When colonists arrived in Madeira in July 1419, the valley they settled was a mass of bright yellow fennel, or funchal in Portuguese. Today the bucolic fields are gone, and the community that replaced them is the self-governing island's bustling business and political center. Funchal is the only town of any size on the island and the base for the the bulk of its tourism thanks to the plethora of hotels, restaurants, bars, cafés, phenomenal coastal and hillside views, and—of course—Madeira wine. Despite the tropical vegetation, Funchal’s center feels decidedly Portuguese, though there's a heavy British influence, which is a holdover from the mid-16th-century marriage of the Portuguese princess Catherine of Bragança to England's King Charles II. The marriage contract gave the English the right to live on Madeira, plus valuable trade concessions. Charles in turn gave Madeirans an exclusive franchise to sell wine to England and its colonies. The island's wine boom lured many British families to Funchal, and many blue-blooded Europeans and famous vacationers such as George Bernard Shaw and Winston Churchill followed the pack to enjoy the mild winters.
Golden Gate Grand Café
Just across from the tourist office in the heart of Funchal, this restaurant-café has been open for business off and on since 1814. Sit in the airy interior, capture one of the tables that flank the sidewalk, or—even better—bag a seat on the balcony. You can pop in for coffee, light local dishes, or British-style afternoon tea, or you can settle in for a feast of creative Portuguese and international dishes. Don't miss the delicious desserts such as delicia Golden Gate com gelado de noz, ananás assado e molho de manga (Golden Gate delight with walnut ice cream, roasted pineapple, and mango salsa).
Casa do Turista
Despite its unpromising name, the Casa do Turista sells museum-quality Madeiran crafts of all types, including embroidery, wicker, ceramics, wine, and liqueurs, in the 19th-century former home to the German consul.
Madeira Wine Company
For the best selection of Madeira wine, check out the Madeira Wine Company (part of Blandy's Wine Lodge), which sells an exhaustive selection of the local tipple, covering virtually every vintage of Blandy's produced on the island since around the mid-'70s. Otherwise you can find Madeira wine sold in most of the island's delicatessens and better supermarkets.
Palácio de São Lourenço
Built in the 17th century as Madeira's first fortress, the St. Lawrence Palace is still used as a military headquarters. At certain times its grand rooms are open to visitors and you can see the grand Ballroom and other state rooms filled with sumptuous works of art and antique furniture.
Museu de Arte Sacra
Funchal's Museum of Sacred Art has Flemish paintings, polychrome wood statues, and other treasures displayed in a former bishop's palace. Most of the pricelss paintings were commissioned by the first merchants of Madeira,who traded sugar for Flemish art so they could decorate their private chapels. The Adoration of the Magi was painted in 1518 for a wealthy trader from Machico and was paid for not in gold, but in sugar. You can tell how important this commodity was to the island by examining Funchal's coat of arms: it depicts five loaves of sugar in the shape of a cross.
Renowned for its ceiling with intricate geometric designs of inlaid ivory, Funchal's cathedral dates from 1514 and reveals an Arabic influence throughout. Don't miss the carved, gilded choir stalls in the side entrance and in the chancel (they depict the prophets and the apostles), or the intricate tile work at the side entrance and in the belfry.
Quinta do Palheiro
Also known as the Blandy Gardens, this 30-acre estate 5 km (3 mi) northeast of Funchal is owned by the Blandy wine family. The formal gardens have flowering perennials. You can stroll the gardens and the grounds, where camellia trees bloom between December and April, but you can't tour the family's house. To get here, head out of town on N101, the road to the airport. At the fork make a left onto N102 and follow the signs toward Camacha. Also, bus 36A departs weekday mornings at 9:45, 11:30, and 12:10 from in front of the Palácio de São Lourenço, on Avenida das Comunidades Madeirenses (next to the marina). It returns at 12:10, 12:35, 2:35, and 5:10.
Teleférico da Madeira
The sleek, Austrian-engineered cable-car service has more than 40 cars that travel from Funchal's old town waterfront up to Monte at 1,804 feet above sea level. The trip takes 15 minutes one way, and there are great views to enjoy as you float silently up and over the city.
