring to amateur regattas that are open to all sailors, rather than professional races like the Vendée Globe or the Ocean Race. Engaging in a race not only exposes you to a different style of sailing but also injects a thrilling dose of adrenaline into your maritime endeavors. Racing within a fleet of 30 boats can be challenging yet immensely rewarding. However, it is crucial to ensure that you have experienced sailors on board who are well-versed in sail trimming, maneuvering the boat, and maintaining an accurate course. In Croatia, noteworthy options include the May Regatta, the Easter Regatta, the Captain's Regatta, or the Champagne Cup. Depending on your preference for difficulty level, there are numerous regattas available to choose from.

8. Cross national borders

Engaging in practical exercises with signal flags and familiarizing yourself with the customs procedures is an invaluable experience we believe every captain should undertake. It offers insight into the process of crossing borders with a ship, creating an unforgettable and unique adventure. No one can take away this firsthand knowledge from you. To prepare for such endeavors, we recommend reading our guide to crossing national borders with a charter boat. And if you don't know exactly where to head, check out our recommendations — Crossing international waters on a charter boat: 5 route tips.

9. A boat of beginners

One of the greatest challenges for a skipper is to navigate a boat filled with inexperienced individuals who are unfamiliar with basic concepts such as a windlass, tying up the boat, or even operating the toilet. The skipper must not only refresh their own theoretical knowledge, as beginners tend to ask numerous questions, but also acquire the ability to teach and explain everything effectively. It is indeed a demanding task, but at the conclusion of the voyage, a sense of accomplishment washes over the skipper as they witness the initial novices confidently furling the sails and throwing ropes with the proficiency of seasoned sailors.

YACHTING.COM TIP: Don't know what exactly to prepare the crew members who are not familiar with the sailing life? Check out the article — Crew briefing: 7 essentials to tell your crew before setting sail. And when teaching them to tie a knot, don't forget the 9 essential sailing knots. If you're a beginner crew member, make sure to check out — First time on a sailboat: 10 things you need to know before setting sail.

10. Rent an additional sail

Sailing with a gennaker or spinnaker is a wonderful experience that will take your sailing knowledge to the next level. When booking a boat, ask the dealer if additional sails can be ordered. Still hesitant? Read our 5 reasons to rent a gennaker.

gennaker cruise

Sailing with additional sails is a great experience.

11. Buy your own sailing gear

If you are a regular sailor, there comes a time in your sailing journey when acquiring your own sailing gear becomes a significant milestone. Depending on rentals or makeshift solutions like outdoor trousers or overalls made from work clothes will no longer be necessary. While it may appear to be a materialistic aspect, owning your sailing gear represents a substantial leap towards enhanced comfort during your sailing adventures. It also signifies a deeper commitment to the sailing lifestyle, which you will likely find difficult to leave behind. If you can't think of what else to get, take a look at —  What else to take sailing: tried and tested pieces of kit from experienced sailors

12. Subscribe to a yachting magazine

There is a large number of yachting blogs and magazines available but, of course, we highly recommend our Yachting°com magazine.

Turn your sailing dreams into reality. Get in touch and I'll find the right boat for you.