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Lisbon and Madeira Itinerary: 11 Days of Culture & Island Adventure
11 Days
3 Stops
Hybrid tour
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From$3,600
per personAccommodations
Transportation
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Meals
Tourlane App
Travel plan
Flights
Flexible cancellation policies
Trip curated by Roman Karin
ExpertThe EN101 along Madeira's northern coast from Porto Moniz to Santana is the road that justifies the rental car, and I always flag it first when clients are planning this itinerary. It hugs the cliff through tunnels and single-track stretches above a sea that looks nothing like the south coast, and stopping in São Vicente for lunch places you at the exact point where the island's character shifts most dramatically. In Funchal, the cable car and the Monte botanical garden pair naturally into a single morning that gives the ascent a purpose beyond the view. Book the dolphin watching for first thing before ocean chop builds; the corridor between Funchal and Calheta is one of the most reliably productive in the Atlantic, and a flat sea changes the encounter entirely.
The EN101 along Madeira's northern coast from Porto Moniz to Santana is the road that justifies the rental car, and I always flag it first when clients are planning this itinerary. It hugs the cliff through tunnels and single-track stretches above a sea that looks nothing like the south coast, and stopping in São Vicente for lunch places you at the exact point where the island's character shifts most dramatically. In Funchal, the cable car and the Monte botanical garden pair naturally into a single morning that gives the ascent a purpose beyond the view. Book the dolphin watching for first thing before ocean chop builds; the corridor between Funchal and Calheta is one of the most reliably productive in the Atlantic, and a flat sea changes the encounter entirely.
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Lisbon
Day 1 - 4
Lisbon, Portugal's hilly capital on the Tagus estuary, where the river meets the Atlantic Ocean, combines historic neighbourhoods, grand squares and waterfront districts with a lively contemporary atmosphere. A vibrant European capital, it is known for its distinctive yellow trams, tiled facades, winding streets and viewpoints overlooking the Tagus River. Travellers can explore the UNESCO-listed Jerónimos Monastery and Belém Tower, wander through the atmospheric lanes of Alfama, or ride Tram 28 through the city's historic quarters. Praça do Comércio and Rossio serve as lively gathering places, while the waterfront offers opportunities for dining and leisurely strolls. Lisbon also makes an excellent base for exploring nearby coastal scenery and cultural attractions, including Sintra. With its mild climate, rich maritime heritage and relaxed café culture, Lisbon offers a varied city break with plenty of character.
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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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.
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.
From$3,600
per personAccommodations
Transportation
24/7 support
Activities
Meals
Tourlane App
Travel plan
Flights
Flexible cancellation policies
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Plan with professionals who are explorers themselves.
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11+ Bookings managed
Everything is bundled in one place and perfectly planned.
6+ Transfers coordinated
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Excellent
Why plan with an expert?
200+
Plan with professionals who are explorers themselves.
26+ hours of time saved
Our experts plan and book for you.
11+ Bookings managed
Everything is bundled in one place and perfectly planned.
6+ Transfers coordinated
For optimal transport and comfort.
Excellent
Itinerary inspiration
Four nights in Lisbon and then the flight to Madeira for a self-drive through the island's northern coast before settling into Funchal — the combination works because the contrast between a historic European capital and a subtropical volcanic island sharpens both halves of the trip. Lisbon's trams and tiled facades read differently after two days on a coast shaped by lava fields and Atlantic swells.
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Porto Moniz on the northern tip of the island is what most visitors to Madeira miss. The natural volcanic pools carved into the rock at the sea's edge — cold, clear, and framed by basalt — are unlike anything on the southern coast, and the road from Funchal along the northern shore to reach them is as dramatic as anything the island offers behind the wheel.
Day 1–4: Lisbon
Hotel: Portugal Boutique City Hotel
Four nights gives Lisbon genuine depth. The hop-on hop-off city exploration, the Belém monuments, and the Sintra, Cabo da Roca, and Cascais day trip each reveal a different dimension of the city and its surroundings. The Sintra palaces in the morning before the coaches arrive from Lisbon are the most rewarding version of that excursion — particularly the Palácio da Pena on its cloud-level promontory above the town.
Day 5–6: Porto Moniz
Hotel: Aqua Natura Bay
The rental car is collected in Funchal and the drive north along the ER101 coastal road is the introduction to Madeira's scale. The cliffs, the deep gorges, and the ocean below change character with every kilometer. Porto Moniz on the island's northwestern tip gives you two nights away from the tourist circuit and immediate access to the volcanic pools at dawn, before anyone else arrives.
Day 7–11: Funchal
Hotel: Quinta Da Penha De Franca
Four nights with the cable car and botanical gardens, the dolphin watching excursion, the food and wine tour, and the scenic island drives across the remaining days. The Quinta Da Penha De Franca sits above the bay with the Atlantic below and the mountains rising behind it — a place that gives Funchal a different quality from the main hotel zone. The food and wine tour is the activity I'd prioritize earliest: the Madeira wine tradition, the espada fish, the bolo do caco bread with garlic butter — all of it is more interesting with someone who can explain where it comes from.
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Tips for your 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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