Calling all experienced skippers! These are waters you'll want to conquer

Pushing your boundaries, challenging yourself to greater feats and exploring new territories has always been an integral part of sailing. When selecting your next sailing destination, consider locations that will test not only your captaincy skills but also your crew's endurance and determination. Within reason and safety of course.

These destinations are not for the faint of heart, but for those who seek to challenge their skills and learn from experience. Even seasoned sailors will find these locations to be a true test of their abilities. We recommend that you first sail to these destinations with a different skipper on board as a crew member, to get a feel for sailing in more challenging conditions. This way, the responsibility will not be solely on your shoulders, and you can benefit from the guidance of a more experienced colleague.

Brittany is renowned for its stunning scenery, quaint old towns, delicious cider, and excellent sailing conditions. For sailors, the northern region of Brittany is often the top choice, with Saint Malo being one of the most famous ports and a gateway to the English Channel for sailors and endurance swimmers alike. The English Channel is a destination that almost every experienced skipper wants to visit sooner or later, and if you're fond of big waves, you'll certainly enjoy it. However, we actually recommend southern Brittany as an ideal location for your first challenging sailing adventure.

The southern Brittany coastline is characterized by its rugged, rocky terrain, with many underwater rocks protruding above the water, some of which are unmarked. The region's waters are also known for their strong currents and significant differences in tide levels, which can be surprising to those accustomed to the Mediterranean or Baltic. However, the sheltered bays of Quiberon and Morbihan, along with the surrounding islands, offer an ideal starting point for your first Brittany sailing adventure. We recommend trying the route: La-Trinité-Sur-Mer — Les Glénan — Groix — Hoëdic — Ile aux Moines — Houat — La-Trinité-Sur-Mer, which takes you through stunning harbours that are as beautiful as they are diverse, and provides a moderately challenging yet exhilarating nautical experience. 

Sailing the Baltic Sea is an experience like no other, offering a unique and thrilling challenge that stands in stark contrast to the calm and safe reputation of the Mediterranean. The Baltic is known for its cold waters, strong winds, and big waves that can test the resolve and stomachs of even the most experienced sailors. But those who have sailed it will forever love it, perhaps because it can make them even better sailors. Newbies will learn to trim their sails while battling the wind, and navigators will be kept on their toes by the numerous shoals and obstacles in the water. The Baltic's boating infrastructure and signage are second to none, making it a safe and enjoyable destination for sailors of all levels. We have a great fondness for the Baltic ourselves, so we recommend a fantastic challenging route from Germany to Sweden and Denmark.

The Mediterranean Sea is a unique and challenging sailing destination due to its geographical features. With mountains to the north and African deserts to the south, the temperature differences between sea and land can create significant pressure differentials, resulting in seasonal winds that are infamous for terrorizing both the sea and ports with their hurricane force. We have previously covered in detail all 7 of the most common Mediterranean winds in our magazine. It's important to note that these winds, at their full force, can be dangerous even when you are moored in a marina, and we do not recommend attempting to sail in them. But we'd be lying if we didn't admit that in certain circumstances experienced crews can (and do) use them as an turbo-boost for sport sailing. Specifically, these winds and areas:

The Tramontane and Meltemi are two winds that frequently visit the Aegean Sea every year. Both winds blow from the north and are often confused with each other because of their cold nature. Experienced sailors often choose to sail with the weaker Tramontane and Meltemi winds and use them as propulsion when sailing south. However, it's essential to note that both winds can cause unpleasant rocking in the confined Aegean Sea. Furthermore, due to the rugged coastline and numerous islands, sailors need to be cautious of gusts. The Meltemi, in particular, can be accompanied by a swell, which is a series of waves that form in the ocean tides and move towards the shore at regular intervals. Unless you can find a sufficiently sheltered anchorage on the leeward side of a land or island, you will not enjoy anchoring very much.

The Mistral is a cold wind that forms in winter and early spring in the Bay of Biscay and then blows across France into the Mediterranean. In some areas it can reach a force of up to 12 degrees Beaufort (180 km/h). It is strongest on land and in the Gulf of Lions off the Côte d'Azur, gradually loses its strength as it travels across the sea, yet it can be felt as far as the west coast of Italy. For experienced crews, a Mistral of up to 4 or 5 Beaufort degrees can help with sailing. From Marseille, the Mistral spins by the action of the Italian cyclone to St. Tropez and on to Corsica and Sardinia, providing steady tailwinds and sternwinds without gusts. Some skippers use it to help them sail south to the Balearics.

The Jugo, also known as the Sirocco, is a warm and humid wind that originates over the Sahara and blows from the south to southeast across the Mediterranean Sea into Europe. This wind is most noticeable at sea, where it can serve as a turbo at lower intensity. However, at higher intensities, it can create large waves and even drive the boat ashore, which can be a significant problem when anchoring.

If you're looking to try ocean sailing for the first time, the Canary Islands are an excellent place to start. With relatively short distances between the islands and well-protected anchorages against swells, these waters are well-explored by experienced sailors, with plenty of tried and tested routes to inspire your journey. You can find more information on two popular routes in our article on sailing in the Canary Islands, making it easier for you to plan your sailing adventure with confidence.

While Cape Verde may not feature as prominently in sailing guides compared to the Canaries, it is equally accessible and boasts breathtaking beauty, perhaps even surpassing its better-known counterpart in some ways. Some even describe Cape Verde as similar to the Caribbean, yet unspoiled by tourism. The islands are smaller, less populated, and less touristy than the Canaries, with longer distances between them. Therefore, Cape Verde is an ideal destination for experienced sailors who prioritize ocean sailing, privacy, and peace away from the bustling tourist crowds.

For truly confident skippers, a sailing trip across the Atlantic Ocean is the ultimate challenge. Many choose to sail from Europe, either via the Azores to Miami or via the Canaries and Cape Verde to the Caribbean. However, both routes require careful preparation for a several-week stay on the boat, during which you must carry enough supplies, particularly water, and all the necessary equipment from the start. Most crews typically set sail between October and February, when the likelihood of hurricanes in the Caribbean is lower. Ocean sailing presents its own unique challenges and risks, even for experienced sailors and large cargo ships. Nevertheless, approximately 2,500 sailing ships cross the Atlantic each year, proving that this daunting feat is achievable with the right preparation and mindset.

The Caribbean is a dream holiday destination for many sailors, with calm, clear turquoise waters that are perfect for sailing, except during hurricane season. However, what makes this destination challenging for sailors is the lack of yachting infrastructure and the limited number of signal lights. As a result, sailing is only allowed during the day. Additionally, the area is abundant with rocks and reefs, and while some may be marked by wooden stakes, navigating around them can be difficult, especially in coral reef areas where neither paper nor electronic charts can be relied upon. We recommend sailing during the day, with a crew member stationed at the bow to check the depth and spot obstacles as the sun is high in the sky.

But with all this, the Caribbean offers a chance to get back to the basics and the very roots of seafaring, test your own captaincy skills and vigilance. You'll be rewarded with distinctive islands, diverse culture and gastronomy, and, of course, locally produced rum.

Don't feel the need to venture out of the safe areas you enjoyed as a novice just the year before. Raise the bar on your skippering skills with a night voyage that will test your sense of direction. A non-stop cruise, such as a crossing from Croatia to Greece with minimal or even no stops, will also keep you busy. Both of these options have the advantage that you can get to land pretty quickly at any time if you happen to overestimate the crew's abilities. For those who prefer solitude, an solo voyage is a great option, where you can spend a week avoiding marinas and people, relying solely on the supplies on board.