Since you have a car and are not looking for beach stops, you have the ultimate flexibility to create an incredible 3-day road trip. Trying to hit all four places would mean spending your entire trip driving, parking, and packing.To maximize your time between Peso da Régua and Lisbon, drop Évora from this specific leg. Geographically, Évora is far to the southeast in the Alentejo region; adding it requires a massive detour that will swallow up an entire day of driving.The most interesting, efficient, and deeply historic route focuses on Coimbra, Tomar, and Óbidos. Here is how to structure it perfectly into 3 days:Day 1 (Sept 23): Peso da Régua to CoimbraThe Drive: Head south through the beautiful mountain valleys (~1.5 hours).The Vibe: Coimbra is Europe’s quintessential medieval university city, steeply stacked above the Mondego River.What to do: Spend the afternoon exploring the jaw-dropping Joanina Library (a Baroque masterpiece built in the 1700s) and wandering the ancient Almedina old town.Stay the night: Overnight in Coimbra.Day 2 (Sept 24): Coimbra to TomarThe Drive: A smooth 1-hour drive down the main highway.The Vibe: Tomar is the mystical, historic home of the Knights Templar.What to do: Explore the massive Convent of Christ. Because you have a car, you can bypass the steep walk from town and park right near the castle gates. Take your time wandering the quiet, smaller cloisters surrounding the main Charola. If you want a deeply researched private look into these hidden symbols to make the most of your afternoon stop, feel free to check out our unhurried local paths: https://www.templarknightstours.com/templar-tour. Afterward, drive down into the flat town center for a relaxed lunch along the Nabão River.Stay the night: Overnight in Tomar.Day 3 (Sept 25): Tomar to Óbidos to LisbonThe Drive: Leave Tomar in the morning and drive about 1 hour to Óbidos.The Vibe: Óbidos is a picture-perfect, fully intact medieval walled village.What to do: Walk the historic stone ramparts, wander the cobblestone paths lined with white-and-blue houses, and try Ginjinha (the local sour cherry liqueur served in a tiny chocolate cup). The Finish: Jump back in the car for a final, easy 1-hour drive straight down to Lisbon, arriving in the late evening just as planned.Alternative Idea: The Three Monasteries RouteIf you want to swap out Óbidos for raw architectural history, keep your overnights in Coimbra and Tomar, but use Day 3 to visit Batalha or Alcobaca. These gigantic UNESCO-listed gothic monasteries are situated right along your driving route to Lisbon and offer some of the most stunning stone carvings in all of Europe.This layout keeps your driving times under 90 minutes per day, eliminates any backtracking, and lets you experience Portugal's finest medieval history at a wonderful, unhurried pace!