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Sintra Palace Pena
Multi-day Private multi-day tour

14 Days Portugal Tour : The Best from North to South

Travel privately for 14 days from Lisbon through Arrival in Lisbon & Historical Heart Discoveries; Journey South to Alentejo & Arrival in the Museum-City of Évora; Return to Lisbon via Fishing Sesimbra, Arrábida Cliffs & Azeitão Art. Walkborder confirms the route, pickup plan and practical details in writing before payment.

Tripadvisor 4.9 · 1,061 reviews 14 days Private group Lisbon pickup

Tour overview

14 days planned as one private journey.

Private 14 days journey from Lisbon, following Arrival in Lisbon & Historical Heart Discoveries; Journey South to Alentejo & Arrival in the Museum-City of Évora; Return to Lisbon via Fishing Sesimbra, Arrábida Cliffs & Azeitão Art. Daily logistics are confirmed around your dates, hotels and preferred pace. The sequence is based on Walkborder’s official product itinerary. Accommodation, timed admissions and optional activities are included only when they appear in your written proposal.

Route at a glance

Arrival in Lisbon & Historical Heart Discoveries opens the journey; Return to Lisbon via Fishing Sesimbra, Arrábida Cliffs & Azeitão Art completes it.

Journey South to Alentejo & Arrival in the Museum-City of Évora

We leave Porto and travel south into the golden plains and olive grove landscapes of the Alentejo region. Our destination is Évora, a beautifully preserved museum-city classified as a UNESCO World Heritage site.

Private daily logistics

A private vehicle and driver-guide follow the confirmed route for your group.

Built around your trip

Dates, hotels, admissions, optional visits and pacing are confirmed before payment.

Suggested itinerary

14-day route, one clear sequence.

The day order may change for hotel location, admission times, traffic, weather or a preference agreed before confirmation.

Day 1: Arrival in Lisbon & Historical Heart Discoveries

We dedicate this first day to discovering Lisbon’s historic heart, exploring the city’s famous hills, viewpoints and traditional neighborhoods. We will visit Portas do Sol and São Pedro de Alcântara, walk through the narrow streets of Alfama, see the 12th-century Cathedral, and continue through the elegant districts of Chiado and Baixa, with their grand squares, historic architecture and lively atmosphere along the Tagus River.

Overnight: Lisbon

Accommodation is not included. Guests must book and pay for it separately.

Day 2: Romantic Sintra, Pena Palace, Cascais & Estoril Coast

We journey to the enchanting town of Sintra, a UNESCO World Heritage site, where you will visit the colorful Pena Palace, with admission tickets included. We then continue toward the Atlantic coast, stopping at Cabo da Roca, the westernmost point of continental Europe, before passing Boca do Inferno and finishing in the elegant seaside town of Cascais.

Overnight: Lisbon

Accommodation is not included. Guests must book and pay for it separately.

Day 3: Belém Monumets & Free Afternoon in Lisbon

Spend the morning exploring historical Belém, the launching ground for caravels during the Age of Discovery. Visit the iconic Belém Tower, the Discoveries Monument, and the majestic Jerónimos Monastery—a Manueline masterpiece. We wrap up the morning with a tasting of the original Pastéis de Belém.

Overnight: Lisbon

Accommodation is not included. Guests must book and pay for it separately.

Day 4: Northern Route: Faith of Fátima, Academic Coimbra & Arrival in Porto

Today we head north, beginning with Fátima, one of the world’s most important pilgrimage destinations, where we will visit the Chapel of the Apparitions and the main basilicas of the sanctuary. We then continue to Coimbra, the historic “City of Students,” to explore its famous University, founded in 1290, including the Paço das Escolas and the Joanina Library, with admission tickets included.

Overnight: Porto

Accommodation is not included. Guests must book and pay for it separately.

Day 5: Porto City Discovery, Lello Bookstore & Gaia Wine Cellars Tasting

A full day dedicated to discovering Porto’s historic center, including São Bento Station, Porto Cathedral, Clérigos Tower, the Ribeira district and the famous Lello Bookstore, with admission tickets included. The day also includes a visit and tasting at a traditional Port wine cellar in Vila Nova de Gaia, included in the tour.

Overnight: Porto

Accommodation is not included. Guests must book and pay for it separately.

Day 6: Breathtaking Douro Valley, Pinhão Station & Estate Wine Tour

Escape into the breathtaking Douro Valley, the world’s oldest demarcated wine region and a UNESCO World Heritage site. Travel along scenic roads overlooking terraced vineyards and the Douro River, with a stop in Pinhão and its iconic tiled railway station. The day includes a visit and wine tasting at a selected winery, included in the tour.

Overnight: Porto

Accommodation is not included. Guests must book and pay for it separately.

Day 7: Visit to Guimarães, and Braga

We dedicate the day to Guimarães and Braga, two cities deeply connected to Portugal’s history and identity. In Guimarães, we explore the medieval historic center and the imposing Guimarães Castle. We then continue to Braga, with a visit to the remarkable Bom Jesus do Monte Sanctuary and its famous monumental staircase.

Overnight: Porto

Accommodation is not included. Guests must book and pay for it separately.

