Portugal's Islands & Capital: Lisbon, the Azores & Madeira

Explore a unique blend of Portugal by combining its bustling capital city with its magical islands.

With its breathtaking landscapes, historic sites, and friendly locals, Portugal is an ideal place to explore and enjoy!

What's Included?

All flights and connections
Accommodations for your destinations
Expert trip manager
All taxes & fees

Why we love this deal:

  • Lisbon, Madeira, and São Miguel Island in the Azores are one of the top destinations for travelers looking to experience the unique beauty and vibrant culture of Portugal. 
  • The Portuguese capital of Lisbon offers something for everyone: vibrant city life with chic boutiques and restaurants; historical landmarks such as the Jerónimos Monastery or the Belém Tower; wonderful outdoor activities like kayaking on Tagus Estuary or simply taking in the beauty of its cobblestone streets. 
  • For travelers who want to get off the beaten track, Madeira is an excellent option. This island boasts some of Europe’s most stunning scenery with dramatic cliffs, picturesque villages, lush vegetation, and unspoiled beaches. Of course no visit to Madeira without tasting its world-class wine and traditional drink "poncha".
  • São Miguel is known as ‘Green Island’ due to its lush vegetation, where visitors can explore volcanoes that are still active today or take swimming trips around thermal pools created by volcanic activity - Terra Nostra Park, Poça da Dona Beija, Caldeira Velha and more. 
  • In short, our Portugal's Islands & Capital package offers travelers an array of incredible experiences that will make them fall in love with Portugal. Whether you're seeking relaxation on world-class beaches or adventure activities such as scuba diving or hiking along ancient trails through nature reserves – this beautiful corner of Europe has something for everyone!
  • Customizable: Add more nights to your stay, a rental car or even local excursions!

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Day 1
Arrival in Lisbon

Suggestion for the day:

  • Visit the Chiado, Baixa, Belém and Bairro Alto districts (Bairro Alto is known for its nightlife scene). Highlights: São Roque church, São Pedro de Alcântara garden, the ruins of Carmo church, Santa Catarina viewpoint, Luís de Camões Square, Torre de Belém, Mosteiro dos Jerónimos, Pastéis de Belém, Augusta street, Terreiro do Paço, Santa Justa lift. Or book here your Lisbon Foodie Walking Tour.
  • Suggestion for dinner: Lisbon Fado Night With Dinner

Suggestion for the day (Évora or Sintra):

  • We suggest taking a stroll around downtown Évora. Highlights: Capela dos Ossos, Évora Cathedral, The Roman Temple of Évora, Diana’s Garden, Évora’s winding streets, Évora University. Visit Évora’s City Walls, Aquecut of Évora, Mosteiro da Cartuxa, Almendres Cromlech and Monsaraz. Or book here your Évora Guided Tour with a Wine Tasting Experience! 
  • At Sintra, visit the Old Town and one of the following monuments: Pena Palace, Quinta da Regaleira, Monserrate Palace, Sintra National Palace, or the Moorish Castle. Or book here your Sintra Guided Tour. 

Suggestion for the day:

  • Take the afternoon to stroll around Funchal’s historical streets and gardens. 


  • Monte Palace Tropical Garden
  • Madeira Botanical Garden
  • Funchal Cable Car
  • Church of Nossa Senhora do Monte
  • Monte Toboggan Ride
  • São Tiago Fortress
  • Mercado dos Lavradores
  • Or book here your Food & Wine walking tour of Funchal. 

Suggestion for the day:

  • Madeira's West Coast.


  • Ribeira Brava
  • São Vicente
  • Seixal
  • Porto Moniz
  • Calheta 
  • Ponta do Sol
  • Or book here your southwest guided tour. 

Suggestion for the day:

  • Discover Madeira’s Eastern Wonders 


  • Santana
  • Machico
  • Pico do Arieiro
  • Ponta de São Lourenço
  • Or book here your full-day guided tour. 

Option #2: Take the Day for a Hiking Adventure 

Suggestion for the day:

  • Take the afternoon to stroll around Ponta Delgada’s city streets. Ponta Delgada, the main city, is not only the hub of the island but the capital of the Azores. Ponta Delgada evokes all the charms of Europe with cobbled streets, sidewalk cafes, and a thriving culinary scene. Or book here your Ponta Delgada City Tour. 

