I am writing this in Portals Vells on a rainy day in Mallorca. My buddy Rick left me a bottle of Flor de Caña 12-year-old rum which I am using to ease the pain of multi-year voyage planning, and Samantha and her boyfriend Brandon are in the galley making cookies. So the conditions for thinking through complicated things are, on balance, acceptable.

The thing I am trying to do today sounds simple. I’m finishing the plan that takes S/V Spindrift from where she is in the western Mediterranean to Greece, back through Sicily, out the gate at Gibraltar, down to the Canaries, across the Atlantic with the ARC, and up the east coast of the US. Along the way, Sarah wants to be in Boulder for a Parents Day weekend in October, and we both need to be in the States for Sam’s graduation in spring 2027.
Easy peasy. Get out a chart and draw some lines. Right? Well. Not so fast. It is actually full of constraints. 3 sets of rules cover this voyage, none of them coordinated with the others, and the moment you try to lay the route on the chart all 3 start arguing. Then lay in the weather and you now know why I need rum and cookies.
The Three Rings
There are 3 frameworks layered on top of each other. They overlap. They are not coordinated. Each one is manageable on its own. The trick, and the trouble, is the interaction. And the weather. And Sam’s graduation. And Parents Day weekend. And our desire to be on LBI in the summer.
S/V Spindrift is here under EU Temporary Admission (TA). When a non-EU flagged vessel, like S/V Spindrift, sails into EU waters, it enters under TA. The Union grants the boat 18 months. After that, you must either import the boat by paying VAT, or leave EU waters entirely. VAT runs between 17% and 22% of the boat’s value depending on the country of importation. For a cruising yacht our size, that is a tax bill well over $100,000. So when I say “we are leaving on time,” I mean it.
You can take the boat outside EU waters whenever you like. What matters for the clock is the paperwork, not the length of the trip. A clean exit from EU customs territory, documented at a non-EU port with a fuel receipt and a customs stamp, followed by a re-entry, starts a brand-new 18-month period. A short stop with the right paperwork does the job. A long one without it does nothing. The most common places to plan that exit are Gibraltar, Tunis, Montenegro, and Turkey. We have our eye on Gibraltar.
The next ring is Schengen. 27 countries, mostly EU, share a single immigration regime. Third-country nationals like us get 90 days inside any rolling 180-day window. Overstay it and you collect fines and a stamp that can keep you out of the zone for years. You really do not want to be barred from re-entry while your boat is still sitting in a marina in a Schengen country.
The third ring is our visa. Sarah and I both hold French long-stay visas (VLS-TS). Here is where most cruisers get the next part wrong. A French long-stay visa does not exempt you from the 90/180 rule across all of Schengen. It exempts your time in France from counting against the 90/180 clock. The days you spend in Italy, Spain, or Greece still count. So the visa is not a magic wand that erases Schengen. It is a tool that lets you treat France, including French Corsica, as outside the clock.
That is the architecture of the plan. There are 2 master constraints. The TA clock runs out in fall 2027. The ARC leaves Las Palmas in late November of the same year. Together they fix the western end of our timeline. Everything else, the Schengen budget, the family events, the weather, has to fit before them. The alternative is another full season in the Med, which we are not inclined to plan at this point.
The Greek Problem
Imagine for a minute that none of the 3 rings existed. Sarah and I look at a chart and we say, let’s go to Greece. We are in the Balearics. Greece is roughly 1,000 nautical miles east. We sail out of the Balearics, cruise Corsica, Sardinia, and Sicily. Eventually we find our way to the Greek islands, sail back in the fall, exit at Gibraltar, and cross the Atlantic in November. Easy enough.
Now turn on the rings one at a time and watch the plan break.
Turn on Schengen. Every day from here to Greece and back is a day in Schengen. Except those in Corsica. The sail to Sicily eats Schengen days. The Sicily-to-Corfu hop eats Schengen days. Every Greek island eats Schengen days. By the time we have actually arrived in the place we wanted to go, our 90-day window has very few days left in it.
Turn on the French visa. A relief. Time we spend in France or French Corsica is free. But Italy is not free. Greece is not free. The trip out and the trip back still cost us, every mile. The visa rescues our summers in France. It does not rescue the Greek season.
Turn on the Meltemi. Greek summer is not on a free calendar. The Meltemi, the northerly honking wind that closes the Aegean Sea in July and August, forces a serious Greek cruise into late spring and early summer. Which means we have to be there in May and June. Which means we have to be sailing east in April. Which means the Schengen days we burn on transit are burned right when our 180-day window opens, leaving nothing for a westward push out of the Med.
Turn on Parents Day weekend. October 2026. Right in the middle of the eastbound run from southern France through Corsica and Sardinia to our Sicilian winter haul. We step off the boat for the week, fly to Colorado, and step back on. October weather windows close fast in the Tyrrhenian. The week we are away is a week the calendar runs without us.
