8-Day Lisbon & Alentejo Countryside Escape

A Slow Luxury Journey by Portugal Magik Private Tours

Introduction — Where Time Slows and Portugal Shines

There are trips you take to see things, and trips you take to feel things.
The 8-Day Lisbon & Alentejo Countryside Escape, designed by Portugal Magik Private Tours, belongs to the latter.

It’s a private, relaxed journey that invites you to linger — over a glass of wine in the shade of an olive tree, over tiled streets bathed in sunlight, and over meals that seem to last forever.
For eight gentle days, you’ll experience the rhythm of Portugal’s capital and the serenity of the Alentejo plains — a land of cork forests, vineyards, and quiet medieval towns that feel suspended in time.

Your personal English-speaking driver-guide will take care of everything. You’ll travel in a luxury Mercedes-Benz vehicle, at your own pace, between Lisbon’s cultural treasures and the slow-living charm of Évora, Monsaraz, and the Alentejo countryside.

Every day has purpose — and every day has peace.

Day 1 – Arrival in Lisbon | Welcome to the City of Light

Arrive at Lisbon Airport, where your private driver-guide will greet you and assist with your luggage before transferring you to your selected hotel.
After check-in, enjoy a short panoramic tour to get oriented — the Avenida da Liberdade, the Rossio, and the Commerce Square, ending at a scenic viewpoint over the Tagus River.

The evening is free for rest or a casual walk through the Chiado neighborhood.

Dinner suggestion: Solar dos Presuntos (website: https://solardospresuntos.pt), a Lisbon icon known for its classic seafood and warm service.

Day 2 – Lisbon Heritage & Gourmet Delights

Your private tour begins in the old quarter of Alfama, Lisbon’s oldest neighborhood, where fado music drifts from balconies and laundry lines cross sunlit alleys.

Visit the Jerónimos Monastery and Tower of Belém, two of Portugal’s greatest architectural landmarks. Stop at Pastéis de Belém (website: https://pasteisdebelem.pt) for warm custard tarts dusted with cinnamon.

Afternoon is free — unwind at a rooftop café or enjoy a spa treatment at your hotel.

Dinner recommendation: Belcanto (website: https://www.belcanto.pt), Lisbon’s two-Michelin-star restaurant, for a contemporary take on Portuguese flavors.

Guest Review:

“Portugal Magik found the perfect rhythm for us — a bit of history, a bit of leisure, and no stress at all.”
— Helen and Brian T., USA – May 2024

Day 3 – Sintra & the Atlantic Coast

Your driver takes you west to Sintra, a UNESCO World Heritage town of pastel palaces and misty forests. Visit Pena Palace, an icon of Romantic architecture, and stroll through the gardens of Quinta da Regaleira.

Continue to the coastal village of Cascais, stopping at the dramatic Cabo da Roca, Europe’s westernmost point.

Lunch suggestion: Mar do Inferno (website: https://www.mardoinferno.pt) — legendary seafood by the ocean.
Return to Lisbon by evening for a relaxing night at your leisure.

Day 4 – Journey to Évora | The Heart of the Alentejo

Depart Lisbon and drive east through golden hills dotted with cork oaks and olive trees.
Arrive in Évora, the capital of the Alentejo, a city that feels both timeless and alive.

Visit the Roman Temple, the Cathedral, and the haunting Chapel of Bones.
Lunch at Degust’Ar (website: https://www.conventodoespinheiro.com/en/restaurant-bar/), featuring local produce paired with fine Alentejo wines.

Check in to your countryside accommodation — perhaps a converted monastery or a vineyard estate — and enjoy a free afternoon to rest by the pool, explore the grounds, or sip a glass of wine at sunset.

Guest Review:

“Arriving in Évora felt like exhaling. The landscape, the calm, the kindness — it was pure magic.”
— Amy C., UK – June 2024

Day 5 – Alentejo Wine & Olive Oil Experience

The day unfolds gently among vineyards and olive groves.
Visit Herdade do Esporão (website: https://www.esporao.com), one of Portugal’s most celebrated wineries, for a private tasting and tour. Learn the secrets of the region’s olive oil production, followed by a farm-to-table lunch with local delicacies.

