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Madeira’s Greatest Trails: Big Hikes, Comfy Nights
Date and group size

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Accommodation options

Price is based on twin-share rooms. Choose how many members of your group would like to stay in single occupancy rooms during the trip.

Select your adventure protection

Redpoint travel protection
Weather shifts, flights cancel. Core and Premium include Redpoint travel protection to cover you when they do. Standard follows 57hours' booking policy. See full coverage
Every booking, whichever you pick
Cancel within 48h of booking 100% refund
Cancel 60+ days before departure (Any or no reason) 70% refund
Full coverage details
Basic Standard terms Most popular Core protection Recommended Premium protection
Cancel within 48h of booking
100% refund 100% refund 100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund 70% refund 70% refund
Cancel any time (Covered reason)
75% refund 100% refund
Cancel any time (Any or no reason)
75% refund
Cancel under 60 days (Any or no reason)
75% refund
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p. Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p. Up to $100,000 p.p.
Basic Standard terms
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
Cancel any time (Any or no reason)
Cancel under 60 days (Any or no reason)
Travel: canceled flights, lost baggage, delays
Rescue, evacuation, and medical coverage
Most popular Core protection
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
75% refund
Cancel any time (Any or no reason)
Cancel under 60 days (Any or no reason)
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p.
Recommended Premium protection
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
100% refund
Cancel any time (Any or no reason)
75% refund
Cancel under 60 days (Any or no reason)
75% refund
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p.
Cancellation policy

The percentages in the table above are of the full trip price, not of what you’ve paid at the time of booking.

Cancellations made within 48 hours of booking receive a full refund on all plans, including booking fees and insurance. After the 48-hour window, your refund depends on your selected protection plan and when you cancel. Core and Premium plans extend your cancellation rights beyond the Standard policy:

  • With Core, a covered reason gets you 75% of your trip cost back — even the day before you go.
  • With Premium, a covered reason gets you 100% of your trip cost back — and any other reason gets you 75%, right up to the day you leave.
What counts as a covered reason
  • Sudden illness or injury — yours, a travel companion’s, or an immediate family member’s, confirmed by a doctor
  • Death of a traveler or an immediate family member
  • A natural disaster affecting your destination or your departure point
  • A government travel advisory against travel to your destination

Changing your mind isn’t a covered reason. Premium is the only plan that covers that. Documentation is required for all insurance claims.

Everything the travel insurance covers

Both plans include travel insurance through Redpoint Travel Protection. Core insures 75% of your trip cost; Premium insures 100%.

Maximum per person:

  • Trip cancellation — up to 100% of your trip cost
  • Cancel for any reason — up to 75% of your trip cost (Premium only)
  • Trip interruption — 150% of the trip cost limit
  • Trip delay — $200 a day, $1,000 max
  • Itinerary change — $250
  • Single occupancy supplement — up to 100% of trip cost
  • Missed connection — $1,000
  • Travel inconvenience — $250 each, $750 max
  • Pet return — $1,000 per pet
  • Baggage and personal effects — $2,500, max $300 an item
  • Baggage delay — $600, after 12 hours
  • Baggage delivery — $100 per trip
  • Emergency medical expenses — $100,000
  • Medical evacuation and repatriation — up to $1,000,000

These are maximums. What a claim actually pays depends on what you can document and on the policy’s exclusions — pre-existing conditions and undeclared activities among them. We’ll send the full policy wording with your confirmation.

Reserve deposit (30%) $0
Second Payment Amount: $0
Madeira’s Greatest Trails: Big Hikes, Comfy Nights
Itinerary
Madeira’s Greatest Trails: A Deluxe Hiking Experience
Date(s)
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Number of travelers
1 Person
Cancel in the first 48h for free
Pay deposit now, the rest by
Travel and medical insurance available
Earn $0.00 Adventure credits
  • Over 8 days of hiking and relaxing, you will visit the most beautiful and emblematic part of this Atlantic pearl. Your guides will take care of all the transfers and meals as you make your way through the gigantic rainforests, lush levadas, golden beaches and basalt cliffs. As the sun sets, return to the comforts of 4-star hotels located in towns boasting beautiful architecture and vibrant communities. Explore the cultural and natural heritage with expert guides and make this a trip you’ll never forget.

    • You will meet your guide at the airport and be transferred to your accommodation. It’s best if your plane lands between 10 am and 5 pm—you will notify us in the post-booking process of your approximate landing time, and you will be individually picked up. A 30-minute ride gets you to Santana, a small town famous for its traditional thatched houses. Depending on your arrival time, feel free to explore the quaint city before dinner time.

