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Essential Guide to Madeira

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This stunning subtropical Portuguese island has it all: romance, adventure, history, food, and, well, Madeira wine.  I was reluctant to go because I feared I'd be reluctant to leave, and I was right.   Use this guide to get the most out of a week on this “Island of Eternal Spring.”
Sections
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Adventures

Explore the island's many adventures, from hiking, to markets, to Madeira wine tastings.

 
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Spend a half-day exploring this incredibly diverse and lush tropical garden maze, offering everything from a palace, to a Japanese Garden, to an olive tree growing when Caesar reigned in Rome.  Or take the Tuk Tuk Tour at the link.  You can lunch there too.
Monte Palace Tropical Garden
 
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This church's interior is almost as stunning as the panoramic view.  This is also the starting point for careening downhill on a wood and wicker sledge.
Igreja de Nossa Senhora do Monte Church
 
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We weren't sure we'd like the island's namesake sweet wine. But we signed up for the Vintage Tour on an afternoon when rain threatened, and the tour made us Madeira lovers.
Blandy's Wine Lodge – Home of Madeira Wine
 
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This colorful and bustling 3-level, indoor/outdoor market offers fish fruits, vegetables, quality corkware (I bought a great cork fedora and Sarah was overwhelmed by the purse selection), olive oil, spices, etc.. I didn’t see any T-shirts. 😀 The fru...
Mercado dos Lavradores
 
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The nuns went to the valley in 1566 to escape pirates and stayed for the great view. There's a lot of unclear information about hiking down to the village, Curral das Freiras. Take the 81 bus at 11am from the cable car station in Funchal. It costs a ... Hike down from there, have lunch, and take the bus or taxi from the village back to Funchal. It's an easy hike.
Curral das Freiras | Valley of the Nuns hike
 
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We took a day trip to this small village on the northwest coast, which offers plenty of lunch spots and natural tidal pools for soaking up the sea, sun, and air, which we did.
Porto Moniz

Eats

Among the many restaurants in Funchal and around the island, these stand out.

 
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Our upstairs 2-top along the rail was the best in the house, but beware of other guests dining directly below. I worried we'd accidentally wine-bomb the unsuspecting diners below. I suggest the restaurant provide helmets for guests at the first floor...
RESTAURANTE DOS COMBATENTES, Funchal
 
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Although this restaurant is located on the touristy Street with the Painted Doors (Rua de Santa Maria), it seems different from its neighbors, which implore passersby to dine with them.  This restaurant doesn’t and doesn’t seem to need to. It’s hard to describe exactly what makes it different. Maybe it’s all the white and the weird and strangely spelled name.  The menu choices seemed different and a cut above the competition. Reservation recommended.
COMTRADIÇÕES, Funchal
 
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This is one of many outdoor/indoor places in Câmara de Lobos, a short bus ride from Funchal. We sat perpendicularly to each other to sip our wine while viewing the fishing boats in the small harbor and the banana-laden hills above, and to people watc...
ESPADEIRO by Jose De Sousa, Câmara de Lobos
 
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This Fine Food spot is very different from most restaurants in Funchal's tourist area: industrial-chic, open and exposed, revealing everything most restaurants want to keep hidden. We chose to dine inside because we love this kind of restaurant, and ...
OLIVIA, Funchal
 
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After our hike from Eira do Serrado down to Curral das Freiras, we were famished. This spot's sleek glass and steel construction and indoor/outdoor seating say “We're not just another tourist restaurant. We're doing something different.” The menu?  Think all chestnuts, all the time because Curral das Freiras is the heart of Madeira’s copious chestnut production. We ordered only chestnut-centric dishes and loved them.
SABORES DO CURRAL, Curral das Freiras
 
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At this spacious indoor/outdoor restaurant, every table has a great view of the ocean and the town’s salt water tide pools, and the menu promised Mediterranean and Japanese Cuisine (how could we go wrong?).  The plating was beautiful and tasty, especially the Jenga-like scabbard fish sticks. For a great view in a great setting while enjoying a tasty lunch, this is a really good choice.
Sea View Rooftop - Porto Moniz

Digs

These two apartments in the heart of Funchal and one luxury hotel overlooking the city should satisfy any tastes and budget.  Funchal can be your base to explore the whole island.

 
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Rated 9.6 on Expedia, this well-appointed 1 bedroom apartment is central to everything you'll want to see and do in Funchal.
Arriaga Residence - Funchal
 
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Panoramic ocean vistas greet guests from the 16th-floor rooftop infinity pool overlooking Funchal.  The luxurious spa offers rejuvenating treatments after exploring the gardens or relaxing by one of the hotel's pools.
Savoy Palace | 5-star hotel - Funchal
 
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Rated 10 on Expedia, this fully equipped 2-bedroom, 3-bath apartment is walking distance to everything.
Aqua City by Farmer's Market, Funchal