Madeira, Portugal

THE PURSUITMADEIRA

An island conjured out of the sea — and everything it has traded, hidden and sailed toward since.

Two experiences  ·  Funchal old town, on foot  ·  Built & ready
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The invitation

Six hundred years ago, this island wasn't on any map.

Then sailors blown off course found it — all forest and fog — and set it alight to make room. What grew back was a wine the world fought over, a harbour raiders couldn't resist, and a young navigator who would one day go looking for something far bigger.

You'll be handed sealed envelopes, one at a time, and sent out on foot through the oldest streets in Funchal to follow it for yourself.

An island this rich was never left alone for long.

Two ways to walk it. Pick your story.

Three ways to play

One island. Three stories.

The Pursuit comes to Funchal in three editions — all self-guided, entirely on foot through the old town, roughly two to three hours. Pick the one that fits your group.

For any group

The Wine Run

Charm a cask across the old town.

Madeira wine once crossed oceans as currency — and came home better for the journey. Rival trading houses move their cargo through the market, the painted-door lanes and the cellars, trading up by charm alone. First house to land its cask at the water wins the trade.

  • Every checkpoint verifies — the island hands you nothing
  • Equal parts tasting, bartering and foot-race
  • The Trade-Up with locals — charm only, never money
Enter the Wine Run
For the restless

Dead Reckoning

Learn to read the sea, the way he did.

Before he crossed an ocean, a young navigator lived in this town — trading sugar, marrying into the family that found the island, learning to read wind and star and current. Follow the lines he would have walked, piecing together a route that was never meant to leave the harbour. Some charts were worth more than gold.

  • A trail of navigation, maps and the open Atlantic
  • The history they teach — and the history they don't
  • A finale that points due west
Enter Dead Reckoning
For the bold

The Sack of 1566

The year the sea came for the city.

A French fleet once fell on this harbour and held it for days — churches stripped, homes burned, the nuns fleeing into the mountains. Race the raid through the old town, from the fortress that failed to the yellow fort the city built so it would never happen again. Somebody always knew the corsairs were coming.

  • A darker trail — fortresses, betrayal, and a city on fire
  • Every checkpoint verifies, out on the stone where it happened
  • Secret roles in play — not everyone is who they say
Enter the Sack
How it works

Sealed envelopes. One old town. No guidebook.

Whichever story you pick, the shape is the same: a trail that unfolds in your hands as you walk — phones-down on sealed envelopes, or live on the app — and a reckoning at the end.

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The Sealed Envelopes

Open them one at a time, in order, on the honour system. Each sends your team somewhere new in the old town — the story deepening with every seal you break.

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The Trade-Up

Optional — switch it on if your group wants it. Every team starts with one small token and trades it up, charm only and no money, into something better. Best item and best story win at the Tribunal.

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Verified Checkpoints

No "tap done." You prove you were there and that you found it — on the stone, in the cellar, by the water — before the next envelope opens.

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The Tribunal

Everyone reconvenes for the reveal over dinner, where the whole night turns on its head and every team renders its verdict.

The answers aren't in a guidebook.

They're in the market, the painted doors, the cellars and the fortress by the sea. You bring the curiosity. Funchal brings the rest.

Bring it to Madeira

Some of it they'll pour you.
Some of it only the island remembers.

Dates for the Funchal editions are being set now. Choose your story — or get in touch to bring The Pursuit to your group.