Madeira Island Portugal Cruise from Funchal to Lisbon — 15 Days

Funchal, Portugal

Funchal sits in a broad, sunlit amphitheatre above Madeira’s deep Atlantic harbour. Its compact centre rewards exploration, from the Old Town’s painted doors to the cathedral’s carved cedar ceiling. Ride the cable car uphill to Monte for sweeping views, then descend through gardens or by traditional wicker toboggan. Madeira’s wines and market produce offer a taste of the island before your ship sails.

At Sea (At Sea)

Santa Maria Island Azores, Portugal

Santa Maria is the Azores’ southernmost island. Its warmer, drier climate sets it apart from the archipelago’s greener, cloud-touched islands. Explore Vila do Porto, the Azores’ oldest settlement, then follow lanes past vineyards and whitewashed houses. At Praia Formosa, pale sand and Atlantic surf invite an unhurried pause. Inland, Barreiro da Faneca’s red clay hills offer a striking change of scene.

Ponta Delgada, Portugal

Ponta Delgada is the Azores’ Atlantic gateway, set on São Miguel, the archipelago’s largest island. Roads from the city lead to crater lakes, steaming fumaroles and the green caldera of Sete Cidades. In town, tiled churches and handsome squares reward an unhurried walk, while cafés serve local cheese and pineapple. Choose a scenic island drive, or explore the historic centre before returning to the waterfront.

Sao Jorge Island Azores, Portugal

São Jorge is a long, green volcanic island in the central Azores, known for dramatic cliffs and coastal fajãs. From Velas, its principal port, roads climb toward viewpoints, pastures and villages above the Atlantic. Fajãs—small coastal platforms formed by lava or landslides—reward walkers with quiet lanes, lagoons and sea views. Sample the island’s celebrated cheese, then choose a trail or an unhurried drive through this landscape of striking contrasts.

Corvo Island Azores (Scenic Stop)

Flores Island Azores, Portugal

Flores Island, Portugal’s westernmost Azorean island, rewards visitors with volcanic cliffs, crater lakes and waterfalls. At Fajã Grande, cascades descend the green escarpment toward the Atlantic, while Monchique Islet marks Europe’s western edge. Inland, Lagoa Negra and Lagoa Comprida fill volcanic calderas, reached by roads that reveal the island’s changing landscapes. Come ashore for uncrowded trails, intimate villages and a side of Portugal far removed from the mainland.

Pico Island Azores, Portugal

Pico is the Azores at its most elemental: black lava, Atlantic light and a volcanic peak that commands the island. Mount Pico reaches 2,351 metres, Portugal’s highest summit, and rewards fit walkers with a demanding ascent. Along the coast, a UNESCO-listed vineyard landscape shelters vines behind basalt walls against wind and salt. At Lajes do Pico, a museum recalls the island’s whaling past; finish with a glass of local Verdelho.

Horta, Portugal

Horta sits on Faial, one of Portugal’s Azores, with Pico’s volcanic peak rising across the channel. Its marina is a landmark for Atlantic sailors, whose painted messages cover the breakwater. On shore, Peter Café Sport has welcomed generations of visiting crews. The nearby Scrimshaw Museum displays carved whale teeth and bones. Beyond town, drive to Capelinhos, where a 1957–58 eruption reshaped the coast, or walk the rim of Faial’s vast Caldeira.

Graciosa Island Azores, Portugal

Graciosa is a small Azorean island of volcanic landforms, vineyards and quiet rural villages. Santa Cruz pairs whitewashed houses with red-domed windmills in a landscape recognized as a UNESCO Biosphere Reserve. Descend into Furna do Enxofre, a volcanic cavern with an underground lake and a natural fumarole. Along the coast, Carapacho’s thermal waters invite a restorative pause; local cheese and Verdelho reward the table. Here, the pleasures are open views and unhurried discovery.

Angra do Heroismo, Portugal

Angra do Heroísmo is the Azores’ most compelling historic port, set on Terceira’s south coast. Its sheltered bay once served ships crossing the Atlantic, and the streets still reflect that maritime wealth. UNESCO-listed since 1983, the centre rewards an unhurried walk among pastel façades, churches and Praça Velha. Climb toward Monte Brasil for wide harbour views, then explore the vast 16th-century São João Baptista fortress.

At Sea (At Sea)

Lisbon, Portugal

Lisbon is a city best approached with time and comfortable shoes. Its seven hills rise above the Tagus, linking tiled lanes, grand squares and viewpoints with wide river views. In Alfama, narrow streets preserve the feel of old Lisbon. In Belém, the Jerónimos Monastery and Tower recall Portugal’s age of discovery. Pause for coffee and a warm pastel de nata between sights.