Three islands, one afternoon. On the chart it looks easy. Out on the water it almost never is, and the reason is dull: every mile costs time, and time spent sailing is time you don’t spend swimming, eating lunch somewhere with a view, or getting into a quiet anchorage before dark. So how much sailing can you realistically fit into a day on a sailing holiday? Less than the map suggests. How much less depends on the boat’s true speed, the hours you’re actually moving, the conditions and the sort of week you’re after. What follows is a way to build a sailing itinerary that keeps room for the good parts.
Nobody can hand you a daily distance that works for everyone. Boats differ. So do winds, and so does people’s patience. You can work out your own figure, though. A knot is one nautical mile (NM) an hour. A nautical mile runs a bit longer than the land kind, and skippers plan in them. Take your average speed, multiply it by the hours underway, and there’s a rough day. Averaging 5 knots for 4 hours gives about 20 nautical miles. That’s an example, not a promise about any boat. What matters is the average, not the maximum printed in a brochure, because tacking, patches of light wind and adverse current all drag the real number down, and most of us guess too high before we set off. A short day sail also isn’t a long passage, so don’t picture the boat moving all day on a holiday. Take any daily sailing distance you read as a place to start, then work out the sailing distances that suit your group.
Wind sets the tone. Which way it blows decides whether you’re reaching along comfortably or zigzagging, and how hard it blows decides the speed. A foul tide, or short, steep waves, can take off more speed than you’d guess. The route matters too, because you’ll rarely sail the straight line between two harbours. A gap that looks small on the map can become extra nautical miles and extra sailing time if the wind is right on the nose. Then there are the people. The skipper’s reading of the day counts, and so does how comfortable everyone is, since nobody enjoys a rough passage just to make an arrival time. All of it shifts by the hour. A skipper treats any estimate as a draft.
Think in hours underway, not just miles. A relaxed sailing holiday is often short hops and long stops. Two hours of sailing, a swim, lunch, a wander ashore. Longer days make sense when you need to reach somewhere specific, but you pay for them with time at anchor, and that’s what most people booked the trip for. Six hours of sailing can start to feel like a job. A late departure squeezes the swim, because the planned arrival doesn’t move. And the skipper may change the plan for wind, swell or a forecast that turned overnight. A good one will tell you why.
Most of a day happens at anchor anyway. Finding a bay and approaching it slowly takes time. So does anchoring, or picking up a mooring where that’s allowed. Then comes lunch, a swim, just sitting somewhere, maybe a trip ashore for a village, a restaurant or a short walk, and finally the leg to tonight’s anchorage. Add it up and a route with fewer miles often gives a fuller day. That’s the idea behind a good sailing itinerary: sailing holidays are about the places between the passages. Not every bay allows overnight anchoring, and not every stop has a landing, so check first. Our guide to choosing an overnight anchorage explains what makes a stop suitable. And there’s no correct number of hours for every group. Decide how you want the evening to feel, then work backwards.
Start with what the day is for, say a swim and a village lunch. Estimate distance and passage time cautiously, then add time for stops, arrival and the night, and pick a backup in case the wind refuses. Now the numbers, all of them illustrative. You leave at 9:30 and sail two and a half hours at 5 knots, which is about 12.5 NM. You anchor for a swim and a long lunch until 14:00. Two more hours at the same speed adds 10 NM, and you’re in at 16:00 with the evening ahead. In total that’s around 22.5 nautical miles and 4.5 hours underway. On a catamaran charter a day like that leaves the group unrushed and the arrival easy, and our catamaran-selection guide covers how layout affects comfort on the longer legs. Swap in your own boat and route.
The place you’re heading for isn’t the furthest point you can reach before sunset. It’s somewhere you picked in advance, with time to spare once you get there. So choose the overnight stop before you leave, give the skipper time to judge shelter, local restrictions and the anchoring or mooring options, and keep a second choice up your sleeve. Good sailing itinerary planning starts from arrival and works back to departure. On a boat with skipper, those decisions are theirs, and they’ll rely on current local information. Sailing Aeolian Islands waters, for example, means dealing with steep seabeds and busy anchorages, which our guide to anchorages in the Aeolian Islands covers.
The skipper assesses conditions and manages the route. You say what matters to you and how fast you like to go, and the plan still bends to weather, sea state and practical limits. Catamarano Skipper is a guide to curated skippered catamaran options if you’d like to look at some.
A good day balances passage, stops and arrival against what your group wants and what the sea allows. The mileage is whatever it turns out to be. When you’re ready to build your week, our sailing guides and Catamarano Skipper’s curated charter options are a place to start.
