Adrenaline and Beauty in Madeira (If You Survive the Flight!)

The wind-swept eastern peninsula of Madeira. (Vereda da Ponta de Sao Lourenço)

Don’t let the flight into Madeira and the island’s treacherous roads scare you off. Once your knees stop shaking, you’re in for a magical time on this outdoor oasis off the coast of Portugal!

For a week, we hiked and mountain biked from Madeira’s mist-shrouded peaks to cliffs overlooking the ocean. It’s one of the coolest places I’ve traveled.

To keep it interesting, Madeira’s airport is Europe’s most dangerous and pilots need special training to land there. Picture intense crosswinds, a short runway, and mountains and ocean as constraints.

Our flight landed as gusting wind slapped our plane updownsideways like a malevolent hand of God. Terrified passengers shrieked, then clapped and cheered when the plane landed.

Next step: revving our tiny rental car on the twisty roads, jousting with the “laid back” locals who drive like their cars are engulfed in flames. Grades I wouldn’t even consider walking up (30+%!) are a feature on any drive into the mountains. I’ve never driven in 1st gear so much. (Make sure you can drive a manual if you rent a car.)

Ah, but those treacherous roads are worth it!

If you can handle that…

Oh. Yes. Madeira is sweet. A nugget of fun and beauty sparkling in the Atlantic. Coming from bike touring to the island was a shift from adventure to pure vacation. We embraced it!

I alternated days hiking with Chelsea and mountain biking, whereas she hiked every day. ​If our days apart were a video cutting between me and Chelsea:
BAMBAMBAM downhill rocky mega testosterone mtb madness
CUT to Chelsea: twittering birds, fields, flowers, smiling farmers, and pretty views
CUT jumps, fist bumps, roots, dust, woot wooting, high fives.
CUT quiet sugarcane fields, mama cat with nursing kittens, lizards, more flowers to smell…

Thus passed our magical days in Madeira. Simplicity and complexity need one another, right?

Chelsea disappearing into the looking glass during a lavada hike through laurel forest.
Don’t worry Mom, I wasn’t going (too) fast! #contrast

Mountain Biking in Madeira

Two days before our flight from Porto, I couldn’t have placed Madeira on a map. The island pinged my radar thanks to mountain biking.

Since our visit to Madeira was a trip pivot from bike touring, I needed to rent a mountain bike. Enter Freeride Madeira. This small local company has created a top-notch mountain bike destination that brought the Enduro World Series to the island twice. They offer well-priced guiding and shuttling services that make exploring the trail systems easy.

The trails aren’t ragged, overgrown hiking trails. Since a solid chunk of Freeride’s revenue goes to trail building, everything is custom-built for mountain biking. No need to wear a bell on your bike: hikers steer clear and the trails only point one way: DOWNHILL.

To prevent eye-rolling, I won’t go all BroDuro on you describing jumps, berms, and rocks. YAWN. I’ll skip the word shred and gnar too. (I for SURE won’t say braaap.)

Know that trails in Madeira vary widely, from flowy to steep roots and rocks, and that you’ll encounter all kinds of terrain. If you’re a mountain biker who likes enduro riding in beautiful places, you’ll dig Madeira!

Hiking in Madeira

Everything on Madeira is steep!

Don’t let wanna-be bros like me scare you off if you aren’t a mountain biker. The hiking in Madeira draws people from all over Europe as well. For good reason: it’s varied, beautiful, challenging, and easily accessible.

From the popular wind-swept peninsula at the eastern end of the island with falcons soaring above to peak to peak hiking above the clouds to lush, moody laurel forest to traversing irrigation canals through terraced fields, you can’t go wrong.

Speaking of fields, Madeira grows and was almost entirely self-supporting for centuries. (It was discovered uninhabited only 600 years ago by Portugal.)

“Lavadas” or irrigation channels carry water in a network across the island and their access paths are the backbones for much of the hiking. We saw ox-strong old men hauling food and farming equipment just as their grandfathers did.

All you need to navigate ALL the hikes: the excellent WalkMe app. For $5, it guided our hiking efforts for our stay.

Hiking PR1: Pico do Arieiro and Pico Ruivo

Misty mountains and me descending some stairs on the PR1 hike.

There are plenty of blogs talking about favorite hikes in Madeira, so I’ll only describe my favorite, PR1: hiking above the clouds between Pico do Arieiro and Pico Ruivo, the two tallest peaks in Madeira. It’s a destination-worthy hike and one that attracts serious hikers kitted out in their finest gear with carbon trekking poles.

To get there, we drove straight up from sea level to 6,000’ on roads that felt like walls. Roaring along in 1st gear, our car felt like it might flip over backward if the road got any steeper. Chelsea gouged finger marks in the door panel she was so excited to get to the hike. (There’s a less-direct, well-graded option that we took on the way back.)

In the ten miles of hiking out-and-back, the trail features a dozen tunnels, thousands of stairs, and enough exposure to send people with vertigo into lockdown. To the north, a giant bank of clouds hovered below us; to the south, steep mountains dropped away to the ocean. A hike to remember.

A Destination Worth Visiting

In short, Madeira is SO COOL. The hiking. The mountain biking. The views of sunsets while sitting on a balcony overlooking the ocean. The stories about terrifying roads and plane landings… What else do you need for a magical trip?

View from the top of Pico Arieiro before heading back to Pico Ruivo. Such a cool hike!

