Lisbon and Madeira Itinerary: 10 Days of Culture & Island Adventure
11 Days
3 Stops
Hybrid tour
From$2,000
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Itinerary inspiration
Experience the perfect mix of culture and nature with this 10-day Lisbon and Madeira itinerary. Begin in Lisbon, Portugal’s vibrant capital, where trams rattle through Alfama’s cobbled streets and Belém’s monuments tell stories of the Age of Discovery. A day trip to Sintra, Cabo da Roca, and Cascais adds fairy-tale palaces, dramatic cliffs, and seaside charm to your stay.More...
Lisbon
Day 1 - 4
The beautiful city of Lisbon lies draped across a string of seven hills on the western Iberian Peninsula and is the westernmost and oldest city in western Europe. Its long and tumultuous history has resulted in an aesthetic characterised by a haphazard combination of old and new; however, the aesthetic chaos of Lisbon only adds to its appeal and its undeniable charm. Bright yellow centenarian trams rattle their way up steep, tree-lined, cobbled streets; ornate ironwork balconies overrun with bougainvillaea sit above elegant outdoor cafes housed in ancient whitewashed, red-roofed stone houses; and a flurry of detailed mosaics decorate the sidewalks. Ancient statues adorn grand squares and hidden gardens. A diverse culinary scene, a plethora of fascinating museums, and numerous castles make it easy to see why Lisbon is one of Europe’s most misunderstood and underrated cities.
Your accommodation
Portugal Boutique City Hotel
Portugal Boutique City Hotel is located in the heart of Lisbon, Portugal, with easy access to attractions such as the slopes of Castelo de São Jorge, Rossio Square and Igreja de São Roque. Accommodation consists of a variety of guest rooms and suites, each equipped with air conditioning, a hairdryer, a minibar, a safe and a flat-screen TV. Guests can enjoy delicious meals at any of the on-site restaurants and refreshing drinks at the hotel bar.
Your activity
Lisbon Hop on Hop Off Classic 24h
The Lisbon Hop-On Hop-Off Classic 24h ticket allows you to explore Lisbon and its surroundings flexibly in one day. With just one ticket, you can hop on and off five different tours as often as you like – from the historic districts of Belém and Alfama to modern Oriente and the charming coastal town of Cascais. Discover the diversity of the region at your own pace.
Main attractions: São Jorge Castle, Alfama, São Vicente Church, Graça viewpoint, Praça do Comércio, the cathedral, the National Pantheon, the flea market, Martim Moniz, Restauradores, El Corte Inglés, Eduardo VII Park.
Porto Moniz
Day 5 - 6
Resting on the rugged northwestern edge of the island of Madeira, Porto Moniz is a picturesque town shaped by sheer basalt cliffs, narrow ravines, and constant Atlantic swells. Originally a 16th-century fishing and farming village, it spread across terraced slopes where vine-growing and subsistence crops once dominated. The town’s most prominent feature is its natural lava pools—sea-filled basins formed by volcanic rock and made accessible with walkways, ladders, and changing facilities. Nearby, the Madeira Aquarium occupies a restored 18th-century fort and contains tanks showcasing a multitude of marine species native to Macaronesian waters. Restaurants along the seafront serve scabbardfish, octopus, and dishes rooted in local fishing traditions. About 15 kilometres inland, Achadas da Cruz sits at 576 metres and connects by cable car to Fajã da Quebrada Nova, a narrow coastal plain used for traditional agriculture, reachable only by the steep descent or a strenuous footpath. Within Porto Moniz itself, Miradouro da Santa offers a panoramic lookout beside a roadside chapel, with views over the lava pools and Atlantic horizon. Although not inside the municipality, the Levada da Ribeira da Janela trail begins to the east, and follows a historic irrigation channel through the UNESCO-listed Laurissilva forest.
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Your accommodation
Aqua Natura Bay
The Aqua Natura Bay is a remarkable hotel with an idyllic seaside setting in the paradisiacal Vila of Porto Moniz, on the North Coast of Madeira Island. With its excellent location, the hotel is the perfect starting point for exploring the stunning Laurissilva Forest. Designed to ensure a comfortable stay, the hotel offers a range of beautifully appointed rooms, each has casing contemporary decor and equipped with modern amenities such as a minibar, Nespresso machine, wireless internet and a private bathroom. Leisure facilities include a wellness centre and an outdoor heated swimming pool with breathtaking views over the Atlantic Ocean and the imposing North Coast.
Funchal
Day 7 - 11
Set within a natural amphitheatre along the south coast of Portugal’s island of Madeira, Funchal is the capital city of the Madeira Archipelago. This picturesque city is perfectly positioned against a breathtaking backdrop of dramatic cliffs, crystal-clear waters and forested mountains. Funchal is renowned for its variety of beautiful flowers, rich heritage, vibrant nightlife and scores of superb al fresco cafes and eateries. Visitors can look forward to a number of exciting activities including dolphin and whale watching tours, surfing magnificent waves, hiking through the lush landscape, and wine tasting at the famed Madeira Cellars. Don’t miss the amazing Gothic and Romanesque architecture of the Se Cathedral, the 15th-century Sao Tiago Fortress, housing Funchal’s Contemporary Art Museum, and the hillside Madeira Botanical Gardens which are decorated with over 2000 plants.
Your accommodation
Quinta Da Penha De Franca
Located in Funchal on the island of Madeira, Quinta Da Penha De Franca is surrounded by magnificent tropical gardens and is an ideal option for leisure travellers looking for a relaxing and convenient accommodation option. The hotel offers a selection of rooms, suites, and villas, all of which feature air-conditioning, flat-screen TVs, and free Wi-Fi access. Certain units also feature kitchenettes. During their stay, guests can enjoy delicious meals and refreshing drinks at the on-site restaurants and bars. The hotel features two swimming pools, one of which is heated. Nearby attractions include Funchal's Museum of Natural History, Madeira Botanical Garden, and the Sacred Art Museum.
Your activity
Swimming with dolphins
Experience an unforgettable dolphin and whale watching experience in Madeira. Accompanied by a dedicated team of experienced marine biologists, you'll begin with an informative introduction explaining the upcoming adventure and sharing insightful details.
During the Atlantic Ocean excursions, you'll have the opportunity to marvel at the rich diversity of dolphins, whales, and even turtles in the waters around Madeira up close. Swimming with dolphins is an unforgettable experience!
This activity always depends on the sea conditions and the dolphin species observed. Snorkeling equipment is provided.
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Tips for your 10-day Lisbon and Madeira trip
The best time to travel to Lisbon and Madeira is during the shoulder seasons of spring and fall. These seasons offer a perfect balance of pleasant weather for exploring cities and outdoor activities, while avoiding the intense heat of summer. Since Madeira is a year-round destination, it is a great choice to visit at any time.
On a mid-range budget, a trip to Portugal starts at around $140 per person per day, excluding flights. For a 10-day trip, a good estimate would be around $1,400 per person. This budget covers a stay in a 4-star hotel and a mid-range rental car for exploring Madeira. A budget-friendly trip starts at approximately $55 per day.
A trip to Lisbon and Madeira is a mix of culture and nature. Highlights include a ride on Lisbon's historic streetcars, visiting the colorful Pena Palace in Sintra, and exploring Madeira's unique volcanic landscapes. For activities, you can take a culinary walk in Lisbon or go wine tasting in Madeira's vineyards.
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