Madeira Boys Trip: Six Days of Adventure, Cliff Jumps, Coasteering and Canyoning
After several smaller trips together, we decided to go bigger this time. Nine guys. One trip. Portugal.
This was our biggest boys trip yet, and we knew from the beginning that getting nine guys to agree on everything was going to be an adventure of its own.
Porto: Food, Wine, and Getting Everyone Together
Everyone arrived in Porto on June 28th, so we kept the first day pretty relaxed. After the long flights, we spent the day walking around some of Porto’s most famous areas, including Santa Catarina, Bolhão, and the Cathedral of Sé. Nothing too crazy—we just wanted to eat, explore, and let everyone recover.
Amazon Product: Travel Backpack
The next day, we joined a food tour we found through GetYourGuide, which was a great way to experience some of Porto’s food without having to figure everything out ourselves.
GetYourGuide: Porto Food Tour
Later that day, we headed across the river to Vila Nova de Gaia for a wine tour and tasting at Húmus Pinto Winery. Besides the wine, one of the best parts was simply seeing Porto from the Gaia side. The views across the Douro River are incredible.
We finished the evening watching the sunset from Jardim do Morro—a perfect way to end our short time in Porto.
GetYourGuide: Port Cellar Wine Tour
Madeira: The Flight That Didn’t Want to Land
The following day, everyone headed to Madeira, but we didn’t all fly together.
Four of us booked an EasyJet flight, and let’s just say…we learned a lesson.
The plane attempted to land in Madeira three times but couldn’t make it and eventually returned to Porto. At that point, we had no choice but to bite the bullet and buy extremely expensive last-minute TAP Air Portugal tickets for later that day.
We finally made it to Madeira around midnight.
Our biggest lesson? Sometimes the cheapest flight isn’t actually the cheapest flight. Madeira’s airport can be challenging because of the wind and surrounding mountains, so if you’re flying there, it’s worth considering TAP and its reputation for operating flights into Madeira.
Be sure to have a power bank or charger if you have to take the same flight for 2 hours twice!
Amazon Product: Power Bank
Canyoning: Level 3 Adventure
The next morning, we didn’t waste any time.
We signed up for a Level 3 canyoning adventure, and it ended up being one of the highlights of the entire trip. There were jumps, waterfalls, swimming, climbing, and plenty of moments where you question whether you really agreed to do this.
It was scary, but in the best possible way.
And judging by the smiles afterward, all nine guys loved it.
The following day was intentionally slower. We did a food tour, walked around town, explored a little, and mostly enjoyed being together without having to rush from one activity to another.
Pico do Arieiro to Pico Ruivo
Then came one of the big ones: the PR1 trail from Pico do Arieiro to Pico Ruivo.
The hike was absolutely worth it. The scenery is incredible, with dramatic mountain peaks, steep ridges, clouds below you, and views that seem almost impossible to be real.
One important tip: book your PR1 tickets ahead of time. Access is now controlled, and tickets can sell out quickly.
PR1 Trail Tickets / Madeira Hiking Information
After the hike, we headed back to our Airbnb, which was about 45 minutes outside the city. Honestly, the location couldn’t have worked out better.
It was right by the beach, and having a place where all of us could hang out, swim, eat, drink, and just laugh together became a huge part of the trip.
Where to stay in Madeira
We stayed in an Airbnb about 45 minutes outside Funchal, right by the beach. If you want to be closer to town, look at Funchal.
Products we recommend:
Amazon Products: Comfortable Hiking Boots, Merino Wool Socks, Sunglasses, Hat, Water Bottle, Day Pack
Coasteering and Cliff Jumping
Our final adventure was coasteering.
A boat dropped us off along the coast, and from there we worked our way through the water, swimming along the cliffs and jumping from different heights into the ocean.
It was one of those activities that sounds slightly crazy when you explain it—but once you’re doing it, it’s incredibly fun.
And yes, there were plenty of moments of hesitation before jumping.
Until the Next Boys Trip
On July 5th, we all packed up and headed home.
Six days, nine guys, a failed flight, canyoning, hiking, wine, food tours, cliff jumping, beach time, and a whole lot of laughing.
That’s really what these trips are about for us. The activities are great, but it’s the stories we come home with that make them memorable.
Madeira definitely gave us plenty of those.
And after this trip, one thing is pretty clear: nine guys might be our new minimum.
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