8 Days in Madeira (10-18 May 2026)
Maderia, Portugal - Hiking Adventure
Discover One of the Planet’s Most Breathtaking Locations
Venture to a land where emerald peaks pierce the clouds and the Atlantic Ocean crashes against dramatic cliffs. This is Madeira, and it's calling to you.
Imagine an island where every day offers a new story—a place where the thrill of adventure and the joy of discovery go hand-in-hand with stunning natural beauty and incredible local culture. This is our Madeira adventure, and it’s a journey designed to awaken all your senses.
We'll start where the heart of the island beats: its breathtaking landscapes. Our boots will take us deep into the lush, emerald heart of Madeira, along ancient levadas that wind through fairytale forests and up to dramatic volcanic peaks. Stand atop Pico do Arieiro and feel on top of the world, gazing out at a sea of clouds that parts to reveal the rugged beauty of the island below.
But the adventure doesn’t stop on land. We'll set sail on the deep blue Atlantic, trading our hiking trails for the open water. From the deck of a boat, we’ll witness the island's magnificent cliffs from a completely new perspective, a sight that will leave you in awe of nature’s power.
Back on solid ground, the cultural journey begins. We’ll immerse ourselves in the vibrant capital of Funchal, a city of cobbled streets, colorful markets, and historic charm. And for a truly unforgettable thrill, we’ll experience the famous Monte Toboggan ride, a one-of-a-kind, high-speed descent on a traditional wicker sled.
No adventure is complete without amazing food and drink. We’ll taste the rich, complex flavors of authentic Madeiran wine at a local vineyard, and every meal will be a celebration of the island’s incredible cuisine—fresh seafood, delicious fruits, and hearty local dishes that tell a story of their own.
This trip is for those who want it all: the challenge of the trail, the serenity of the sea, the charm of a vibrant city, and the unforgettable taste of a new culture.
This is your chance to explore, to indulge, and to connect. Join us, and let's experience the magic of Madeira together.
Are you ready to answer the call of Madeira Island?
Contact me today to reserve your spot on this unforgettable journey!
Trip cost is $1890 USD
(Airfare and transport to/from Madeira is not included. See link to FAQ below for what’s included.)
*Itinerary
10 May: Arrive in Madeira, Portugal. I can provide recommendations on getting there from wherever you need. I’ll either pick you up at the airport or arrange for transportation. We’ll meet at our amazing lodging for the trip for welcome drinks and dinner. Lodging is TBD.
Provisions
11 May: This morning we’ll hike
12 May: Funchal cable car
13 May: 25 falls hike
14 May: Porto Moniz swim
15 May: Pico do Arieiro sunrise hike
16 May: Valley of Nuns
17 May: hike
18 May: Depart Madeira towards your home or next destination.
*We may make slight modifications to the itinerary to enhance the experience
Meet Your Host: Chris
I’ve loved the outdoors and traveling since a very young age. I’ve visited almost 40 countries, and many of them keep calling me back. Norway is one of those for sure! I am excited to return to Norway and share the beauty of the Lofoten Islands with you! You can read more about me in my bio here: About Me
“There’s nobody I trust more to travel with than Chris. His organization and attention to detail are unmatched!” - Charles S., Alexandria, VA
“It’s difficult for me to trust anyone except myself when planning experiences of a lifetime, but I trust Chris without question. His innate ability to tailor experiences that achieve clients’ desires is rare. He thrives on making dreams come true!” - Tara L., Wash DC
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