Lisbon's Multi-Day Trips South and Inland
The Algarve’s A22 highway went toll-free in 2025, which is the version of this route most travel forums repeat. The A2 heading south out of Lisbon, the road that actually gets you there, is still tolled, and a rental car needs an electronic Via Verde transponder fitted before you leave the lot or the tolls simply don’t get paid. Lisbon works well as a base for two multi-day routes that don’t involve Porto at all: south to the Algarve coast, and inland to a cluster of UNESCO monasteries.
Route B: south to the Algarve coast
A CP Intercidades train from Lisboa Oriente or Entrecampos to Tunes or Faro takes about 3 to 3.5 hours for roughly 24 to 30 EUR, or drive the A2 in about 2 hours 30 minutes with the toll transponder sorted first. Base yourself in Lagos or Tavira for 3 to 4 days. From Lagos, the limestone sea stacks at Ponta da Piedade are walkable, a shared boat tour to the Benagil sea cave runs about 25 to 35 EUR from Portimao, and the Seven Hanging Valleys trail covers the clifftop scenery on foot rather than by boat. Book a private 2-day Algarve tour from Lisbon if you’d rather not manage the train-plus-local-transport logistics yourself.
Route C: the central monasteries circuit
This one is genuinely best done by rental car over 2 to 3 days: Alcobaca Monastery, holding the tombs of King Pedro I and Ines de Castro, then Batalha Monastery, a Dominican masterpiece of late Gothic and Manueline architecture built around its Unfinished Chapels, then Tomar, home to the Convent of Christ and former headquarters of the Knights Templar, then Coimbra for its Baroque university library. None of these sit conveniently on a single train line together, which is exactly why a car works better here than it does for the Algarve route. Compare rental car options for Lisbon before you commit to this route, since pricing and pickup locations vary a lot by company.
What this route isn’t
Don’t fold the Azores or Madeira into either of these plans without flagging the obvious: both are mid-Atlantic island groups reached only by a 1.5 to 2.5-hour flight, not an extension of a train or driving route, and treating them as a rail add-on will wreck a travel budget built around ground transport.
Current Intercidades fares and timetables are on CP - Comboios de Portugal ; for guided multi-day itineraries covering some of the same ground, Intrepid Travel runs small-group options. For the day trips that fit inside a Lisbon base rather than requiring an overnight elsewhere, see the day trips guide , and for a full week’s structure, the 4-day Lisbon itinerary shows how much of the city to see before heading out on either route.
Verdict: pick the Algarve for beach and coastline, and the monasteries circuit for architecture and history; trying to do both in one trip usually means neither gets enough time.
One concrete tip: activate the Via Verde transponder in your rental car paperwork before you leave the depot, not after you’re already on the A2, since retroactively paying an unregistered toll from abroad is far more of a hassle than the five minutes it takes at pickup.