This 9-day itinerary starts in Lisbon, where you'll savor local treats and traditional music as you explore the capital by foot and tram. Hit the road and head north to Porto, where world-class wine cellars and riverside views await, then hop over to Madeira to end your adventure among the verdant, volcanic landscapes of Portugal's "Island of Eternal Spring."

Highlights

  • Hear live fado music over dinner in Lisbon
  • Stroll through the beautiful whitewashed village of Óbidos
  • Explore Porto's riverside Ribeira district
  • Test your nerve on the glass walkway over Cape Girão
  • Soak in the seawater tide pools of Porto Moniz

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon Lisbon
Day 2 Self-Guided Lisbon, Fado Dinner Lisbon
Day 3 Day Trip to Sintra & Cascais Lisbon
Day 4 Drive to Porto via Óbidos Porto
Day 5 Discover Porto & Guimarães Porto
Day 6 Fly to Funchal, Madeira Funchal
Days 7-8 Explore Madeira Funchal
Day 9 Depart Funchal  

Detailed Itinerary

Day 1: Arrive in Lisbon

Tiled rooftops in Lisbon's Alfama district
Welcome to Lisbon! Upon arrival, your driver will be waiting to transfer you to your hotel in the city center. After checking in, you can unwind after your long journey or head out for a stroll. You'll find Lisbon to be an unheralded gem of a European capital. Hilly waterfront neighborhoods are dotted with grand plazas and pastel-colored buildings, many dating back hundreds of years. Old cable cars lurch up winding cobbled roads, and medieval castles sit perched atop the highest points in the city.

The quickest way to acquaint yourself with Lisbon's culture is through its traditional cuisine. This includes pastéis de bacalhau (cod fritters), grilled sardines, squid stuffed with sausage and onions, queijo de azeitão (a creamy cheese made from sheep's milk), pastéis de Nata (egg custard tarts), and the quintessential street food, the bifana. This sandwich of pork marinated in white wine is pure heaven after one too many Vinho Verdes.

Day 2: Self-Guided Lisbon, Fado Dinner

Lisbon's Torre de Belém at sunset
Spend today exploring Lisbon—one of the world's oldest and most beautiful cities— at your leisure. Walk its narrow and hilly streets, admire its intricately tiled sidewalks, visit important historic sites, climb to panoramic viewpoints, and taste the delicious local gastronomy. You'll also spend some time getting to know the Belém quarter, famous for its monuments from the age of the Portuguese Discoveries and one of the most renowned Portuguese delicacies, the pastel de Belém (custard tart).

Visit Lisbon's fascinating Museu Nacional do Azulejo or National Tile Museum to discover one of the city's hidden gems. Not only is it beautiful in and of itself, but the museum also helps to explain Lisbon's unique decorative appeal and architectural history. As evening falls, head back into Bairro Alto to enjoy a night at one of the city's best fado restaurants, where good food, the perfect setting, and the melancholy tones of Portugal's beautiful fado music come together for a truly authentic night in Lisbon.

Day 3: Day Trip to Sintra & Cascais

Pena Palace overlooking the forests of Sintra Cascais National Park

After breakfast, pick up your rental car and hit the road for today's adventure in Sintra. Located just half an hour east of the city, this resort town in the Sintra Mountains is known for its forested hills, upscale villas, and Moorish palaces. Start with a visit to the Palacio Nacional da Pena (Pena Palace). This 19th-century romanticist castle mixes Moorish and Portuguese late-Gothic architectural styles with distinct features like gargoyles, ornate battlements, and colorful terraces. 

After touring the palace, you'll have a break for lunch, at which point you can also stroll through the historic village of Sintra and do some shopping or sightseeing. Then it's off to Sintra Cascais Natural Park. Some can't-miss locales in this area include the dramatic coastal cliffs of the Cabo de Roca, the wide and inviting Guincho Beach (a popular surf spot), and the glamorous towns of Cascais and Estoril. After a day of sightseeing, you'll return to Lisbon for the evening. 

