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 Ponta do Sol, Anjos Paradise Eden, for welcome drinks and dinner.

Depending on everyone’s arrival time, there may be time to make a stop for any provisions you will want to have on hand at our villa or we will find time the next day.

~7:00 PM: Dinner at the villa. For anyone arriving later, we will save you some!

12 May: Nearby Levada Hike, Porto Moniz, West Coast

7:30 AM: This morning we will have an early start and make our way to the Levada Nova - Levada do Moinho hike. It’s a moderate, 10.5 km / 6.5 mile, 2.5 - 3 hours, 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. A levada is a narrow irrigation channel or aqueduct unique to Madeira, designed to carry water from the rainy north to the dry southern agricultural regions. Dating back to the 16th century, these, 2,500 km of, stone-walled channels now serve as famous, scenic hiking trails. 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/waterproof shoes) and a flashlight or headlamp for the tunnel (if you don’t have one, your phone flashlight should be enough).

11:30 AM (earlier if ready earlier): After our hike and a quick change and freshen up at our villa, we’ll drive (about 45 mins) 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.

I recommend you bring water, sunscreen, hat, layers and maybe a swimsuit and towel if you want to take a swim!

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 very steep but scenic hike down (1.77 km / 1.1 miles, 1 hour) or the cable car. We’ll all return by cable car back up the cliff.

From here we will head to Ponta do Pargo, the westernmost point of Madeira, where we can see the lighthouse and take in stunning coastal views.

Next, we will take the scenic route through winding roads back for a provision stop then to our villa where we can chill until dinner. This is probably a good time to check out the very nearby spectacular waterfall Cascata dos Anjos (walking distance and maybe bring an umbrella!) and/or explore the quaint village of Ponta do Sol.

Dinner time and location is TBD

13 May:‍ Eastern Wonder Hike, Banana Plantation Tour, Special Dinner

7:45 AM: We’ll start today’s adventure early driving east to the Vereda da Ponta de São Lourenço, a stunning coastal hike with dramatic, volcanic landscapes. This moderate hike (PR8) is about 6 kilometers round trip (depending on the route we take) and takes about 2-3.5 hours to complete depending on how we walk. It offers incredibly dramatic sea views!

I recommend you bring snacks, water, sunscreen, hat, layers, and maybe a swimsuit and towel if you want to take quick refreshing dip!

After the hike, we will stop for lunch in the nearby town of Caniçal. From there we will drive back to our villa to freshen up before our next event.

At 2:45 PM, and only a short drive from the villa, 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.

6:00 PM: This evening we will have a very special 3-course dinner and drinks at a plantation in Funchal. This unique experience begins with a welcome drink, tour of the plantation, and culminates with a seasonal menu prepared by a phenomenal local chef. The views are spectacular as well!

14 May: Pico do Areeiro - Pico do Ruivo Hike, Valley of the Nuns

7:15 AM: This morning we will have an early start for the Pico do Areeiro hike (hard, 9 km/5.6 miles, 1000 meters/3200 feet elevation gain, 5 hours). Although the full hike is currently closed, it is expected to open before we arrive. Assuming it opens, we will complete the full hike using a transportation service since it is point to point. A truly spectacular and unforgettable experience, it is often described as a highlight of a trip to Madeira and the most spectacular hike on the island. It's a journey into a surreal, high-altitude landscape that feels far removed from the rest of the island.

I recommend you bring snacks or packed lunch, 2-3 liters of water, sunscreen, hat, and layers.

If you are unsure about completing the full hike, there may be other ways to experience this beautiful area, and we can discuss 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. After our visit here, we will return to the villa to chill before dinner.

Dinner time and location TBD

15 May: Funchal, Dinner Boat Cruise

8:30 AM: We’ll drive into the vibrant atmosphere of the Zona Velha (Old Town) of Funchal, famous for its painted doors and narrow streets. You’ll want to bring your stuff for the entire day to include comfortable walking attire, water, sunscreen, hat, and possibly a swimsuit and towel plus whatever else you’ll want for the boat trip later in the day.

From there, we’ll take the cable car up to Monte. At the top, we’ll have about 1-2 hours to explore the beautiful Monte Palace Tropical Garden and take a quick peek inside the quaint little nearby church. Afterward, you will have the option to embrace the thrill of a lifetime by riding the traditional wicker toboggan sleds back down the hill (additional cost depending on number of people in each sled). You may also choose to walk down, take the cable car, or we can arrange other transportation. From the bottom of the toboggan ride, there is a 20-30 min walk back to central Funchal. Due to variety of factors, the toboggan ride may not be available to us (e.g. weather, long queues, etc.) but we will do our best for those that are interested!

We can have a quick lunch and start our guided walking tour of the area at 1:00 PM. We’ll likely visit the lively Mercado dos Lavradores to see the colorful local produce and fresh fish and other interesting spots. After the walking tour, we will have a little free time for everyone to wander around the area until around 5:15 PM when we need to board our boat for a spectacular sunset dinner cruise! Please note the departure point is about a 20 min walk from central Funchal.

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

Today we will start early 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.

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.

From here we will like make our way back to the villa where we will be picked up and taken to São Vicente to a very small, family run, winemaking space for a very special Madeira wine tasting. This is one of my favorite things on the island, and the hosts / winemakers are amazing people.

After the wine tasting, we will have dinner in the village before returning to the villa for the night.

Dinner time and location TBD.

17 May: Last Hike (25 Falls, Levada do Caldeirão Verde, or others)

Today we will take our last group hike of the trip. We have many options including the more challenging 25 Falls (there are several ways to do this one) or the easier but spectacular PR 9 - Levada do Caldeirão Verde (assuming we can get reservations still) or the steep but beautiful PR19 - Caminho Real do Paúl do Mar. We will discuss options, I’ll provided recommendations, and we can decide as a group. Afterword, 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.

Dinner time and location TBD.

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

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