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above clouds in madeira

Madeira’s Greatest Trails: Big Hikes, Comfy Nights

8 days | Moderate
From $3,240 ()
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I chose Madeira for this all-women hiking trip because it immediately felt special to me—the dramatic scenery, incredible hiking, local wine, and a beautiful 4-star hotel at the end of each day felt like the perfect balance of adventure and comfort.

Over eight days on the Flower Island, we’ll walk levadas through the Laurisilva forest, cross the ridge from Pico Arieiro to Pico Ruivo, and explore wild plateaus and coastal paths with a local guide. We’ll stay in three hotels with pools, in Santo da Serra, in Porto Moniz beside the natural lava pools, and in Funchal. Along the way, we’ll visit a volcanic-soil vineyard for a tasting and a traditional Madeiran lunch, and swim in Porto Moniz and at São Lourenço.

Tanya
Tanya
Hiking guide

Adventure Highlights

  • The island's famous ridge walk: We climb from Pico Arieiro through tunnels and stone staircases to Pico Ruivo at 1,861 m (6,106 ft)
  • Levadas and laurel forest: Narrow channels lead us through UNESCO-listed Laurisilva, past waterfalls, century-old trees, and the old crater of Fanal
  • Wine, skewers, and a swim: A volcanic-soil vineyard visit with tasting, a traditional Madeiran lunch, and the natural pools of Porto Moniz waiting next door
Duration
8 days
Season
Spring
Group size
Up to 10 people
Accommodation
Comfort: Three 4-star hotels, each with a pool
Difficulty
Moderate: Good fitness required, hiking up to 14 km (8.7 mi) per day, with up to 500 m (1,640 ft) of elevation gain
What's included
Guide, lodging, all breakfasts and dinners, picnics, transfers, wine tasting, and more

The adventure, day by day

We spend eight days on Madeira with six full days of walking, moving across the island as we go. The first three nights are in Santo da Serra, our base for the Caldeirão Verde levada and the Pico Arieiro to Pico Ruivo traverse. Then two nights in Porto Moniz, right beside the natural pools, with a vineyard visit, a traditional lunch, and the Paul da Serra plateau in between. The last two nights are in Funchal, where we walk the wild São Lourenço peninsula, swim, explore the city, and sit down to a farewell dinner. All hotels are 4-star with pools, and breakfasts, dinners, and trail picnics are included.

Day 1: Welcome to Madeira
madeira road

Arrive at Madeira Airport, where your local hiking guide will be waiting to welcome the group. From there, we drive up to Santo da Serra, a quiet village in the green hills above the island’s east coast and our home for the next three nights. Once we’ve settled into our 4-star hotel, we sit down to our first dinner together and get ready for the week of hiking ahead.

Meals: Dinner
Accommodation: Porto Bay Serra Golf (4-star hotel), Santo da Serra

Day 2: Caldeirão Verde
waterfall of caldeirao verde

We start with one of Madeira’s best levada walks. Levadas are the narrow irrigation channels cut into the island’s slopes, and the paths beside them make for some of the most scenic walking on Madeira. Ours leads through the Laurisilva laurel forest, through four tunnels and along cliffside sections secured with a safety wire, to Caldeirão Verde, the Green Cauldron, where a waterfall drops into a lagoon. After a picnic, we descend to the remote village of Ilha. Bring a headlamp for the tunnels, and if heights bother you, you can turn back halfway.

Meals: Breakfast, picnic, dinner
Hiking: 14 km (8.7 mi), approx. 4.5 hours
Elevation: +110 m (+361 ft) / -620 m (-2,034 ft)
Accommodation: Porto Bay Serra Golf (4-star hotel), Santo da Serra

Day 3: Pico Arieiro to Pico Ruivo
pico arieiro view

Today we hike between two of Madeira’s most famous peaks. We start at Pico do Arieiro (1,818 m / 5,965 ft) and follow an alpine trail of tunnels and staircases carved into the rock to Pico Ruivo, the island’s highest point at 1,862 m (6,109 ft). The views over Madeira’s jagged volcanic interior keep coming the whole way. Our guide picks the perfect picnic spot along the trail, and once we’re done, a taxi waits for us at Achada do Teixeira to take us back to the hotel.

