Architectural arches of the Jeronimos Monastery in Lisbon

Self-Drive Portugal Itinerary: Iconic Cities to Charming Towns

Ratings of Zicasso's Service

Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Lisbon, Evora, Alentejo, Estremoz...

See all

Suggested Duration

10 Days

Creating a loop from the vibrant capital city of Lisbon, this 10-day self-driving tour is an adventure into the soul of Portugal. Connect with the locals, venture away from the tourist trail, and discover the dazzling diversity of destinations that make the country so distinctive. Indulge in the coastline, castles, marble towns, salty harbors, sunbaked plains, spire-packed cities, and much more. With this unique route, you celebrate all the highlights that Portugal loves to hide.

Customizable Itinerary

Expand All

Trip Highlights

  • Follow a unique self-drive route that has been handcrafted to celebrate the complete allure of Portugal, with each destination offering a different version of history and culture
  • Explore the dazzling open landscapes of Portugal, crossing the dusty Alentejo plains, green Minho valleys, and cliff-strewn coastlines
  • Enjoy sublime accommodation in some of Portugal’s oldest destinations, like a castle town from the eighth century and a charming walled city of cobblestone and whitewashed houses
  • Discover many of the country’s World Heritage Sites, including the cities of Evora and Guimaraes, Coimbra University, and the monasteries at Alcobaca and Batalha
  • Uncover Portugal’s most recognizable highlights with two guided days in Lisbon and a full day in and around Porto
  • Meet with the locals and enjoy traditional Portuguese hospitality as you travel to destinations that are far from the tourist trail
  • Stop at dozens of panoramas along the way, including castles above the Atlantic waves and the highest mountains in Portugal

Detailed Description

Portugal’s landscapes encourage discovery. Weave through green valleys, and you come across a Gothic monastery from the 15th century, an epic symbol of history standing on its own. Drive down the coastline, and there is always an empty beach to spend an hour on. Cross open plains and the castles beckon you forward, compass points from a now-forgotten century. This is a country that rewards the inquisitive eye, one that is tailor-made for a soul that likes to wander. With this unique 10-day route, you connect the landscapes and the destinations, the history and the culture, and the people and the places that make Portugal such an exciting place to be. En route, there will be fortresses, marble cities, culinary temptations, Roman odes, and such architectural diversity that it is hard to believe that everything you see was built in the same country.

The handcrafted route is a loop starting and ending in the capital city, Lisbon. First, journey southeast through the rural Alentejo region, where hilltop villages and evocatively narrow streets make for real fascination. Wind north along the border of Spain, a region packed with castles and tightly-packed walled cities. By the middle of the tour, you will find yourself in Minho, the region where the country has most of its cultural roots. The old cities are close together, and the route allows for ample time to explore places like Braga and Guimaraes on foot. Spend a couple of nights in Porto, then return to Lisbon along the coast as you connect the dots of history and the feeling of solitude that the windswept Atlantic can provide.

Hotels have been handpicked for their accessibility. Each provides a safe place to park so you can continue the discovery on foot. While a couple of destinations can feel busy in the day, most of them are quiet and authentic throughout the evenings. With a self-drive route, you can spend the night in these relatively remote destinations and savor a culture that only becomes more apparent after dusk. With each hotel, there is a collection of restaurants and cafes within walking distance, so you can take a daily break from the driving. And with such unusual destinations, you will find that meeting the locals is part of the everyday experience.

For additional Portugal travel inspiration, consider browsing the other Portugal vacation packages offered on Zicasso.

Starting Price

$1,995 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

Reviews of Zicasso's Referral Service

4.94 stars based on 672 reviews.

Portugal Travel Review: Waves of Nazare, Obidos, Alentejo...
"We will be traveling with this company again!"

Reviewed By Denise B.

Portugal Travel Review: Coimbra, Sintra, Cascais, Douro...
"The travel designers and their team were wonderful."

Reviewed By Fred R.

Solo Tour of Portugal Travel Review: Marvao, Braga, Guimaraes,...
"My recent trip to Portugal felt effortless due to the exceptional,...

Reviewed By Jeanne J.

Portugal Vacation Review: Lisbon, Sintra, Nazare, Palacio...
"We visited some unique places and enjoyed some incredible...

Reviewed By George G.

Portugal Travel Review: Lisbon, Aveiro, Douro River, Castles,...
"The owners [of our travel agency] were at the airport to...

Reviewed By Sue A.

Portugal Mother-Daughter Trip Review: Lagos, Lisbon, Benagil...
"It was obvious [our travel agency] wanted us to enjoy Portugal...

Reviewed By Laurie B.

Your Dream Vacation

in 3 simple steps

  1. 1

    Describe your dream trip

  2. 2

    Get matched with top travel specialists

  3. 3

    Book the trip

Free service - no credit card required