Transatlantic Crossing – The Ultimate Yachting Adventure and Autumn Alternatives
- Brainz Magazine
- 2 days ago
- 10 min read
Updated: 3 hours ago
Written by Eldin Basic, Yacht Charter Manager
Eldin is a well-known yacht charter broker, arranging private yachts for sailing holidays in all the main sailing destinations, with a specific expertise in long-term yacht charters and luxury yacht charters in particular.
As the European sailing and boat hire season begins to wane, and marinas from West Mediterranean to the most Southern parts of the Med start to quieten, a unique yacht migration starts taking shape across the Atlantic. Monohulls, catamarans, and superyachts alike begin their journey westward, crossing thousands of nautical miles toward the East Caribbean for the winter season.
For many sailors and yacht charter guests, this adventure is not merely a passage; it’s the pinnacle of ocean adventure, a blend of freedom, endurance, and possibly a luxury that few other experiences can match.
The crossing itself usually starts in the second part of November, when the autumn paints the Northern Hemisphere in shades of gold, the weather turns colder, and Europe shuts down its yacht charter industry.
This is the time when the seasoned sailors and adventure-seekers begin to look west, toward the ultimate seafaring voyage: the ‘’Transatlantic Crossing’’. This, possibly the grandest of yachting passages, steeped in maritime tradition and increasingly so in the modern ambition, undoubtedly remains one of yachting’s most remarkable benchmarks.
Indeed, the transatlantic crossings hold a magnetic pull for those who crave more than a holiday. They embody freedom, resilience, and the spirit of discovery, where the horizon is not a limit but an invitation, and personal self-development, and possibly mind-development, reach a new level.
Even though this adventure merges endurance and exploration into one awe-inspiring experience, in recent years it has also become a part luxury experience. A2A Yachting, namely, now offers not only bareboat charter crossings, but also skippered, luxury crewed, and superyacht transatlantic crossing experiences.
The spirit and practicality of the Atlantic crossing
Yacht charter is usually defined as a short-term rental or hire of a boat, primarily for enjoying a relaxing weekly or fortnightly sailing holiday. On the other side, a transatlantic voyage is often described as the purest form of sailing. The route, most commonly from the Canary Islands to the Caribbean via the trade winds, offers a mix of challenge, rhythm, and meditative isolation. Days are spent surrounded by endless horizons, most nights illuminated by the Milky Way, and each sunrise brings a renewed sense of rebirth and possibly a new perspective.
It lasts at least 3 weeks, with our clients typically sailing for 1 to 2 months. While the crossing once belonged exclusively to seasoned sailors and highly experienced crew, advances in yacht design and navigation have opened it to a broader audience of adventure-minded travellers. Many now choose to participate as guests or co-sailors aboard modern bluewater yachts, which are equipped for long-range cruising and luxury yacht charters in general.
Historically, at least when it comes to timing and tradition, the transatlantic passages from Gibraltar, the Canary Islands or Cape Verde to the Caribbean coincide with the trade wind season, beginning in late November after the hurricane period in the Caribbean subsides. For many yacht owners and charter guests, the crossing is not only a voyage of discovery but also a logistical transition, relocating vessels from Europe to the Caribbean for the winter charter season, maximizing charter income, or paying off monthly leasing rates.
As yacht brokers, we use this opportunity to generate additional revenue and provide our clients with unique sailing experiences. Using this opportunity to book a suitable yacht for your own party, department, group, or team is a rare opportunity to live the essence of seamanship, witness celestial navigation in practice, and experience the ocean in its purest form, while gaining in both personal development, communication skills, and team bonding too.
Yachts built for the blue horizon
While the most experienced sailors and boat owners may take their exquisite vessels, which are designed and built for crossing the oceans and often for their own holidays, such as a Hallberg-Rassy 57CC, a CNB 76, a Swan 88, or possibly an Oyster 125, the availability of charter yachts is more limited. Most yachts offered for bareboat or skippered transatlantic crossing charters are modern catamarans, such as the Bali 5.4, or a sailing monohull, such as a Hanse 575.
These boats provide good value for money, as well as stability and space, making them ideal for crews seeking comfort and safety over long distances. For those seeking ultimate luxury and capability, yachts such as the Oyster 825 or, in particular, the Alegria 67 and Sunreef 80 Eco represent the new era of sustainable sophistication, offering long-range autonomy with hybrid propulsion and solar-assisted systems. Larger expedition-style superyachts, equipped with the necessary fuel capacity and self-sufficiency, provide an unmatched level of comfort, even mid-ocean.
A few of those yachts may also consider welcoming guests for this ultimate passage, although the cost of doing so may turn out to be prohibitively expensive. Whether crewed or bareboat, all these vessels are designed to meet the demands of the Atlantic while offering all the indulgences of a floating villa.
