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Portugal Historic Towns & Lisbon: Cultural Road Trip
8 Nights: 5 Historic Portuguese Towns (Sintra, Óbidos, Tomar, Évora & Monsaraz) + Lisbon with Car Included


Dates and Prices
Why We Love This Deal

Embark on a 9-day self-drive journey through Portugal’s most historic towns and medieval treasures, with a rental car included. Explore the fairytale palaces of Sintra, the medieval village of Óbidos, the Templar city of Tomar, and the UNESCO-listed gems of Évora. Continue to Monsaraz for breathtaking views over Alqueva Lake before ending in vibrant Lisbon, discovering its historic neighborhoods and maritime landmarks. A seamless blend of culture, history, and scenic landscapes, this Portugal road trip is the perfect way to explore at your own pace and get to know the country's hidden gems.
2 nights Sinta → 1 night Óbidos → 1 night Tomar → 1 night Évora → 1 night Monsaraz → 2 nights Lisbon
Plan This Trip to Fit Me!
Your Trip Itinerary

- Day 1Arrive in Lisbon & Drive to Sintra (approx. 35 minutes)
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Welcome to Lisbon! Let's explore together: pick up your car rental on arrival and get ready for adventure by driving to Sintra. It's an easy 35-minute drive via the A37 route, covering 17.27 miles (27.8 km).
* Want to maximize your time in paradise? Consider pre-booking an early check-in during the booking process. This way, you can hit the ground running and start exploring sooner! Don't hesitate to contact our booking agents if you have any questions or need assistance setting this up.
Suggestion for the day: Arrival & First Evening in Sintra
- Stroll in Sintra Historic Center: Wander around the cobbled streets, admire the traditional houses, and maybe stop for a travesseiro pastry at Piriquita.
- Sintra National Palace (Palácio da Vila): If time allows, visit the palace right in the town center – recognizable by its twin conical chimneys. It’s less demanding than other monuments and gives a nice introduction to Sintra’s royal past.
- Dinner: Enjoy a local dinner in town. Good options include Tascantiga (petiscos/tapas-style) or Cantinho Gourmet (Portuguese cuisine in a cozy setting).
- Day 2Sintra

Suggestion for the day: Full Day Exploring Sintra
Morning & Afternoon
- Pena Palace & Park: Drive (or take the tourist bus) up to Palácio da Pena, the colorful Romantic palace surrounded by lush gardens. Allow 2–3 hours to explore both the interiors and the park.
- Moorish Castle (Castelo dos Mouros): Just next door, visit the medieval fortress with panoramic views across Sintra, Lisbon, and the Atlantic. Great for photos and a lighter walk.
- Lunch: Stop in town for a quick bite, or try Taverna dos Templários for something hearty.
- Afternoon – Quinta da Regaleira: A must-see with its magical gardens, underground tunnels, and the famous Initiation Well. Plan around 2 hours here.
Late Afternoon/Evening:
- Option 1: Relax with a drive to Cabo da Roca (30 minutes from Sintra) to catch the sunset at mainland Europe’s westernmost point.
- Option 2: Stay local and enjoy a calmer evening walk around Sintra village with a light dinner and maybe a glass of local Colares wine.
- Day 3Drive to Óbidos (approx. 1h)

Say goodbye to Sintra and hit the road for Óbidos, a scenic drive of approximately 58 miles (92 km), taking around 1 hour.
Suggestion for the day: Exploring the Medieval Village of Óbidos
- Enter through Porta da Vila: The decorated main gate with azulejos sets the mood right away.
- Stroll Through the Village: Wander the narrow whitewashed streets with bougainvillea and craft shops. The main street, Rua Direita, leads straight to the castle.
- Óbidos Castle & Walls: Explore the medieval castle (now a pousada) and walk along the fortified walls for sweeping views over the town and surrounding countryside.
- Igreja de Santa Maria: A charming 16th-century church in the main square with ties to Portuguese royal history.
- Chocolate or Ginja Liqueur: Try a shot of ginja de Óbidos served in a chocolate cup — a local specialty.
- Dinner inside the walls: Cozy options include Alcaide (traditional Portuguese with a modern twist) or Pontinha (regional specialties).
- After dinner, enjoy the village at night — beautifully lit and much quieter after day-trippers leave. The medieval atmosphere is especially magical in the evening.
- Day 4Drive to Tomar (approx. 1.15 hour)

If time allows, consider a quick stop before leaving Óbidos and driving to Tomar:
- Sanctuary of Senhor da Pedra (just outside the walls, a unique hexagonal baroque church).
- Aqueduto de Óbidos, visible near the town.
The drive from Óbidos to Tomar will take about 1 hour and 15 minutes - approximately 51 miles (82 km).
Suggestion for the day: Unveiling Historic Tomar
- Convent of Christ (Convento de Cristo): The must-see. A UNESCO site tied to the Knights Templar and later the Order of Christ. Allow at least 2 hours to explore the famous Charola (rotunda), Manueline window, cloisters, and fortress grounds.
- Castle of Tomar: Within the convent complex, offering views over the town and the Nabão River.
- Lunch Tip: Try Taverna Antiqua (medieval-inspired dishes) or Café Paraíso for lighter bites in the center.
- Stroll through the historic center: Charming squares, tiled façades, and riverside walks along the Nabão.
- Synagogue of Tomar: A small but important 15th-century synagogue (now a museum) — visit if it’s still open.
- Dinner: Options include Alminhas Restaurante (Portuguese classics) or O Tabuleiro (regional cuisine).
- Nighttime: The city center is calm and atmospheric; enjoy a quiet evening drink in Praça da República.
- Day 5Drive to Évora (approx. 2.30 hours)

