14-Day Best of Islands Portugal

14-Day Best of Islands Portugal

Unleash your inner explorer on a 14-day adventure through Portugal's Azores & Madeira archipelagos. Explore vibrant cities, charming villages, and dramatic volcanic landscapes. Hike the UNESCO-listed Laurissilva forest, witness Sete Cidades' colorful lakes, and unwind on pristine beaches. Savor delicious regional cuisine and local wines.

This island-hopping adventure offers the perfect blend of relaxation, exploration, and cultural immersion. Discover Portugal's hidden gems - book your unforgettable journey today!

  • Days:14±
  • Best for:First-timers, nature lovers
  • Best time:Jun. - Sep.
  • Departure date:up to you
  • Sample price:US$ on request

Brief Itinerary for Best of Islands Portugal Tour

Day Highlights
Day 1 Lisbon arrival
Day 2 Lisbon Highlights
Day 3 Lisbon Free & Easy
Day 4 Day trip to Sintra
Day 5 Lisbon to Funchal, Madeira
Day 6 Exploring Madeira's East Island
Day 7 Off-Roading Adventure in West Madeira
Day 8 Dolphin & Whale Watching & Sunset Cruise
Day 9 Funchal to Ponta Delgada, Azores
Day 10 Sete Cidades & Lagoa do Fogo
Day 11 Azorean Delights & Tea Culture
Day 12 Azores Adventure: Marine Life & Canyoning
Day 13 Free & Easy in Azores
Day 14 Departure from Ponta Delgada
Seeking a time-efficient trip, to explore the major attractions within a limited timeframe? I'm here to assist you in planning and optimizing your trip.
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  • Monica Mo
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Tour Highlights

Here are the awesome attractions, the most must-do activities selected by Highlights Travel (HT Hand-Picked), and exclusive cultural experiences offered by Highlights Travel (Only With HT) included in this tour:

Explore Portugal's Island Paradises: Discover Madeira and the Azores in one unforgettable combo!

Swimming natural pools of volcanic lava, Madeira island, Portugal

Hike along lush levadas built centuries ago, soaking in the island's verdant beauty.

On the way on the city levadas of Funchal with a fantastic view on the Atlantic Ocean, Madeira, Portugal

Experience unforgettable dolphin watching adventures.

dolphin near the island

Witness the stunning beauty of Sete Cidades crater lake in the Azores.

couple holding hands while walking towards the Grota do Inferno viewpoint at Sete Cidades on Sao Miguel Island, Azores

Become a marine birdwatching expert on a thrilling expedition.

A common chaffinch (Fringilla coelebs maderensis) is photographed on the island of San Miguel, Azores, Portugal

Unveil Lisbon's treasures by exploring iconic landmarks.

Praca do Comercio with yellow tram, Lisbon, Portugal

Escape to Sintra's fairytale palaces.

National Palace of Pena, Sintra, Portugal

Unwind with a relaxing tea tasting, a traditional Azorean activity.

Tea plantation on the island of Sao Miguel island, Azores, Portugal

Enjoy hassle-free private transfers between cities and to the airport for a seamless journey.

Driver turns over his shoulder as a passenger with a smile

Rest and recharge in comfortable accommodations throughout the adventure.

Night view of the island of Corvo Azores, Portugal

Journey Map (Suggested Route)

14 days Portugal tour map

Suggested Itinerary for Inspiration

Your preferences design the real journey. We're ready to create a wonderful tour for you.

