Four Weeks, Fifty Doors: How We Built Madeira's First Fully Digital City Pass at Madeira Startup Retreat

I spent two months on Madeira earlier this year.

I walked the levadas, swam in the natural pools, ate at restaurants that have fed locals for generations, and met the people behind the businesses that give this island its character. By the time I left, one thing was clear: Madeira deserved a product built specifically for it.

So we built one. In four weeks.

The Tripnly Madeira City Pass (a trademark of Tripnly) is now live — a first for the Portuguese archipelago. This is the story of how we built it.

Why Madeira?

Tripadvisor has crowned Madeira the #1 Trending Destination in the World for 2026: dramatic volcanic landscapes, natural swimming pools carved into lava rock, ancient levada trails through laurel forests, and a food culture all its own.

The Madeira island group sits in the Atlantic Ocean about 600 kilometres west of Africa.

And yet, until now, no fully digital city pass existed for Madeira.

That gap was impossible to ignore. Madeira’s travelers deserve better, and its local businesses — the family-run restaurants, the independent surf schools, the cultural institutions keeping centuries-old traditions alive — deserve a product that works as hard as they do.

When we arrived in February for the Madeira Startup Retreat (7th Edition), we didn’t waste a day.

Four Weeks, 50+ Partners, and a Lot of Doors

Building a city pass from scratch, on an island where you have no network, is hard. There’s no shortcut for it. You knock on doors. You have conversations. You listen. You convince people, one at a time, to trust something that doesn’t exist yet.

That’s most of what those four weeks actually were: showing up, explaining the idea, and earning a yes. In the end, 50+ local businesses gave us one — museums, transport providers, tours, cafés, outdoor experiences, surf schools, and accommodation, independent businesses run by people who’ve devoted their lives to this island. We’re still adding more every week.

Moments before one of the best lunches of our lives at A Pipa Restaurant & Bar, with Tripnly Global Ambassador Nurgül at Porto da Cruz, Madeira.

What I didn’t expect was how much the island itself would shape the product. Living here while we built it meant every decision was grounded in a real place and real people, not a spreadsheet. The pass is projected to generate over €5 million in annual value for local partners and the broader Madeira tourism economy, channeling visitor spending directly to the businesses that define the island. That framing — building infrastructure for a community rather than just another travel product — came from being here, not from a plan.

The Madeira Startup Retreat, backed by Turismo de Portugal and recognized by the Câmara Municipal do Funchal, made a lot of those first doors easier to open. Innovation and sustainable tourism, hand in hand.

What We Actually Built

No physical card. No app to download. No complicated activation.

You buy it, you get a QR code, and Madeira opens up.

The Tripnly Madeira City Pass comes in 1–5 day options from €22.90 and gives instant digital access to 50+ of Madeira’s top attractions and experiences — museums, cultural landmarks, levada tours, restaurants, coffee shops, surf schools, coworking spaces, and local brands. It can be activated any time within 12 months of purchase.

Does it actually save money?

We spent a lot of the build worrying about this exact question, because a pass that doesn’t clearly pay for itself isn’t worth making. On a typical 3-day trip, the net saving is over €160. On a 5-day stay, up to €339. The math is straightforward, and it pays off on day one.

Save on more than 50 experiences in Madeira, including whale watching cruises.

Tripnly Madeira City Pass is available at madeiracitypass.tripnly.com and through GetYourGuide, Viator, Tripadvisor, and 10+ other OTAs worldwide.

What the First Months Taught Us

Since March 20th — and before we’d even reached July 1st — we crossed into the hundreds of sales across all our channels. And we’re still counting.

But the number that means the most to me isn’t the sales figure. It’s this: rated 5.0 on Google by 80+ travelers, with 100% customer satisfaction from day one. Every single traveler who has used the pass has given it five stars.

When you’ve built something this fast, that’s the signal you’re really watching for — proof that speed didn’t come at the cost of the experience.

Why This One Was Personal

The Tripnly Madeira City Pass is our second city pass, after Lisboa, with Torino and several more already in the works.

Exploring the Immersive Museum of Madeira (IMOM), a contemporary digital art space in Funchal

But it’s the one that feels most personal — because I was there. I lived the destination while we built the product, so I understood why it mattered. Travel technology only works when it’s built on real understanding, when the people building it have actually experienced what they’re trying to serve. That’s the whole lesson of these four weeks, and it’s what we mean when we say we want to make every trip count.

A Note on What Made This Possible

This is Tripnly‘s achievement, but it didn’t happen in a vacuum. Startup Madeira, Turismo de Portugal, Nova School of Business and Economics, and the Câmara Municipal do Funchal believed in this vision early, and their institutional support made the difference.

And Nejat Aksoy, my co-founder, who builds the technology that makes all of this possible.

We came to Madeira with a vision. We left with a product, a community, and a deep connection to an island that will always be part of Tripnly’s story.

De Madeira para o mundo.

Made with ❤️ in Madeira, for lovers of Madeira.