After lunch, return to your hotel for free time — perhaps a spa session or a slow walk through the fields.

Evening suggestion: a private dinner arranged at a local restaurant or winery, depending on your preferences.

Day 6 – Monsaraz & Alqueva Lake | Castles and Horizons

Today’s journey takes you deeper into the Alentejo countryside.
Perched high above the plains, Monsaraz is a medieval village of whitewashed houses and cobbled alleys, offering one of the best panoramic views in Portugal.

Visit the Monsaraz Castle, explore local pottery shops, and stop by a small family-run winery for a tasting overlooking the Alqueva Lake, Europe’s largest artificial lake.

Enjoy a leisurely lunch in the village or by the water before returning to Évora in the late afternoon.

Guest Review:

“Monsaraz was breathtaking — quiet, genuine, untouched. Portugal Magik’s timing and local contacts made it perfect.”
— Patricia & Charles M., USA – September 2024

Day 7 – Évora at Leisure | Optional Day Trips

Your last full day is intentionally flexible — a free morning to sleep late, enjoy a spa treatment, or explore Évora’s artisan shops.
For those seeking a bit more adventure, your driver can organize optional short excursions:

• Arraiolos, famous for its hand-embroidered carpets.

• Estremoz, known for marble and charming markets.

• Vila Viçosa, the former royal residence of Portugal’s dukes.

Return to Évora for a final evening of wine, good food, and starlight over the countryside.

Dinner suggestion: Fialho Restaurant (website: https://www.restaurantefialho.com) — a local institution serving classic Alentejo recipes.

Day 8 – Farewell to the Alentejo | Return to Lisbon

After breakfast, enjoy a scenic drive back to Lisbon, stopping along the way for coffee or a final vineyard visit.
Your driver ensures a smooth airport transfer or an optional drop-off at your Lisbon hotel if you plan to extend your stay.

As the rolling plains fade in the rearview mirror, you’ll understand why the Alentejo is called “Portugal’s soul under the sun.”

Why Travelers Love This Journey

• Relaxed pacing: No rushing — time to enjoy long lunches, free mornings, and peaceful evenings.

• Balanced itinerary: City culture and countryside calm in equal measure.

• Private and personal: English-speaking driver-guide with luxury Mercedes-Benz vehicle.

• Gastronomy and wine: Handpicked experiences that celebrate Portugal’s culinary heartland.

• Authentic atmosphere: Boutique hotels, vineyard stays, and historic charm.

This 8-day escape is ideal for couples, families, and solo travelers seeking a smooth, scenic, and meaningful introduction to Portugal’s most soulful regions.

About Portugal Magik Private Tours

Founded over 14 years ago, Portugal Magik Private Tours has become one of the most trusted names in luxury private travel across Portugal.
We design bespoke multi-day journeys that combine cultural depth, comfort, and local authenticity.

Guests travel in Mercedes-Benz vehicles, accompanied by professional English-speaking driver-guides who provide insight, flexibility, and discreet service.

Most of our guests book tours of 7 to 12 days, often combining Lisbon, the Alentejo, and the Douro Valley — creating experiences that balance discovery with rest.

Guest Reflection:

“Portugal Magik is exactly what its name suggests — calm, elegant, and completely seamless.”
— Janet W., USA – October 2024

Pricing

Starting from 4,450 EUR per person, based on two guests traveling privately in a luxury Mercedes-Benz vehicle with professional driver-guide service throughout.
Our team will assist you in selecting and booking the best 5-star or boutique hotels to suit your preferences and travel dates.

Book Your Lisbon & Alentejo Escape

Discover Portugal at your own rhythm — slow, scenic, and unforgettable.
Let Portugal Magik Private Tours design your 8-Day Lisbon & Alentejo Countryside Escape, blending city culture, rural tranquility, and world-class gastronomy.

Book Your Portugal Experience:

• Explore our bestseller multi-day tours: https://portugal-magik.com/multi-day-tours/

• Best private day tours around Lisbon: https://portugal-magik.com/private-day-tours/

• Read top guests’ reviews: https://portugal-magik.com/reviews/

• Contact us: https://portugal-magik.com/contact/

Fill in the form below to request your custom itinerary and begin planning your Lisbon & Alentejo Escape today.