Four products share this phrase and the price gap between them is larger than the gap between any two destinations. You can take the whole boat and sail it, take the whole boat with a professional, take the whole boat with a crew who cook, or buy one cabin on a boat somebody else is running. Working out which one you actually want is the first and most valuable decision.
The whole boat, sailed by you
Bareboat is the cheapest and the most demanding. Sunsail publishes about $3,500 for a low season seven day bareboat monohull in the British Virgin Islands and about $5,700 for a low season catamaran. You need a recognized certificate in most of the Mediterranean, though not in the BVI, and you need to be willing to berth a strange boat in an unfamiliar harbour on a Friday evening.
The whole boat, with someone to run it
A skipper sails the yacht and leaves the rest to you; a crew adds a cook or host and takes on the provisioning and the meals. The step between them is large. The Moorings publishes a 7 day bareboat charter for 2 in the Abacos from $5,579 and skippered packages from $12,479, which is the clearest published picture of what putting professionals aboard does to the price.
One cabin, on somebody else's boat
A cabin charter or catamaran trip sells you a berth rather than a yacht, with a skipper aboard and other guests in the other cabins, priced per person. It is much the cheapest way for one or two people to spend a week sailing, and you give up the route, the anchorages and the saloon. For a family it usually works out worse on both money and comfort.
Which one fits which group
A couple who do not sail: a cabin charter or a skippered week. A family with children: the whole boat, probably a catamaran, probably with a skipper the first time. A group of six who sail: bareboat, and take the savings in a better boat. The commonest mistake is a group booking bareboat on price and then hiring a skipper at the dock, which costs more than having booked skippered.
What none of them include
Flights, transfers and food, in every case. Fuel, berthing and local taxes on everything except a fully crewed charter with an Advance Provisioning Allowance, where they are paid from a float you hand over in advance and reconcile at the end. Budget the week rather than the boat, or the boat will be the smaller half of what you spend.
Questions people ask about sailing vacations
How much is a sailing vacation?
Sunsail publishes about $3,500 for a low season seven day BVI bareboat monohull and about $5,700 for a low season catamaran, read on 11 September 2026. A crewed week costs several times that.
What is a cabin charter?
A berth on a boat with a skipper aboard and other guests in the other cabins, sold per person. The cheapest way for one or two people to sail for a week, at the cost of the route and the privacy.
How much more is a crewed sailing vacation?
Roughly double for a skipper, and more again for a cook. The Moorings publishes Bahamian bareboat from $5,579 against skippered packages from $12,479 for the same seven days.
Do I need to know how to sail?
Only for bareboat. Skippered, crewed and cabin charters all have a professional aboard, and in most of the Mediterranean a bareboat needs a recognized certificate checked at handover.