Day 1
Lisbon arrival
  • Welcome to Portugal! Arrive in Lisbon and enjoy a private transfer to your centrally located hotel.
  • Relax and unwind after your flight, or explore the surrounding area at your own pace.
Day 2
Lisbon Highlights
  • Dive into Lisbon's historic heart, Alfama, with its iconic terracotta rooftops.
  • Explore the city's vibrant neighborhoods and iconic landmarks like Belem Tower and the Jernimos Monastery.
  • Indulge in a delightful Pastel de Nata baking experience - a local pastry specialty!
  • Ride the iconic Tram 28 and witness the Monument to the Discoveries (Padrão dos Descobrimentos).
  • Explore the majestic São Jorge Castle (Castelo de S. Jorge) for breathtaking city views.
The Jeronimos Monastery or Hieronymites Monastery is located in Lisbon, Portugal
The Jeronimos Monastery or Hieronymites Monastery is located in Lisbon, Portugal
Day 3
Lisbon Free & Easy
  • Recharge or Explore!
  • Unwind on beaches, indulge in a spa, or sip coffee soaking in the city vibes. Or wander charming neighborhoods, visit historical sites, or ride a historic tram. Choose your adventure!
Panoramic view over Baixa and Castelo de Sao Jorge from Alfama, Lisbon, PortugalInside the Lello Bookshop, Porto, Portugal
Panoramic view over Baixa and Castelo de Sao Jorge from Alfama, Lisbon, PortugalInside the Lello Bookshop, Porto, Portugal
Day 4
Day trip to Sintra
  • Embark on a day trip to Sintra, a charming town nestled in the hills.
  • Explore the stunning Pena National Palace, Park and Palace of Monserrate, architectural masterpieces.
  • Take in breathtaking ocean views from Cape Roca, the westernmost point of mainland Europe.
Cape Roca
Cape Roca
Day 5
Lisbon to Funchal, Madeira
  • Bid farewell to Lisbon and catch a flight to Funchal, the capital of Madeira.
  • Upon arrival, a private transfer whisks you to your hotel.
  • Enjoy the rest of the day, have a good rest or discover the neighboor on your own.
Bird's-eye View of Madeira Island
Bird's-eye View of Madeira Island
Day 6
Exploring Madeira's East Island
  • Embark on a scenic walk through Laurissilva forest, a UNESCO World Heritage Site. Enjoy the lush vegetation, waterfalls, and unique flora and fauna.
  • Visit the village of Camacha, known for its wickerwork production. Watch artisans skillfully craft traditional baskets and furniture.
  • Discover Santana, a charming village famous for its colorful, thatched-roof houses.
  • Savor a delicious Azorean buffet lunch at a local restaurant, featuring fresh seafood, regional specialties, and local wines.
couple walking by levada on Madeira island
couple walking by levada on Madeira island
Day 7
Off-Roading Adventure in West Madeira
  • Traverse dramatic landscapes, witnessing towering mountains, cascading waterfalls, and hidden coves.
  • Take a refreshing dip in volcanic natural pools, a unique experience surrounded by stunning scenery.
  • Discover Seixal, a charming village known for its black sand beach.
  • Enjoy breathtaking panoramic views from Cabo Girão, Europe's highest cliff with a glass skywalk (optional).
Cabo Girao from the air, Madeira island
Cabo Girao from the air, Madeira island
Day 8
Dolphin & Whale Watching & Sunset Cruise
  • Search for dolphins, whales & sea turtles. Snorkel with these amazing creatures & enjoy sparkling wine & refreshments.
  • Sail past dramatic cliffs, charming harbors, and lush gardens. Enjoy sparkling wine, snacks & breathtaking views during Sunset !
sunset at sea
sunset at sea
Day 9
Funchal to Ponta Delgada, Azores
  • Travel from Funchal to Ponta Delgada, the capital of the Azores archipelago.
  • Upon arrival, a private transfer takes you to your hotel.
  • Savor the remainder of your day, relax well, or venture out to explore the neighborhood independently.
Top view of Islet of Vila Franca do Campo. Crater of an old underwater volcano. San Miguel island, Azores, Portugal
Top view of Islet of Vila Franca do Campo. Crater of an old underwater volcano. San Miguel island, Azores, Portugal
Day 10
Sete Cidades & Lagoa do Fogo
  • Explore the breathtaking Sete Cidades crater lake and the volcanic scenery of Lagoa do Fogo.
  • Witness the unique beauty of these natural wonders.
Sete Cidades landscape in Sao Miguel island, Azores, Europe
Sete Cidades landscape in Sao Miguel island, Azores, Europe
Day 11
Azorean Delights & Tea Culture
  • Savor the flavors of Ponta Delgada on a culinary adventure, indulging in local specialties.
  • Discover the traditional Azorean tea culture with a walking tour and tasting at Gorreana Tea Plantation.
Traditional tea plantation in Sao Miguel, Azores. Portugal
Traditional tea plantation in Sao Miguel, Azores. Portugal
Day 12
Azores Adventure: Marine Life & Canyoning
  • Witness incredible island birdlife on aeco-friendly cruise. Responsible close-up encounters with majestic birds in their natural habitat.
  • Unleash your inner adventurer on a thrilling canyoning expedition! Hike, rappel waterfalls (optional), and jump into crystal-clear pools.
Traveler canyoning climbing on an waterfall
Traveler canyoning climbing on an waterfall
Day 13
Free & Easy in Azores
  • After an exhilarating journey, enjoy a free day in Ponta Delgada to unwind and recharge.
  • (Optional) Soak up the sun on a pristine beach, indulge in a spa treatment, or simply savor a coffee at a sidewalk cafe and watch the world go by.
Aerial view of a small port and the village of Ponta Delgada in the Azores
Aerial view of a small port and the village of Ponta Delgada in the Azores
Day 14
Departure from Ponta Delgada
  • Enjoy a relaxing final day in Ponta Delgada.
  • A private transfer takes you to the airport for your departing flight home.

Ideas for Making This Trip Uniquely Yours

Special experiences can be added to brighten a honeymoon trip, a family vacation, a birthday, or satisfy personal interests.

Hand-Picked Hotels

We select hotels with style and local features. Let us know your preferences and we'll find your ideal hotel.

Portugal Boutique Hotel, Lisbon
Portugal Boutique Hotel
Three House Hotel, Funchal
Three House Hotel
Pêro Teive Bay Apartments Hotel, Ponta Delgada
Pêro Teive Bay Hotel
EPIC SANA Lisboa Hotel
EPIC SANA Lisboa Hotel
Les Suites at The Cliff Bay - PortoBay, Funchal
Les Suites at The Cliff Bay
Octant Ponta Delgada
Octant Ponta Delgada

Our Service Includes:

14 days from
US$ on request
*The price is based on a private tour for 2 people staying in 4-star hotels during the low tourist season. (tour code: gh-pt-15)

Groups of 4 or more enjoy a more competitive price.

  • One-to-one consultancy
  • Knowledgeable local guides
  • Private drivers/driver guides and vehicles as listed
  • Accommodations Mentioned
  • Breakfasts and meals as listed
  • Entry to all attractions on the itinerary
  • Transportation as listed
  • A 24/7 helpline while travelling

Tour code: gh-pt-15

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