Portugal: Madeira Island

Self-Guided Walking Tour, Portugal: Madeira IslandSelf-Guided Walking Tour, Portugal: Madeira Island

Portugal

Madeira Island

overview

Three hundred miles off the African coast lies the island of Madeira, a subtropical Shangri-la known as the “Atlantic’s floating garden,” a perfect destination for year-round walking. With tremendous summit vistas and infinite ocean views, this enchanting nature-lover’s paradise has a vast traffic-free trail network that follows its unique levada water channels. You’ll venture into a lush world of mountain habitats, terraced vineyards, and colorful villages where you experience generous Madeiran hospitality. It’s a moderate tour with some ascents and descents, following trails from the sleepy wine village of Santana in the north to bustling Funchal in the south. Visit the delightful A-frame houses in Santana, and the famous wicker shops of Camacha. Head to Santo da Serra to savor a glass of poncha in its vibrant square, and on your layover day, you may choose to explore the 18th-century fort in 14th-century Machico. Whether Headwaterit’s a refreshing waterfall, a tranquil cove, lush tropical forests or botanical gardens, busy outdoor markets, local cuisine and distinctive wines, Madeira has all the ingredients for the ideal independent walking adventure.

 

Activity Level
Moderate;
6-12 miles daily
Meet
Funchal, Madeira (Portugal)
Depart
Funchal, Madeira (Portugal)
Daily Itinerary
Download printable
itinerary
Reading List
Recommended
pre-trip reading
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From our blog

Self-Guided Walking 
8 days, 7 nights Trip Includes 

Trip Includes

  • Breakfast daily, two lunches (days 4 and 6), and dinner daily; beverages not Included
  • All accommodations (with private bathrooms) while on tour
  • Local transfers as noted in the itinerary
  • Luggage transfers between the hotels
  • Detailed route notes and maps
  • Basic travel insurance coverage
  • 24-hour emergency service
  • The unbeatable and cumulative experience of the CW and Headwater staff
Compare Dates & Prices
Prices Starting From...
Departure Dates
2+ travelers
Single Supplement
Solo Surcharge
2014
Feb 13, 20, 27, Mar 6, 13, 20, 27, April 3, 10
$1,749
$378
$308
April 17
$1,807
$378
$308
April 24
$1,749
$378
$308
May 1, 8, 15, 22
$1,717
$378
$308
May 29, June 5, 12, 19, 26
$1,608
$378
$308
July 3, 10, 17, 24, 31, Aug 7, 14, 21
$1,768
$378
$308
Aug 28, Sept 4, 11, 18, 25, Oct 2, 9, 16
$1,799
$378
$308
Oct 23, 30
$1,838
$378
$308
2015
Feb 12, 19, 26, Mar 5, 12, 19, 26
$1,849
$378
$308
April 2
$1,909
$378
$308
April 9, 16, 23
$1,849
$378
$308
April 30, May 7, 14, 21
$1,819
$378
$308
May 28, June 4, 11, 18, 25
$1,709
$378
$308

*Price is based on per person, double occupancy.

Number of Travelers
Total in your party
Price From
per person double occupancy
Single supplement + $0 

Call 800.234.6900 to book this trip.

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Itinerary and Accommodations

Days
Destination
1
Santana
View on map
2
Santana
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3
Santana
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4
Santo de Serra
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5
Santo de Serra
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6
Funchal
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7
Funchal
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8
Funchal
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Day 1

Santana

Arrive in Madeira

We meet you at the airport and take you to your hotel near Santana (30 mins) where our agent will brief you on the week’s walking.

Hotel Quinta do Furão

Santana, Madeira

This four-star, cliff-top hotel has an exceptional location with ocean views surrounded by vineyards (September guests may join the grape harvest!), vegetable plots, orchards, and rare dragon trees and proteas, and a backdrop of two peaks. Rooms are spacious and tastefully appointed with solid dark wood furniture and earth-toned paints and fabrics. Amenities include a heated indoor/outdoor swimming pool, fitness room and sauna, two bars, a reading room, and private wine cellar with occasional tastings. Separately housed, the restaurant has a sea-view terrace and serves an original three-course menu of locally sourced products such as fish and tropical fruit.

