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Lisbon and Madeira Itinerary: 11 Days of Culture & Island Adventure
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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
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.
Portugal Boutique Hotel
With a stay at Portugal Boutique Hotel, you'll be centrally located in Lisbon, just a 3-minute walk from Rossio Square and 8 minutes by foot from Avenida da Liberdade. This hotel is 0.3 mi (0.5 km) from Santa Justa Elevator and 0.3 mi (0.4 km) from Castle of São Jorge.
Enjoy recreation amenities such as an attached winery or take in the view from a rooftop terrace. This hotel also features complimentary wireless internet access and concierge services.
Make yourself at home in one of the 53 guestrooms featuring minibars and LCD televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Bathrooms feature bathtubs, complimentary toiletries, and bidets. Conveniences include safes and desks, and housekeeping is provided daily.
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
Located in Porto Moniz, Aqua Natura Bay is a 5-minute walk from Lava Pools and 8 minutes by foot from Porto Moniz Natural Pools. This spa hotel is 4.9 mi (8 km) from Laje Beach and 6.2 mi (9.9 km) from Seixal Beach.
Pamper yourself with a visit to the spa, which offers massages, body treatments, and facials. If you're looking for recreational opportunities, you'll find a 24-hour health club, an outdoor pool, and an indoor pool. Additional features at this hotel include complimentary wireless internet access, a communal living room, and tour/ticket assistance.
Make yourself at home in one of the 47 individually decorated guestrooms, featuring minibars and plasma televisions. Rooms have private balconies. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have hair dryers and bathrobes.
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.
Hotel Quinta da Penha de França
With a stay at Hotel Quinta da Penha de França in Funchal, you'll be within a 5-minute drive of Funchal Farmers Market and Funchal Marina. This beach hotel is 1.4 mi (2.2 km) from Lido Bathing Complex and 1.4 mi (2.2 km) from Town Square.
Spend the day on the private beach or dip into one of the 2 outdoor pools. This hotel also features complimentary wireless internet access, concierge services, and an arcade/game room.
Make yourself at home in one of the 108 air-conditioned rooms featuring minibars. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms have complimentary toiletries and hair dryers. Conveniences include phones, as well as free tea bags/instant coffee and blackout drapes/curtains.
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.