Resources We Used:

My wise-and-awesome guide, Pedro. He’s taking a break from electrical engineering to guide awhile. Smart man!

This post ain’t sponsored, so the below is simply a reflection of the services we used:

  • Flying: Unless you’ve got a teleporter or a yacht (or can stomach a cruise ship), you’ve got to fly to Madeira. The landing is going to suck (I surveyed other tourists and 100% agreed), so steel yourself for that. There are lots of cheap flights from the European mainland.
  • Driving: We rented from Insular Car and they were awesome! Our car (a Clio) was billed as underpowered, but I found it to be a fun little rocketship. Second reminder: make sure you are SOLID at driving a manual transmission or driving will be a nightmare vs just entertaining. Lots of buses and shuttle services are available.
  • Lodging: Great deals abound. Lots of apartments in the $50-75/night range on Airbnb and tons of options on
  • Mountain bike guiding services: Look no further than Freeride Madeira. The guys are all cheery, friendly, helpful and excellent riders. Can’t go wrong with their services in my experience!
  • Finding Trails: Trailforks has many (but not all) of the mountain biking trails. The WalkMe app has all the hikes.

Once you get to Madeira, you’re in for a treat. HAVE FUN!

The coastline of Madeira seen while hiking Vereda da Ponta de Sao Lourenço.

A First Date in Prague

Meeting in Prague

Today is special. Ten years ago to the day, Chelsea and I met for the first time.

In Prague.

At the time, I was studying abroad in Gothenburg, Sweden. (Ok, mostly having fun.) Chelsea had just moved to Portland. Through an introduction from her brother, my college roommate, she and I wound up chatting online, then Skyping.

An offhand comment from me about traveling in Europe resulted in her booking a plane ticket to fly across the Atlantic for a first date. It was my bushy fro that wooed her.

I know, I know - I'm a serious charmer.

I know, I know – I’m a serious charmer.

We united in a square in Prague and kicked off a month journey through red-roofed Czech villages and Croatian islands with spectacular views and free house wine. Just in case we didn’t hit it off, Chelsea brought shirts emblazoned with FUN, the theme of the trip. She also brought fake buck teeth and temporary tattoos with sayings like Girl Love to embarrass me.

Turns out that we liked each other.

Two months later, she was back in Portland. Meanwhile, I took the Trans-Siberian Railroad across Russia with my brother. (A story for another day.) Then Chelsea soldiered through a long trip to meet me in Beijing to kick off our second date – 2.5 months exploring the far reaches of SE Asia from China to Thailand.

Top of a holy mountain somewhere in SW China.

Top of a mountain somewhere in SW China.

Let’s just say traveling together 24 hours per day is a quick way to get to know someone. We decided life together would be fun, so I got on a flight to Portland and moved in with her.

Since then, the saying about time flapping its wings has proven true. We’ve worked hard on businesses, dug into a community of friends in Portland, and built a life together. There were small trips, all woven into a busy work, social, and city life. The end of 2013 was major life shift when we headed out on a “four month” van trip that continues to evolve and has transformed how we aspire to live.

Alright, you caught me - this one is from a day exploring Vietnam by scooter. Everyone needs a pink umbrella while scootering...

Wait, that’s not our van! Exploring Vietnam by scooter in 2006. Pink umbrellas for rain protection are mandatory.

We get along well, even in a small space like a van or pedaling thousands of miles together, but we’re not perfect. There are fights, misunderstandings, and moments when she tells me to go for a run or force-feeds me to send my Hangry Alter-Ego (NARG) into retreat. (Check out my Happy Wife Happy Life post for tips on keeping it together on the road.)

Still, I figure we must be doing something right. When I think about it, there’s one thing that’s the bedrock of our successful partnership:

We never stop learning, or more importantly, being open to what the other person is learning.

It’s as simple as that. There are books about the five love languages, techniques on non-violent communication, and plenty of expensive therapists available. For us, continuing to learn, exploring the world, and growing keeps life interesting and aligns us on a path together.

Hanging with our favorite lambs at Farm Sanctuary.

Hanging with our favorite lambs at Farm Sanctuary.

To celebrate our ten year anniversary of meeting with a fitting gift, I dug deep into our photo collection. First, I picked over 1,000 photos of the two of us, starting April 5, 2006. Shots of us laughing, hiking, hanging with friends, doing handstands, wearing hats sideways, riding bikes, and all the fun of 3,650 days as a couple.

Then I made a photo mosaic with Mosaically using those photos to create a big print to surprise Chelsea. The shot I chose is a goofy one from our wedding day wearing those original FUN shirts. When you look at it from afar, it’s a portrait of the two of us. Upon closer inspection, it’s a 1,000 tiny moments we’ve spent together.

One of my favorite shots, now built from 10 years of fun moments.

One of my favorite shots, now built from 10 years of fun moments. (Here’s the original.)

After all, what is a relationship but a compilation of the moments shared with someone you care about? When I look at this print, I think of not just the times Chelsea made me smile, laugh, or feel special. I also dream of the expanding landscape of our lives, how many more adventures we will have, and how much we’ll learn and explore together. We’re just getting started.

Chelsea, thanks for being my life partner. Here’s to filling the next mosaic with many more photos of us sporting temporary tattoos or doing handstands. I love you.

I finally found a place to use a dorky wedding photo! It's amazing what those photographers can talk you into...

Yesssss – I finally found a place to use a dorky wedding photo! It’s amazing what those photographers can talk you into.