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Highlights

  • Enjoy private, guided tours showcasing Lisbon's historic quarters, maritime heritage and iconic landmarks
  • Discover Sintra, Cabo da Roca and Cascais, from fairy-tale palaces to dramatic Atlantic coastlines
  • Stay at the elegant Royal Savoy, overlooking the Atlantic in the heart of Funchal
  • Explore Madeira's spectacular landscapes, including Pico do Areeiro, Santana and the Laurissilva forest
  • A perfect blend of culture, history and island relaxation, seamlessly combining two of Portugal's most compelling destinations

Discover the rich history, culture and landscapes of Portugal on a journey that combines the highlights of Lisbon with the natural beauty of Madeira. Begin in the capital with privately guided tours exploring Lisbon's historic neighbourhoods, the maritime heritage of Belém and the enchanting town of Sintra, before continuing along the coast to Cabo da Roca, Cascais and Estoril. Then fly to Madeira for five nights in Funchal, where you'll uncover the island's diverse scenery, from dramatic mountain peaks and ancient laurel forests to traditional villages and rugged Atlantic coastlines. Complemented by time to explore Funchal and relax at the elegant Royal Savoy, this itinerary offers an ideal balance of culture, history, sightseeing and island relaxation.


Day 1

Welcome to Lisbon

On arrival in Lisbon we will arrange a private transfer to your hotel, one of Lisbon’s historic landmark properties.

Step outside this small and luxurious hotel to find yourself a short stroll will bring you to many of Lisbon’s main sights, along with typical Portuguese neighbourhoods for you to explore.

Breakfast included

Lisbon, Portugal

Lisbon, Portugal


Day 2

Lisbon's historic old town & Belém

Accompanied by a private driver-guide, discover the many facets of Lisbon on a full-day tour encompassing both its historic landmarks and more contemporary districts. Begin in Belém, the city's celebrated Age of Discovery quarter, where you'll visit iconic monuments including Belém Tower, the Monument to the Discoveries and Jerónimos Monastery, all closely linked to Portugal's maritime heritage. You'll also stop by the famous Pastéis de Belém bakery, founded in 1837, for a taste of Portugal's famed custard tarts. Continue into the heart of the city, taking in Rossio Square and Praça do Comércio before exploring the atmospheric streets of Alfama, home to Lisbon Cathedral and views towards St George's Castle. Your tour also includes the characterful neighbourhoods of Chiado and Bairro Alto, along with panoramic viewpoints such as Portas do Sol and Santa Luzia. Conclude the day at Parque das Nações, Lisbon's modern waterfront district. 

On your return to the hotel, perhaps 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

Sintra, Cascais & Cabo da Roca

Today, you'll explore some of the highlights of Portugal's coastline on a full-day tour taking in Sintra, Cabo da Roca, Cascais and Estoril. Begin in the UNESCO-listed town of Sintra, where you'll visit the colourful Pena Palace, the former summer residence of the Portuguese royal family, dramatically perched atop the Sintra mountains. Afterwards, enjoy free time to wander the town's historic streets, lined with traditional shops and overlooked by the distinctive National Palace of Sintra. Following lunch at leisure, continue to Cabo da Roca, the westernmost point of mainland Europe, before travelling along the Atlantic coast past Guincho Beach. The day concludes in the elegant seaside town of Cascais, once a traditional fishing village and now one of Portugal's most popular resorts, before returning via neighbouring Estoril, famous for its connections to the Second World War and Ian Fleming's inspiration for the James Bond novels.

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

After breakfast, transfer to the airport for your short flight from Lisbon to Madeira. On arrival in Funchal, continue by private transfer to the elegant Royal Savoy, your home for the next five nights. With a privileged seafront location overlooking the Atlantic Ocean, this refined hotel combines spacious accommodation, excellent facilities and easy access to the heart of Madeira's capital. Spend the rest of the day settling into your surroundings and taking advantage of the hotel's oceanfront setting, providing the perfect base from which to explore the island over the coming days.

Stay: Royal Savoy, Funchal

Breakfast included

Funchal, Madeira

Funchal, Madeira

Royal Savoy, Funchal, Madeira

Royal Savoy, Funchal, Madeira


Days 5 – 8

Madeira's landscapes, culture & cuisine

During your time in Madeira, you'll have the opportunity to discover the island's diverse landscapes, rich culture and unique natural heritage. Explore Funchal at your own pace, perhaps taking in the colourful Workers' Market, wandering the historic centre or riding the cable car to Monte, where tropical gardens and the island's famous wicker toboggans await. Those looking to experience Madeira's renowned scenery may wish to venture into the mountains and walk alongside the island's historic levadas, which wind through forests, valleys and dramatic coastal viewpoints.

A full-day guided excursion showcases some of Madeira's most celebrated sights. Travel via Camacha to Pico do Areeiro, the island's third-highest peak, where panoramic views stretch across the central mountain range. Continue through the lush landscapes of Ribeiro Frio, home to endemic Laurissilva forest, before visiting Santana and its distinctive thatched houses. The tour also includes Porto da Cruz, known for its sugar cane rum production, and the dramatic headlands of Ponta de São Lourenço, whose rugged cliffs provide some of the island's most impressive coastal scenery.

Back at the Royal Savoy, make the most of the hotel's seafront setting and excellent facilities, whether relaxing by the pools, enjoying the spa or taking in views across the Atlantic. In the evenings, Funchal's restaurants, bars and traditional music venues offer plenty of opportunities to experience the island's celebrated hospitality and cuisine.

Stay: Royal Savoy, Funchal

Breakfast included

Cliffs, Madeira

Hike to Cliffs of Madeira's Coastline

Madeira

Explore the Picturesque Villages on the Island of Madeira


Day 9

Farewell Madeira

Finally, we’ll arrange a private transfer to the airport where your journey concludes.

Breakfast included


About the itinerary

"Combining the cultural treasures of Lisbon with the dramatic scenery of Madeira, this indulgent itinerary will leave you head-over-heels with the romance of Portugal. From exploring the historic streets of the capital and the fairytale palaces of Sintra to discovering Madeira's mountain peaks, coastal landscapes and vibrant island traditions, every experience has been chosen to provide an authentic insight into the destination. The highlight is a five-night stay at the elegant Royal Savoy in Funchal. "

Andy Austen

Destination Specialist

Pricing information

Guide price from £2,480 pp excl. flights

Price includes £29 taxes & charges to be paid locally
  • This price is converted to show you the approximate cost in GBP. You'll pay in the local currency. The exchange rate may change before you pay.
  • Your card issuer may charge you a foreign transaction fee.

Nov 2025 to Mar 2026 from: £2,480 pp
Apr - Oct 2026 from: £2,845 pp

Validity: February to October

Includes

  • Private transfer from Lisbon Airport to Lisbon Hotel
  • 3 nights Lisbon accommodation on a BB basis
  • Private guided tour of Historical Lisbon Old town and Belem
  • Private guided tour of Cascais and Sintra
  • Private transfer from Lisbon Hotel to Lisbon Airport
  • One way flight from Lisbon to Funchal, Madeira
  • Private transfer from Funchal Airport to Hotel
  • 5 nights Funchal accommodation on a BB basis
  • Private full day East Island tour (Santana)
  • Private transfer from Madeira Hotel to Madeira Airport

Why are international flights excluded?

We believe that luxury and flexibility go hand in hand. That’s why our prices exclude international flights. Flight availability and fares vary daily, so when you’re ready to book, we’ll provide a quote based on your chosen airline, dates and departure airport. Or, if you prefer, you’re welcome to book your own flights. Either way, every detail is tailored to suit you.

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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