The allure of the transatlantic crossing
Unlike coastal cruising, a transatlantic passage offers uninterrupted days at sea, where life finds its rhythm in waking up to the sound of waves, regular watch schedules, following weather patterns, and possibly enjoying the sheer beauty of the ocean. It's also an obvious social experience, as you share space with familiar, albeit new, people whom you will get to know very well in the coming days.
The essence of it, though, at least for the majority, is not simply about reaching the Caribbean or Europe; it’s about the transformation that comes from navigating one of the world’s great bluewater highways. Whether one chooses a bareboat or a skippered adventure or a luxurious crewed experience, the essential element remains the same: the thrill of crossing an ocean under sail.
Formal participation or a bespoke adventure
Apart from a charter experience, many crews tend to join the famous ARC (Atlantic Rally for Cruisers), which departs from Las Palmas de Gran Canaria. Gathering hundreds of yachts for a safe and sociable crossing to Saint Lucia, the rally offers additional security and assistance for less experienced crews. Joining such a fleet provides the perfect balance of independence and camaraderie, as socialising is a big part of yachting in any case.
As a part of the crew or the fleet, this experience allows you to participate as much or as little as you wish. It’s an opportunity to disconnect entirely from the digital world and reconnect with the timeless rhythm of the sea. Most of our clients join the ARC, although some sail in complete independence. Others, though, are choosing routes of the WORLD ARC and following their Atlantic crossing.
The following year, they are booking one-way charter experiences that depart from the Grenadines, they then travel across the ABC Islands, make a stopover in Bogota, Colombia, with a final stop in the San Blas Archipelago of Panama. Very few decide to do what is an even more extraordinary experience and sail even further, at a significant cost, one may add, across the Panama Canal all the way to Galapagos. At the same time, one family dared to sail all the way to Australia. They did so with a malfunctioning autopilot, too, which made the actual transpacific journey even more remarkable. In other words, we at A2A Yachting can arrange most extraordinary, one-way or ultimate sailing adventures on request, as anything is possible with a suitable budget, good planning and an open mind.
Sailing beyond the season: Autumn alternatives for the sea-loving traveler
Of course, not everyone seeks to cross an ocean at this time of the year. For those craving a shorter maritime escape before winter, October offers some of the finest sailing conditions in the Mediterranean. The Amalfi Coast, Croatia’s Dalmatian Islands, and Greece’s Saronic Gulf still bask in warm seas and gentle breezes, with fewer crowds and attractive late-season charter opportunities.
Further afield, and mostly in November, the Red Sea, particularly around Egypt’s Hurghada and the emerging marinas near Saudi Arabia’s coastline, NEOM’s futuristic Sindalah Island, or Jeddah in particular, presents crystal-clear waters, coral reefs, and ideal sailing weather in the autumn shoulder season.
These regions are becoming increasingly popular for luxury yacht charters and eco-conscious explorers alike, with some yachts offering availability that is not to be missed. A new Lagoon Eighty 2, for example, chartering from 70,000 Eur per week, is one of the finest yachts cruising the Red Sea this Autumn for the first time, as not everyone dreams of weeks on the open sea.
The spirit of yachting and the sea
Whether crossing the Atlantic or exploring the quiet bays of the Mediterranean, sailing in autumn carries a special rhythm, one of transition, reflection, and renewal. Many crews and guests report back amazing experiences, tranquil beaches, and still warm waters.
The combination of clear sea, empty anchorages, and good food creates a fantastic yacht charter experience in the Mediterranean beyond the primary summer season. On the other hand, a transatlantic passage challenges both skipper and spirit, rewarding them with nights beneath untouched skies and days propelled by trade winds once harnessed by explorers centuries ago.
And for those who prefer a gentler course, the shoulder season’s serenity across Southern Europe and the Red Sea offers all the magic of the sea, distilled in golden light and tranquil waters. For every sailor, there comes a moment when the horizon beckons. Whether that journey stretches across an ocean or along a coastline, it remains above all a voyage of the soul. For the inexperienced, starting on a cabin charter on yachts such as the spacious Upwind 50 catamaran in Croatia, with rates from as low as 2,000 EUR per couple, per week, represents an ideal introduction to sailing.
Notch it up: West to East transatlantic crossing
And while East to West is the traditional crossing, now completed by many, the West to East represents another type of challenge. This is not for everyone, for sure. These passages are another type of significant bluewater milestone, undertaken mainly through experienced crews and well-found boats, often returning to Europe or the Mediterranean after a Caribbean season.
These types of crossings are mostly completed by the crew, yet an increasing number of our clients both enquire about, or actually complete, such adventures, a 3,500nm voyage, completed in two stages. Our clients usually start in Saint Martin and cross directly to the Azores (2,500nm approximately). This route requires sailing against prevailing winds and currents, often involving variable and less predictable weather.
