14-Day Best of Islands Portugal

Island Hopping Adventure: Unveiling the Azores & Madeira

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±

Price:

on request

Best For:

First-timers, nature lovers

Best Time:

Jun. - Sep.

Cancellation Policy:

100% Refund 22 Days before Arrival

* The price is based on a private tour during the low tourist season.

Discover real reviews of Highlights Travel Family's best-rated service across trusted platforms.

Trip Advisor 2024 certificate Tour Review

14 days in Portugal Tour Map (Suggested Route)

14 days Portugal tour map

Brief Itinerary for 14 days in Portugal

Day Highlights
1-3
Libon
Explore iconic landmarks & charming Alfama district. Take a fairytale Sintra day trip
4-8
Funchal (Madeira)
Discover volcanic landscapes & lush levadas. Embark on jeep tours & dolphin watching adventures
9-13
Ponta Delgada (Azores)
Island hop, explore Sete Cidades & canyons, see birds, savor cuisine & sip tea
14 Azores departure

Tour Highlights

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

Suggested Itinerary for Inspiration

Craft your dream Portugal adventure (Azores & Madeira) - explore, unwind, and savor on a personalized 14-day itinerary!

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
The Jeronimos Monastery or Hieronymites Monastery is located in Lisbon, PortugalThe awe-inspiring Jerónimos Monastery, a highlight of any Lisbon exploration
  • 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 Jerónimos 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.
Day 3
Lisbon Free & Easy
Panoramic view over Baixa and Castelo de Sao Jorge from Alfama, Lisbon, PortugalInside the Lello Bookshop, Porto, PortugalAlfama Magic: Lisbon's beauty unfolds!
  • 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!
Day 4
Day trip to Sintra
Cape RocaEnjoy the view at Cape Roca
  • 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.
Day 5
Lisbon to Funchal, Madeira
Bird's-eye View of Madeira IslandExperience the Lush Subtropics of Madeira Island
  • 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.
Day 6
Exploring Madeira's East Island
couple walking by levada on Madeira islandHand-in-hand on a Madeira levada walk.
  • 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.
Day 7
Off-Roading Adventure in West Madeira
Cabo Girao from the air, Madeira islandWitness the majesty of Cabo Girão, Europe's crown jewel of cliffs.
  • 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).
Day 8
Dolphin & Whale Watching & Sunset Cruise
sunset at seaSunsets & sea whispers - a magical end to our day trip!
  • 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!
Day 9
Funchal to Ponta Delgada, Azores
Top view of Islet of Vila Franca do Campo. Crater of an old underwater volcano. San Miguel island, Azores, PortugalAzores magic from the start! First glimpse of Vila Franca do Campo's dramatic volcanic crater lake.
  • 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.
Day 10
Sete Cidades & Lagoa do Fogo
Sete Cidades landscape in Sao Miguel island, Azores, EuropeIsland paradise found! Sete Cidades, São Miguel unveils volcanic beauty!
  • Explore the breathtaking Sete Cidades crater lake and the volcanic scenery of Lagoa do Fogo.
  • Witness the unique beauty of these natural wonders.
Day 11
Azorean Delights & Tea Culture
Traditional tea plantation in Sao Miguel, Azores. PortugalSipping history in the Azores - a traditional tea plantation in São Miguel, where Europe's oldest tea tradition thrives!
  • 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.
Day 12
Azores Adventure: Marine Life & Canyoning
Traveler canyoning climbing on an waterfallAzorean adrenaline rush! Canyoning through waterfalls - just another day in paradise!
  • 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.
Day 13
Free & Easy in Azores
Aerial view of a small port and the village of Ponta Delgada in the AzoresAzores exhale - Ponta Delgada's charming port, a perfect chill spot after island adventures!
  • 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.
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.

Hand-picked 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

Price Includes

*Price from: 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)

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

Your 1:1 travel consultant will reply within 1 working day.

How would you travel?

When would you travel?

What's your hotel choice?

I am also available on:

Get Inspired with Some Popular Itineraries

10-Day Portugal and Spain Family Tour 14-Day Family Trip to Spain and Portugal 14-Day Best of Spain and Portugal Tour 7-Day Portugal Family Beach Vacation

More Travel Ideas and Inspiration

10 Days in Portugal: 5 Top Family/Couples Itineraries How to Plan a Trip to Portugal in 2025 Best & Worst Times to Visit Portugal 2025: How to Choose An Ultimate Guide to Planning a Trip to Portugal and Spain (2024)
We are here to help you...
start planning your tailor-made trip with 1-1 help from our travel advisors.
Create Your Trip

Sign up to Our Newsletter

Be the first to receive exciting updates, exclusive promotions, and valuable travel tips from our team of experts.

Where Can We Take You Today?

Global Highlights logo
tour review Rated 4.6 out of 5 | Excellence
China Highlights International
Travel Service Co., LTD
Featured on
We are recommended by these social medias.

Address: Building 6, Chuangyi Business Park, 70 Qilidian Road, Guilin, Guangxi, 541004, China