Portugal packs sun-drenched coastlines, medieval hilltop castles, and world-class wine into one compact, road-trip-ready country that rewards every detour. Cruise from Lisbon's electric tram-lined streets to Porto's riverside wine lodges and finally unwind on the Algarve's jaw-dropping golden cliffs — all in 10 unforgettable days.
Morning: Pick up your rental car at Humberto Delgado Airport, drop bags at a Bairro Alto guesthouse, and fuel up with a pastel de nata and espresso at Pastéis de Belém.
Afternoon: Walk the cobbled lanes of Alfama to São Jorge Castle for panoramic views over the terracotta rooftops spilling down to the Tagus.
Evening: Join locals at a tiny tasca on Rua dos Remédios for bacalhau à brás and a carafe of Alentejo red, then catch live fado drifting from an open doorway.
Morning: Ride the vintage yellow Tram 28 to Belém, visit the UNESCO-listed Jerónimos Monastery before the tour buses arrive, and photograph the ornate Manueline stonework in golden morning light.
Afternoon: Cross the street to the Museu Nacional dos Coches for the world's finest royal carriage collection, then stroll the riverside promenade to the Tower of Belém.
Evening: Head to Príncipe Real for craft cocktails at Park Bar rooftop — a hidden gem above a car park with unbeatable sunset views over the city.
Morning: Drive 40 minutes west on the A37 to Sintra; arrive before 9 a.m. and climb directly to Pena Palace to beat the crowds and catch mist still clinging to the eucalyptus forest.
Afternoon: Hike 20 minutes downhill through the park to the Moorish Castle for sweeping Atlantic views, then descend into the village for a travesseiro pastry at Piriquita.
Evening: Drive 15 minutes to Cascais for a seafood dinner at Taberna Cais — try the grilled sea bass — before checking into a Cascais guesthouse for the night.
Morning: Drive south across the Tagus via the April 25th Bridge, stopping at Arrábida Natural Park for a swim in impossibly turquoise water below limestone cliffs.
Afternoon: Continue an hour south to the Alentejo coast and the rice-paddy village of Comporta, walk the 10 km of wild, dune-backed beach, and let the pace drop completely.
Evening: Dine at Ilha do Arroz for clam rice cooked in river water with coriander — a hyper-local Comporta dish you will not find elsewhere — as the sun melts into the Atlantic.
Morning: Drive 90 minutes inland to Évora and explore the eerie 16th-century Capela dos Ossos — its walls lined with the bones of 5,000 monks — early before tour groups arrive.
Afternoon: Wander the Roman Temple of Diana and the walled medieval old town, then drive 20 minutes to Herdade do Esporão winery for a guided tasting of their flagship Reserva red.
Evening: Back in Évora, eat at Tasquinha do Oliveira for slow-roasted black pork with migas — the definitive Alentejo meal — paired with a full-bodied Alentejo Aragonez.
Morning: Drive two hours south on the A2 and IP1 to Lagos, check into a guesthouse in the old town, and explore the whitewashed 17th-century Forte da Ponta da Bandeira guarding the harbor mouth.
Afternoon: Walk south along the cliff path to Praia Dona Ana, rent a kayak, and paddle through the amber sea arches and grottos carved into the sandstone coast.
Evening: Head to the buzzing Rua 25 de Abril for grilled cataplana seafood stew at Casinha do Petisco, and cap the night with a craft beer at Lagos Brewing Company.
Morning: Drive 30 minutes west to Sagres, the windswept promontory where Henry the Navigator plotted the Age of Discovery; stand inside Fortaleza de Sagres as Atlantic gusts tear off the headland.
Afternoon: Walk five minutes to Praia do Tonel, one of the best beginner surf beaches in Europe — rent a board and wetsuit from Sagres Surf School for a two-hour lesson.
Evening: Drive back to Lagos and eat at No Patio for wood-fired lamb chops with rosemary, dining in a candlelit courtyard beneath orange trees.
Morning: Drive east along the EN125, stopping at Praia da Marinha — consistently rated among Europe's top beaches — and hike the clifftop trail for views of the layered ochre and rust sea stacks below.
Afternoon: Continue to Albufeira's old town, browse the market at Praça Miguel Bombarda, and take a 90-minute jeep safari into the Serra do Caldeirão hills behind the coast.
Evening: Eat dinner at Adega do Peixe for charcoal-grilled bream straight off the boat, washed down with vinho verde poured ice cold.
Morning: Drive an hour east to elegant Tavira, the quietest and most authentically Portuguese of all Algarve towns; cross the Roman bridge over the Gilão River and climb to the ruined castle for rooftop views.
Afternoon: Take a ten-minute ferry to Ilha de Tavira, a barrier island with 11 km of undeveloped Atlantic beach, and spend the afternoon swimming in the calm lagoon-side waters.
Evening: Return to Tavira for dinner at Aquasul — try the cataplana de lingueirão (razor clams) cooked with garlic, white wine, and tomato in the traditional copper pot.
Morning: Rise early, return the car to Lisbon airport or drop it in Porto (one-way fees are reasonable with major companies), then fly or drive five hours north to Porto, checking into a guesthaus in the Ribeira waterfront quarter.
Afternoon: Cross the iconic Dom Luís I Bridge on foot to Vila Nova de Gaia, tour the historic cellars of Graham's Port Lodge, and sample aged tawny direct from the barrel.
Evening: Back in Ribeira, eat your final Portuguese dinner at Cantinho do Avillez for roasted suckling pig and a bottle of Douro red — toast ten days of the finest roads, wines, and coastlines in Europe.
All tracked partners in one place — you support TonyPlan at no extra cost.
More options: Kiwi.com · Oojo · seats.aero · Arangrant · QEEQ · GetTransfer · Saily · Yesim · GigSky · Klook · EF Ultimate Break · EF Adventures · AirHelp Plus · CruiseDirect
Tell Tony your dates, style and budget — get your own itinerary in seconds.
Plan my Portugal trip →