      Accommodation: Enotel Santo da Serra, Santo da Serra or similar
      Meals: Dinner

      Small colorful houses that Santana is known for
    • After a nice continental breakfast, your guide will transfer you to the start of your walk where you will discover one of the most spectacular Levada hikes of Madeira. You will enter the famous Laurisilva – remains of the humid and subtropical laurel forest. After passing through several (safe) tunnels and cliffside passageways, you will get to the famous “Green Cauldron” — Caldeirao Verde. Your guide will prepare a delicious picnic for you. After a well-deserved break, continue along the way and back down to the remote village of Ilha, with its magnificent ocean views. Your guides will take you back to your accommodation.

      Walking: 4.5 hrs, 14 km (8.7 miles)
      Elevation: +110 m / -620 m (+360 ft / -2,034 ft)
      Accommodation: Enotel Santo da Serra, Santo da Serra or similar
      Meals: Breakfast, lunch box, and dinner

      Important: You will go through 4 tunnels so don’t forget your headlamp. The second part of the walk can be slightly dizzying if you are afraid of heights. Cliff edge path with a safety wire. It is possible to turn back half-way.

      Holding onto rail Madeira
    • *We set off from Pico Ariero (1,810 m) on one of Madeira’s most spectacular alpine trails, winding through tunnels and up staircases toward the island’s highest point. The route rewards us with sweeping panoramas of jagged peaks, deep valleys, and the Atlantic Ocean along the way. Our guide picks out the perfect spot to stop for a picnic before we continue to Achada do Teixeira, where a cab takes us back to the hotel.

      Walking: 4 hrs, 10 km (6.2 miles)
      Elevation: +500 m / -700 m (+1,640 ft / -2,297 ft)
      Accommodation: Enotel Santo da Serra, Santo da Serra or similar
      Meals: Continental breakfast, picnic lunch, and dinner

      Please note that today’s trail will be closed for a few days in September due to installation of a walkway (14–17 and 21–22). In that case, an alternative hike will be done instead.

      pico arieiro view
    • Depart from the hotel and head down an ancient paved royal road, through dense vegetation, as if you were in the jungle, crossing a charming little river then climbing to reach the village of Arco de Sao Jorge and its magnificent viewpoint. Enjoy a well-deserved lunch break in a restaurant overlooking the sea, and try out a brochette, island’s specialty! Next, follow a paved path along the coast, with a splendid panorama of the ocean and waves crashing on small rocky islets. Continue on to a zig-zag descent back to the sea and a final climb to the meeting point. Transfer to Porto Moniz, a sea-resort famous for its natural pools which you can enter and relax in for about 3 EUR. Check in to your splendid hotel where you will stay for two nights.

      Walking: 3 hrs, 7 km (4.4 miles)
      Elevation: +550 m / -550 m (+1,800 ft / -1,800 ft)
      Accommodation: Aqua Natura Madeira Hotel, Porto Moniz or similar
      Meals: Breakfast, skewer lunch, and dinner

      Boaventura Madeira
    • This morning, reach the Paul da Serra plateau (5,250 ft / 1,600 m). Your group will set off for a hike through the enchanted landscapes, crossing the plateau and reach the ancient crater of Fanal, a UNESCO World Natural Heritage Site that is home to rare specimens of century-old laurel trees. Continue along the Levada dos Cedros, one of the oldest in the region, built in the 17th century and dug directly into the ground. After exhilirating hikes, transfer to your hotel in Porto Moniz and spend some quality time with fellow hikers over dinner.

      Walking: 4.15 hrs, 8 km (5 miles)
      Elevation: +150 m / -300 m (+492 ft / -984 ft)
      Accommodation: Aqua Natura Madeira Hotel, Porto Moniz or similar
      Meals: Breakfast, lunch box ,and dinner

      Madeira wildlife
    • After a hearty breakfast, your guides will transfer you to Paul da Serra’s plateau — the start of a charming walk in the middle of an enchanted forest and a UNESCO World Heritage Site. Take in the stunning scenery of streams and waterfalls and discover the endemic flora that Madeira is so famous for. As usual you will enjoy a delightful picnic. Drive to Funchal, the capital of the island where you will stay for two nights.

      Walking: 4.5 hrs, 14 km (8.7 miles)
      Elevation: +250 m / -485 m (+820 ft / -1590 ft)
      Accommodation: Enotel Magnolia or Hotel Caju, Funchal or similar
      Meals: Breakfast, lunch box, and dinner

      Clouds Madeira view
    • The Peninsula of Sao Lourenço is located to the east of the Island. The landscape is very different from the rest of the island because of the semi-arid climate and its basalt cliffs carved by wind and waves. This nature reserve allows you to observe the unique flora and fauna of Madeira. Then, head with a taxi to Pico Arieiro for a short walk along the island’s impressive ridges to the Rija viewpoint. Return on foot to Pico do Arieiro and transfer to Funchal. On your last night in Funchal, the whole group will meet for a final dinner in a restaurant.

