Discover Portugal on a 2-week road trip that covers the country’s iconic destinations alongside hidden gems. This itinerary connects our favorite places from more than a year of living in Portugal on a road trip loop. With less than 2 weeks, you can easily shorten the itinerary by leaving out some of the blocks.

Lisbon & Sintra: 3 Days

Day 1: Chiado, Alfama & Graça

Upon arrival in Lisbon, start by exploring its elevated neighborhoods. Visit iconic viewpoints Miradouro São Pedro de Alcântara and Miradouro de Santa Luzia, board tram 28 to Graça and end the day with sunset drinks on a rooftop bar. My favorite rooftop views of Lisbon are served at Memmo Alfama Rooftop Terrace and Rooftop Bar at Hotel Mundial.

Day 2: Baixa & Belém

On the second day in Lisbon, visit the neighborhoods bordering the river Tagus. Explore the elegant streets and imposing squares of Baixa, before lunch at a traditional Portuguese tasca like A Merendinha do Arco Bandeira. Board the train from Cais to Sodré station to Belém and visit the monuments from the Age of Discovery. Try the original pasteis de Belém before heading to Chiado for a rooftop dinner at Silk Club (sushi) or Entretanto Rooftop Bar (small plates).

Day 3: Day Trip to Sintra

The fairytale land of Sintra is an easy day trip away from Lisbon, either by train, car or organized tour. Visit the colorful Pena Palace, the National Palace of Sintra and Quinta da Regaleira, which tower out above Sintra’s picturesque historic town center. Continue for 30 minutes through the Sintra mountains to the scenic coast, including westernmost point Cabo da Roca and the coastal village of Azenhas do Mar.

Alentejo Coast: 2 Days

Day 4: Setúbal Peninsula & Comporta

Explore Alentejo’s pristine coastline on the way south from Lisbon to Algarve. The first stop is Parque Natural da Arrábida, one of Portugal’s seven natural wonders. Follow the park road to Miradouro do Portinho da Arrábida and complete the loop to Azeitão, where you can have lunch and paint your own tile at Leiveiro Azulejos. Continue to hip Comporta for boutique shopping and dinner on the beach at Sal Carvalhal.

Day 5: Vicentina Coast

Start the day in Alentejo’s most charming coastal town. Porto Covo is surrounded by beautiful beaches and coves, connected by the first stretch of the Fishermen’s Trail. Hike 5 km (3 miles) along the coast from Porto Covo to Bar da Praia Vieirinha for a relaxed lunch overlooking the ocean. In the afternoon, explore the picturesque town of Vila Nova de Milfontes. Restaurant A Choupana grills fresh catches on a large outdoor grill, served with ocean views.

Algarve: 3 Days

Day 6: Sagres & Lagos

Alentejo’s rough west coast becomes almost still at Cabo de São Vicente, Algarve’s westernmost point. Follow the road up to the lighthouse and explore the relaxed surfers’ town of Sagres. Spend the afternoon in Lagos, one of the most quaint towns in the Algarve. Pack up a picnic to enjoy a spectacular sunset from Miradouro da Praia do Canavial, accessed by the Ponta da Piedade walkway in the west.

Day 7: Ponta da Piedade & Benagil Cave

The Ponta da Piedade area covers a network of boardwalks and trails that lead up to unique rock formations. Follow the boardwalk from Praia do Pinhão to the tip of the coast, or access from the water by kayak or boat tour. In the afternoon, take a speedboat tour from Portimão to Benagil sea cave, passing the stunning Algarve coastline. Enjoy a seafood dinner in Ferragudo, a picturesque fishing village across the river from Portimão.

Day 8: Carvoeiro & Seven Hanging Valleys

The Seven Hanging Valleys trail is considered one of Europe’s most beautiful coastal trails. Hike 6 kilometers (one-way) from spectacular Praia da Marinha to Praia de Vale de Centeanes, with lunch at O Stop before returning. Spend the afternoon in the colorful holiday town of Carvoeiro. A scenic boardwalk leads to Algar Seco, a maze of tunnels, caves and windows carved into the cliffs by erosion. Have dinner surrounded by this unique landscape at Boneca Bar & Restaurant.

Interior: 3 Days

Day 9: Monsaraz

Return from Algarve to Central Portugal through the interior of Alentejo, past cork trees and olive groves. On the way to Monsaraz, make a stop at São Pedro de Corval, Portugal’s pottery village. Start your visit at the small museum Casa do Barro, which displays several pieces from each artist with a workshop in town. Continue to Monsaraz, a walled medieval town on a hilltop near the Spanish border. Stroll the enchanting streets before watching the sunset from Monsaraz Castle.

Day 10: Evora & Alentejo vineyards

Evora’s historic center dates back to Roman times. Admire the Diana Temple with coffee from Quiosque Jardim Diana. Climb the Cathedral of Evora for 360-degree views over the city and visit the unique Chapel of Bones. Before heading into Alentejo wine country, stop by wine museum Rota dos Vinhos do Alentejo in Evora to map out your wine route. You can sip on wines by the glass at the beautiful wine bar of Fitapreta Vinhos.

Day 11: Parque Natural da Serra da Estrela 

Break up the drive from Alentejo to the Douro Valley with a stop in Parque Natural da Serra da Estrela, Portugal’s largest protected area. You can stay the night in Manteigas, a mountain town next to the river. Take a scenic drive around the park past viewpoints of the many lakes, with a picnic at Covão d’Ametade. Hike the easy Rota das Faias (PR-13) trail for expansive views of the valley and beautiful fall foliage in October and November.

Porto & the Douro Valley: 3 Days

Day 12: Douro Valley

You can visit the Douro Valley on a day trip from Porto or explore the stunning scenery at your own pace. In the morning, take a one-hour river cruise by traditional Rabelo boat. Enjoy a farm-to-table lunch with amazing views at Quinta do Pôpa, followed by a port tasting at Quinta Santa Eufémia overlooking the Douro River. Stay the night in one of the towns along the river or tackle the 90-minute drive to Porto.

Day 13: Porto

With just one day in Porto, start with a guided tour of riverfront Ribeiro, a maze of narrow streets and colorful façades. Grab lunch at Mercado do Bolhão and visit the nearby Chapel of Souls. In the afternoon, cross the iconic Dom Luis I Bridge to Vila Nova de Gaia, where all major port houses are located along the riverbank. Visit a port wine cellar followed by a port tasting, ending the day with a stunning sunset from Roof Terrace Espaço Porto Cruz.

Day 14: Obidos, Nazaré & Return to Lisbon

Return to Lisbon via Óbidos, one of Portugal’s best preserved medieval towns. Stretch your legs by walking all around town on the former defense walls. Take a 30-minute detour to visit surf mecca Nazaré if traveling in winter, when waves often reach 20 meters (65 feet) or more. After another 90-minute drive, you will complete the road trip loop and reach the capital.

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