• Timeless elegance and traditional Portuguese hospitality
  • An immersive tour of Lisbon with a local guide
  • An exploration of the Estoril coast and superb beaches plus an introduction to the secret retreat of Sintra
  • A chance to explore Madeira and discover the hidden delights of this attractive island
  • A stay in one of Europe’s exquisite grande dame hotels

From sensuous Lisbon to the island of Madeira, this luxury holiday to Portugal offers an idyllic combination of culture, urban adventure and elegant style. We’ll show you Lisbon’s unmissable sights and its secret spots, from postcard-perfect viewpoints to cobblestone alleyways and gorgeous, white-domes churches, before jetting you over to Funchal on Madeira. Here, you'll settle in for a seriously stylish stay in one of Europe’s grande dame hotels and the chance to discover the island’s wild coastlines, pretty villages and sublime seafood.

Day 1

Fly to Lisbon

Start your luxurious short break in Lisbon by enjoying a complimentary chauffeur-driven ride to the airport and exclusive airport lounge access before your flight to Portugal. On arrival we will arrange a private transfer to your hotel, the Tivoli Avenida Liberdade, one of Lisbon’s landmark properties.

Step outside this sleek hotel to find yourself on bustling Avenida de Liberdade, with its fashionable haunts and hip boutiques. A short stroll will bring you to many of Lisbon’s main sights as well, along with typical Portuguese neighbourhoods for you to explore.

Exterior of Tivoli Avenida Liberdade Lisboa, Lisbon

Tivoli Avenida Liberdade Lisboa

Lisbon's old-town skyline

Lisbon's old-town skyline

Day 2

Lisbon's historic old town & Belem

Spend your day immersing yourself in Lisbon. Your private guide will help you explore the oldest part of the city, next to Lisbon's Castle, you will find preserved Roman and Moorish vestiges, and the most amazing viewpoints in the city. Next your guide will show you the beautiful neighbourhood of Belem, from where vessels departed during the Age of Discovery. To end the tour visit one of the oldest pastry shops in the city to taste the famous custard tart - Pastel de Belem, the secret recipe inherited from the convent just across the street

On your return to the hotel, hunt out the hidden swimming pool surrounded by century-old botanical trees. Arrange a massage or slip into the spa for a tailored treatment. In the evening, settle into the Cervejaria Liberdade for a celebration of all things Portuguese, from fish and seafood to beer. Maybe you’ll then lose yourself in traditional fado music while enjoying a performance of Portuguese song at a traditional Casa de Fados; ask us about arranging backstage access as well.

Breakfast included

Lisbon Trams

Iconic Trams of Lisbon

Belem Tower, Lisbon

Belem Tower, Lisbon

Day 3

Journey to the Estoril Coast

Escape from Lisbon by letting us take you to explore the bucolic Estoril coast. A private driver will lead you to the delightful fishing village of Cascais, where you will be able to amble along the quay, soak up the port’s atmosphere and admire some of the finest beaches in the area. A short drive through the lush forest will bring you to the secret some-time summer retreat of the Portuguese royal family. The town of Sintra is a magical stop, now recognised by UNESCO as a World Heritage Site. Walk slowly through the sunny alleyways and stumble on pretty squares and superb examples of Moorish architecture.

Once you’ve drunk in the atmosphere, we will whisk you to one of the most westerly vineyards in Europe where a leading wine producer will guide you through a tasting session. On your return to the hotel, consider treating yourself to a gourmet experience at Terraco, the Tivoli’s renowned restaurant. Afterwards, ascend to the hotel’s much-raved about rooftop Sky Bar for cocktails and people watching among Portugal’s hip crowd.

Breakfast included

Cascais, Portugal

Port of Cascais, Portugal

Beach, Cascais

Beautiful Beaches of Cascais

Pena National Palace, Sintra, Portugal

The Magical Pena Palace in Sintra

Day 4

Fly to Madeira

Swap the Portuguese mainland for the laid-back island of Madeira and, after a short flight from Lisbon to Funchal, experience five nights of unabashed luxury in your next base, Belmond Reid’s Palace. Overlooking the Atlantic Ocean and set among tropical gardens, Reid’s Palace is one of Europe’s grande dame hotels.

Follow in the footsteps of more than a century of European royalty and aristocracy and settle yourself into this stylish property, awash with old-school elegance and impeccable service.

Breakfast included

Belmond Reid's Palace

Belmond Reid's Palace, Madeira

Belmond Reid's Palace, Madeira

Pool Area at Belmond Reid's Palace, Madeira

Days 5 – 8

Madeira's landscapes and luxury

During your stay, discover that there’s more to Madeira than meets the eye. We suggest that you spend your days exploring. Enjoy a guided botanical tour of the hotel’s subtropical gardens with an expert horticulturalist. Set out from Reid’s Place to explore Funchal on a guided tour, taking in the sights and smells of the Workers’ Market. Visit the picturesque village of Camara de Lobos, once a favourite haunt of Winston Churchill and climb to the Skywalk Lookout Point for unprecedented panoramic views of the island. Trek into the hills and to walk Madeira’s famous levadas. Take a cable car ride to Monte Palace tropical gardens and pilot a traditional wicker toboggan back down the hill. Ask us about borrowing one of the hotel’s boats so that you can explore the hidden coves of the coast. Back at the hotel, sign up for a dance class with a seasoned professional ahead of the weekly dinner dance.

Take afternoon tea on the black and white marble terrace with the Atlantic laid out below you and spoil yourself with a delicious glass of champagne. In the evening, dress for dinner and mingle with fellow guests in the glitzy bar for perfectly prepared cocktails. Dine at the hotel’s main, Michelin-starred restaurant or, one evening, ask us to arrange an intimate supper for just the two of you on your private terrace or balcony, under indigo skies and with the ocean before you. Satiated, sip a digestif and drink in the views, or carry on into the night with an evening of traditional fado music in Funchal.

Breakfast included

Cliffs, Madeira

Hike to Cliffs of Madeira's Coastline


Explore the Picturesque Villages on the Island of Madeira

Day 9

Depart for home

Finally, we’ll arrange a private transfer from Reid’s Palace to the airport for the return flight from Funchal to London.

Breakfast included

About the itinerary

"Seamlessly blending city meanders with island treks, this indulgent itinerary will leave you head-over-heels with the romance of Portugal. From the historical capital Lisbon, the magical town of Sintra and the sun-soaked island of Madeira, you’ll be treated to only the best of the best – the pinnacle being your stay at Belmond Reid’s Palace, a grande dame hotel that I have hand-picked to ensure that you're treated like royalty. "

Andy Austen

Destination Specialist

Pricing information

Guide price from £2,425 pp incl. flights

Low Season from: £2,425 pp
High Season from: £2,785 pp


  • Complimentary Return Chauffeur transfers to/from airport
  • Complimentary access to UK departure airport VIP lounge
  • Flights from UK to Lisbon to Madeira and return
  • Private arrival and departure transfers
  • 3 nights accommodation at the Tivoli Avenida Liberdade on a B&B basis
  • Private Half day guided tour of Lisbon Downtown - Old town & Belem including private English speaking host, hotel pick-up and drop-off, luxury private car and custard tart tasting
  • Private Full day guided tour of Cascais, Sintra & the most Western Coast of Europe
  • 5 nights accommodation at Reids Palace on a B&B basis
  • Return private airport transfers in Madeira