From the enchanting fantasy land hidden in the hills of Sintra to the charming villages of rural Alentejo and the sun-kissed coves of the Algarve, there is an authentic Portugal just waiting to be discovered. Explore ancient castles, take to the waves with a surf lesson and enjoy fresh seafood complemented by the distinct wines of the region.
Here’s how a weeklong road trip starting and ending in Lisbon will take you off the beaten track to give you a taste of the real Portugal. As always, check for travel guidelines and closures before planning your trip.
Day 1: Take the High Road into the Magical Hills Around Sintra
After picking up your car in Lisbon, take the scenic N6 drive north to discover one of the most stunning stretches of coastline in Europe. With its cluster of beachside seafood restaurants, a stop at the fishing port of Cascais is a must, before following the N247 along sculptural cliffs and past near-deserted golden-sand beaches. Surfer’s paradise Praia do Guincho is well worth a look, as are the views at Cabo da Roca with its lighthouse that marks continental Europe’s westernmost point.
An inland turn brings you to the Sintra-Cascais Natural Park, where you can explore the lush wooded hills and architectural treasures that made Sintra the summer playground of Portuguese aristocracy for centuries.
After an afternoon touring onion-domed mansions, labyrinthine gardens and fairytale grottos, Penha Longa Resort awaits — the epitome of luxury set within a converted 14th-century monastery and boasting two restaurants with Michelin stars.
Day 2: Linger in Lisbon Before Enjoying Dramatic Vistas and Crystalline Waters
Bid farewell to Penha Longa Resort and return to Lisbon for a day and night in the Portuguese capital before setting off south. With its rooftop views, outdoor pool and — perfect for road-trippers — on-site parking, the Lisbon Marriott Hotel is one of the city’s most appealing places to stay. Or opt for the Sheraton Lisboa Hotel & Spa, where the outdoor pool and spa ensure moments of well-deserved relaxation.
Don’t leave Lisbon without stopping off at the 16th-century Torre de Belém and tasting pastéis de Belém, the famous custard tarts served warm from the blue-tiled Pastéis de Belém bakery — you might even get some to take away as snacks for the drive to come.
Back behind the wheel, cross the Ponte 25 de Abril suspension bridge spanning the Tejo Estuary and meander your way south through the Arrábida Natural Park to the dramatically windswept Cabo Espichel headland. The route along the N-379 promises stunning vistas from chalk cliffs over sparkling waters and past ruined hilltop castles.
In Sesimbra, family-run restaurants offer delicious, simply grilled sardines — irresistible. You might even find time for a swim at the sandy Portinho da Arrábida beach before the sun goes down.
Day 3: Discover Some of the Alentejo’s Hidden Gems
Following the coast through the Alentejo region, the next stage of your road trip offers a glimpse of Portugal far away from the tourist crowds. The journey south takes you through pastures of holm oaks where free roaming Iberian pigs feast on acorns, and past family-owned vineyards, whose wines will provide the perfect pairing to the catch of the day.
The landscape is dotted with historic towns, whitewashed seaside villages and some of the best beaches in Europe. Don’t miss the dizzying cliffs of Cabo Sardão, the only maritime spot in Europe where storks make their nests, while the charming fishing village of Zambujeira do Mar makes for a perfect lunch spot.
Afterwards, criss-cross the landscape until the rugged coastline softens into a cove at Odeceixe, where the River Ceixe spills into the sea, forming a natural border between Alentejo and the Algarve.
Day 4: Travel to the Historical Ends of the Earth at Cabo de São Vicente
By staying off the highway, you can follow atmospheric local roads to explore the southwestern reaches of the Algarve. You might stop to stretch your legs with a stroll beneath the imposing cliffs at Praia de Arrifana and take a break to explore the quaint fishing village of Vila do Bispo. If you happen to be here at dusk, be sure to watch the sun sink into the horizon at the Cabo de São Vicente. Up until the 15th century and circumnavigation of the globe, this headland was believed to be the end of the world.
Some 6 kilometers south, Sagres attracts surfers and watersports enthusiasts. If you fancy an afternoon on the beach, head to the sheltered golden sands of Praia da Mareta.
When the time comes to round off your fourth day, an hour’s drive east will bring you to W Algarve, an ultra-modern sanctuary with ocean views and a spa that blends cutting-edge design with traditional Portuguese style.
Pine Cliffs Hotel, a Luxury Collection Resort, Algarve, meanwhile, is a destination in itself with 172 acres of parkland, breathtaking views and a nine-hole golf course.
Day 5: Hop from Lively Lagos to Portimão and the Benagil Caves
Heading east through the Algarve, you can explore a craggy coastline of coves and beaches — some of the finest are only accessible by rural tracks. Plan to spend a few hours exploring Lagos, a lively town with a thriving fishing fleet. It’s buzzing during the summer months with bars and restaurants lining the cobbled streets of the old quarter and craft boutiques offering the chance to pick up some souvenirs to take home.
A short drive to the east is Portimão, a port city with a busy marina and a museum detailing the history of the region. Adventurers can take a boat trip from here to explore the nearby Benagil caves.
Come the end of the day, hop behind the wheel for a leisurely 45-minute drive further east to a tranquil lakeside sanctuary: Domes Lake Algarve, Autograph Collection, where the concierge service is second to none.
Day 6: Experience Olhão’s Special Light and Some Island Beaches
Two gems of the Eastern Algarve are the fascinating towns of Olhão and Tavira. Famed for its special light, Olhão has attracted an artsy crowd who have been restoring the town’s traditional tiled houses, making a pre-dinner wander through the old cobbled streets a must.
From Olhão, leave the car behind for a few hours to take a boat to the islands of Armona, Culatra and Fuseta, their spectacular beaches teeming with birdlife. Back on the mainland and along the coast, Tavira spreads across two banks of the Gilão River and boasts a Roman bridge, Moorish ruins and a wealth of Baroque churches.
Day 7: Travel into the Hills and Back in Time
Leaving the golden coast behind you, head north into the hills to encounter a completely different Portugal. The walled town of Silves has a rich history and one of the best preserved castles in Portugal — enter through its arched gate dating back to Moorish times and take a step back into the past, wandering through cobbled streets scented with orange blossom.
Further up into the hills is Monchique, where in summer you’ll catch the cooler breeze whistling through the eucalyptus trees. Be sure to visit the 16th-century Miguelino church and browse the local handicraft shops where weaving is a specialty.
From here, it’s less than three hours north to Lisbon. You’ll cross into the city over the Vasco de Gama bridge. This astonishing 17-kilometer-long structure spans the Tagus estuary, where you’ll see flamingos wading in the shallows.
What better way to end your adventure than with a stay at explorer-themed The Ivens, Autograph Collection? This pastel pink former warehouse dating to the 19th century has been converted into an opulent hotel located in the heart of Lisbon’s historic Chiado neighborhood.
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