Day 2

Santana

Circular Walk to São Jorge 10km/7mi/3.5hr or 13km/8 mi/4hr

A panoramic coastal path leads you to the ancient cobbled route linking Santana to São Jorge. Agapanthus and cactiline the descent to the seaside ‘resort’ of Calhau. Then walk along the base of the cliffs, where big Atlantic rollers come sweeping in, before climbing and enjoying balcony views. Fabulous coastal views as you ascend to São Jorge, with the village’s lighthouse glimmering above the azure waters. Mighty Pico Ruivo frames the horizon as you return to Santana.

Hotel Quinta do Furão

Santana, Madeira

This four-star, cliff-top hotel has an exceptional location with ocean views surrounded by vineyards (September guests may join the grape harvest!), vegetable plots, orchards, and rare dragon trees and proteas, and a backdrop of two peaks. Rooms are spacious and tastefully appointed with solid dark wood furniture and earth-toned paints and fabrics. Amenities include a heated indoor/outdoor swimming pool, fitness room and sauna, two bars, a reading room, and private wine cellar with occasional tastings. Separately housed, the restaurant has a sea-view terrace and serves an original three-course menu of locally sourced products such as fish and tropical fruit.

Day 3

Santana

The Caldeirão Verde Levada 14km/9mi/5hr

A transfer takes you on the 10-minute ride up to the Parque das Queimadas—all the hard climbing is done for you! The walk follows the beautiful (and shady) Levada Caldeirão Verde (the Green Cauldron Levada) into the Vale da Lapa. The scenery is magnificent: the views of the sea, of hilltop villages, and of the lofty central peaks are unforgettable. You head up the valley through a series of impressive levada tunnels to the magnificent waterfall at Caldeirão Verde. Then it’s back down the Lapa Valley to Ilha before taking the local bus back to Santana.

Hotel Quinta do Furão

Santana, Madeira

This four-star, cliff-top hotel has an exceptional location with ocean views surrounded by vineyards (September guests may join the grape harvest!), vegetable plots, orchards, and rare dragon trees and proteas, and a backdrop of two peaks. Rooms are spacious and tastefully appointed with solid dark wood furniture and earth-toned paints and fabrics. Amenities include a heated indoor/outdoor swimming pool, fitness room and sauna, two bars, a reading room, and private wine cellar with occasional tastings. Separately housed, the restaurant has a sea-view terrace and serves an original three-course menu of locally sourced products such as fish and tropical fruit.

Day 4

Santo de Serra

Ribeiro Frio to Santo da Serra 14km/8mi/4hr

A scenic 30 min ride takes you to Ribeiro Frio. You join the Levada do Furado, a verdant paradise of laurel, heather and pine with waterfalls tumbling into the gushing river. Tiny firecrest and tame finches flit between the trees, which occasionally part to reveal stunning views of white hilltop hamlets. You descend to Santo da Serra’s vibrant square with its lively market; wood smoke fills the air as meats grill al fresco—try the traditional espetada (delicious meat skewered on laurel twigs)!

Porto Bay Serra Golf

Santo da Serra, Madeira

Built in the 1920s, this four-star hotel, formerly a tea house and later a golf clubhouse, has reopened its doors after a complete refurbishment. Guest rooms are spacious and modern. The property features extensive grounds and gardens, and is located near a 27-hole golf course (preferential rates for guests). A traditional three-course dinner is served in a bright dining room next to an inviting salon for before- or after-dinner drinks. Situated on the edge of a charming village with a main square, bars, shops, a park and zoo, and a market on weekends.

Day 5

Santo de Serra

São Lourenço 8km/5mi/3hr

Starting with a transfer (30 mins), today’s walk takes you to the most eastern point of Madeira, to Ponta de São Lourenço’s Nature Reserve, where you will walk the hugely popular peninsula loop, with sweeping views, jagged peaks and masses of flora and fauna.

Porto Bay Serra Golf

Santo da Serra, Madeira

Built in the 1920s, this four-star hotel, formerly a tea house and later a golf clubhouse, has reopened its doors after a complete refurbishment. Guest rooms are spacious and modern. The property features extensive grounds and gardens, and is located near a 27-hole golf course (preferential rates for guests). A traditional three-course dinner is served in a bright dining room next to an inviting salon for before- or after-dinner drinks. Situated on the edge of a charming village with a main square, bars, shops, a park and zoo, and a market on weekends.