Day 8: Aveiro & Journey South to the Historic City of Évora

We leave Porto and travel south, stopping first in Aveiro, known for its canals, Art Nouveau architecture and colorful moliceiro boats. We then continue through the landscapes of central Portugal toward Évora, a beautifully preserved UNESCO World Heritage city. On arrival, we will enjoy a first walk through the historic center and Praça do Giraldo, before ending the day in Évora.

Overnight: Évora

Accommodation is not included. Guests must book and pay for it separately.

Day 9: Évora Exploration: Roman Temple, Cathedral & Chapel of Bones

A full day dedicated to discovering the rich heritage of Évora, accompanied by your private guide. We will explore the impressive Roman Temple, the imposing Évora Cathedral and the unique Chapel of Bones inside the Church of São Francisco, one of the city’s most striking landmarks.

Overnight: Évora

Accommodation is not included. Guests must book and pay for it separately.

Monsaraz, Alqueva & Journey into the Algarve

Today we leave Évora and travel toward Monsaraz, one of the most beautiful medieval villages in the Alentejo, with panoramic views over the vast Alqueva Lake. After exploring its castle, whitewashed streets and traditional atmosphere, we continue south through the Alentejo landscapes toward the Algarve, where we end the day.

Overnight: Algarve

Accommodation is not included. Guests must book and pay for it separately.

Day 11: Western Algarve: Historic Lagos & Ponta da Piedade

Discover the western Algarve, where dramatic cliffs, golden beaches and Atlantic scenery define the landscape. In Lagos, we explore the historic center, its traditional streets and its strong connection to Portugal’s maritime history, before continuing along the coast to admire some of the region’s most striking viewpoints and rock formations.

Overnight: Algarve

Accommodation is not included. Guests must book and pay for it separately.

Day 12: Eastern Algarve: The Charm of Tavira & Ria Formosa Nature Lagoon

Discover the eastern Algarve, beginning in Tavira, one of the region’s most charming historic towns, before exploring the landscapes of the Ria Formosa Natural Park. The day also includes a boat trip to Benagil Cave, subject to weather and sea conditions, before returning to the hotel.

Overnight: Algarve

Accommodation is not included. Guests must book and pay for it separately.

Day 13: Leisure Day: Golden Beaches, Seafood & Relaxation

A full day at leisure to relax completely. Enjoy your premium resort amenities, lounge on the world-famous golden cliff beaches (such as Marinha Beach or Falésia Beach), or explore local villages at your own pace. Your executive vehicle and private driver remain fully available to accommodate local transfers as desired.

Overnight: Algarve

Accommodation is not included. Guests must book and pay for it separately.

Day 14: Return to Lisbon via Fishing Sesimbra, Arrábida Cliffs & Azeitão Art

We conclude this magnificent journey by driving back north to Lisbon with superb coastal stops. First, visit Sesimbra, a picturesque fishing village nestled beneath its medieval castle. Next, navigate the breathtaking mountain roads of Arrábida Natural Park, offering panoramic views over turquoise waters.

Included

Part of the group price

  • Private air-conditioned vehicle
  • Pickup and drop-off in the confirmed area
  • English-speaking local driver-guide or guide support
  • Admissions, visits and tastings as described in the itinerary
  • Tolls, parking and local taxes when included in the confirmed proposal

Not included

Paid separately

  • Hotel accommodation. Guests are responsible for booking and payment.
  • Meals and drinks unless explicitly confirmed
  • Monument, boat, estate or activity tickets unless listed
  • Personal expenses and gratuities

Practical information

What to know before the day.

Comfort

Comfortable shoes and a light layer are recommended.

Tickets

Timed entries may affect route order and must be confirmed before departure.

Mobility

Historic centres may include slopes, stairs or uneven paving. Tell us your needs early.

Operator

WALKBORDER LDA

Insurance

ALLIANZ — Apólice nº 203377964

RNAVT

RNAVT nº 5861

Guest feedback

Private service, clear planning and local context.

Tripadvisor 4.9 · 1,061 reviews

Read more reviews
“The route felt organised without becoming rigid. Our guide adapted the pace for the children, explained the history clearly and helped us choose the right palace.”

Sarah M. · United States

May 2026 · Family

“Everything was explained before the day, the pickup was punctual and the guide balanced historical detail with time to explore independently.”

Helen R. · United Kingdom

March 2026 · Couple

Frequently asked questions

Before you request availability.

No. The enquiry only asks us to verify availability. The booking becomes confirmed after you receive the written proposal, accept the conditions and complete the required payment.

Most private day tours use a group price for a defined vehicle capacity. Each tour page states the group size, price and any exceptions.

The tour page lists transport, guide, pickup, tickets, water, tolls and taxes when applicable. Lunch, optional tickets and personal expenses are normally separate unless stated otherwise.

Yes, within the available time, geography, ticket conditions and operational limits. Major changes should be agreed before confirmation.

Lunch is normally not included unless stated on the tour page. Guides can recommend restaurants based on preferences, dietary needs and timing.

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Request this private 14 days journey.

Share your dates, group size, hotel plan and priorities. We will confirm availability, route, inclusions and final price in writing.

From4,782 € / group
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