Itinerary #1: Ultimate Portugal: Porto, Lisbon & Lagos
Portugal boasts a host of treasures. This eight-day adventure focuses on three of its most iconic jewels: historic Porto and the wine estates of the Douro Valley, the lovely capital city of Lisbon, and the golden beaches and towering cliffs of the Algarve.
|Day 1||Arrive in Porto, Afternoon City Tour||Porto|
|Day 2||Wine Tasting Experience in the Douro Valley||Porto|
|Day 3||Transfer to Lisbon, Local's Lisbon Tour||Lisbon|
|Day 4||Day Trip to Sintra, Cascais & Estoril, Evening of Fado||Lisbon|
|Day 5||Transfer to Lagos & the Algarve||Lagos|
|Day 6||Explore Lagos & the Algarve's Beaches||Lagos|
|Day 7||Free Morning in Lagos, Transfer to Lisbon||Lisbon|
|Day 8||Depart Lisbon|
Begin in Porto, where you'll be transferred to your hotel, then enjoy a tour of this historic and culturally vibrant UNESCO-listed city, including such iconic sites as the Porto Cathedral. The next day, explore the Douro Valley wine region with your expert guide: you'll visit venerable wineries and enjoy a traditional lunch at one of the quintas (wine estates) before a winding scenic drive back to Porto. You'll then head south to Lisbon and hop aboard a yesteryear tram to explore the Bairro Alto, Chiado, and Alfama districts, with their narrow cobblestone streets and such sites as the 12th-century Sé de Lisboa Cathedral.
On Day 4, you'll transfer to the lovely resort town of Sintra, in the Sintra Mountains. You'll visit the flamboyant romanticist Palacio Nacional da Pena, the dramatic Cabo de Roca cliffs (the westernmost point of mainland Europe), Guincho Beach, and the lovely towns of Cascais and Estoril. Next, head to cobblestoned Lagos and the beautiful beaches of the Algarve, perhaps taking time to hike in Costa Vicentina Natural Park. You'll then have a full day at leisure to relax on a beach and enjoy kayaking and/or snorkeling before heading back to Lisbon and—the next day—boa viagem! Learn more
Itinerary #2: Portugal's Food & Wine: Lisbon, Porto & the Douro Valley
From the antiquities and gourmet enclaves of Lisbon, and the pastries and port wines of Porto, to the wine estates and scenic delights of the Douro Valley, this eight-day road trip combines the best of Portugal's culinary and cultural treats.
|Day 1||Arrive in Lisbon & Enjoy the City||Lisbon|
|Day 2||Guided Walking Tour of Lisbon||Lisbon|
|Day 3||Explore the Seaside Resort of Cascais & Castles of Sintra||Lisbon|
|Day 4||Visit the Ancient Roman City of Évora||Lisbon|
|Day 5||Drive to Porto via Óbidos, Nazaré, Batalha, Coimbra, or Aveiro||Porto|
|Day 6||Porto Walking Tour & Wine Tasting||Porto|
|Day 7||Discover the Wine Country of the Douro Valley||Douro Valley|
|Day 8||Drive to Lisbon & Depart|
Arriving at Lisbon airport, pick up your rental car, check in to your hotel, then explore Portugal's historic capital city by hopping on and off iconic trams. Don't miss the Graça neighborhood, the Estrela Basilica, and the culinary delights of Rossio Square and Bairro Alto. Next day, a guided walking tour of labyrinthine Alfama includes 11th-century Castelo de São Jorge, and Jerónimos Monastery plus pastéis de Belém custard in the Belém quarter. Day 3, visit Cascais, the seaside resort of Estoril, Cabo de Roca, and the fairy-tale village of Sintra, with its medieval Castle of the Moors and romantic Palacio Nacional da Pena.
Then head to exquisite Évora, a UNESCO World Heritage Site, where you'll explore the 2,000-year-old Roman Temple and medieval Évora Cathedral and savor local fare in the Praça do Giraldo. Continue via Óbidos for a seafood lunch in Nazaré, then on to Aveiro to sample ovos moles pastries and explore its canals by boat before arriving in Porto, where a guided walking tour hits all the must-sees, including a tasting experience in the Casa Ferreirinha wine cellars. Finally, drive to Portugal's premier wine-growing region—the Douro Valley—to visit famous estates before returning to Lisbon. Learn more
Chat with a local specialist who can help organize your trip.
Itinerary #3: Portugal Scenic Coastal Hike: Cascais, Azóia, Colares & Sintra
This eight-day coastal hiking itinerary combines a foodie tour of Lisbon plus relaxing downtime in Cascais and Sintra to bookend four days of trekking in mountainous Sintra-Cascais Natural Park.
|Day 1||Arrive in Lisbon & Gourmet Food Tour||Lisbon|
|Day 2||Transfer from Lisbon to Cascais||Cascais|
|Day 3||Hike from Cascais to Azóia||Azóia|
|Day 4||Complete the Azóia Loop||Azóia|
|Day 5||Hike from Azóia to Colares||Colares|
|Day 6||Colares to Sintra Hike & Palace Visit||Sintra|
|Day 7||Tour of Sintra Palaces & Sintra-Cascais Natural Park||Sintra|
|Day 8||Transfer from Sintra to Lisbon & Depart|
Arriving at the Lisbon airport, you'll be met and transferred to your hotel. You'll have the afternoon free to relax or explore must-see sites like Castelo de S. Jorge and Praça do Comércio before a guided gourmet foodie tour in the Campo de Ourique district. The next day, transfer to the resort of Cascais to explore its charming old town, laze on a beach, and savor delicious local seafood specialties. Begin your hiking adventure on Day 3 from Guincho Beach to traverse the scenic Estoril Coast, ending at the 13th-century Convent of São Saturnino—today a luxury hotel tucked into a coastal valley outside Azóia.
