Sailing is the art of using an invisible force to move through a medium that covers 71% of the planet. When you get it right – sheets trimmed, boat heeled just so, the keel carving a clean line through water – there is no machinery involved. Just physics. And nothing else sounds like it.
How sailing works
A sailboat moves using the aerodynamic lift generated by sails shaped to act like vertical aerofoils. Wind flowing faster over the leeward (downwind) face of a sail creates lower pressure, which generates a lateral force. The keel converts this lateral force into forward motion. On a close-hauled point of sail (sailing toward the wind at about 45°), the aerodynamic principle is dominant. Downwind sailing uses drag – the wind simply pushes from behind.
Points of sail: Close-hauled (45° into wind), Close reach, Beam reach (90°), Broad reach, Running (180°, dead downwind). Most sailing is done on a beam or broad reach – the fastest and most comfortable angles.
Sailing certifications
The two main international frameworks are RYA (Royal Yachting Association, UK-standard, widely recognised in the Mediterranean and Caribbean) and ASA (American Sailing Association, standard in North America). Both are recognised globally for chartering.
- RYA Day Skipper – Sail a yacht by day in familiar waters. Typically 5 days + theory.
- RYA Coastal Skipper – Day and night sailing in unfamiliar waters.
- RYA Yachtmaster Offshore – Globally recognised qualification for skippering up to 200 nm offshore.
- RYA Yachtmaster Ocean – Offshore passages, celestial navigation, ocean meteorology.
For chartering a bare boat (without a skipper), most charter companies require at minimum a Day Skipper or equivalent. A Yachtmaster or proof of significant logged miles is standard for larger yachts.
Types of sailing boats
- Monohull sloop (25-50 ft) – The standard cruising yacht. Stable, simple rig. Best all-around for coastal and offshore sailing.
- Catamaran (38-50 ft) – Two hulls, wide beam, stable platform. Less heeling, more interior space. Preferred by liveaboard sailors. More expensive to charter.
- Ketches and yawls – Two-masted rigs. More sail area options, better for bluewater passages.
- Dinghy (8-15 ft) – Single-handed or two-person. The best way to actually learn sailing by feel – dinghies capsize, which accelerates learning.
Bareboat chartering
A bareboat is a yacht chartered without a skipper – you are the captain. Charter companies operate in the British Virgin Islands, Greece, Croatia, Thailand, Maldives, Tahiti, Seychelles, and dozens of other locations. A one-week bareboat charter for a 40 ft yacht in the BVI costs $2,500-4,500 (split between 6-8 people = $300-750 per person). In Greece or Croatia, comparable boats cost 20-30% less.
The BVI is the most beginner-friendly bareboat area in the world – benign trade winds, short passages between anchorages, clear charts, well-marked channels. The Mediterranean in summer (May-September) is ideal: predictable thermal winds (Meltemi in the Aegean), stunning anchorages, low swell.
Best sailing destinations
- British Virgin Islands – The world’s most popular bareboat destination. Perfect trade winds, stunning anchorages, swim-stop culture. Best November-May.
- Greece (Dodecanese, Ionian, Cyclades) – Ancient history, brilliant blue water, reliable Meltemi breeze. Best May-September.
- Croatia (Dalmatian Coast) – 1,000+ islands. World Heritage old towns. Affordable. Best June-September.
- Tahiti and the Tuamotus – Remote atolls, crystal lagoons, sharks and rays. Best May-October.
- Seychelles – Granite islands, trade wind sailing, exceptional marine life. Best April-May and October-November.
- Caribbean (Eastern Caribbean arc) – Martinique to Grenada. Trade wind sailing, excellent provisions, lively anchorage communities.
Bluewater passage sailing
Offshore passages require significantly more preparation than coastal sailing: storm sails, life raft, EPIRB, SSB radio or Iridium satellite communicator, sufficient water and provisions, and a crew experienced in standing watches. The ARC (Atlantic Rally for Cruisers) departs Las Palmas, Canary Islands every November for Barbados – the world’s best-organised ocean rally, perfect for a first Atlantic crossing.
Most bluewater sailors work toward crossing in the trade wind belt (15°N to 20°N for the North Atlantic passage) where downwind sailing makes passage-making comfortable. The Caribbean to Mediterranean passage in spring (April-May, via the Azores or Bermuda) completes the Atlantic circuit.
Plan your sailing trip
Our Bareboat Charter Checklist covers everything from provisioning to marina booking to passage planning. Use our destination guides for anchorage reviews, marina costs, and local weather patterns. The Marine Animal Finder helps you understand what marine life you’ll encounter at each destination and season.