2-Day Lisbon Road Trip via Sintra, Cascais, and Óbidos

2-Day Lisbon Road Trip via Sintra, Cascais, and Óbidos

Journey Through Portugal

Start a lovely journey through Portugal, beginning and ending in Lisbon, and enjoy a route filled with charm and calm coastal views. Wander through Sintra’s dreamy palaces and leafy gardens, breathe in the sea air in Cascais with its golden beaches and relaxed town feel, and step back in time in the medieval streets of Óbidos. This road trip blends history, culture and beautiful landscapes, giving you a warm taste of Portugal at every stop.
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Historical Landmarks

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Coastal Beauty

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Cultural Richness

About This Road Trip

This Portugal road trip highlights the country's cultural depth and stunning landscapes. Designed for culture and history enthusiasts, it offers visits to the iconic Belem Tower in Lisbon, the romantic Quinta da Regaleira estate in Sintra, the scenic seaside town of Cascais, and the medieval charm of Óbidos Castle. Each stop presents unique experiences blending historical grandeur with natural beauty, perfect for photography and immersive travel.
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Starting Station: Lisbon Airport (LIS)

Trip Duration: 2 days

Mileage Distance: 232 km

Perfect For: History Enthusiasts, Photography, Culture, Nature
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Reddit Reviews

👍 80 % positive|👎 20 % negative

Begin Your Portugal Adventure

Kick off your journey in Lisbon, a city full of history, colour and easy coastal charm. Take your time exploring landmarks like Belém Tower and Jerónimos Monastery, then rent a car with Abbycar and set off on the open road. From here, your Portugal road trip unfolds at your own pace, giving you the freedom to enjoy the country’s bright coastlines, peaceful countryside and all the small moments in between.
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Where To Stop

Road Trip Stops

<p>Explore the captivating stops on this Portuguese road trip, each offering rich history, scenic views, and cultural gems.</p>

1
First stop
View in Lisbon

Lisbon

Belem Tower in Lisbon is a historic fortress symbolizing Portugal's Age of Discovery. Visitors can explore its intricate Manueline architecture and enjoy scenic views along the Tagus River, making it a cultural highlight of your roadtrip.
Based on 38332 reviews
(4.2/5)
2
Second stop
View in Sintra

Sintra

Quinta da Regaleira in Sintra is a magical estate featuring lush gardens, mysterious tunnels, and exquisite architecture. This UNESCO World Heritage site captivates visitors with its romantic and esoteric atmosphere, perfect for cultural and nature lovers.
Based on 14221 reviews
(4.8/5)
3
Third stop
View in Cascais

Cascais

Boca do Inferno is a spectacular cliff formation near Cascais, offering visitors dramatic ocean views and the chance to witness powerful Atlantic waves crashing against the rocks, creating a mesmerizing natural show along Portugal's coast.
Based on 4206 reviews
(4.2/5)
4
Fourth stop
View in Óbidos

Óbidos

Óbidos Castle is a well-preserved medieval fortress dominating the town of Óbidos. Visitors can stroll the historic walls, explore charming streets filled with traditional shops, and experience the medieval ambiance coupled with scenic views over the surrounding countryside.
Based on 1896 reviews
(4.5/5)
5
Fifth stop
View in Lisbon (Jerónimos Monastery)

Lisbon (Jerónimos Monastery)

Jerónimos Monastery in Lisbon is a masterpiece of Manueline architecture and a UNESCO World Heritage site. Visitors can admire its intricately carved cloisters and rich maritime history, making it a cultural cornerstone of Portugal's golden age of exploration.
Based on 33014 reviews
(4.5/5)
All you need to know before you go!

Frequently Asked Questions

Yes, this road trip is ideal for a short break. The distances between Lisbon, Sintra, Cascais, and Óbidos are short, making it easy to explore iconic landmarks, coastal scenery, and historic towns within a few days without feeling rushed.
 

Visitors to the Algarve region often plan to take boat trips from Portimão to visit caves and see dolphins.
Traveling from Lisbon to Sintra does not require a car; Ubers are affordable, and public transport like trams provide a charming experience.

While public transport exists, renting a car offers much more flexibility. With a car, you can visit attractions like Quinta da Regaleira, Boca do Inferno, and Óbidos Castle at your own pace, avoid crowded timetables, and reach scenic viewpoints not easily accessible by train or bus.
 

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AbbyCar Travel Experts

Car Rental & Travel Industry Specialists

AbbyCar Travel Experts are the experienced professionals behind AbbyCar, one of Europe’s most trusted and value-for-money car rental brands, operating in over 30 countries. With more than 14 years of hands-on experience in car rentals and road-trip travel, the team has helped more than 1.5 million travellers explore their destinations with comfort and confidence. Drawing on in-depth knowledge of local routes, travel trends, and driving conditions, AbbyCar Travel Experts provide reliable, experience-based advice to help every traveller enjoy a safe, smart, and stress-free journey. 

For more road-trip ideas and expert travel inspiration, visit our Road Trips Section