Meals: Breakfast, picnic, dinner
Hiking: 10 km (6.2 mi), approx. 4 hours
Elevation: +500 m (+1,640 ft) / -700 m (-2,297 ft)
Accommodation: Porto Bay Serra Golf (4-star hotel), Santo da Serra

Day 4: Madeiran vineyard and Porto Moniz
madeira's vineyards of sao vicente

We leave Santo da Serra and head for the hills of São Vicente on the north coast. Here, we take a guided walk through vineyards planted on volcanic soil and cooled by sea breezes, followed by a tasting of six local wines with a small cheese board. Lunch is a traditional Madeiran feast: espetada, beef skewered on bay laurel sticks, served with boiled potatoes, salad, and bolo do caco with garlic butter. Dessert is passion fruit pudding with a glass of Madeira wine and coffee. In the afternoon, we take a gentle levada walk above Porto Moniz, then transfer to our hotel, right next to the town’s natural lava rock pools.

Meals: Breakfast, skewer lunch, dinner
Hiking: 7 km (4.3 mi), approx. 3 hours
Elevation: +50 m (+164 ft) / -50 m (-164 ft)
Accommodation: Aqua Natura Madeira (4-star hotel), Porto Moniz

Day 5: Fanal and Levada dos Cedros
Natural pools of Porto Moniz

From Porto Moniz, we cross the high Paul da Serra plateau to Fanal, an old crater dotted with century-old laurel trees. It’s part of the Laurisilva, which is a UNESCO World Natural Heritage Site. From there, we continue along the Levada dos Cedros, one of the island’s oldest, dug into the ground in the 17th century. Back in Porto Moniz, there’s time to cool off in the natural pools before dinner.

Meals: Breakfast, picnic, dinner
Hiking: 8 km (5 mi), approx. 4 hours 15 minutes
Elevation: +150 m (+492 ft) / -300 m (-984 ft)
Accommodation: Aqua Natura Madeira (4-star hotel), Porto Moniz

Day 6: Levada Alecrim, 25 Fontes, and Garagem
Funchal on Madeira island

Today’s hike starts on the Paul da Serra plateau and leads us through an enchanted forest, where we pass streams, waterfalls, and plenty of Madeira’s endemic flora. We stop for a picnic along the trail, then transfer to Funchal, the island’s capital, where we spend our last two nights in a 4-star hotel.

Meals: Breakfast, picnic, dinner
Hiking: 14 km (8.7 mi), approx. 4.5 hours
Elevation: +205 m (+673 ft) / -485 m (-1,591 ft)
Accommodation: Enotel Magnolia (4-star hotel), Funchal

Day 7: São Lourenço Peninsula and Funchal
sao lourenco madeira

Our final hike shows a completely different side of the island. The São Lourenço Peninsula is Madeira’s semi-arid east, with basalt cliffs carved by wind and waves and a nature reserve home to unusual flora and fauna. It’s also our chance for a swim at the beach. Back in Funchal, we take a short guided visit of the city, and the rest of the afternoon is free to explore at your own pace. In the evening, we gather for a farewell dinner at a local restaurant.

Meals: Breakfast, picnic, dinner
Hiking: 8 km (5 mi), approx. 3 hours
Elevation: +400 m (+1,312 ft) / -400 m (-1,312 ft)
Accommodation: Enotel Magnolia (4-star hotel), Funchal

Day 8: Departure
Street in Funchal

Our adventure wraps up after breakfast. A taxi takes you from the hotel to Madeira Airport, timed so you arrive 2 hours and 30 minutes before your flight. Note that guiding services end on Day 7.

Meals: Breakfast

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Meet your hosts

Seasoned pros, local legends, and passionate adventurers—your trip is in the best hands.
Tanya
5.00
Tanya
Hiking guide
Travel has always been one of the things that brings Tanya the most joy, especially when it combines beautiful places, meaningful connection, and a little adventure. Madeira is a destination she hasn’t yet explored herself, which makes it even more exciting for her to experience it for the first time alongside an amazing group of women!
Andreia
5.00
Andreia
Hiking guide
There is no place like home and that’s exactly what Andreia thinks! Borned and raised at Madeira Island, you won’t find a better guide to show your around. Her friends used to say she was a big fish for a small pond, so she found a way to travel without leaving the Atlantic Pearl: through her guests! Working as florist for more than a decade, she has been working as a guide for 8 years now. She enjoys sharing her knowledge of stories, local food and wine while enjoying the warm sun on your skin and drinking a Poncha. She wants you to come over and her main goal is to make you fall in love with her island! And for sure this is what will happen!