Fueled with a hearty breakfast the next day, you'll hike a scenic loop through the Sintra Mountains to the Peninha Sanctuary, offering a breathtaking panoramic view. Next, hike along the coastal cliffs to Cabo da Roca before continuing for lunch on Adraga Beach, then overnight in Colares. Continue with a forest hike ending at the neo-Gothic Monserrate Palace in Sintra, with time to explore this historic town. Finally, you'll have a full day to explore the hilltop Palacio Nacional da Pena and Quinta da Regaleira, and other sites of interest, before heading back to Lisbon the next day for your departure. Learn more
Itinerary #4: Self-Drive Adventure in Madeira
This eight-day road trip packs in the best of Madeira as you enjoy charming Funchal and hike the island's highest peaks, then hop a ferry to Porto Santo for downtime on stunning beaches.
|Day 1||Arrive in Funchal & Discover the City||Funchal|
|Day 2||Explore Funchal at Your Leisure||Funchal|
|Day 3||Journey through Western Madeira||Funchal|
|Day 4||Experience Eastern Madeira||Funchal|
|Day 5||Mountain Hike from Pico do Areeiro to Pico Ruivo||Funchal|
|Days 6-7||Take Ferry to Porto Santo Island & Enjoy Beach Time||Funchal|
|Day 8||Depart from Funchal|
Welcome to Madeira, where after picking up your rental car and checking into your hotel, relax with a glass of Madeira's famous wine. The following day, begin your island discovery by exploring Funchal's Old Town—"Zona Velha"—and renowned Madeira Botanical Garden, then ride the cable car up Monte to wander the Monte Palace Tropical Garden and admire the panoramic vistas. On Day 3, drive along the western shore, ticking off Cape Girão (Europe's highest sea cliff), picturesque Ponta do Sol, the mysterious Fanal Forest, and a swim in the lava lagoon of Porto Moniz.
The next day, explore eastern Madeira, including the Curral das Freiras viewpoint, the dramatic Ponta de São Lourenço cliffs, a cable-car ride up to Fajã da Rocha do Navio, and an easy hike in Ribeiro Frio National Park. More hiking awaits on Day 5 as you follow the scenic mountaintop trail between Pico do Areeiro and Pico Ruivo. For your last two days, hop a ferry to nearby Porto Santo island to relax on its golden beaches and swim in its turquoise Atlantic waters before returning to Funchal for your departure on Day 8. Learn more
Itinerary #5: Self-Drive Azores Adventure: São Miguel & Terceira
Get behind the wheel and enjoy an eight-day self-drive celebration of the Azores' natural beauty as you explore geothermally active São Miguel and lush Terceira islands, including whale watching plus kayaking a volcanic crater lake.
|Day 1||Arrive in São Miguel & Explore Ponta Delgada||São Miguel Island|
|Day 2||Visit the Lagoons of Western São Miguel||São Miguel Island|
|Day 3||Whale Watching & Drive to Furnas via Central São Miguel||Furnas|
|Day 4||Experience the Volcanic Activity of the Furnas Valley||Furnas|
|Day 5||Guided Tour of Eastern São Miguel's Pristine Landscape||Furnas|
|Day 6||Fly to Terceira & Enjoy Angra do Heroísmo||Angra do Heroísmo|
|Day 7||Self-Guided Tour of Terceira||Angra do Heroísmo|
|Day 8||Drive to Lajes Airport & Depart Terceira|
Upon arriving at Ponta Delgada, on São Miguel, pick up your rental car, and check in to your hotel before exploring the capital city, including 16th-century Nossa Senhora da Esperança Convent, Carlos Machado Museum, and ancient Gruta do Carvão lava tube. The next day, explore western São Miguel, including kayaking at Sete Cidades volcanic crater lake and a swim in Ponta da Ferraria ocean hot spring. On Day 3, thrill to whale watching before exploring the waterfalls of Caldeira Velha and jade-colored Lagoa do Congro, and perhaps Ilhéu de Vila Franca do Campo for snorkeling.
Then head to Furna Valley to marvel at its hot springs, fumaroles, and geothermal pools, which are great for bathing. Feast on a lunch cooked in the super-hot ground at Furnas Lagoon. On Day 5, drive through the eastern agricultural district, with stops for canyoning at Ribeira dos Caldeirões Park waterfalls, coastal vistas at Ponta da Madrugada and Ponta do Sossego, and in Pico da Vara subtropical forest. Then fly to Terceira, with the afternoon to explore historic Angra do Heroísmo. On your last day, explore Algar do Carvão volcanic chimney and the natural pools of Biscoitos before departing for home the next day. Learn more
More Great Portugal Itineraries
Looking for more inspiration for your trip to Portugal? Check out these other Portugal itineraries, with outdoor adventures, family-friendly trips, and best-of tours to hit the highlights.