Parque Santa Catarina
Abloom with flowers all year-round, St. Catarina Park covers an area of around 43,000 square yards with fantastic views over Funchal and its bay up to the Ponta do Garajau. In the center of the park rests the tiny Capela de Santa Catarina (St. Catherine's Chapel), built by Madeira's discoverer João Gonçalves Zarco in 1425. It's one of the island's oldest buildings. Just above the park is a pink mansion called Quinta Vigia, the residence of the president of Madeira—it's closed to the public but you can visit its eighteenth-century chapel, lined with beautiful tiles.
Museu do Historia Natural do Funchal
Animals found on Madeira and in its seas—including a ferocious-looking collection of stuffed sharks—are on display in the natural history museum. Attached is a small aquarium, where you can watch the graceful movements of an octopus and view a family of sea turtles.
The stately Old Customs House is home to Madeira's parliament (closed to the public). From here deputies govern the island, which is part of Portugal but enjoys greater autonomy than the mainland provinces. The building's original 16th-century Manueline style was given baroque touches during renovations that followed the devastating 18th-century earthquake that almost leveled faraway Lisbon.
Fortaleza do Pico
It's a steep walk to get to the fortress, but it's worth the effort for the dazzling views of the city. The "Fort of the Peak" was built in 1611 to protect the settlement against pirate attacks. It's been in the possession of the navy since 1933, but you can view parts of the ramparts, and there's a small museum that has prints of the building over the years on display.
Museu de Arte Contemporânea at Fortaleza de São Tiago
A former governor's house inside the old fort has been transformed into the Museu de Arte Contemporânea, which has changing exhibitions of works from the 1960s and later, most by local artists. The robust fortaleza was started by 1614, if not earlier, when French corsairs began to threaten Funchal's coveted deepwater harbor. Thanks to continuous use—by British troops when their nation was allied with Portugal against Napoléon, and during the visit of the Portuguese king Dom Carlos in 1901—much of the military stronghold has been preserved. You can wander around the ramparts which offer interesting views over the old town and sea below.
The Botanical Garden is on the grounds of an old plantation 3 km (2 mi) northeast of Funchal. Its well-labeled plants—including anthuriums, bird-of-paradise flowers, and a large cactus collection—come from four continents. Savor wonderful views of Funchal, and check out the petrified trunk of a 10-million-year-old heather tree. There's also a natural-history museum, and a small exotic-birds garden. You can get here on bus 29, 30, or 31, which stop across the street from the market in front of Madeira's Electric Company. You can also take another cable car from the top of the gardens to Monte (April to Sept., daily 9:30–5:30; Oct. to Mar., daily 9–5; €8.25 single, €12.75 round-trip).
Convento de Santa Clara
Inside the working seventeenth-century Santa Clara Convent (ring for entry), the painted wood walls and the ceiling are lined with ceramic tiles, giving the sanctuary an Arabic look. There are two beautiful internal cloisters; one is filled with orange trees. The adjacent church contains the tomb of Zarco, the discoverer of Madeira.
Museu da Quinta das Cruzes
Once the home of a Genoese wine-shipping family, the 17th-century building and grounds of this museum are as impressive as its collection of antique furniture. Of special interest are the palanquins—lounge chairs once used to carry the grand ladies of colonial Madeira around town. Don't miss the small garden filled with ancient stone columns, window frames, arches, and tombstone fragments rescued from buildings that have been demolished around the island. It also has an alluring café.
Mercado dos Lavradores
In the center patio of the farmers' market, women—sometimes in Madeira's native costume of a full, homespun skirt with yellow, red, and black vertical stripes and an embroidered white blouse—sell orchids, bird-of-paradise flowers (the emblem of Madeira), anthuriums, and other blooms. The bustling lower-level seafood market displays the day's catch. Note the rows of fierce-looking espada. Their huge, bulging eyes are caused by the fatal change in pressure between their deepwater habitat and sea level.
Adegas de São Francisco
The St. Francis Wine Lodge takes its original name from the convent that once stood on this site. Today the operation is owned by the island's famous wine-making Blandy family and is also known as the Blandy's Wine Lodge. Here you can see how the wine and wine barrels are made, visit cellars where the wine is stored, and hear tales about Madeira wine (book your tour in advance online). One legend has it that when the Duke of Clarence was sentenced to death in 1478 for plotting against his brother, King Edward IV, he was given his choice of execution methods. He decided to be drowned in a "vat of Malmsey," a barrel of the drink. There's plenty of time for tasting at the end of the visit and a shop for purchasing the wine.