Wild WorkationGuides
Evergreen answers to the real questions people ask before booking a sailing workation — written from our own experience running these trips.
What a week working from a sailboat actually looks like
An honest, hour-by-hour account of a real working week at sea — the morning focus block, the afternoon sail, what the internet is actually like, and who it suits.
How to plan a remote-team offsite people remember
Why most offsites fall flat, what actually bonds a distributed team, and a practical plan — venue, budget, and agenda — for a week that sticks.
The best sailing-workation destinations in 2026
Five coasts ranked for working from a boat — by connectivity, season, cost, visa, and time zone, from people who run trips on all of them.
How much does a sailing workation cost? (2026)
The full price of a week at sea — what one all-inclusive price covers, what you spend ashore, and how shared, team, and vacation trips compare.
Starlink on a sailing yacht: what actually works in 2026
The honest state of satellite internet at sea — what Starlink delivers, where it fails, and why a 4G SIM is still in every crew bag.
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.
How to pitch a sailing team offsite to your CFO
The numbers, the risk frame, and the three-page memo that gets a team offsite through budget — without killing the reason you wanted it.
Best Mediterranean destinations for remote work in 2026
Turkey, Greece, Croatia, Montenegro — ranked by the things that actually matter for a workation: connectivity, timezone, cost, and schedule-friendliness.
Is a team offsite tax-deductible? What founders should know
When an offsite counts as a business expense, what documentation survives an audit, and whether the venue being a yacht changes anything. Not tax advice — a checklist for the conversation with your accountant.
A sailing workation with kids: what actually works
Which ages work on a boat, how the working day changes with a family aboard, safety, cabins, and when to pick the vacation format instead.
Seasickness on a sailing workation: the honest guide
How likely it actually is, why the working day happens on flat water, what prevention works, and who should test themselves on a day sail first.