This captivating two-week trip through Portugal unlocks the diverse wonders of Lisbon, Madeira, and the Azores. Start in Lisbon to delve into the city's vibrant atmosphere, exploring hidden gems and the local way of life. Fly to Madeira, where 4WD safari tours unveil dramatic landscapes and enchanting terraces. End on the Azorean island of São Miguel, discovering geothermal wonders at Furnas, marveling at the beauty of Sete Cidades, and whale watching, horseback riding, and canyoning.


  • Explore Lisbon like a local among its backstreets and markets
  • See the magnificent palaces of Sintra and Cascais
  • Explore the wild side of Madeira Island with 4WD tours
  • Feel the volcanic core of the Azores in Furnas on São Miguel Island

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Free Afternoon Lisbon
Day 2 Get to Know Lisbon with a Local, Explore Lisbon Markets Lisbon
Day 3 Free Day in Lisbon Lisbon
Day 4 Private Day Trip to Sintra, Cascais & Estoril Lisbon
Day 5 Fly to Funchal, Madeira Funchal
Day 6 Nature & Wine 4WD Experience Funchal
Day 7 Enchanted Terraces & Porto Moniz Tour Funchal
Day 8 Madeira West 4WD Adventure Funchal
Day 9 Fly to the Azorean Island of São Miguel, Culinary Walking Tour São Miguel Island
Day 10 Sete Cidades Jeep Adventure São Miguel Island
Day 11 Whale Watching Cruise, Canyoning Experience São Miguel Island
Day 12 Volcanic Excursion in Furnas São Miguel Island
Day 13 Horseback Riding, Sunset Boat Trip São Miguel Island
Day 14 Depart São Miguel  

Detailed Itinerary

Day 1: Arrive in Lisbon, Free Afternoon

The view from Miradouro da Graça offers breathtaking views over Lisbon

Olá and welcome to Portugal! You've landed in vibrant Lisbon where a driver will be waiting to transfer you to your hotel. Drop your bags and freshen up—the rest of the day is yours to explore the Portuguese capital at your own pace. 

Get lost in the colorful city streets, seek out the sights of the Belém district, hunt for the best Portuguese custard tart, and explore day-to-day life. Visit the city's biggest traditional daily market, Mercado da Ribeira, and order food next door at the trendy Time Out Market food hall. Or visit the LX Factory, a former cloth and textile factory that has been transformed into a buzzing district filled with small shops, restaurants, and bars. Explore Lisbon's cultural heritage and tile traditions at the National Azulejo Museum, or seek out European art at the Museu Calouste Gulbenkian.

Day 2: Get to Know Lisbon with a Local, Explore Lisbon Markets

Santa Justa Elevator
The beautiful Santa Justa Elevator was inaugurated in 1902

Discover the real Lisbon with a local this morning when you join a walking tour of the city center. Uncover the city's top sights along with some well-kept secrets as you explore the cosmopolitan Chiado and bohemian Bairro Alto neighborhoods. Feel the authentic character of Lisbon as you trek along cobbled streets and hear about life in the city from a local. Visit the beautiful Santa Justa Lift, a century-old ornate iron tower that connects downtown to Chiado, rising 148 feet (45 m) above. Enjoy views across the city and then seek out lunch.

Use the rest of the day to explore at your own pace. Lisbon's markets give insight into the city's day-to-day rhythms. Each Tuesday and Saturday, the Feira da Ladra flea market offers everything from vintage clothing to quirky antiques. For produce, try the city's most prominent traditional market, the daily Mercado da Ribeira, and then visit the buzzing Time Out Market food hall next door, if you haven't already. Make sure you try a pastel de nata from Manteigaria!

Day 3: Free Day in Lisbon

Jeronimos Monastery
The Jerónimos Monastery is one of the best examples of the late Portuguese Gothic Manueline architecture

Lisbon has a number of special places that are worth visiting, and today is yours to explore as you wish. You could start by strolling through the historic neighborhoods of Alfama and Mouraria. Let yourself get lost in the winding, cobbled streets, soak up the vibrant atmosphere, and admire the colorful tiled facades.

If you didn't make it to Belém on your first afternoon, choose to visit the iconic Torre de Belém and Jerónimos Monastery. Both are UNESCO World Heritage sites that allow you to delve into the city's rich history. While here taste a warm custard tart from the world-famous Pastéis de Belém nearby. Later you could board a canary yellow tram and take a self-guided tour through the city's inner neighborhoods. Finally, end the day by enjoying breathtaking views of the city from the Miradouro da Senhora do Monte or the picturesque São Jorge Castle.

Day 4: Private Day Trip to Sintra, Cascais & Estoril

Sintra's hilltop setting near Lisbon
Pena Palace sits at the top of Sintra's highest peak near Lisbon

UNESCO World Heritage-protected Sintra, with its romantic palaces, Moorish castle, and mystical forested hill, is Lisbon's best day trip. Explore Pena Palace, a 19th-century romanticist beauty that mixes Moorish and Portuguese late-Gothic architectural styles, with your guide. Next, enter Monserrate Palace to enjoy the beauty of Sintra-Cascais Natural Park before venturing toward the coast.

