Your First Voyage – How to Begin Sailing From Cabin Charters to Yacht Ownership
- Brainz Magazine
- Nov 14, 2025
- 9 min read
Updated: Dec 1, 2025
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.
When it comes to sailing, many say that it is the best holiday there can be. To be enjoyable, it must first and foremost be a safe and relaxing experience. Even if it is a challenge, an adventure, or, as it can happen, an over-the-top, unexpected, and slightly dangerous experience, it is undeniable that there is something irresistibly alluring about the sea, the freedom of open water, the rhythm of the waves, and the promise of destinations only accessible by boat. Yet for many, the world of sailing can seem as distant as a far horizon. How do you begin? Do you need a license, a crew, or even your own yacht?
The truth is, you can start sailing in luxury, comfort, and safety, without years of training or owning a boat. The modern yacht charter industry offers a range of pathways for newcomers, from simple skippered charters aboard an affordable yacht to a manageable bareboat flotilla, to cabin charters on exquisite catamarans, and eventually, for those with deeper pockets, even yacht ownership with professional management. To begin sailing, the most accessible route is through a private yacht charter. Cabin charters on crewed catamarans stand out as the ideal first experience for new sailors. In contrast, flotilla holidays, powerboat training, luxury yacht charters or superyacht hire, and flexible ownership options are perfect for progressing further or for new boat owners seeking worry-free usage.
1. Cabin charter: The safest way to start enjoying sailing luxury
For most beginners, a cabin charter is the easiest and most enjoyable way to introduce them to the sailing lifestyle. Think of it as booking a luxury hotel suite that floats, complete with an experienced crew, gourmet dining, and ever-changing sea views. You book a cabin aboard a high-end sailing catamaran, share the experience with a small group of like-minded travellers, and let the professional skipper handle everything from navigation to anchoring in secret bays.
Cabin charters are ideal for couples or small groups who want to experience yachting without committing to chartering a full boat or learning to sail themselves.
Top cabin charter experiences in the Mediterranean and beyond
There are several cabin charter options in all major sailing destinations across the world. It would be impossible to mention them all. Here, I mention some of the most apparent, affordable options, as well as the most luxurious ones that are easily accessible with a simple enquiry and may suit a single couple, a family, or a larger group, ideally consisting of three to four couples.
Croatia: Sail the Adriatic aboard the Upwind 50 from as low as €2,000 per week per couple, exploring smaller islands, medieval towns, hidden coves, rare bays and anchorages, and tasting food that you will most likely not have come across anywhere else.
Italy: Discover the picturesque Amalfi Coast on a Lagoon 55 from €4,000 per week per couple, with prosecco sunsets and seaside dining.
Greece: Experience the magic of the Cyclades aboard a Samana 59 from €6,000 per week per couple, island-hopping between Santorini and Mykonos with stopovers on islands such as Paros, Milos, and Folegandros, among many other options.
South of France: Cruise the Riviera between Monaco and St Tropez and across the Lerin Islands, Cap d’Antibes, and Nice in style on board a Sunreef 60 from €10,000 per week per couple, with Michelin-inspired cuisine and chic coastal stops.
Red Sea: Indulge in ultimate exclusivity on the Lagoon Eighty 2 from €20,000 per week per couple, exploring untouched coral reefs and desert-fringed anchorages.
East Caribbean: All the above options, with costs usually around 10 to 30 percent higher, including the option to sail on a 145 ft megacatamaran with rates from €40,000 per week per couple.
Cabin chartering is not just a vacation, it is a gateway to a lifestyle. You gain a sense of the rhythm of life at sea, learn how yachts operate, and discover which destinations or boat styles resonate most with you before taking the next step. As a 20-year experienced yacht charter brokerage agency, A2A Yachting is in a great position to arrange a fabulous first-time sailing experience on board a crewed catamaran or any other type of yacht.
It may also be worth knowing:
All-inclusive packages cover the cabin, crew, meals, and water sports equipment.
