Perfect Pairings: Lisbon & Rural Alentejo

Portugal
6 nights private tour from $9,500
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Perfect Pairings Lisbon Rural Alentejo
At a glance
  • Jump on board the iconic yellow tram and discover Lisbon through its flavours, medieval architecture, lively soul and buzzing café culture

  • Enjoy private tours, wine tastings and gourmet delights in Lisbon, Sintra and the lesser known Alentejo 

  • Unearth palace secrets at the dramatic Quinta da Regaleira and iconic Pena Palace

  • Devour farm to table food with incredible local produce, cheeses and wine 

Journey highlights
  • Jump on board the iconic yellow tram and discover Lisbon through its flavours, medieval architecture, lively soul and buzzing café culture

  • Enjoy private tours, wine tastings and gourmet delights in Lisbon, Sintra and the lesser known Alentejo 

  • Unearth palace secrets at the dramatic Quinta da Regaleira and iconic Pena Palace

  • Devour farm to table food with incredible local produce, cheeses and wine 

Our tailor made journeys include:
  • Your dedicated Travel Consultant who will take care of arrangements
  • Private international airport transfers in destination
  • Your own private, English-speaking local guides
  • Unique experiences, hand-picked by our Journeys team
  • Entrance to must-see local sites
  • Dedicated 24/7 team providing in-country support and guidance
  • Complimentary access to My Scott Dunn – industry-leading travel app providing pre-departure information and in-journey support

When to visit

  • J
  • F
  • M
  • A
  • M
  • J
  • J
  • A
  • S
  • O
  • N
  • D
Best time to visit
Good time to visit
Average time to visit

Lisbon is a year-round destination, although the city can be busy during the summer months. Spring and autumn are some of the best times to visit.

The south of Portugal has a mild climate with more that 300 days of sunshine a year. The weather generally warm and sunny in May with the risk of the odd shower of rain. Sometimes it can be cool in the evenings. By June the weather generally settles in a pattern of long hot sunny days and balmy evenings especially in July and August. June and September are particularly pleasurable months.

Your Itinerary

Let us take you on a thrilling adventure as we guide you through the lesser known gems of Lisbon and Alentejo. Taking you along the road less travelled you will submerge in bespoke private out of hours tours, the secret nooks of Sintra and unearth palace secrets as our expert guides share their passion and knowledge. Along with awe-inspiring beauty, exquisite crafts, world renowned wineries and delicious cuisine, you will discover this corner of Portugal like never before.

Palace of Pena

Your Itinerary

Your bespoke luxury break is raring to go. Arrive at the gorgeous Bairro Alto Hotel, boasting a mix of boho style and contemporary elegance with exclusive access to the roof terrace overlooking the city, the perfect base to relax!

Devour breakfast and set off on a tour of the city with your private guide. Be wowed as you visit the magnificent Jeronimos Monastery before opening hours, with no one else there travel back in time to when the Hieronymite monks lived here, and silence was the motto. Board your very own private yellow tram and wind your way through the seven hills of Lisbon, discovering the enchanting neighbourhoods and vibrant atmosphere of the city. Explore downtown Lisbon with an exclusive visit to the Church of São Roque, where the nooks of the church are usually hidden away from the public.

The following day lose yourself in an exceptional guided tour through the rolling hills of Sintra. On the way, you will understand the passion and love put into running the magnificent estate of Quinta de Santana. You'll be guided through the vineyards, winery, barrel room and 17th century chapel ending with a tasting of their delicious wines, followed by a delicious picnic in the grounds. Next, on to the divine World Heritage Site of Sintra where hundreds of years of history and culture await you. Pass by amazing royal palaces, chalets and aristocratic residences in the most incredible combination of architectural styles, colours, and shapes. In the old centre lies a one-of-a-kind mansion, Quinta da Regaleira. Travel through the magical labyrinth of trees and walk down the steps of the initiation well to Quinta da Regaleira's underground passageways. After hours visit the iconic Pena Palace, a mesmerising hilltop palace of whimsical design with sweeping views of the valley, forest and sea.

Wine Tasting

Your Itinerary

Time for a slower pace of life as you head to São Lourenço do Barrocal, an idyllic farm estate. Surrounded by endless wheat fields, cork forests and olive groves with hiking, wine tasting and horse riding waiting for you here, a hidden retreat far from the tourist trail. Firstly, visit Quinta do Casal Branco, where you’ll enjoy the almost forgotten magical world of manor houses, falconry, and rural traditions. Taste the superb wines and devour a sumptuous lunch in the grounds. Return to your hotel for the afternoon, boasting a pool and spa set amongst its extensive grounds, the perfect setting to unwind and be pampered. The estate has archaeological sites that can be explored, along with many walking and biking trails. Horse riding and wine tastings can be arranged.

Quinta Dona Maria awaits you the following day, a landmark for its beauty and history, now producing top-quality wines. You will be delighted to sample these followed by an informative lunch with the owners. In the evening prepare to be wowed as you visit a local observatory where the astronomers will take you on a walk to remember under the night sky. Stargaze far from the light pollution of cities taking in the view from the observation platform and marvel at the incredible stars above.

Another exclusive tour awaits you the following day at the Cadaval Palace, the residence of the Duchess of Cadaval and her family. Take in the unique combination of Mudéjar, Gothic and Manueline styles, featuring a vast residential area, two inner gardens and church. You will be invited to share a meal with the Duchess of Cadaval, during which you will absorb centuries of tradition and history, accompanied by the wines produced at the property. Lastly visit Sao Pedro do Corval, famed for its pottery workshops. Experience the clay being moulded by the expert hands of the master potter, as you then take your turn at the wheel, before returning to your hotel for a final evening on this exhilarating itinerary.