      Walking: 3 hrs, 8 km (5 miles)
      Elevation: +445 m / -445 m (+1,460 ft / -1,460 ft)
      Pico Arieiro extension: 1 hours, 2.4 km (1.5 miles), +100 m (330 ft), -100 m (-330 ft)
      Accommodation: Enotel Magnolia or Hotel Caju, Funchal or similar
      Meals: Breakfast, lunch box and dinner

      Panoramic views Madeira
    • About 3 hours before your flight, a taxi will transfer you back to Madeira airport. Depending on the time of your flight, you might have some time to visit the local market and grab a few souvenirs before going home!

      Meals: Breakfast

      Market in Madeira full of fresh fruits and produce
    • Hiking routes may change due to weather conditions, landslides, and other natural factors. Please note that route conditions and availability can vary.

    • Included:

        • An experienced, local hiking guide with extensive knowledge of the area
        • 8-day Madeira adventure (6 days of guided hiking)
        • Accommodation for 7 nights in 4-star hotels (double/twin room with ensuite bathroom)
        • Hotel taxes
        • All meals, from dinner on Day 1 through breakfast on Day 8
          • 7 breakfasts
          • 6 lunches (5 picnic lunches & 1 skewer lunch)
          • 7 dinners
        • All transfers as listed in the itinerary
        • Airport transfers — individual pick-up between 10 am and 5 pm on arrival day

      Add-ons (pricing shown at checkout):

        • Single occupancy room

      Not included:

        • Airfare to and from Madeira
        • Meals not mentioned in the itinerary
        • Drinks
        • Insurance — available to add at checkout
        • Guide gratuities — optional
    • This Madeira hiking trip is ideal for those with previous hiking experience and great fitness. You’ll be hiking for 3-5  hours per day, covering up to 14 km (8.7 mi) per day. Don’t underestimate this wonder of an island—the elevation changes are what make this adventure challenging, with up to 550 m (1,805 ft) of ascent each day, i.e., up to 700 m (2,300 ft) of elevation loss.

      Please note that this tour isn’t appropriate for those with a fear of heights due to occasional exposed trails.

    • Here’s a list of the equipment you need to bring:

        • Duffle bag to pack all of the things you need for the tour
        • Day pack large enough to carry all the items you need in a day (around a 25-40L bag)
        • Hiking poles — optional
        • Water bottle or hydration bladder (2L capacity)
        • Comfortable hiking clothes
        • Clothes for everyday activities and restaurant
        • Shoes for everyday activities and hotel
        • Hiking shorts and t-shirts
        • Light fleece jacket
        • Spare clothes for layering
        • Water and windproof rain jacket
        • Swimwear
        • Sunhat
        • Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.)
        • Headlamp or flashlight
        • Sunglasses
        • Camera — optional (but recommended)

      Madeira, small as it is, has its very own climate zones. Whilst it may be pouring down with rain on the northern coast, the south could be enjoying blue skies and warm sunshine. Make sure to check the weather before packing. 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.

      Got everything you need? Grab your gear through Active Junky and earn cash back on top outdoor brands — plus a $10 bonus on your first $25+ purchase. Shop now at Active Junky!

    • Group sizes and prices:

        • For this group adventure, the usual client-to-guide ratio is 10:1.
        • It takes a minimum of 3 people for this tour to operate.
        • Solo travelers are welcome—they can either share a room with another same-gender solo traveler at no extra cost, or guarantee a private room by paying a single occupancy fee. In case your guides aren’t able to find another traveler to share a room with you, you’ll be required to cover the single occupancy fee.

      Hiking in Madeira can be arranged for larger groups. Contact us to make arrangements.

      Min. age requirements:

        • If you are older than 18, you’re good to go.
        • Minors younger than 18 may be permitted to join the hike on a case-by-case basis, but must be in the presence of a parent or legal guardian.

      If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

    • The price for 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.

      Solo travelers are welcome—they can either share a room with another same-gender solo traveler at no extra cost, or guarantee a private room by paying a single occupancy fee. In case your guides aren’t able to find another traveler to share a room with you, you’ll be required to cover the single occupancy fee.

    • To get to Madeira, most people fly into Madeira (Funchal) Airport (FNC). The airport is well connected and offers direct flights to many European and US cities.

      You will meet your guide on Day 1 at the airport and be transferred to your accommodation. It’s best if your plane lands between 10 am and 5 pm—you will notify us in the post-booking process of your approximate landing time, and you will be individually picked up.

    • 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.

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