Week 4 - Madeira Island

Yes, it is in Portugal but 600 miles away from the mainland

As I sit on the balcony of our Airbnb in Funchal, Madeira (a Portuguese island closer to Morocco than mainland Portugal), I’m already thinking about how much we’ll miss this place. We’ve been here for a week, and while we’ve seen and done a lot, it feels like we’re still leaving plenty on the table.

Quick geography note: Madeira is part of Portugal, though it sits way out in the Atlantic. Portugal discovered this island in 1419. Nearby islands include the Azores (also Portugal) and the Canary Islands (Spain). Oddly enough, our old neighbor in Midway owns a place here—they bounce back and forth depending on the season.

We’re staying in Funchal, the main city (see blue dot below), where houses are stacked on steep hillsides like LEGO bricks. When we arrived, a rum festival was happening just feet from our place. Rum is a big export here, made from locally grown sugarcane. We later “toured” a rum factory on the other side of the island—basically watched sugarcane turn into sugar and then into booze. That sugar also fuels poncha, a local drink that tastes like a rum-based margarita with a tropical twist.

The island is loaded with hiking trails, sheer cliffs, tiny villages, and rocky coastlines. Most beaches on the island are rocky, but one highlight: a black sand beach—something you usually only find in volcanic areas. The beach itself wasn’t the most beautiful we’ve ever seen, but the black sand and steep mountain drop-offs gave it a unique vibe. Also, black sand sticks to your body like you’ve been working in a coal mine. On the plus side, it makes it easier to see what you need to rinse off. It also makes everyone look like they’re in some kind of DIY body paint photoshoot. Maybe that’s the real draw.

We rented a car through Europcar for just €71 for the week. Total steal. Having a car gave us the freedom to explore every corner of the island. Downsides? The streets here are pure madness—30% inclines, narrow lanes, tight corners. Driving a manual transmission in these conditions is not for the faint of heart. I kept stalling on a steep hill until Tara saved me with a quick “Use the emergency brake, genius!” reminder. I simply ran out of feet.

Road conditions are generally great, but the tiny village roads definitely demand a small car and big guts. Pro tip: If the weather sucks, just drive through a tunnel—seriously. On the other side, it’s sunny. No idea why this works, but it does. Tunnel = cheat code.

Highlights of the week:

• Hiked to Madeira’s highest point: Pico Ruivo.

• Got pushed down a mountain road in a wicker basket (Monte Toboggan Ride—10/10 chaos).

• Climbed the “Stairway to Heaven” in the fog—creepy but epic.

• Found parking in packed trailheads and considered flipping the spots for cash to fund the trip.

• Knocked out a 7+ mile hike ending at a huge waterfall in Fanal Forest (plus haunted-looking trees).

• Witnessed a pilot land in serious wind—applause all around.

• Strava says I hit my biggest climb ever (6k ft). Only one young girl applauded. Everyone else judged the spandex.

• Discovered a secret trail with killer views that ended at a cliffside bar. That’s how hikes should end.

Things we learned:

• Farm animals make any landscape better. They’re like nature’s Easter eggs.

• Manual cars = less distracted driving. You have to pay attention.

• Haircuts abroad are cheaper and just as good.

• We’re better than cruise people. (Kidding… mostly.)

• 4am flights are for masochists.

• Don’t pay for gardens when the whole island is a garden.

• Combo washer/dryers do both jobs poorly.

• A 47-liter hot water tank doesn’t cut it. (Airbnb tip: Go tankless.)

• One person’s “lagoon” is another person’s sad pond.

• Online travel videos should come with expiration dates—things change.

• Food delivery = smaller portions. Order in person if you’re hungry.

The weather was solid all week—just a bit of rain at the end. Big improvement from the storms mainland Portugal has had. And thanks to everyone who checked on us about the power outages in Spain and Portugal… but Madeira is about 600 miles away. So no, we weren’t affected—but appreciated the love!

We’ll miss Madeira. It’s exactly our kind of place: outdoorsy, scenic, and just the right mix of chill and challenge. It’s firmly on our return list. Next up: Italy—heading to Tuscany this Thursday where we’ll also be overseeing the Conclave in Rome briefly.

Portugal Destination Rankings (by us):

1. Funchal (Madeira Island)

2. Lagos & Porto - tied for 2nd

3. Lisbon