We will be open at 9:00 am. Call 020 7590 0610

Our favourite Portugal routes through Lisbon, Madeira & the Azores

Article content

7 June 2018 by Claire Benktander

Every year on 10th June, Portugal celebrates its annual national holiday, commemorating the death of national literary icon Luis de Camoes on 10th June 1580 and observed throughout the world by Portuguese citizens and emigrants. In honour of the aptly-named Portugal Day, we’ve picked our favourite routes and places to stay in Lisbon and its surrounds, as well as the rugged delights of Madeira and the Azores, to immerse yourself in the famed pousadas, cobblestone villages and world-class gastronomy of this Iberian gem.

Capital city Lisbon is a natural starting point for many Portugal holidays, but it's more than just a stopover – Lisbon's easy combination of ancient charm and metropolitan allure make it an unmissable stop. From vibrant Bairro Alto buzzing with bars and street-side restaurants to the winding streets of Lisbon’s oldest district Alfama, the pastel buildings, ochre-red roofs and coastal crescents are charm embodied. The city centre provides boundless delights, from the engineering marvel Elevador de Santa Justa lift, linking the upper and lower levels of the city, to the 1930s-restored Route 28 tram, attention-grabbing as it winds through cobbled streets. We particularly like the Tivoli Avenida Liberdade Lisboa hotel, situated among the palm trees of Avenida Liberdade and Chiado’s exclusive boutiques, with semi-tropical gardens and a swimming pool.


Head just west and you’ll find Sintra, a fairytale town dwarfed by its eponymous mountain range, surrounded by forested plains and dotted with rainbow palaces and villas. The highlight is undoubtedly the Moorish-style castle and the Romanesque national palace, glittering over the ocean below and offering sweeping valley vistas. The Tivoli Palacio de Seteais is an unbeatable choice for a stay in Sintra, charmingly situated at the foothills of the mountain range with spectacular countryside views. Frescoes and chic furnishings add to the delights, as well as massages in the hotel’s gardens and a stunning bar terrace. For something more contemporary, we also recommend Penha Longa Resort, a wonderful mix of medieval architecture and ultra-modern features. Enjoy a two-Michelin star restaurant looking over 300 acres of lush woodland, as well as indoor and outdoor pools, a romantic monastery, spa and the enchanting Estoril coast in the distance.

Pena Palace, Sintra

If it’s coastal charm you’re after, neighbouring Estoril and Cascais offer it by the bucketload. The latter is all luxurious beachside villas, Revivalist palaces, cobbled squares, designer boutiques and al fresco fresh fish restaurants, edged by a trio of golden crescents, craggy sea caves and clinking yachts in the marina. For those preferring a more laidback trip, Estoril’s spired villas, palm-edged seafronts and beautiful beaches abide, particularly with a stay at Hotel Palacio Estoril, one of our favourite Estoril hotels. Situated right on the shore, it’s just a 20-minute walk to the city centre but idyllic beaches also lie just moments away. Enjoy the hotel’s private golf course, then come back to elegant décor, landscaped gardens and a terrace restaurant with stunning ocean views.


Away from the mainland, Porto’s good-looking charms, Madeira’s rugged hills or the dramatic landscapes of the Azores are easily reached from Lisbon via boat or flight. Porto’s historic gems are boundless, from the baroque and gold gilded décor in the São Francisco Church to hidden gems like the religious mosaics in the Sao Bento train station. Pastel houses frame imposing bridges and charming ports, and the riverside region is all winding cobbled laneways, the quayside ideal for relaxing with a glass of the famous local port.

Douro River, Porto

Further afield, the subtropical archipelago of Madeira, all volcanic landscapes and soaring cliffs, is just a short flight from Lisbon, making it an ideal combination trip. Stroll along waterways that criss-cross the verdant scenery, hike mountain canyons and cosy forest trails in Laurissilva, and relax or go scuba diving on the plethora of pebbly beaches. Madeira is also home to one of the world's most renowned hotels, Reid's Palace, whose reputation for excellence goes back over a century. Set amid ten acres of subtropical gardens on clifftops that overlook the Atlantic Ocean, it’s true old world charm at its best. Each room is elegantly draped with florals and dark wood, with patios over the ocean alongside poolside dining, tennis courts, dolphin watching and even helicopter flights.