Perfect for couples and solo travellers wanting to explore classic Mediterranean routes without handling the yacht themselves.
Flexible itineraries allow for local cuisine exploration, swimming, snorkelling, and an effortless entry into yachting culture.
2. Flotilla sailing: For the adventurous beginner
For those who may have caught the sailing bug and want to take the helm themselves, flotilla sailing is one of the best ways to embark on independent sailing vacations. It is ideal for newly qualified skippers who may have earned their RYA Day Skipper or ICC recently, but still want the reassurance of sailing in company with a lead boat to follow.
In a flotilla, you command your own yacht while following a lead boat crewed by professionals who handle navigation, logistics, daily briefings, and, when necessary, come aboard your yacht to support you and provide further instructions. You gain confidence, improve your skills, and enjoy the camaraderie of fellow sailors, all within the safety net of expert support.
The Mediterranean offers some of the best flotilla destinations in the world, the best ones being in the Ionian Islands of western Greece, the Croatian Dalmatian coast, and the Spanish Balearics. You can explore at your own pace by day and join the group for social dinners or beach barbecues by night. BBQ parties most nights, stopovers for swimming and snorkelling, carefully selected night anchorages, and a relaxed itinerary create easy sailing conditions and shorter distances where new sailors can feel safe and relaxed while enjoying a sense of adventure.
Tips for those interested in flotilla sailing
Join a group of yachts led by experienced crew who assist with daily itineraries and docking, suitable for newcomers to Mediterranean sailing.
Flotilla routes are available throughout Greece, Croatia, and Italy, offering supportive environments for learning and camaraderie.
Enrolled courses, such as the Mediterranean Flotilla Skipper's Course, from around €800 for three days, offer hands-on skills and navigation practice for those ready for more independence.
3. Powerboat licenses: Motor yacht charters with power on demand
If sailing is not your style and you prefer the sleek appeal of motor yachts, consider taking your Powerboat Level 2 licence. These short, practical courses can be completed in a few days and open the door to chartering smaller motorboats independently, usually those up to 30 to 35 ft, perfect for daily trips along the coast or exploring islands near your resort or navigating shorter overnight distances. These courses have a low participant ratio, are taught on coastal waters, and use continual assessment rather than exams.
Aspiring motor yacht charterers can complete RYA Powerboat Level 1 and 2, which cover boat handling, navigation, close-quarters operation, and safety in two to three beginner-friendly days. These are available in all major Mediterranean sailing destinations, from the Atlantic coast of Portugal to the southern shores of the Greek Islands and Malta.
Powerboat hire and motor yacht charters are a fast, exciting, and accessible way to enjoy the sea, especially if you value speed and simplicity. Once you feel comfortable navigating boats up to 10 metres, you can opt for an RYA Intermediate Powerboat licence, which allows you to charter or own larger and more powerful motor yachts. With this experience, you can engage in more advanced boat handling and longer passage planning. The final level for potential boat owners or those keen on more regular yacht charters would be the RYA Advanced Powerboat licence, which can be commercially endorsed and allows you to work on vessels up to 24 metres or charter yachts up to 65 ft on a bareboat basis without crew, as well as sail up to 20 miles away from a safe haven. A2A Yachting can easily arrange powerboat charters, including powerful RIBs with cabins or luxury motor yachts in the 40 to 65 ft range on a bareboat basis.
4. From charter guest to yacht owner
For those who fall in love with the lifestyle, buying your own yacht becomes a natural progression. Yet ownership does not mean you need to handle the complexities of management, crew, or maintenance yourself. It can be costly to run a yacht on your own, unless you can afford it easily or use it regularly.
Many luxury yacht owners today hire a professional skipper or management company to maintain and sail the vessel year-round. The skipper ensures the yacht is ready whenever the family wishes to use it, stocked, serviced, and positioned in the ideal cruising area for the season. This hybrid approach combines the freedom of ownership with the convenience of charter, a best-of-both-worlds solution for busy professionals and families.