Before leaving Tomar and driving to Évora, we recommend a few stops:
- Mata Nacional dos Sete Montes: A peaceful park near the convent, perfect for a morning stroll.
- Church of Santa Maria do Olival, a beautiful Templar burial site.
Say goodbye to Tomar and start driving to Évora. The drive will take about 2 hours and 30 minutes - approximately 143 miles (230 km).
Suggestion for the day: Évora Historic Center
- Roman Temple of Évora (Templo de Diana): Iconic ruins right in the heart of the city, with gardens and panoramic spots nearby.
- Sé de Évora (Évora Cathedral): Climb to the rooftop for sweeping views over the town and Alentejo countryside.
- Historic Streets & Squares: Wander through Praça do Giraldo, the lively central square, and along the narrow lanes lined with whitewashed houses and yellow trim.
- Chapel of Bones (Capela dos Ossos) inside Igreja de São Francisco: Striking and thought-provoking, best visited before evening.
Dinner Options:
- Fialho – classic Alentejo cuisine, long-standing and elegant.
- Taberna Típica Quarta-Feira – authentic, traditional set-menu experience.
- Dom Joaquim – refined local dishes with a modern twist.
After dinner, enjoy the calm streets of Évora by night; the historic center is beautifully lit and quieter once day-trippers leave.
- Day 6Drive to Monsaraz (approx. 1 hour)

Recommendations for your morning before leaving for Monsaraz, if you have time:
- University of Évora (Colégio do Espírito Santo): Elegant cloisters with azulejo-covered walls.
- Aqueduto da Água de Prata: Renaissance aqueduct that runs into town; some houses are built right into its arches.
- Local Shopping: Consider cork products, olive oil, or Alentejo wines before heading on.
Hit the road for a quick dribbling session of about 1 hour. From Évora to Monsaraz, the distance is approximately 33 miles (53 km).
Suggestion for the day: Monsaraz Hidden Gems
- Wander the Walled Village: Enter through the stone gates and explore the cobbled lanes, whitewashed houses, and charming corners.
- Monsaraz Castle: Climb up the castle walls for panoramic views of the Alqueva Lake, Europe’s largest artificial lake. The castle’s arena (once used for bullfights) is still intact.
- Igreja Matriz de Nossa Senhora da Lagoa: The main church in the village square, simple but historically significant.
- Craft Shops & Local Products: Browse small artisan shops for Alentejo pottery, textiles, cork items, and regional wine.
- Sunset Over Alqueva Lake: The view from the castle walls or the village terraces is unforgettable — golden plains meeting the deep blue of the lake.
Dinner:
- Taverna Os Templários – hearty Alentejo dishes with lake views.
- Sabores de Monsaraz – cozy spot with traditional cuisine.
- Stargazing: Monsaraz is part of the Alqueva Dark Sky Reserve, one of the best stargazing destinations in the world. If the sky is clear, you’ll see an impressive night sky with minimal light pollution.
- Day 7Drive to Lisbon (approx. 2.15 hours)
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Bid farewell to Monsaraz and drive to Lisbon for the last part of your trip. The drive will take approximately 115 miles (185 km).
Suggestion for the day: Stroll Around Downtown Lisbon
Lace up your walking shoes and embark on a journey through Lisbon's captivating historical neighborhoods. It’s time to explore Lisbon's vibrant neighborhoods on foot.
- Start in Chiado, a charming district with elegant shops and cafes. Don't miss Livraria Bertrand, a historic bookstore.
- Move to Baixa, the bustling downtown area with Praça do Comércio, a grand waterfront square. Climb the Arco da Rua Augusta for city views.
- Immerse yourself in Bairro Alto's lively nightlife scene. Wander its maze-like streets filled with bars, restaurants, and traditional Fado music venues.
Can't-Miss Sights:
- São Roque Church: Admire its opulent interior.
- São Pedro de Alcântara Garden: Relax and enjoy panoramic views.
- Ruins of Carmo Church: Reflect on Lisbon's history.
- Santa Catarina Viewpoint: Capture stunning cityscapes.
- Luís de Camões Square: Pay homage to Portugal's literary icon.
- Terreiro do Paço: Soak in the lively atmosphere of this vast waterfront square.
- Santa Justa Lift: Enjoy a unique perspective from this neo-Gothic elevator.
- Day 8Lisbon

Suggestion for the day: Unveiling Belém's Maritime Marvels
Head to Belém, a UNESCO site showcasing Portugal's maritime past. See the iconic Torre de Belém and Mosteiro dos Jerónimos, and savor Pastéis de Belém, a delicious custard tart.
Don’t Miss:
- Torre de Belém (Belém Tower): Start your exploration at this imposing 16th-century fortress. Marvel at its Manueline architecture, a unique Portuguese style characterized by nautical motifs and intricate stonework. Padrão dos Descobrimentos (Monument to the Discoveries): A short walk away stands this impressive monument commemorating Portugal's Golden Age of Exploration.
- Mosteiro dos Jerónimos (Jerónimos Monastery): Immerse yourself in the grandeur of this magnificent 16th-century monastery. A UNESCO World Heritage Site, it's a masterpiece of Manueline architecture, showcasing intricate stonework and stained-glass windows.
- Pastéis de Belém: No visit to Belém is complete without indulging in the world-famous Pastéis de Belém, a traditional Portuguese custard tart. This iconic bakery, established in the 18th century, follows a secret recipe that has been passed down through generations.
- MAAT – Museum of Art, Architecture, and Technology: If you have extra time, consider visiting the MAAT, a contemporary museum housed in a striking modern building on the waterfront.
- Day 9Return Flight Home
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One last stop: returning your rental car.
Thank you for choosing us to be your travel companions on this adventure! It's been a pleasure assisting you in creating unforgettable memories. We wish you happy travels and until next time!
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