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

Highlights

• 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

Detailed Itinerary

Day 1: Arrive in Lisbon, Free Afternoon

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

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

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

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

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

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.

Day 7: Enchanted Terraces & Porto do Moniz Tour

Day 8: Madeira West 4WD Adventure

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

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

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.

Day 11: Whale Watching Cruise, Canyoning Experience

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.

Day 12: Volcanic Excursion 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. 

Day 13: Horseback Riding, Sunset Boat Trip

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 

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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