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Lisbon and Portugal`s Islands by Air (Madeira - Sao Miguel - Terceira)

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9 to 13+ Nights from $1,954*
* Sample price: priced within the past 7 days for a 8/31/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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Add Outbound & Return Flights

This 9 night sample itinerary includes:

  • Flight into Lisbon and out of Terceira Island (Azores)
  • Hotel for 3 nights in Lisbon
  • Flight from Lisbon to Funchal (Madeira Island)
  • Hotel for 2 nights in Funchal (Madeira Island)
  • Flight from Funchal to Ponta Delgada (Sao Miguel Island)
  • Hotel for 2 nights in Ponta Delgada (Sao Miguel Island)
  • Flight from Ponta Delgada (Sao Miguel Island) to Terceira Island (Azores)
  • Hotel for 2 nights in Terceira Island (Azores)

Portugal is offering four of its glorious and beautiful cities, three of which are islands, to all travelers with this customizable package. Start in Lisbon (the capital of Portugal; full of medieval charm and modern sensibilities) then, take a flight to Funchal, the capital city of Madeira Island (situated between wide stretches of beach and imposing mountains) and after that, to Sao Miguel (a glorious island filled with ocean views and volcanic scenery). Finally, catch a flight to Terceira Island (nestled in the middle of the North Atlantic Ocean, one of the larger islands of the archipelago in the Azores).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
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Flexible Itinerary

  • Lisbon

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  • Funchal (Madeira Island)

    about
  • Ponta Delgada (Sao Miguel Island)

    about
  • Terceira Island (Azores)

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Portugal

Customer Reviews

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Trip Summary

  • Lisbon
    Lisbon

    Lisbon, a dazzling city stretching along the Tagus river, makes an enchanting European capital. Its nucleus, an ancient fortress, is now circled by neighborhoods drenched with medieval charm. Handcrafts - from embroidery to leatherwork - are peddled right on the streets. At night, yellow electric tramcars continue to wind their way up and down the hills to the sound of traditional Fado songs. Ample opportunities exist for seeing popular celebrations, for shopping, and for enjoying the nightlife along the riverbank.

    Visit Alfama, Baixa and Chiado, Se de Lisboa, Sao Roque Church, Mosteiro dos Jeronimos, Torre de Belem, Discoveries Monument, Museu Nacional dos Coches, Parque das Nacos, Elevador de Santa Justa, Tram 28 and so much more!

  • Funchal (Madeira Island)
    Funchal (Madeira Island)

    Funchal is nestled in a great natural amphitheatre, facing the blue Atlantic with a backdrop of dramatic mountains. Located in the stunning south of Madeira Island, on its sunniest coast amidst banana plantations and wonderful gardens, it is an extremely lush, green and relaxed city by day. But scratch Funchal's surface and you will find it to have a vibrant and varied nightlife scene with multiple personalities.

    Explore Zona Velha, Madeira Wine Institute, Fortaleza de São João Baptista do Pico, Mercado dos Lavradores, Fortaleza de São Tiago, Funchal Cathedral, Praca da Autonomia, Palacio de São Lourenco, Madeira Story Centre, Pontinha, Praia Formosa, Lido Promenade, and so much more!

  • Ponta Delgada (Sao Miguel Island)
    Ponta Delgada (Sao Miguel Island)

    Sao Miguel is the largest and most popular of the Azores Islands chain. Portuguese explorers and settlers first inhabited Sao Miguel Island in the 15th century and were so impressed with the tranquil, lush isle that they dubbed it the Green Island. You can stroll down historic avenues in the capital Ponta Delgada, swim with the dolphins, or sun yourself on lakeshores formed by underwater massifs -- all in one day!

    Explore the Portas da Cidade, Lagoa das Sete Cidades, Mercado da Graca, Jardim Antonio Borges, Museu Carlos Machado, and more!

  • Terceira Island (Azores)
    Terceira Island (Azores)

    Terceira Island is part of the Azores island chain. History meets biodiversity in this beautiful part of the world. The island's capital, Angra do Heroismo, is a UNESCO World Heritage Site.

    Explore the UNESCO World Heritage Site of Angra do Heroismo, Algar do Carvao, Monte Brasil, Serra do Cume Viewpoint, Gruta do Natal, and more.

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