When it comes to luxury yachts, if you wish to explore ownership options, SuperSailYachts.com will happily discuss management solutions that may include circumnavigation, allowing your boat to cruise the world’s oceans. You can embark and disembark flexibly while also accumulating charter income that may help cover the cost of ownership. Your boat could become a rare luxury yacht available in remote locations such as the South Pacific, Indian Ocean, or the West Caribbean, or remain positioned in prime destinations around the Mediterranean or East Caribbean.
5. Begin your journey
Sailing is more accessible than ever before. Whether you start with a cabin charter in Croatia or the French Riviera, join a Mediterranean flotilla, or one day step aboard your own yacht, the key is to begin. Once you feel the wind in the sails and the quiet thrill of gliding across the water, you will understand why sailors say the sea calls you back.
When choosing your yacht charter
Choose your yacht broker wisely. A2A Yachting for bareboat and crewed charters, and SuperSailYachts.com for luxury yachts, superyachts, and megayachts, are experienced, knowledgeable, and committed to supporting your project from the outset to disembarkation.
Check preparation routines. Understand how the yacht works, inspect safety gear, and familiarise yourself with basic manoeuvres.
Confirm comprehensive insurance and what is included. Meals, bedding, and local taxes can add to the costs of charter. Only the price of the boat is included. Flights, transfers, food, and crew tips are typically additional.
Travel outside peak season. Consider a modest first itinerary for greater enjoyment, especially outside school holidays and major holidays, when prices can be as much as 75 percent lower.
Consider a skippered charter. Even though you may be qualified, for your first experience, especially with no formal qualifications, a skipper handles everything related to the boat and navigation, allowing you to relax and learn.
6. Final thoughts
For those already sailing or with experience, or as a next step after choosing how to begin your sailing lifestyle, these are some of the other main options offered within the yacht charter industry, all provided by A2A Yachting.
Regular Bareboat sailing holidays
Luxury yacht charters in the Mediterranean and the Caribbean
Superyacht hire in the Mediterranean and the Caribbean
Transatlantic crossings on superyachts, cabins, or bareboat yachts
One-way yacht charters, both bareboat or crewed (for example, Split – Dubrovnik in Croatia or St Martin, Grenada in the Caribbean)
Long-term yacht charters (for example, bareboat charter over 5 months from Turkey, the South of France or in the East Caribbean)
Tandem charter – Chartering one boat for your family while another one for your extended family or friends
Cultural or cycling tours boat, if your group is keen to experience something new and unusual
De-luxe motor sailor charters in the Mediterranean
Corporate exclusive charters – Grand Prix in Monaco or Abu Dhabi, MIPIM or Cannes Film Festival
Tennis and Golf yachting holidays
Full Seabbatical long-term bareboat charters
Deluxe 5-star gullet sailing holidays
Powerboat and superyacht tender hire
Motor yacht charters in the Mediterranean
Other types such as nudist charters, gay charters, parties, etc
If none of the charter options appeal for now, why not just join one of the many sailing courses available around the amazing Solent, within the spectacular English Riviera, or even be part of the World's Famous COWES WEEK, as the spirit of sailing is nowhere better experienced than here.
If this text inspired you to start sailing or book your next yacht charter holiday, I would be pleased to hear from you. You can contact me at eldin@a2a-yachting.net or on WhatsApp at +447792052007 to discuss your plans, even if they are not immediate. For experienced sailors, I am particularly skilled in long-term charters lasting from two months to full sabbaticals of up to 18 months. These may include transatlantic or transpacific crossings, one-way charters, and long-distance cruising.
However, for those inexperienced, starting with a cabin charter on a skippered or crewed catamaran provides both comfort and a hands-on introduction. Meanwhile, flotilla holidays, powerboat training, and professional management for owners cater to a range of skill levels and ambitions. Every step can be tailored for maximum enjoyment in the world’s best sailing destinations.
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.
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