Day 4: Drive to Porto via Óbidos

Fortress walls surrounding the beautiful whitewashed village of Óbidos

After breakfast at your hotel, it's time to make the journey to Porto, Portugal's second-largest city. It won't be a direct route, though: about halfway through the drive, you'll make a morning stop in adorable Óbidos. Surrounded by a classic crenelated wall, this fortified village's historic center is a labyrinth of cobblestoned streets, riotous flowers, and whitewashed houses livened up with dashes of vivid yellow and blue paint.

Historically, Óbidos was recaptured from the Moors and presented to the Queen of Portugal on her wedding day—in a long-lasting tradition that began with Queen Urraca in 1214 and continued until the 19th century. Take your time as you explore the historic center and its stunning castle, which dates back almost a thousand years. After lunch, you'll get back on the road and continue north.

Other optional scenic stops along the way include the coastal fishing village of Nazaré, Batalha, famous for its 14th-century monastery, and Coimbra, one of the most important cities in Portuguese history and home to one of Europe's oldest universities. You could also stop in Aveiro for a look at the "Venice of Portugal," where streets, bridges, and canals intertwine. When you've had your fill of sightseeing, you'll continue to Porto, where the remainder of the day is free for you to settle in and get your bearings in the city.

Day 5: Discover Porto & Guimarães

Porto
Explore Porto's riverside Ribeira district
Today's half-day guided walking tour immerses you in the colorful neighborhoods and rich history of Portugal's second city. Stroll through the cobblestone lanes of the UNESCO-listed Ribeira district, admire soaring Gothic churches, wander the bustling stalls of world-class food markets, and climb to breathtaking views over the Douro River.

In the afternoon, you can join a guided tour of a famous port wine cellar for an immersive tasting experience. If you feel like exploring further afield, drive northeast to visit the small city of Guimarães, considered the cradle of the Portuguese Nation and the birthplace of its first king, D. Afonso Henriques. Among its exquisite medieval center, don't miss the imposing Guimarães Castle, the Dukes of Bragança Palace, and the church of Santa Maria da Oliveira.

Day 6: Fly to Funchal, Madeira

The port of Camara de Lobos near Funchal
After breakfast, you'll head to Porto's airport to drop off your car and catch your flight to Funchal, the capital of Madeira. Known as the "Island of Eternal Spring," Madeira is part of a tiny archipelago located in the mid-Atlantic, just northwest of Africa and about 669 miles (1,077 km) from mainland Portugal. The remote paradise teems with biodiversity, with the perfect blend of rich volcanic soils, lush flora, and a year-round subtropical climate.
 
Upon arrival, pick up your car at the airport. Depending on the time of arrival, you can go for a walk in the city center for your first glimpse of the island, climb to the Botanical Garden for a spectacular array of flowers and plants, or choose to visit Curral das Freiras (Nun's Valley), a tucked-away settlement where a convent of nuns once hid from pirates among the steep and scenic valleys.

Days 7-8: Explore Madeira's Coasts

Volcanic rock pools at  Porto Moniz
The next two days are free for you to explore Madeira's many wonders at your leisure. Drive around the island with no destination in mind, discovering hidden beaches, breathtaking vistas, and charming villages. On the island's west coast, you'll find Cape Girão, the highest cape in Europe that offers dizzying views from its glass-bottomed skywalk. Hike to the spectacular Garganta Funda Waterfall, then head to the rock pools of Porto Moniz, where cooled lava has formed natural tidal pools perfect for a refreshing swim. 
 
To the east, you can visit rugged sea cliffs and traditional houses in Santana and São Lourenço or take a breathtaking hike along a levada (a traditional trail along irrigation channels) into the island's magical laurisilva—one of Europe's last primeval, subtropical laurel forests.

Day 9: Depart Funchal

Madeira
Sunset over Cape Girão
After breakfast, it's time to bid your island paradise farewell. Drive to the Funchal Airport to drop off your rental car and catch your departing flight. Safe travels and boa viagem!

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Map

Map of Lisbon, Porto & Madeira - 9 Days
Map of Lisbon, Porto & Madeira - 9 Days