IDEAL LENGTH 10 nights
Price From $6,400 pp
When to Go Apr, May, Jun, Jul, Aug, Sep, Oct

Portugal’s Islands & Icons: Lisbon & the Azores

Discover a side of Portugal where ancient cities meet volcanic wonders. From the cobbled elegance of Lisbon to the lush, elemental beauty of São Miguel in the Azores, this itinerary is designed for those seeking culture, nature, and a sense of place.

This is a suggested itinerary – we will tailormake your route and recommend hotels based on your individual preferences, whether you're travelling as a couple or with your family or friends.

Day 1
1 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 1
Arrival in Lisbon

Upon arrival, you’ll be privately transferred to the elegant Palácio Ludovice, your home for the next four nights. A former royal architect’s residence, it now offers a refined stay in the heart of Lisbon’s Chiado and Bairro Alto districts.

Day 2
2 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 2
The Soul of the City

Today’s guided tour reveals the layers of Lisbon – from its Roman and Moorish foundations to its Golden Age grandeur. Highlights include Alfama, Baixa, and the Belém area. The afternoon culminates in a private workshop at the Fábrica de Sant’Anna, where you’ll hand-paint your own Azulejo tile.

Optional dinner at Alma, a Michelin-starred restaurant just moments from your hotel.

Day 3
3 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 3
Sintra, Cascais & a Sunset Sail

Venture to fairytale Sintra for a private visit to Pena Palace, then stroll the historic centre. After a picnic lunch in the gardens of Seteais, continue to the stylish coastal town of Cascais. End the day with a private sunset sail along the Tagus River, admiring Lisbon’s skyline from the water.

Day 4
4 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 4
Trams, Tiles & Fado

Enjoy a curated tram tour through Lisbon’s most charismatic quarters – Alfama, Chiado, and the downtown core – before a Real Fado concert in the elegant Príncipe Real district. The evening’s mood continues with an optional reservation at Belcanto, a temple of modern Portuguese cuisine.

Day 5
5 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 5
To the Azores

Fly to São Miguel in the Azores, where volcanic peaks and crater lakes define the island’s dramatic topography. You’ll check into Octant Ponta Delgada, a well placed base with sweeping sea views and a rooftop pool.

Day 6
6 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 6
Volcanic Valleys & Hidden Lagoons

Explore the island’s western side by 4x4, from the twin lakes of Sete Cidades to the steaming hot springs of Caldeira Velha. Pause for lunch in a local town before an afternoon at Lagoa do Fogo, one of the island’s most breathtaking crater lakes.

Day 7
7 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 7
Whales & Dolphins

This morning, head out on a semi-rigid boat for a private whale and dolphin watching experience. These waters are home to a diverse array of marine life, from playful pods of dolphins to migrating giants like the blue whale.

Day 8
8 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 8
Leisure in São Miguel

Enjoy the island at your own pace. Suggested activities include hiking scenic trails, visiting the Gorreana Tea Plantation, or canyoning through lush waterfalls. Alternatively, relax at your hotel’s rooftop bar and savour Azorean tapas.

Day 9
9 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 9
Furnas: Geothermal Wonders

Canoe across Furnas Lagoon and witness traditional volcanic cooking – the iconic Cozido slow-cooked in underground heat. After lunch, explore Terra Nostra Garden, one of Europe’s most impressive botanical parks, and enjoy a soak in its warm, iron-rich pool.

Day 10
10 Boca do Inferno Viewpoint on São Miguel Island in the Azores, Portugal

Day 10
Departure

You’ll be privately transferred to Ponta Delgada Airport for your return flight home, bringing with you memories of volcanic vistas, soulful cities, and truly unforgettable experiences.

Belinda Profile Photo
our destination expert

Meet Belinda

or
itinerary highlights
  • Explore Lisbon’s historic quarters aboard a restored 19th-century tram
  • Visit the Pena Palace in Sintra and enjoy a private sunset sail back to Lisbon
  • Experience a hands-on tile-painting workshop at a heritage factory
  • Whale watch and 4x4 through volcanic landscapes in the Azores
  • Canoe across Furnas Lagoon and bathe in iron-rich thermal springs
Looking for something else?

Get in touch with our Lightfoot Travel experts and they will create a bespoke itinerary designed to your exact needs and budget.

Why Book With Lightfoot Travel

Lightfoot Travel is a fully licensed global tour operator with a 24/7 support line for our guests, giving you peace of mind on your holiday . We have three core values that underpin our commitment to creating meaningful holidays for our guests.

Choose Lightfoot Travel
Authentic Personal Expert
Book Now
Enquire Now
+1 917 4709 804