The word "charter" covers three fundamentally different experiences, and the gap between them is wider than most first-time clients expect. A bareboat charter is a self-drive holiday on the water — the boat is yours to command, provision, and navigate. A skippered charter adds a professional captain who handles the sailing while you handle the holiday. A crewed charter adds a full team — captain, cook, steward — and the experience shifts from sailing holiday to floating hotel. The choice shapes everything: cost, freedom, effort, the relationship between you and the sea.
Bareboat: the self-drive option
A bareboat charter puts you in command. The charter company hands over a yacht — inspected, fuelled, provisioned if you have ordered in advance — and you sail it for the week. You plan the route, handle the navigation, cook the meals, manage the anchoring, and return the boat in the condition you found it.
This is the purest form of charter sailing and the cheapest. A bareboat is typically 40-60% less expensive than the equivalent skippered charter and a fraction of the cost of a crewed yacht. The trade-off is responsibility: everything that happens on board is yours to manage.
Requirements: Most charter companies require the lead skipper to hold a recognised sailing qualification — an ICC, RYA Day Skipper, ASA 104, or national equivalent. Some also require a VHF radio licence. A sailing CV (a written summary of experience) is commonly requested and occasionally scrutinised.
Best for: Experienced sailors who want full autonomy; couples or small groups with at least one confident skipper; return charterers who know the destination; anyone who finds the idea of being told where to sail by a hired captain slightly grating.
Not ideal for: First-time sailors; large groups where no one holds qualifications; destinations with demanding conditions (strong winds, complex tides, poorly charted waters); groups where the "skipper" would rather be on holiday than on watch.
Skippered: the guided option
A skippered charter adds a professional skipper — typically a local sailor with extensive knowledge of the cruising area. The skipper handles navigation, passage planning, anchoring, and docking. You can participate as much or as little as you want: some clients crew actively, learning as they go; others sit in the cockpit with a book while the skipper manages the boat.
The skipper sleeps aboard (usually in the smallest cabin or a forepeak berth) and eats with the crew. Their daily fee — EUR 150-250 in the Mediterranean, slightly more in the Caribbean — covers their time and expertise. Food and drink for the skipper are traditionally the charterer's responsibility.
The advantage is confidence. A good skipper knows the local waters intimately: which anchorages are protected from tonight's wind direction, which restaurants are worth the walk, where to find fuel on a Sunday, when to leave early to beat the afternoon swell. This knowledge is worth more than its cost, particularly in unfamiliar waters.
The risk is chemistry. You are sharing a confined space with a stranger for a week. Most professional skippers are socially adept — it is a requirement of the job — but a mismatch in temperament or expectations can strain the holiday. Communicate clearly at the briefing: how involved you want to be in the sailing, what kind of pace you prefer, when you want suggestions and when you want to be left alone.
Best for: Groups that include non-sailors; first-time charterers who want to learn; charterers visiting an unfamiliar or challenging destination; anyone who wants to sail without the full responsibility of command.
Crewed: the full-service option
A crewed charter is a different category of experience. The yacht comes with a professional crew — at minimum a captain and a cook, on larger vessels a full complement including steward, engineer, and deckhand. The crew handles everything: sailing, navigation, meal preparation, cleaning, provisioning, and itinerary planning.
The cost reflects this. Crewed charters are priced as all-inclusive packages — yacht, crew, food, drink, fuel, port fees — and the weekly rate for a 50ft sailing yacht with captain and cook starts at EUR 8,000-15,000 in the Mediterranean, rising sharply with vessel size and crew complement. A 60ft catamaran with three crew might run EUR 15,000-25,000 per week. Large motor yachts and superyachts operate in a different financial stratosphere entirely.
What you receive for this money is a holiday without logistics. Meals are prepared to your preferences, the boat is immaculate, the itinerary is curated but flexible, and the captain's local knowledge is encyclopaedic. The best crewed charters feel like staying in a private waterfront villa that relocates every day.
Best for: Non-sailors who want to experience sailing without any of the work; celebrations and special occasions; families with young children who need the extra hands; corporate entertaining; anyone for whom the holiday budget is less important than the holiday experience.
The caveat: A crewed charter is not really a sailing holiday. It is a luxury holiday that happens to take place on a boat. If you want to learn to sail, feel the tiller, understand the wind — a crewed charter will not deliver that. The crew will let you take the wheel if you ask, but the dynamic is fundamentally that of guest and staff, not of sailor and sea.
Cost comparison
For a 40ft yacht, one week, Mediterranean high season, crew of six:
| Charter type | Hull/package cost | Skipper | Provisions | Total |
|---|---|---|---|---|
| Bareboat | EUR 5,500 | — | EUR 800 | EUR 6,300 |
| Skippered | EUR 5,500 | EUR 1,400 | EUR 1,000 | EUR 7,900 |
| Crewed | EUR 12,000-18,000 (all-inclusive) | Included | Included | EUR 12,000-18,000 |
Per person per week, that translates to roughly EUR 1,050 for bareboat, EUR 1,320 for skippered, and EUR 2,000-3,000 for crewed. The bareboat and skippered figures exclude eating ashore; the crewed figure includes everything.
The hybrid approaches
Skipper for day one only: Some charter companies offer a skipper for the handover day at EUR 200-400. The skipper sails with you for the first passage, demonstrates the boat's systems, briefs on local conditions, and disembarks at the first overnight stop. This is an excellent option for competent sailors visiting an unfamiliar destination.
Hostess or cook only: In some markets (particularly Turkey and Greece), you can hire a cook without a skipper. The cook provisions and prepares meals while you sail the boat. Daily rates of EUR 80-150 buy excellent food and eliminate galley duties — a significant quality-of-life upgrade on a week-long charter.
Flotilla sailing: A flotilla is a group of bareboat yachts sailing the same route, led by a mothership with a professional skipper and hostess. You sail your own boat but follow a planned itinerary with social events and a support crew on call. Flotillas are popular in the Ionian and Croatia and suit first-timers who want autonomy with a safety net.
The right charter type is not a matter of budget alone — it is a question of what you want from the week. If the sailing is the point, go bareboat. If the destination is the point but you lack the skills or confidence, go skippered. If the experience is the point and the boat is merely its setting, go crewed. Each delivers a different holiday, and all three are valid.
