Plan the crossing before you plan the cottage

It is tempting to fall for a photograph of a whitewashed cottage above a bay, book it, and only then work out how you will actually get there. On the Scottish islands that is the wrong way round. The ferry is the fixed point of the trip; everything else bends around it. Sailings on many routes run a handful of times a day in summer and far less often between November and March, and car spaces for July and August are frequently gone by the previous autumn. Once you know which crossing you can secure, the choice of island and accommodation becomes far clearer.

Start by deciding whether you are travelling as a foot passenger or taking a vehicle. Foot passengers are much more flexible: you can often turn up and travel on the next sailing, and you are not tied to a specific vehicle slot. If you are bringing a car, book as early as you can and be willing to travel midweek or on an early or late sailing, when pressure on deck space eases. Note your check-in window too — cars are usually expected 30 to 45 minutes before departure, foot passengers rather less.

Match the island to the kind of break you want

As a general rule, the shorter the crossing, the easier the island is for a short break. Islands reached by a hop of under an hour suit a long weekend beautifully; you can arrive on a Friday evening and feel settled by supper. Longer crossings — two hours and upwards — change the rhythm of a trip. Add a second ferry and you have used most of a day on travelling, so plan at least four nights, ideally a week, to make it feel worthwhile.

Think about what you want from the days. Some islands reward walking and cycling from the pier, with villages, beaches and cafés within a few miles. Others are spread out, with a single main road and long gaps between settlements, where a car or a well-studied bus timetable makes the difference between a rich week and a frustrating one. If you are travelling without a car, look hard at how far the island's attractions really are from the ferry terminal — an island can look small on a map and still be a nine-mile walk from anywhere you want to be.

Why flexible dates save you money and stress

Island travel rewards those who can move their plans by a day or two. Sailing times shift with the tide on some routes, and timetables change between summer and winter. Weather can cancel or delay a crossing at short notice at any time of year, with autumn and winter storms the usual culprits.

• Build a spare day at each end of the trip, especially if you have a flight or a train to catch on the mainland afterwards.
• Check whether sailings run on Sundays on your chosen route — some do, some do not, and some only in summer.
• Shoulder seasons — late April to June, and September to mid-October — often bring kinder prices, fewer people and settled enough weather for walking.
• Bear in mind midge season in the west from roughly June to August, particularly on still, damp evenings.

Stay close to the pier, or on a reliable bus route

If you are arriving without a car, accommodation within walking distance of the pier is worth paying a premium for. It removes an entire layer of logistics, and it makes a delayed sailing far less stressful — you can walk to your door rather than chase a lift that may not come. Failing that, look for a place on a route where the bus timetable is built around the ferry arrivals, since on many islands the buses meet the boats as a matter of course.

Do check the last bus of the day, and how often it runs. On some islands there are only two or three services a day, and a Sunday service may not exist at all. A property that is a ten-minute drive from the terminal can be an hour and a half on foot with luggage. Ask the host directly: how do most guests without a car reach you, and what happens if the ferry is late?

Questions to settle before you pay a deposit

• What are the exact check-in and key-collection arrangements, and can they accommodate a late ferry?
• Is the ferry fare included in any package, and can the crossing be moved if your dates change?
• What is the cancellation policy on both the accommodation and the sailing?
• Is there a shop, pub or café within walking distance, and does it open in the evening or on Sundays?
• How reliable is the mobile signal and wifi, and is there a landline as a backup?
• Is there somewhere secure to store bikes or outdoor kit?

Pack for the crossing and the first night

Pack layers rather than bulk, and include a waterproof that genuinely keeps out driving rain. Bring cash for small honesty boxes and rural cafés, a torch for dark lanes, and enough food for your first evening in case you arrive after the shop has shut. If you are self-catering, order a grocery delivery to arrive on the day you do, or collect a click-and-collect before you board. Midge repellent earns its place in the bag from late spring onwards.

Above all, allow the islands to set the pace. Build in slack, treat the timetable as a guide rather than a guarantee, and the rewards — empty beaches, quiet roads, a horizon that goes on for ever — arrive all the more easily.