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Portugal

Best of Lisbon & The Islands: Azores, Madeira, Lisbon, Sintra & Cascais

Ponta Delgada → Lisbon 11 days Up to 8

About this trip

This 11-day trip takes you across three of Portugal's most distinct landscapes: the volcanic calm of the Azores, the green cliffs of Madeira, and the history and energy of Lisbon and its coast.

You start on São Miguel, known for its quiet scenery and local produce, before flying to Madeira for guided walks and a taste of poncha across the island. From there it's on to Lisbon, where you get to know the city's neighbourhoods and take in a Fado show.

The trip winds down in Sintra and Cascais, two smaller towns near the capital worth the slower pace after the islands.

What you'll do

  • Explore the landscapes of São Miguel in the Azores
  • Walk guided trails across Madeira and try poncha
  • Visit Lisbon's main neighbourhoods
  • Watch a live Fado performance
  • See the palaces and hills of Sintra
  • Spend time in the coastal town of Cascais
Good to know
  • Covers three separate regions by air, so you'll be packing and moving between stops
  • Partially guided, with both organised visits and free time
  • Requires a minimum of two travellers to run
Tour dupe
Same trip, less money
£2,600 less all-in
Best of the Azores: 7 days in São Miguel
4.6from £6247 days
The trade-off: 4 fewer nights, and a different operator.
See the dupe
How it compares

The same-vibe trips, side by side — price, value per day, and how each is moving. Only we can lay two operators' trips out honestly.

Sorted by fit — never by who paid. Price moves and fill fill in from our own tracking as it builds.

Getting there

Ponta Delgada
One-way · arrive 19 Jul 26

Opens Trip.com, pre-filled — one-way so you can book your return whenever. Prices & booking shown there.

Where to stay

A night before your tour in Ponta Delgada · 19 Jul20 Jul

Booked on their own sites, separate from your tour. We may earn a commission — it never changes your price.

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Best of Lisbon & The Islands: Azores, Madeira, Lisbon, Sintra & Cascais — Portugal · 18-35.travel