11 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 help arrange for transportation. We’ll meet at our amazing lodging in Ponto do Sol, Anjos Paradise Eden, for welcome drinks and dinner.

Depending on everyone’s arrival time, we will make a stop for any provisions you will want to have on hand at our villa.

12 May: West Coast and Ocean Views and Porto Moniz

Our day starts at Ponta do Pargo, the westernmost point of Madeira, where we can see the lighthouse and take in stunning coastal views. Next we will head to Teleférico das Achadas da Cruz, a dramatic cable car ride that takes you down a sheer cliff face to a remote piece of farmland by the sea. We’ll each have the option of taking the steep but scenic hike down (1.77 km / 1.1 miles) or the cable car. We’ll all return by cable car and grab some lunch back at the top or have it at our next destination, Porto Moniz.

Next we’ll drive to Porto Moniz, located on the northwestern tip of Madeira. It is a charming town famous for its dramatic coastal scenery and unique volcanic rock formations. The primary draw for visitors is its natural wonders. If we’ve not had lunch yet, we will take it here. For those that are interested, there are two very unique swimming opportunities in the volcanic natural pools. Those that aren’t interested in swimming can explore the charming town.

From here, we will take the scenic route through winding roads back to our villa where we can chill until dinner.

13 May: Ponta do Sol, Levada Hike, Banana Plantation Tour

This morning we will start our day with a tour of the nearby village of Ponta do Sol, set against a backdrop of steep hills and mountains that rise dramatically from the sea, creating a stunning and rugged landscape. The town center is a small, walkable area with a historic feel. You'll find a beautiful pebble beach protected by a small cove, a charming street lined with cafes and restaurants, and historic landmarks like the 15th-century Nossa Senhora da Luz Mother Church.

From here, we will make our way to the Levada Nova - Levada do Moinho hike. It’s a moderate, 10.5 km / 6.5 mile, wonderful circular route that follows the charming Levadas Nova and Levadas dos Moinhos, surrounded by stunning landscapes that enchant walkers in search of the exuberant nature of Madeira Island. Expect to be treated to lush green landscapes, with the ocean in the background, which make the experience even more special.

It is recommended to bring waterproof clothing (and maybe water shoes) and a flashlight for the tunnel.

In the evening, we will have a guided banana plantation tour, offering a unique, educational, and multi-sensory experience that goes far beyond simply seeing a banana tree. We’ll get in-depth knowledge from a local guide, unique tasting experiences, and understanding about what makes the Madeira banana special.

After the tour, we will head to dinner in Ponta do Sol.

14 May: Pico do Arieiro Hike, Valley of the Nuns, Special Dinner

The Pico do Arieiro hike is a truly spectacular and unforgettable experience, often described as a highlight of a trip to Madeira. It's a journey into a surreal, high-altitude landscape that feels far removed from the rest of the island.

The most defining feature is the chance to witness a "sea of clouds" phenomenon. Since Pico do Arieiro is the third-highest peak on the island (1,818 meters) and is often above the cloud line, you can watch the sun rise above a vast, white blanket of clouds, with other mountain peaks piercing through them like islands.

We have several ways to experience this hike and can discuss our options.

Next we will head to the Valley of the Nuns, known locally as Curral das Freiras. It is one of Madeira's most dramatic and geographically striking locations. Tucked away in the heart of the island's mountainous interior, it's a place defined by its sheer scale and isolation.

The valley is a vast, cauldron-like depression surrounded by a ring of incredibly steep, jagged mountains. Its name, "Valley of the Nuns," comes from a historical event in the 16th century when nuns from the Santa Clara convent in Funchal hid there to escape from French pirates. The valley's inaccessibility and natural fortifications made it a perfect refuge.

This evening we will have a special dinner surprise.

15 May: Funchal and Eastern Wonders

We’ll start today’s adventure driving east to the Vereda da Ponta de São Lourenço, a stunning coastal hike with dramatic, volcanic landscapes. This hike (PR8) is about 6 kilometers round trip and offers incredible sea views. We have several options on the route and length we can discuss.

After our hike, we’ll drive into the vibrant atmosphere of the Zona Velha (Old Town) of Funchal, famous for its painted doors and narrow streets. We’ll visit the lively Mercado dos Lavradores to see the colorful local produce and fresh fish. From there, we’ll take the cable car up to Monte.

At the top, we’ll explore the beautiful Monte Palace Tropical Garden. Afterward, we will embrace the thrill of a lifetime by riding the traditional wicker toboggan sleds back down the hill.

In the evening, we’ll board a boat for a spectacular sunset dinner cruise!

16 May: Fanal Forest, Madeira Wine Tasting, Ribeira de Janela, Seixal

Today we will start by visiting one of the most magical places on the island. Fanal Forest, part of the UNESCO-listed Laurisilva forest on Madeira, is a truly mystical and otherworldly place that feels straight out of a fairytale.

The forest is home to centuries-old laurel trees, specifically the Ocotea foetens. Their trunks are often gnarled, twisted, and bent by the wind, with branches covered in thick, vibrant green moss. The strange, almost fantastical shapes of the trees are what give the forest its distinctive, haunting beauty.

The most famous and sought-after feature of Fanal is the frequent fog that rolls in. Because it's a high-altitude forest on the Paul da Serra plateau (around 1,150 meters above sea level), it's often enveloped in a dense, low-hanging cloud. This mist filters the light, creating a surreal and ethereal glow that makes the forest feel completely timeless and isolated from the rest of the world.

From here we will make our way to very small, family run, winemaking space for a very special Madeira wine tasting.

After this, we will explore the coastal villages of Ribeira de Janela and Seixal with opportunities to take some stunning photographs and even to get in the water.

17 May: Last Hike (25 Falls or others)

Today we will take our last group hike of the trip. We have many options including the more challenging 25 Falls. We will discuss options, I’ll provided recommendations, and we can decide as a group. Afterwords, we can revisit any place or make up for any weather misses. We’ll also have time to relax and enjoy the pool and view one last time before we have our farewell dinner.

18 May: Depart Madeira towards your home or next destination.

*While these are the planned activities, we may adjust days and times to accomodate weather and other factors.