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First-time sailor on a workation: a practical checklist

What to pack, what to expect, and what nobody tells you before your first week on a sailing yacht with a laptop.

·2 min read

If you have never been on a sailing yacht for longer than an afternoon, and you are about to do a week of real work from one, this is everything we wish someone had told us before our first.

What a normal workday actually looks like

07:30 — the boat wakes up at anchor in a quiet bay. Someone makes coffee. 08:00–12:00 — deep work. The boat is still; most guests set up at the main salon table, on deck under the shade, or at the bow. Light breeze, no city noise, no Slack emergencies because nobody near you is triggering them. 12:30 — swim. Lunch. 14:00 — the anchor goes up, the sails go out, we move to the next anchorage. 16:30–19:00 — a second shorter work block if you want one, or nothing if you do not. Dinner on deck.

Packing (the non-obvious parts)

  • Noise-cancelling headphones. Not for noise — for focus when someone else is taking a call two metres away.
  • A USB-C Ethernet adapter. Pair with the captain's 4G hotspot for stable calls.
  • Sunscreen you actually like using. You will put it on four times a day.
  • One long-sleeve sun shirt. Eight hours of deck sun adds up; "I'll just stay in the shade" never survives the week.
  • Soft-sided bag, not a hard suitcase. Cabin stowage is shaped for soft bags.
  • A water bottle with a closable lid. Open cups on a moving boat is a short story with a wet ending.
  • Zero formal clothes. Linen shirt + shorts + boat shoes is the fancy dress code.

Seasickness — the one honest paragraph

Most people are fine. Catamarans are very stable and we only sail in calm weather. If you have no idea how you react to a boat, pick up generic cinnarizine or meclizine at any pharmacy before you fly and take one 30 minutes before the first passage. After the first passage you will know whether you need any more. We have run this with dozens of first-time sailors and the worst outcome has been "a bit green for an hour".

Meeting etiquette on a shared boat

One simple rule: if you are about to take a call, tell the boat. Someone else in headphones might be recording, or the captain might be about to start the engine. The fix is two words: "call in five". We have not had a single missed meeting in three years from getting this wrong.

Money and what to expect to spend

Your published price covers everything on board — groceries, fuel, the captain, the marina. You spend on: dinners ashore (we do 2–3 per week, usually €25–€50 per person at a good tavern), optional excursions at some stops (diving, quad bikes, a visit to a winery — expect €40–€80 if you go), and a crew tip at the end if you enjoyed yourself. 10% of the cruise price is the usual reference.

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