Turn on Sam’s graduation. Late spring 2027. Right when we are supposed to be running Greek islands ahead of the Meltemi. The boat has to sit in a Greek harbor for a week while we fly to the States. In Greece there is no free parking.
Turn on the TA clock. This is the killer. The clock does not care about Greece. It does not care about graduation. It does not care about the Meltemi. It started ticking the day the boat entered EU waters and it will run out on a date already on the calendar. Every nautical mile east is a mile we will have to sail back west, on a hard deadline, with no negotiation possible short of a customs-stamped exit through a non-EU port, is say North Africa.
That is the puzzle. The boat is on a clock. The people are on a clock. The wind is on a clock. The kids are on a clock. None of those clocks were set by the same hand.
What We Tried, And What We Kept
The first plan we sketched was the simple one. Sail east, do Greece, sail back. It fell apart inside an afternoon. The Schengen budget alone would not survive a single round trip with any time left to actually enjoy Greece.
The second was a Turkey escape. Run out of Greece into Turkish waters whenever the 180-day window got tight. Turkey is non-Schengen, so days there do not count against our 90/180 budget, and the rolling window keeps moving forward while we are out. Turkey is also outside the EU customs zone, so the trip can reset the boat’s TA clock. The downside is distance. Turkey adds roughly 800 to 1,200 extra nautical miles round trip depending on how far in we push into Turkish water. With the ARC anchored in Las Palmas, every mile east is a mile we have to sail back west, and a fresh 18-month TA does not help when we are leaving the Med anyway. We may still touch Turkey. We probably will not lean on it.
The third was a Montenegro reset. Run north from the Ionian Sea, check into Porto Montenegro or Kotor Bay, exit EU customs territory, and on re-entry start a fresh 18-month TA clock for the boat. What it does not do is refresh our Schengen budget. The 180-day window only rolls clean if we stay out long enough for prior days to age off, and a single port stop in Montenegro does not buy us that. So the trip helps the boat, not the people. The TA relief is still worth something. The price is an extra 1,000 nautical miles or so. This option is still on the table.
The fourth, and the one we kept as the spine of the plan, is a winter haul in Sicily or Sardinia. The boat comes out of the water this fall, we fly home for the winter, and our Schengen days roll off the back of the 180-day window while we are out of the zone. By the time we splash in spring 2027, we have a fresh 90 days. We run to Greece, cruise the Ionian Sea and the Cyclades ahead of the Meltemi, fly out for Sam’s graduation, fly back, sail the western leg, hit Gibraltar before the TA expires, ride the trades down to the Canaries, and pick up the ARC.
That is the only way the spreadsheet stops bleeding red.
The Ledger
I keep a spreadsheet on this boat called the Schengen Ledger and a ledger for the TA. Every day we have been in a Schengen country is on it. Every day we plan to be in one is on it. Every plan change ripples through it.
Move our July out of French Corsica into Sardinia and the September column turns red. Push the spring departure from Sicily a week later and the Greek season collapses to nothing. Add a week of Croatia and the TA deadline owes us 2 weeks back somewhere else. The ledger is unforgiving in a way the regulations themselves never spell out. Each rule reads as a single tidy sentence in a customs handbook. The ledger is where those tidy sentences finally collide.
This is the part nobody warns you about. The rules themselves are not the burden. The bookkeeping and planning is the burden, because every plan is provisional and every plan changes.
What We Have Learned
The first lesson is to get a long-stay visa early if you can. A French VLS-TS turned out to be the single most useful piece of paper on this boat. Without it, 90 days in Schengen out of every 180 would not be enough to support the route we want to sail.
The second lesson is to plan from your hard constraints inward, not from your wishlist outward. We did not pick the ARC because it was on a bucket list. We picked it as the anchor date and built backward. Then we picked our TA exit window because the ARC required it. Then we picked the Sicilian or Sardinian winter haul because the TA exit and the Schengen reset both required it. Then we picked the Greek window because that winter haul allowed it. The wishlist sits inside the gaps.
The third lesson is to use geography deliberately. France is not a country we are visiting. It is a tool we are using. Corsica is not a destination per se. It is a Schengen pressure-release valve. Gibraltar is not a refueling stop. It is the entry and the exit. Montenegro is not a side trip. It is a TA reset disguised as a passage. Once you see the map this way, the planning becomes less daunting. The countries you cruise are also moves on a board.
The last lesson is that the rules are not punitive. They are just inattentive. Nobody at the EU drew up these 3 frameworks together. Each was built for its own purpose. The fact that the 3 of them collide on the deck of a 60-foot sailboat in May is not the system’s problem. It is ours. But once you accept that, the planning gets, if not easier, at least more honest.
The cookies, by the way, are excellent. The rum is holding up. The plan, for the moment, still works. Oh, yeah, and we still have to plan an Atlantic crossing, Caribbean hurricane season and the move up the east coast of the US. More on that later. Time to jump into my bunk.
Fair winds from S/V Spindrift

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