PRIVATE TOUR: Embark on a 9-day tour of Portugal from Lisbon to Madeira. Begin in the capital with a fado show and a guided walk through Alfama and Bairro Alto, then continue to Sintra’s fairytale palaces and the coastal elegance of Cascais. Travel onward to Evora, a UNESCO-listed gem filled with history and character, before flying to Madeira. Marvel at dramatic cliffs, volcanic pools and lush valleys as the island’s beauty stretches from Cabo Girao to Santana. Conclude in Funchal, embraced by the calm of the Atlantic.
Trip Highlights
Included
Not Included
Itinerary
Arrival in Lisbon
Once you have arrived in Lisbon, a private transfer will take you to your hotel for check-in. You may have some time to explore the city, grab a meal, or relax.
This evening, you will experience the soul of Portugal at a traditional Fado performance, where heartfelt melodies capture the spirit of Lisbon’s historic neighborhoods.
During the show, you will enjoy a welcome dinner featuring some of the most beloved dishes of Portuguese cuisine, a perfect introduction to the country’s rich culinary heritage.
Overnight: Lisbon | Dinner
Discovering Lisbon
Today, a transfer will collect you from your hotel for a half-day city tour with a local guide, who will introduce you to the main sights of Portugal’s capital. The tour begins along Avenida da Liberdade, once a grand promenade for the nobility and royal family.
You will then visit Parque Eduardo VII, the city’s largest central park, named in honor of King Edward VII of England after his visit in 1903 to reaffirm the long-standing alliance between the two nations.
Next, you will explore Lisbon’s most characterful neighborhoods, including Alfama and Bairro Alto, where age-old traditions and cultural influences blend to create a lively atmosphere. The tour concludes at Praca do Comércio, one of Europe’s largest squares, offering sweeping views over the Tagus River and the vibrant city beyond.
In the afternoon, you will have free time to relax or explore more of Lisbon at your own pace.
Overnight: Lisbon | Breakfast
Exploring Sintra, Cascais & Estoril
Lisbon - Sintra - Cascais - Estoril - Lisbon. This morning, you will set off on a private transfer to discover the enchanting towns of Sintra and Cascais. Just 30 kilometers from Lisbon, Sintra feels as though it has been lifted straight from a fairy tale. Its mild climate, lush vegetation and mystical atmosphere make it one of Portugal’s most romantic and inspiring destinations.
You will have the opportunity to visit one of Sintra’s most iconic landmarks.. You may explore the National Palace of Sintra, the colorful Pena Palace, the elegant Palace of Monserrate or the intriguing Quinta da Regaleira, each offering a distinctive glimpse into the town’s rich history and charm.
The journey continues to Cabo da Roca, the westernmost point of mainland Europe. Here, you can take in breathtaking views of the Atlantic Ocean before travelling on to Cascais, a delightful fishing village dating back to the 12th century that has grown into an elegant seaside retreat while preserving its historic character.
Your return to Lisbon will follow the scenic coastal road through Estoril, known for its beautiful beaches and graceful seaside architecture.
Please note: that these monuments close on 24 and 25 December, 1 January and Easter Sunday.
Overnight: Lisbon | Breakfast
Évora and the Flavours of Alentejo
Lisbon - Evora - Lisbon. You will travel to the historic city of Évora for a full-day visit. Recognised as a UNESCO World Heritage Site since 1986, Évora is often referred to as both the White City and the Museum City. This charming Alentejo town captivates visitors with its ornate churches, ancient monuments, lively squares, whitewashed houses, and narrow medieval streets.
After time for lunch, you will visit a local wine estate to learn about the production process before enjoying a tasting of regional wines, a fitting end to your day in the heart of Alentejo.
Overnight: Lisbon | Breakfast
Flight to Madeira
Lisbon – Funchal. After breakfast, check out of your hotel in Lisbon and transfer to the airport for your flight to the beautiful island of Madeira. On arrival at Funchal airport, you’ll be met and taken to your hotel to settle in.
The rest of the day is yours to enjoy as you wish – you may prefer to relax after your journey or head out to explore the island’s charming streets and coastal scenery at your own pace.
Overnight: Funchal | Breakfast
Western Wonders of Madeira
Funchal – Ribeira Brava – Sao Vicente – Porto Moniz – Funchal. Today, you will explore the beautiful western region of the island. You will begin with a visit to the traditional fishing village of Camara de Lobos, known for its colorful boats and lively harbor. Continue on to Cabo Girao, the highest sea cliff in Europe, where you can enjoy spectacular views of the coastline and terraced hillsides.
Next, travel to Ribeira Brava before heading inland through the lush valleys of Serra D’Água. At the top, the viewpoint of Encumeada offers breathtaking panoramas of both the north and south coasts.
You will then continue to Sao Vicente, one of the largest villages on Madeira’s northern shore, before arriving in the charming coastal town of Porto Moniz. Here, you’ll have around an hour for lunch (not included) and time to admire the famous volcanic rock pools.
In the afternoon, cross the island’s highest plateau, Paul da Serra, taking in its vast, open landscapes before returning to your hotel for the evening.
Overnight: Funchal | Breakfast
Eastern Charms of Madeira
Funchal – Santana – Machico – Funchal. This morning, you will first visit Terreiro da Luta before continuing towards Pico do Areeiro. Standing 1,818 meters above sea level, it is the island’s third-highest peak and offers breathtaking views across the surrounding mountains and valleys.
From here, descend through the forest towards the coast to see one of Madeira’s last remaining traditional thatched houses. Passing through picturesque villages and along scenic coastal roads, you will reach the island’s easternmost point, where a single viewpoint reveals both the rugged north and the sunlit south coast.
On the northern slope, stop at Ribeiro Frio, a popular spot for levada walks and home to clear trout ponds surrounded by the ancient Laurissilva forest, a rare remnant of Madeira’s original landscape. You will have time for lunch in Santana, a charming village famous for its colorful triangular houses.
In the afternoon, continue to Ponta de São Lourenço, where dramatic cliffs and striking rock formations meet the sea. The final stop of the day is Machico, a lovely viewpoint overlooking the bay and its golden sandy beach, before returning to your hotel for the evening.
Overnight: Funchal | Breakfast
Day at Leisure in Funchal
Today is yours to enjoy as you wish. You might choose to relax at your hotel, take a gentle stroll through the town, or explore some of Funchal’s nearby attractions at your own pace.
The city offers plenty of shops, cafés, and scenic spots where you can simply unwind and take in the surroundings. However you decide to spend the day, it’s a wonderful opportunity to experience Madeira in your own way.
Overnight: Funchal | Breakfast
Farewell to Madeira
Funchal – Lisbon. After your final breakfast, check out of the hotel and transfer to the airport for your flight back to Lisbon. Once you have arrived, this will mark the end of the tour. Safe travels!
Breakfast
Prices & Dates
Departure dates are guaranteed with 2 travellers. 'Twin/Double' prices are per person when there are 2 people on the same booking sharing a room. 'Single' prices are applicable to solo travellers wanting the privacy of their own room, or if your booking party cannot reach the minimum of 2 persons in a room. Single Rooms can also be booked by any other person wanting the comfort and privacy of their own room.


