Wind your way through the mountainous landscape toward the dramatic coastal cliffs of the Cabo de Roca, continental Europe's westernmost point. Continue along the ocean to Guincho Beach, an expansive stretch of golden sand that's popular with surfers, before reaching upmarket Cascais. This former fishing village is now a premier beach destination and was once the coastal playground of Portuguese royalty. Admire the many lavish mansions and historic manor homes in Cascais and Estoril before returning to the city. 

Day 5: Fly to Funchal, Madeira

Funchal Harbour
Take a ride in a wicker basket, an old form of public transport in hilly Funchal

This morning you're jetting off to explore Madeira, one of Portugal's island archipelagos. After two hours you'll land on Madeira Island where a driver will pick you up and transfer you to your hotel in Funchal. Famous for its lush, subtropical forests, steep cliffs, deep valleys, charming villages, and striking ocean views, Madeira Island is a paradise in the middle of the Atlantic, some 350 miles (560 km) southwest of the Portuguese mainland, and 608 miles (978 km) west of the coast of Morocco in North Africa.

The rest of the day is yours to discover Funchal on your own. Start by exploring the historic center, strolling through the charming streets lined with colorful houses and traditional shops. Visit the Mercado dos Lavradores, a vibrant market where you can find local produce, flowers, and traditional crafts. Immerse yourself in the island's rich history at the Madeira Story Centre. Take a cable car ride up to Monte and visit the stunning Monte Palace Tropical Garden and experience a thrilling ride back down in a wicker basket. End your day at one of Funchal's many excellent restaurants.

Day 6: Nature & Wine 4WD Experience

Nature & Wine 4x4 Experience
The steep landscape and terraced farms of Madeira Island

Embark on an unforgettable 4WD half-day trip in Madeira, where nature and wine take center stage. Your first stop is the picturesque Serra de Agua, a valley nestled in the heart of the island. From there, you'll venture to the Encumeada viewpoint, offering breathtaking vistas of both the north and south of Madeira. Continue your adventure to the enchanting Chão dos Louros Forest Park, renowned for its lush laurel trees. An exhilarating off-road drive awaits, treating you to panoramic views of Porto Moniz, Ribeira da Janela, Paul da Serra, and São Vicente.

Next, visit one of the island's most prominent wineries where you'll savor a selection of fine wines with traditional snacks. An experienced oenologist will guide you through the tasting, sharing insights into local traditions and the island's wine culture. End the day at Cabo Girão, a majestic viewpoint soaring 1,932 feet (589 m) above the Atlantic Ocean. Stand on a suspended glass floor balcony and enjoy spectacular panoramic views over the Atlantic, Câmara de Lobos, and Funchal before returning to the city.

Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

Day 7: Enchanted Terraces & Porto do Moniz Tour

Enchanted Fanal
The enchanted and misty forest of Fanal

On today's extraordinary full-day tour, you'll discover the dramatic landscapes and enchanted terraces of the northwest of Madeira. Board a comfortable 4WD vehicle and venture toward the stunning coastal region, traveling past lush green scenery and through Serra de Água. Catch glimpses of the island's everyday life along forgotten enchanting roads. At Encumeada, where one of the island's famous walking trails leads to Madeira's highest peak, you'll pass through the laurel forests of Chão dos Louros and marvel at the mountains and valleys.

Continue to misty Fanal, set in the middle of Laurissilva forest, an ancient forest ecosystem that dates back millions of years and is known for its exceptional biological diversity. Later, continue to Porto Moniz, famous for its natural swimming pools. If weather permits, enjoy the warmth of the sea, or continue to Seixal known for its black-sand beach, which was named among Europe's best recently. Pass through the coastal town of São Vicente before returning to your hotel. 

Day 8: Madeira West 4WD Adventure

Porto Moniz
The famous pools of Porto Moniz

Madeira is all about nature, so today you'll set off again on a full-day 4WD adventure to explore even more of the wild island. Head toward Câmara de Lobos, the most famous fishing village in Madeira due to Winston Churchill's paintings and its flabbergasting sights. Pause for a quick pitstop before continuing the safari to Ponta do Sol before turning inland. Pass banana plantations, sugar cane, and vegetable gardens as you explore wild off-road tracks on the way to Paul da Serra, the only existing plateau on the island at an altitude of 4,593 feet (1,400 m).

Stop along the route to enjoy the breathtaking sights of Fanal and Ribeira da Janela. Pass through the Laurissilva Natural Park via off-road tracks. On the return to the coast, stop at Miradouro do Redondo to take in amazing views of Porto Moniz, famous for its natural lava swimming pools. Enjoy a swim and lunch before continuing to Seixal. Admire the beautiful black sand beach and watch a waterfall cascade into the ocean. Enjoy the scenic drive back to Funchal, with plenty of photo stops along the way.

Day 9: Fly to the Azorean Island of São Miguel, Culinary Walking Tour

Azores - Food
You must try lapas or limpets while in the Azores

This morning a private driver will transfer you to the airport in time for your flight to São Miguel, the biggest of the nine volcanic Azorean Islands. Known as "The Green Island" due to its lush landscapes, volcanic craters, and vibrant vegetation, São Miguel offers a diverse range of things to do and see. A driver will collect you from the airport at Ponta Delgada and transfer you to your hotel.

