- 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
|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|
Day 1: Arrive in LisbonWelcome 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 DinnerSpend 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
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.
Chat with a local specialist who can help organize your trip.
Day 4: Drive to Porto via 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 & GuimarãesToday'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.