Not to miss:

  • Portas da Cidade
  • Louvre Michaelense
  • Pineapple Plantations
  • Matriz Church


  • Embark on a whale and dolphin-watching experience. The Azores Islands are known for their unparalleled beauty and biodiversity, adored by outdoor adventure enthusiasts and nature lovers alike. But what people may not know is that the Azores is also one of the fastest-growing whale-watching destinations in the world. Located in the Atlantic Ocean between Portugal and North America, the Azores are a permanent home and natural point of passage to more than 20 different types of whale and dolphin species, making the islands one of the world’s largest whale sanctuaries. Book here

Suggestion for the day:

  • In Sete Cidades, visit Lagoa das Sete Cidades, Lagoa de Santiago, Lagoa do Canário and Boca do Inferno Viewpoint, and take this opportunity to visit the neighboring village of Mosteiros - ideal for sunset! Once you’re in the west part of the island you can also indulge in an ocean thermal bath at Ferraria. Book here a guided tour around the western part of the island that will have you discovering this and much more in the company of a local guide. 


  • Take the day for a hiking adventure. 

Recommended hikes:

Suggestion for the day (Lagoa do Fogo & Furnas):

  • Head to the north side of the island to visit the Protected Natural Reserve of Lagoa do Fogo and take this chance to visit (and maybe bathe) the thermal pools of Caldeira Velha. Once you’re here you can also visit the Salto do Cabrito waterfall! On your way to Furnas, we recommend that you stop at Porto Formoso and Gorreana Tea Plantations (the only ones in Europe). In Furnas there’s just so much to explore, such as the lake, the Pico do Ferro Viewpoint, the Grená Park, the caldeiras, the fumaroles, the Terra Nostra Park, the Dona Beija hot springs and so much more. Make sure to try out the local delicacies: the cozido das Furnas and the bolos lêvedos!
  • Book a Furnas guided tour here.

*Itinerary Presented is a suggestion and the length of stay may vary. All tours are suggestions unless specifically stated.

Flexibility Policy

No Amendment Fees on Our End
We don’t charge for our work in changing the initial itinerary.
Full flexibility on Land Arrangements
Change the initial itinerary or cancel your land arrangements for any reason until 14 days before the trip, without penalty*.
Support 7 Days a Week
Our experienced travel agents are are available 7 days a week (16 hours per day) to help with any questions.

About the Destinations:


Lisbon, the cosmopolitan capital of Portugal and Europe's second-oldest capital (after Athens), has now become the new "it" destination for tourists visiting Europe. This is "The City of the Sea", "The City of the Explorers", once home to the world's greatest explorers like Vasco da Gama, Magellan and Prince Henry the Navigator. Lisbon is also the first true world city, the capital of an empire spreading over all continents, from South America (Brazil) to Asia (Macao, China; Goa, India). 

São Miguel Island, the Azores

Often referred to as Europe's “Best Kept Secret”, the Azores have become an increasingly popular destination with year-round appeal for travelers. Just four hours from Boston, the Azores are now easier to access and explore than ever before. 

Enjoy the island's quaint fishing villages, seaside restaurants, and delicious seafood. Taste a superb meal cooked underground, known as cozido, and sample the locally grown sweet pineapple. There are numerous vacation activities to be enjoyed on the island, so take advantage of this great vacation package and come have an amazing adventure!


Discover the charming port city of Funchal, a cruise-ship hub and a historical and colorful city teeming with restaurants, cafés, and friendly locals. Explore the narrow streets paved in black and white stones and the city’s colorful and lively markets, and also indulge in delicious Portuguese food. Try the local fish, savor bolo do caco, and sip poncha as you people-watch under the sunny skies of Madeira. Enjoy the thrill of going down a hill on a traditional wicker toboggan, and admire the island’s typical houses and architecture. The options truly are endless in magical Madeira.

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7.8 Based on 4 reviews
Christopher, North Carolina
04 Aug 2023
Very nice trip, fun to see 3 different aspects of Portugal
Kevin, Connecticut
01 Dec 2022
Great trips, hotels, and loved it
Christopher, North Carolina
04 Aug 2023
Very nice trip, fun to see 3 different aspects of Portugal
Kevin, Connecticut
01 Dec 2022
Great trips, hotels, and loved it
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Portugal's Islands & Capital: Lisbon, the Azores & Madeira
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