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Lisbon and Portugal`s Islands by Air (Madeira - Sao Miguel - Terceira)
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9 to 13+ Nigths from $1,568*
This sample price: priced within the past 7 days for arrival on 10/20/2025, departure from Boston BOS (MA), US. Choose your own departure city, cabin type and dates.
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This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
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, it is subdued by day and lively in the evening) 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). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
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
  • Hotel for 2 nights in Terceira Island
Price history for this itinerary (past 7 days):
From Atlanta ATL (GA), US for 9 nights
2076.90 * incl.tax
From Boston BOS (MA), US for 9 nights
1567.43 * incl.tax
From Denver DEN (CO), US for 9 nights
2144.82 * incl.tax
From New York City NYC (All Airports) (NY), US for 12 nights
1535.19 * incl.tax
From Philadelphia PHL (PA), US for 12 nights
1898.67 * incl.tax
From Sacramento SMF (CA), US for 9 nights
2286.68 * incl.tax
Related Itineraries:
Related Cities:
Lisbon (327)     Funchal (Madeira Island) (5)     Terceira Island (Azores) (9)     Ponta Delgada (Sao Miguel Island) (13)    
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With Int'l Flight     Without Int'l Flight
From:
Cabin:
Destination
Arrival date
Stay
1. Lisbon
  226 hotels
2. Funchal (Madeira Island)
   (72 hotels)
3. Ponta Delgada (Sao Miguel Island)
   (30 hotels)
4. Terceira Island (Azores)
   (17 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
3 nights in 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!



2 nights in 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!



2 nights in 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!



2 nights in 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.



Book This Package
Flexible Itinerary
Lisbon
Day 1
Arrive to Lisbon
Overnight in Lisbon   226 hotels offered
Optional   1157 Things to do
Day 2
Overnight in Lisbon   226 hotels offered
Optional   1157 Things to do
Day 3
Overnight in Lisbon   226 hotels offered
Optional   1157 Things to do
Day 4
Departing from Lisbon
Transportation to next city by: Regional Air
Funchal (Madeira Island)
Day 4
Arrive to Funchal (Madeira Island)
Overnight in Funchal (Madeira Island)   72 hotels offered
Optional   245 Things to do
Day 5
Overnight in Funchal (Madeira Island)   72 hotels offered
Optional   245 Things to do
Day 6
Departing from Funchal (Madeira Island)
Transportation to next city by: Regional Air
Ponta Delgada (Sao Miguel Island)
Day 6
Arrive to Ponta Delgada (Sao Miguel Island)
Overnight in Ponta Delgada (Sao Miguel Island)   30 hotels offered
Optional   82 Things to do
Day 7
Overnight in Ponta Delgada (Sao Miguel Island)   30 hotels offered
Optional   82 Things to do
Day 8
Departing from Ponta Delgada (Sao Miguel Island)
Transportation to next city by: Regional Air
Terceira Island (Azores)
Day 8
Arrive to Terceira Island (Azores)
Overnight in Terceira Island (Azores)   17 hotels offered
Optional   91 Things to do
Day 9
Overnight in Terceira Island (Azores)   17 hotels offered
Optional   91 Things to do
Day 10
Departing from Terceira Island (Azores)
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Lisbon Hotels (226 total)
›
Funchal (Madeira Island) Hotels (72 total)
›
Ponta Delgada (Sao Miguel Island) Hotels (30 total)
›
Terceira Island (Azores) Hotels (17 total)
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Tours in Lisbon (1157 total)
›
Tours in Funchal (Madeira Island) (245 total)
›
Tours in Ponta Delgada (Sao Miguel Island) (82 total)
›
Tours in Terceira Island (Azores) (91 total)
›


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Package Map Picture
Portugal

Thousands of years of history are on full display in vibrant <b>Portugal</b>, fast becoming one of the most popular tourist destinations in western Europe. Each region of Portugal offers something unique to the traveler, like unparalleled beaches and resorts in the Algarve; rolling plains that lead to mountains in the Alentejo; delicious food and drink in the Minho and the Douro River Valley; and of course the country's bustling capital, Lisbon, which boasts the best of everything that Portugal has to offer, from restaurants to historical landmarks.
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Price Guidance

The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected. You can change details after selecting your travel date.

Price history for this itinerary (past 7 days):

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*Sample prices on display include ALL taxes & fuel surcharges... read more
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Lisbon and Portugal`s Islands by Air (Madeira - Sao Miguel - Terceira)
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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 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)
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 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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