Itinerary

Day 1-4

Lisbon, Portugal

Your bespoke luxury break is raring to go. Arrive at the gorgeous Bairro Alto Hotel, boasting a mix of boho style and contemporary elegance with exclusive access to the roof terrace overlooking the city, the perfect base to relax!

Devour breakfast and set off on a tour of the city with your private guide. Be wowed as you visit the magnificent Jeronimos Monastery before opening hours, with no one else there travel back in time to when the Hieronymite monks lived here, and silence was the motto. Board your very own private yellow tram and wind your way through the seven hills of Lisbon, discovering the enchanting neighbourhoods and vibrant atmosphere of the city. Explore downtown Lisbon with an exclusive visit to the Church of São Roque, where the nooks of the church are usually hidden away from the public.

The following day lose yourself in an exceptional guided tour through the rolling hills of Sintra. On the way, you will understand the passion and love put into running the magnificent estate of Quinta de Santana. You'll be guided through the vineyards, winery, barrel room and 17th century chapel ending with a tasting of their delicious wines, followed by a delicious picnic in the grounds. Next, on to the divine World Heritage Site of Sintra where hundreds of years of history and culture await you. Pass by amazing royal palaces, chalets and aristocratic residences in the most incredible combination of architectural styles, colours, and shapes. In the old centre lies a one-of-a-kind mansion, Quinta da Regaleira. Travel through the magical labyrinth of trees and walk down the steps of the initiation well to Quinta da Regaleira's underground passageways. After hours visit the iconic Pena Palace, a mesmerising hilltop palace of whimsical design with sweeping views of the valley, forest and sea.

Accommodation: Bairro Alto Hotel ( 3 nights )
Day 4-7

Monsaraz, Alentejo, Portugal

Time for a slower pace of life as you head to São Lourenço do Barrocal, an idyllic farm estate. Surrounded by endless wheat fields, cork forests and olive groves with hiking, wine tasting and horse riding waiting for you here, a hidden retreat far from the tourist trail. Firstly, visit Quinta do Casal Branco, where you’ll enjoy the almost forgotten magical world of manor houses, falconry, and rural traditions. Taste the superb wines and devour a sumptuous lunch in the grounds. Return to your hotel for the afternoon, boasting a pool and spa set amongst its extensive grounds, the perfect setting to unwind and be pampered. The estate has archaeological sites that can be explored, along with many walking and biking trails. Horse riding and wine tastings can be arranged.

Quinta Dona Maria awaits you the following day, a landmark for its beauty and history, now producing top-quality wines. You will be delighted to sample these followed by an informative lunch with the owners. In the evening prepare to be wowed as you visit a local observatory where the astronomers will take you on a walk to remember under the night sky. Stargaze far from the light pollution of cities taking in the view from the observation platform and marvel at the incredible stars above.

Another exclusive tour awaits you the following day at the Cadaval Palace, the residence of the Duchess of Cadaval and her family. Take in the unique combination of Mudéjar, Gothic and Manueline styles, featuring a vast residential area, two inner gardens and church. You will be invited to share a meal with the Duchess of Cadaval, during which you will absorb centuries of tradition and history, accompanied by the wines produced at the property. Lastly visit Sao Pedro do Corval, famed for its pottery workshops. Experience the clay being moulded by the expert hands of the master potter, as you then take your turn at the wheel, before returning to your hotel for a final evening on this exhilarating itinerary.

Accommodation: Sao Lourenco do Barrocal ( 3 nights )
We design each itinerary around you, so this suggested itinerary is a starting point that we can tweak or transform into something completely bespoke to you.
Call us on 858 523 9000 to start planning your holiday.

Experiences included in this itinerary


Your Hotels


When to visit

  • J
  • F
  • M
  • A
  • M
  • J
  • J
  • A
  • S
  • O
  • N
  • D
Best time to visit
Good time to visit
Average time to visit

Lisbon is a year-round destination, although the city can be busy during the summer months. Spring and autumn are some of the best times to visit.

The south of Portugal has a mild climate with more that 300 days of sunshine a year. The weather generally warm and sunny in May with the risk of the odd shower of rain. Sometimes it can be cool in the evenings. By June the weather generally settles in a pattern of long hot sunny days and balmy evenings especially in July and August. June and September are particularly pleasurable months.

Perfect Pairings: Lisbon & Rural Alentejo
Perfect Pairings: Lisbon & Rural Alentejo

Let's get this Perfect Pairing booked for you. Call us on 858 523 9000 to start planning your trip.

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Why Scott Dunn?

At Scott Dunn, we live and breathe travel. An insatiable appetite to discover the world runs through everything we do. We relish the planning and revel in the detail. We know it’s the smallest touches that make the biggest difference, and we stop at nothing to make every trip not only exceptional but totally unique.

  • Every itinerary is crafted from scratch, based around exactly what’s important to you
  • Packed full of unique experiences, hand-picked by our journeys team
  • Expert local guides enrich your experience in every destination
  • Your own dedicated Travel Specialist who will take care of every detail of your trip
  • We have a 24/7 team providing in-country support and guidance
  • We offer flexibility and financial protection to give you total peace of mind

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