Things to know

  • Included:

      • An experienced, English-speaking local guide from Day 1 to Day 7
      • 8-day Madeira hiking tour (6 days of guided walking), with hiking trail fees included
      • 7 nights in twin rooms in 4-star hotels (Porto Bay Serra Golf, Aqua Natura Madeira, and Enotel Magnolia), with hotel taxes included
      • 7 breakfasts and 7 dinners
      • 5 picnics and 1 traditional skewer lunch (Day 4)
      • Vineyard visit and wine tasting (Day 4)
      • Entry to the natural pools in Porto Moniz
      • All transfers listed in the program, including airport pickup on arrival day (between 10 am and 5 pm) and drop-off on departure day
      • 24/7 phone assistance

    Add-ons (pricing shown at checkout):

      • Single occupancy room

    Not included:

      • International flights to Madeira
      • Drinks
      • Items of a personal nature
      • Travel insurance — recommended, available at checkout
      • Tips for drivers and in restaurants
      • Guide gratuities — optional
  • In order to join this hiking tour, good fitness is required as well as previous experience with full days on the trail. The most you’ll hike within a day is up to 14 km (8.7 mi), with up to 500 m (1,640 ft) of elevation gain. Expect roughly 3 to 5 hours of walking on each of the six hiking days, on levada paths, forest trails, and one alpine ridge with tunnels and staircases between Pico Arieiro and Pico Ruivo.

    You’ll only carry a day pack, since you’re based in hotels and everything else stays in your room. Some levada sections run along cliffsides with a safety wire, so if heights bother you on the Caldeirão Verde walk, you can turn back halfway.

  • Gear:

      • Day pack (25-40L)
      • Water bottle or hydration bladder (2L)
      • Headlamp with fresh batteries (needed for the four tunnels on the Caldeirão Verde walk and the tunnels between Pico Arieiro and Pico Ruivo)
      • Hiking poles (optional)
      • Camera (optional, but recommended)

    Clothing & footwear:

      • Hiking boots or trail shoes with good grip, as levada paths can be wet and muddy
      • Waterproof rain jacket
      • Layers for the high ridges and the Paul da Serra plateau, where it’s cooler and windier than at sea level
      • Lightweight hiking trousers or shorts
      • Sunhat and sunglasses
      • Swimwear and a quick-dry towel for the natural pools in Porto Moniz and the beach at São Lourenço
      • Casual clothes for dinners and free time in Funchal

    Other:

      • Toiletries, including sunscreen, hand sanitizer, and bug spray
      • Any personal medication
      • Some cash for drinks, tips, and personal purchases

    Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

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  • Group sizes and pricing:

      • For this hiking tour, the usual client-to-guide ratio is 10:1.
      • The maximum group size is set at 10 participants.

    Min. age requirements:

      • If you are older than 18, you’re good to go.
      • Minors younger than 18 may be permitted to join the hiking tour on a case-by-case basis, but must be in the presence of a parent or legal guardian.
      • If your group has participants under the age of 18, contact us prior to booking to make arrangements.
  • This Madeira hiking trip is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.

  • The starting point of your Madeira hiking tour is Madeira Airport (FNC), just outside Funchal. To get there, most people fly into Madeira Airport directly.

    You will meet your guide at Madeira Airport on Day 1. It’s best if your flight lands between 10 am and 5 pm, and you’ll be asked to share your approximate landing time after booking.

  • We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.

    Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

  • Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.

    • If canceled within 48 hours of booking, a full refund will be issued.
    • If canceled 90 or more days before departure, a 70% refund of the total trip price will be issued.
    • If canceled within 89 days of departure, no refund will be issued.
    • Booking fees are non-refundable after a 48 hours grace period.
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