Pousadas & Wineries


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Lisbon | Pousadas & Wineries Gourmet Tour

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8 days from


An 8-day self-drive tour that will take you on a journey through the multifaceted landscapes, historic towns & dramatic coastline of Portugal's south. With accommodation in charming Pousadas, visits to renowned wineries & wine tasting along the way, this Wine & Gourmet Tour is sure to leave you with memories for years to come!

Day 1: Lisbon

 Arriving at Lisbon Airport, pick-up your rental car and drive downtown to The One Palacio da Anunciada Hotel, your home for the next two nights. The remainder of the day is at leisure to relax or start discovering Portugal's charming capital city on your own. Lisbon is a must to visit with its World Heritage monuments and medieval quarters. We suggest a walk through the medieval quarters of Alfama and Mouraria, crowned by the magnificent St. George’s Castle, and through the Baixa District, the heart of Lisbon featuring magnificent plazas, avenues & grand 18th-century architecture to feel the atmosphere of this historic town. You may also want to visit the historic quarter of Belém where you can admire the Tower of Belem, the Monument of Discoveries and Jerónimos Monastery. A unique experience awaits you tonight with a 3-course dinner & show in a typical Fado Restaurant. (D)
Lisbon Airport - Lisbon hotel: 9 km approx.

Day 2: Lisbon

Today is free to continue exploring Lisbon at your pace. Or perhaps drive to nearby Sintra, the delightful hilltop village and former summer retreat of Portugal's royal family to visit Sintra National Palace or the nearby romantic Pena Palace. Make sure to stroll through the narrow cobblestone alleys of this picturesque town and taste some of Sintra's famous pastries. Then drive through Sintra-Cascais Natural Park to the windswept cliffs at Cabo da Roca, considered the westernmost point of Europe, and return to Lisbon along the coast passing through Cascais with its "Boca do Inferno" waterspout and magnificent panorama out over the Bay of Cascais, and the elegant seaside town of Estoril with its famous Casino. (B)

Day 3: Lisbon | Sagres

Following breakfast at your hotel, check-out and drive south along the coast to Sagres, the most south-westerly village of the Algarve region overlooking the Atlantic Ocean, where you will stay the next two nights at Pousada de Sagres. Of great historical & maritime significance, it was from Sagres that Prince D. Henrique’s caravels departed in search for news lands 500 years ago. The remainder of the day is free to discover historic Sagres on your own. (B) 
Lisbon - Sagres: 325 km approx.

Day 4: Quinta dos Vales Winery

Today set out to explore the Algarve countryside and make your way to drive to the “Quinta dos Vales” wine producer & cellar in Estombar (77 km from Sagres) where you'll enjoy a guided visit and taste four of the estate’s wines. Only a short drive from Estombar, the region’s old Moorish capital of Silves invites for a stroll along the old city walls that surround the central square and to visit the town's castle, an imposing Moorish stronghold. Then perhaps proceed to Monchique, a lovely SPA town of Roman origins located in the Serra de Monchique mountain range. The journey up to Monchique offers spectacular views of the Algarve countryside. Returning to the coast, make sure to stop in the picturesque town of Lagos with its well-preserved old centre, the richly adorned ‘golden church’ of Saint Anthony, and the Ponte da Bandeira Fort. Overnight accommodation at Pousada do Infante in Sagres. (B)
Sagres - Estombar - Silves - Monchique - Lagos - Sagres: 180 km approx.

Day 5: Sagres | Évora

Following breakfast, check-out and drive north into the centre of the Alentejo, a region known for its wide-open spaces & extensive farms, toward Evora, perhaps stopping to visit Alvito with its 15th-century Manueline castle en-route. Évora is a museum-town that retains much of its Medieval & Moorish charm and a Unesco World Heritage Site. The Giraldo Square, the Roman Temple, the 12th-century Cathedral and São Francisco Church, one of the most important Gothic Manueline monuments in the area and which houses the famous Chapel of the Bones, are not to be missed. Tonight & tomorrow you’ll enjoy accommodation at the Pousada do Convento in Évora. (B)
Sagres - Évora: 300 km approx.

Day 6: Herdade do Esporão Winery

Today make your way to Reguengos de Monsaraz (44 km from Évora) where you’ll enjoy a guided wine & gastronomic experience at the “Herdade do Esporão” wine cellar & vineyard, including a tasting of 4 wines from the estate plus a degustation lunch with wine pairing at the local restaurant, a chance to taste the delicious Alentejo cuisine (drinks not included). Following lunch, we suggest visiting the nearby fortified town of Monsaraz, one of the most typical medieval towns in the Alentejo and totally surrounded by walls, then perhaps continue to Vila Viçosa with its magnificent Ducal Palace which served as a summer residence for the last kings of Portugal, and the medieval town of Estremoz surrounded by 17th-century fortifications. Return to Évora for overnight accommodation. (B.L)
Évora - Reguengos de Monsaraz - Monsaraz - Vila Viçosa - Estremoz - Évora: 171 km approx.

Day 7: Évora | Palmela - José Maria da Fonseca Winery

This morning depart Evora and drive toward the Blue Coast in the direction of Palmela, where you’ll stay in a medieval castle converted into a pousada. Its hilltop setting offers breathtaking panoramic views of the magnificent Natural Park of Arrabida and the Sado river. Make sure to visit the historic centre of Palmela starting your tour at S. Pedro Church with its Baroque tile covered interior, and continue to nearby Setúbal with its beautiful pedestrian streets and gardens. Then enjoy a guided visit to the cellar of “José Maria da Fonseca” wine producer in Azeitão with a tasting of 3 different wines. Tonight's accommodation will be at Pousada Castelo de Palmela. (B)
Évora - Palmela - Setúbal - Azeitão - Palmela: 133 km approx.

Day 8: Palmela | Lisbon

Today marks the end of your Pousadas of Portugal Tour. Following a leisurely breakfast, check-out and make your way to Lisbon airport to return your rental car & begin your journey home. (B)
Palmela - Lisbon Airport: 48 km approx.

Daily Departures

Daily departures with minimum 2 passengers.