Day 6

Funchal

Camacha to Funchal 13km/8mi/4hr

It’s a 15 min transfer to Camacha, where you will have time to visit the wickerwork factory and shop before heading off on the broad, eucalyptus-fringed paths of the Levada da Serra. Lilies, rhododendrons and amaryllis burst with color whilst glimmering sea views open out as you approach Funchal. There’s time to explore historic Monte with its tropical gardens and extrav agant C18 church before descending by cable car (included) to bustling Funchal where you’ll spend your final two nights. Here our five star hotel offers fine dining, beautiful gardens, panoramic pool and tennis.

Quinta da Bela Vista

Funchal, Madeira

This five-star family-run resort commands fabulous panoramic views of Funchal from a hillside location on the city’s edge. In a compound of buildings and established gardens constructed around an original quinta manor house, guest rooms are tastefully furnished with thick carpets and mahogany antiques; with an arboretum, heated outdoor swimming pool, sauna, Jacuzzi, and tennis court. Two formal restaurants with a multi-course dinner menu and two bars are on site. Weekdays, free daytime shuttle bus to the center of Funchal (check at reception for times).

Day 7

Funchal

At Funchal

Spend your last day exploring at leisure in Funchal, perhaps starting in the bustling market near the harbor. It’s full of atmosphere and ablaze with color. Lunch on the harbor—saving room for afternoon cream tea at Reids! Then time to relax by the pool or in the beautiful exotic gardens of your hotel.

Quinta da Bela Vista

Funchal, Madeira

This five-star family-run resort commands fabulous panoramic views of Funchal from a hillside location on the city’s edge. In a compound of buildings and established gardens constructed around an original quinta manor house, guest rooms are tastefully furnished with thick carpets and mahogany antiques; with an arboretum, heated outdoor swimming pool, sauna, Jacuzzi, and tennis court. Two formal restaurants with a multi-course dinner menu and two bars are on site. Weekdays, free daytime shuttle bus to the center of Funchal (check at reception for times).

Day 8

Funchal

Leave Madeira

Itinerary Disclaimer

Bear in mind that this is a typical itinerary, and the actual activities, sites, and accommodations may vary due to season, special events, weather, or transportation schedules. We reserve the right to alter the itinerary since tour arrangements are made up to a year in advance, and unforeseen circumstances that mandate change may arise. Itinerary changes are made to improve the tour and your experience. If you are currently booked on a CW adventure, an itinerary has been sent to you for your exact departure date. Please call CW at 800.464.9255 if you have any questions about the exact itinerary or hotels selected for any of our tours.

Guest Comments

B. McKinlay, Ontario, Canada, May 2013

The hiking on the island was great, lots of challenge, great views, great scenery. Hotels were nice, food was very good, staff were very nice, overall a very good trip.

H. Ames, Ontario, Canada, May 2013

We loved the island of Madeira; it's varied topography, great climate, and wonderfully kind residents. The walks were interesting and just the right length of time and level of difficulty. The accommodation was food was excellent. We enjoyed it all!

C. Meyners, Missouri, April 2013

Dramatic scenery and walks, coupled with good food at comfortable hotels made this a memorable trip.

T. Palmieri, California, March 2012

A truly unique experience. Where else could you see palm trees, pine trees, an ocean, and a mountain all in the same photo?

R. Sharkey, Minnesota, April 2012

The verbiage for the self-guided walks was very detailed and easy to follow. Hiking trail selections gave us a wonderful flavor of the island. The staff in all of the hotels made us feel very welcome. Buffet breakfasts provided a wide selection of fruits, cheeses, breads, and other native foods. Accommodations were excellent Bruno's orientation gave us all the necessary information and assured us that we could call him at any time if we had a problem. Walking amid the actual farming fields, the varieties of flowers, and the vistas made this a memorable trip for us.

M. McCall, Ontario, Canada, September 2012

Very well organized. Excellent choice of hotels. Transfers were flawless.
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