Reid's Palace, Madeira

Head north and you’ll find the Azores, isolated in the middle of the Southern Atlantic. The sub-tropical climate is home to nine individual islands, each with their own unique atmosphere. From the dramatic volcanoes of Pico Island to the beaches and remote coves of Santa Maria, the ‘Hawaii of the Atlantic’ is perfectly explored with our Azores Discovery Tour, an easy flight away from Lisbon. You’ll explore volcanic pools and smoking calderas, walk along spectacular cliff-framed coastlines and discover pretty villages seemingly untouched by time on the islands of São Miguel, Terceira and São Jorge, alongside taking in wonderful gastronomy and wine tours.

Sao Miguel, Azores

The combination of pousadas – a network of state-owned hotels in Portugal synonymous with the history, culture and traditions of their particular region – and the country’s endless allure is an exceptional way to experience Portugal and its past. There’s a stunning range of historic pousadas to be explored, and with our Green Pousadas of Portugal itinerary you’ll explore national parks and the historic village of Braga alongside stays in hilltop pousadas in medieval towns and pousadas perched among rivers and valleys. Or, our Heart of Portugal itinerary takes in Lisbon and the attractive Alentejo region, staying in luxurious small pousadas stunningly set in culturally significant old buildings, palaces, castles, convents and forts, all steeped in a tangible sense of history.

Pousada de Lisboa, Lisbon

Related offers

Lisbon Belem Tower

Lisbon & Porto in Style

8-day tailor-made self-drive from £1,485 pp incl. flights

Link Portugal’s pair of city greats with a scenic road trip, affording you the chance to explore the Douro Valley’s vineyard terraces and Sintra’s storybook beauty. And, exploring the cultural delights of Lisbon and Porto, you’ll stay in two of the country’s finest hotels.

Vila Vicçsa Ducal Palace in Alentejo, Portugal

Pousadas of Portugal: The Heart of Portugal

8-day tailor-made self-drive from £1,000 pp

Explore the history and beauty of Portugal's Alentejo region with stays in characterful pousadas, heritage hotels converted from palaces, castles, convents and forts.

Pena National Palace, Sintra

Lisbon, Porto & Madeira

11-day tailor-made holiday from £0 pp incl. flights

Let private tours, first class rail travel and stays in three luxury hotels show you the best of Portugal. Alongside Porto and Lisbon’s heritage, you’ll also take in the Douro Valley’s wines, Sintra’s regal-rural beauty and Madeira’s endless sun.

Madeira, Portugal

Highlights of Madeira

8-day tailor-made self-drive from £1,470 pp incl. flights

Famed for its natural beauty, mild climate and fabulous fortified wine, Madeira is the perfect year-round destination. Explore the island's myriad highlights on this tailor-made road trip.

Ponta Delgada, Azores, Portugal

Azores Three Island Discovery Tour

8-day tailor-made holiday from £2,935 pp incl. flights

Let included, expert-led tours introduce you to the history, culture, landscapes and food of the Azores – a spectacular volcanic-island paradise in the heart of the Atlantic.

Pousada de Geres, Sao Bento

Pousadas of Portugal: Green Portugal & Porto

8-day tailor-made self-drive from £1,725 pp incl. flights

Discover Portugal's beautiful lush interior and National Parks with this self-drive between some of the finest pousadas – a series of state-owned, characterful hotels that were once monasteries, fortresses, castles and other evocative buildings.

Old Town, Porto, Portugal

Historic Porto and Madeira

8-day tailor-made holiday from £1,250 pp incl. flights

Famous for its friendly people, wonderful local flora, and year-round mild climate, Madeira must be one of the most beautiful islands in Europe. It makes a perfect pairing with Portugal's second city, Porto. Overlooking the mouth of the Douro River, UNESCO-listed Porto has a rich and varied history.

Why book with Wexas Travel?

At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0610 to discuss how we can tailor your holiday.

Learn why Wexas is the leader in creating luxury holidays. What is tailor-made travel?

Expert advice & support

Visit us in our London office

Let our travel specialists curate the perfect holiday:

  • Inspirational ideas based on experience
  • Established for over 50 years
  • Tailor a holiday to your precise requirements
  • Personalised quotes and documentation

Every step of the way

Every step of the way

Our services are with you from start to finish:

  • Dedicated personal consultants
  • Free airport lounges on qualifying bookings
  • Care and guidance pre, post and during holiday
  • Full financial security: ABTA & ATOL protected