On every sailing boat, somebody is keeping an eye on the wind. The real question for your week is whether that somebody is you. If you plan the route, trim the sails and make the weather calls yourself, the trip is entirely yours. If you hand all of it to a professional, those same hours go to swimming, reading and arguing about lunch. Neither makes the better holiday. It comes down to your experience, your qualifications, who’s coming and what you can spend. Catamarano Skipper is a guide to skippered multihull options, so we’ll treat the choice of a boat with skipper fairly against sailing independently, whichever sailing holiday you have in mind.
Picture the day from a deck chair. Coffee, a swim stop, a late lunch in a harbour you’d never have found alone. A professional boat skipper handles the navigation, the boat handling and the weather decisions, and usually starts with a safety briefing and a walk around the boat. After that you shape the week together. Say what matters to you and the route bends around it, within what the sea allows. Local knowledge comes with the arrangement, from quiet bays to the right harbour restaurant. Your own part is lighter but it’s real. You follow the safety instructions, accept that the skipper has the final say on safe navigation, and expect to help with lines when docking. As the person who signs the agreement, you also remain responsible for payments and for your guests. Don’t expect a cook or a cruise director. A relaxed sailing holiday runs on good communication.
Bareboat means the boat arrives without a hired professional, and the work passes to you. That covers passage planning, manoeuvring in tight marinas, weather decisions and running the crew. In return you get independence, since you choose the route and the pace, inside what’s safe and permitted. A bareboat charter asks you to prove you can handle all of it. Across much of the Mediterranean, operators expect a recognised sailing certificate, such as the International Certificate of Competence or a Day Skipper-level qualification, along with some evidence of recent experience, and Croatia adds a radio certificate on top. Many Caribbean destinations are looser, and a sailing résumé can be enough. So the bareboat charter requirements depend on the boat, the flag, the destination and the operator, and a bareboat charter license by itself doesn’t always meet a company’s experience rules. Get the exact list before you pay a deposit.
Start with who runs the boat. On a skippered yacht charter it’s a professional, and on a bareboat charter it’s the qualified charterer and crew. Planning the day works differently too. With a boat with skipper you talk through stops and the skipper shapes the route around wind and safety, but go bareboat and the plan is yours to build, and yours to defend when it goes wrong.
Experience is the next split. A yacht charter with skipper suits people who can’t operate the vessel, or just don’t want to, while bareboat bookings come with formal competence checks. Then there’s how much independence you want. Bareboat gives you direct control of the sailing. A skipper brings professional handling and opens the week up to more people. Put simply, bareboat trades ease for control, and a skipper trades some control for ease. One practical point: the skipper counts as crew on the official list, so they take a place in the boat’s capacity, usually in a cabin of their own.
Neither option is absolute. A skipper can’t promise every stop you fancy, and bareboat crews meet the same weather, safety rules and local restrictions.
Usually the skipper adds a line to the bill, though that’s rarely the whole story. A boat rental with skipper may show the fee separately or fold it into a package, so compare the full booking and not the headline price of the boat. Ask about the skipper’s food, which guests normally cover, and about where they sleep. Then keep in mind that fuel, provisions, marinas and final cleaning apply whether or not a skipper is aboard. That’s why bareboat isn’t automatically the cheaper road once you count the responsibility that comes with it. Rates move with the offer, destination and dates, so ask for a clear total on any skippered charter before you compare. Line up the same dates, the same boat and the same inclusions first, or the gap between two quotes mostly measures what each one leaves out. Our cost guide breaks down each category.
A skipper probably suits you if you’d like to enjoy the week without being in charge of navigation, or if you don’t hold the qualification a bareboat booking demands. It also fits a group that would rather spend its energy on the destination, and anyone who wants professional hands on the boat but still a say in the plans. Travelling with children is another case. Their safety stays your job either way, but you may like someone else carrying the navigation. And if you’re simply curious about sailing, many skippers are glad to involve guests who want to learn, though formal training isn’t a given.
A bareboat charter may suit you instead if you hold the right qualification and meet the local rules, and you enjoy planning passages and carrying the responsibility. Everyone aboard should also be comfortable with what that responsibility involves.
Either way, no option guarantees a particular itinerary. Weather, local rules and safety calls reshape every week at sea.
Before you rent a boat with skipper, or commit to sailing yourself, put a few things to the operator. Is the skipper included in the advertised price? Who covers the skipper’s meals, and where do they sleep? Ask what qualifications and documents a bareboat booking requires, and what the charter price includes. Find out who makes route and safety decisions when conditions change, and whether you can ask for a different skipper if the match isn’t right. And don’t skip the deposit, payment and cancellation terms. Written answers beat verbal ones, so keep them with your booking.
The right choice starts with the week you want and the requirements you can honestly meet. If that week means swimming, slow harbours and someone else watching the wind, a boat with skipper may be exactly right. Catamarano Skipper helps you discover and compare skippered multihull options, so you can shape your sailing holiday around what you want to do, not what you have to.
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