This evening you'll discover some of the best food and wine in the Azores with a guided walk through Ponta Delgada's trendiest eateries and neighborhood bars. Wind through the downtown of the vibrant island capital as you sample a progressive menu of fruit, honey, bread, pastries, seafood, artisanal meats, and homemade desserts—all washed down with delicious, locally-produced wines. Along this flavorful culinary experience, you'll visit some of the main city sights, discover off-the-beaten-path highlights, and pick up some great local recommendations for your time in the Azores.

Day 10: Sete Ciudades Jeep Adventure

Sete Ciudades Jeep Adventure
There is a great legend associated with the blue and green twin lakes of Sete Cidades

Explore the wild side of the Azores' most famous attraction—Sete Cidades—with an off-road excursion. Located on the west side of São Miguel Island, this remarkable area of natural beauty is considered one of the Seven Wonders of Portugal. Lush hillsides and volcanic craters rise between numerous tranquil lakes, each with its own distinctive character. You'll stop at several viewpoints, such as Carvão and Vista da Princesa, where you can contemplate this breathtaking landscape accessible only by foot or with a 4WD vehicle.

If the weather is playing nice you'll stop for a hike along the iconic Cumeeiras Trail, which follows the volcano's rim and offers stunning views from both sides. Continue to the charming local church and enjoy a cup of tea or coffee in the village located inside the crater. On the way back to Ponta Delgada, a trail around the lake's edge passes through a small peninsula shrouded in trees and flowers— giving you one last chance to capture the wilderness of this pristine landscape with your camera.

Day 11: Whale Watching Cruise, Canyoning Experience

São Miguel - Azores
São Miguel is one of the best places to go whale watching in the world

The Azores is considered to be among the best whale watching destinations in the world. Here you can spot more than 20 different species found in the archipelago's waters. Today after breakfast you'll board a boat to spot these fantastic and majestic marine creatures with the help of a local biologist and naturalist guides. Search for whales, dolphins, turtles, and more, discover the islands' scenic coastline and sandy beaches, and take a tour around the islet of Vila Franca do Campo for a closer look at the volcanic marvel and its resident wildlife.

Later the adventure continues with a thrilling canyoning experience. Explore the island's lush valleys, cascading waterfalls, and volcanic rock formations in a unique way. An experienced guide will lead you through narrow gorges, rappel down waterfalls, and plunge into crystal-clear pools. This adrenaline-pumping activity combines the excitement of exploration with the stunning beauty of the Azores.

Day 12: Volcanic Excursion in Furnas

Volcanic Experience in Furnas Full Day
Feel the raw volcanic energy in Furnas

From secret gardens and natural thermal pools. to steam vents and fumaroles, to a magnificent gastronomic experience cooked with the power of the volcanoes, experience nature's power on today's visit to Furnas. One of the most emblematic villages of the Azores, the Furnas Valley is where the volcanic nature of the islands is most readily apparent. Join a day trip to the area, first stopping at Pico do Ferro circuit trail to take in one of the best sights of Furnas Lake

Your next stop will be Terra Nostra Botanical Garden, the first and oldest botanical garden of the Azores. Dip in the iron-rich orange thermal pools and natural Jacuzzis surrounded by vibrant green scenery. For lunch, you can choose to try a traditional dish called cozido, a stew that's cooked underground using volcanic power. After, explore the area's volcanic steam vents, fumaroles, and mineral waters fountains with various temperatures and flavors. On the way back to Ponta Delgada, pause at Gorreana Tea Factory to enjoy the local tea and wander the plantation.

Day 13: Horseback Riding, Sunset Boat Trip

Portas da Cidade, the city symbol of Ponta Delgada in Sao Miguel Island
Portas da Cidade is the city symbol of Ponta Delgada

For nature lovers, a horseback ride is an unforgettable way to explore the most beautiful and unknown corners of Sāo Miguel. Jump into the saddle on your final full day in Portugal and ride along charming, quiet paths getting to know the lush green area of Mata Santa. Admire the lush eucalyptus, acacia, and laurel trees and experience the nature of the island from a different vantage point.

This evening feel the cool breeze of the wild Atlantic Ocean as you cruise along the beautiful coastline. Explore different volcanic structures including caves, lava tubes, and the islet of São Roque. Enjoy the Atlantic waters and have a dip in the deep sea before drying off and enjoying your final sunset in Portugal. Watch as the sun hits the horizon, spreading a spectrum of warm colors across the landscape.

Day 14: Depart São Miguel 

Sao Miguel Island
Wave goodbye to the lush, vibrant greens of São Miguel Island

It's the final morning of your two-week vacation through Portugal and its unique islands. When the time is right, take a transfer from your hotel to Ponta Delgada airport for your departing flight. Safe travels!

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Map of Explore the Beauty of Portugal: Lisbon, Madeira & São Miguel - 14 Days
Map of Explore the Beauty of Portugal: Lisbon, Madeira & São Miguel - 14 Days