It is still the best route as it relies on sailing to the north of the "Azores High" pressure system, a key factor in planning a west-to-east crossing. Some may head to Bermuda as an additional stopover, an experience, and a holiday-type stay lasting a couple of nights or longer if desired so. Once heading across, you are at the mercy of the mighty Atlantic, though.
One unfortunate crew had to sail 200 miles in the wrong direction due to a combination of insufficient fuel on board (we usually organize 20 canisters of 20 liters as spares) and unfavorable winds, before finally turning back. The Azores route keeps yachts north enough to catch favorable southwesterlies and westerlies, avoiding the doldrums and hurricane belt. It’s the safest and most common route for yachts under 100 ft in any case, and one that has been completed many times by now.
Due to unpredictable weather, our clients mostly motor up, at least up to the Azores and sail to Portugal and Gibraltar the last 1000nm after a deserved rest in the diverse landscapes, dramatic cliffs, natural hotsprings, fertile valleys and attractions of islands such as Sao Miguel, Sao Jorge, Pico or Faial and the Terceira’s historic city of Angra do Heroismo, the UNESCO World Heritage site.
Who should consider the transatlantic crossing?
A transatlantic voyage is not for the faint-hearted. It requires good experience, preparation, resilience, and a willingness to embrace days far from land. But for those ready to commit, the reward is extraordinary: star-filled skies without light pollution, wildlife encounters in the open ocean, the profound satisfaction of making landfall after weeks at sea, and possibly a friendship for life with one of the crew or another guest.
It takes about 3 weeks to reach the Caribbean from the Canary Islands and 4-5 weeks to reach islands like the Grenadines or Martinique if starting in Southern Spain. Many of our clients begin in the West Mediterranean locations, such as Sardinia, as early as mid-October, or even in the East Mediterranean locations as early as the last week of September. Flexibility is the norm, and adding special equipment like code-0, a full spinnaker for faster downwind sailing, a couple of water toys such as a SUP or sea scooters, and a Starlink for unlimited internet access is standard nowadays. Thus, highly experienced sailors can do a transatlantic crossing on a bareboat basis, adventure-seeking individuals looking for an experience can do so with their friends, and families keen to avoid flying across can do it with a selected crew.
Choosing your autumn adventure
Whether you seek the life-changing challenge of a transatlantic crossing or the relaxed indulgence of a Mediterranean or Red Sea escape, autumn is a season that offers both. With the right yacht, be it a high-performance monohull, a spacious catamaran, or a state-of-the-art superyacht, we at A2A YACHTING and SuperSailYachts.com can help you tailor the adventure to suit your spirit, skill level, and time frame.
In the end, sailing is about freedom: the freedom to chase horizons, wake up at a new location every night, discover hidden bays and anchorages, or to disconnect from the noise of everyday life. And few experiences embody that freedom more profoundly than harnessing the wind to cross an ocean.
Final thoughts on the autumn season
At the end of the Summer season, the yachting industry congregates at major boat shows, from Cannes, Genoa, and Monaco, to Split, Barcelona, and Annapolis. Some start planning for the summer season 2026 as early as the 1st of September, when booking calendars for most boats are opened.
Last-minute yacht charters in October offer fantastic value too, as recent weather patterns have allowed many sailors and holidaymakers to extend their summer into the first week of November in some locations, particularly in the south of the Adriatic, Greece, and Turkiye.
Historically, many yacht races, flotillas, and regattas take place during this period, most notably the Barcolana in Italy. This international sailing regatta features the largest fleet of sailboats racing in the World, with the start on Sunday, 12th October 2025. Despite all this, the most crucial development in the yachting industry, both in general and in yacht charter in particular, takes place elsewhere.
Thus, why not get out of your comfort zone, join a sailing club, hire a sailboat for one of the autumn regattas, or explore a new found destination such as the Red Sea or further afield where the Caribbean season starts as early as late October. Alternatively, do something amazing and take your family, a team, department, or simply best mates to plan a once-in-a-lifetime sailing adventure across the Atlantic.
Eldin Basic, Yacht Charter Manager
Eldin is the Charter & Sales manager at A2A Yachting (SuperSailYachts.com), where he overseas all aspects of business & marketing operations. With over 20 years of experience in the industry, Eldin brings a wealth of expertise and insight to this role.
He holds a degree from the University College Birmingham, supplemented by leadership training from Harvard Business School and ThePowerMBA, giving him a solid foundation in strategic management.
Known for his talent in developing innovative Blue Ocean Strategies, Eldin is also a certified breathwork practitioner & an active supporter of various charitable initiatives. Passionate about helping others, he is committed to turning dreams into reality & inspiring all to live more fulfilling lives.
.jpg)
