Explore Mainland Portugal & Madeira Island - 16 Days

Day 1: Arrive in Lisbon, Sunset Boat Cruise

Welcome to the vibrant capital of Portugal, Lisbon! Meet your driver at the airport for a transfer to your hotel and relax until this evening's two-hour boat tour. When it's time, jump on board a traditional canoa, a wooden sailing boat, to cruise along the Tagus River's tranquil waters. Look out for landmarks, like the UNESCO-listed Torre de Belém (Belém Tower) and the towering Padrão dos Descobrimentos (Discoveries Monument), which pays homage to Portugal's Age of Exploration. Listen as your guide highlights the city's rich history as you sail down the river.

As the sun begins to set over the city, pass under the 25 de Abril Bridge, named after the date of the Carnation Revolution in 1974 CE when the ruling dictator was deposed. Return to shore as darkness closes in and stroll to Cais do Sodré, the city's waterfront district, for dinner. If you're unsure what to choose, visit Mercado da Ribeira, better known as Time Out Market, to browse the stalls selling a diverse array of local and international delights. End the night with a sweet treat of pastel de nata, Portugal's beloved custard tart.

Day 2: Guided Tuk-Tuk Tour, Explore Lisbon's Markets

Have fun exploring today as you navigate Lisbon's hills and discover the city's vibrant neighborhoods on an electric tuk-tuk, a three-wheeled vehicle. Join your guide and begin in central Baixa, known for its elegant squares and neoclassical architecture. Weave through the charming streets and along Praça do Comércio, a grand waterfront square facing the river, before driving uphill to the bohemian district of Bairro Alto. Follow the narrow cobblestone streets to admire buildings adorned with azulejos, intricately decorated tiles depicting historical events, religious scenes, or detailed patterns.

Stop at panoramic viewpoints like São Pedro de Alcântara, Parque Eduardo VII, Senhora do Monte, and Santa Luzia for a new perspective of the cityscape below. After the two-hour tuk-tuk tour, the rest of the day is yours to spend as you wish. If you feel like shopping, browse the stalls full of antiques, vintage items, and secondhand goods at Mercado de Santa Clara. The market is only open on Tuesdays and Saturdays, though, so if you're visiting another day, head to the more local Mercado de Alvalade instead, which is only closed on Sundays.

Day 3: Helicopter Ride Over Lisbon, Free Afternoon to Explore the City

Soar above Lisbon today in a helicopter to get a bird's-eye perspective of the city. As you lift off, admire the mosaic landscape of red-tiled roofs, winding rivers, and architectural marvels below. Spot landmarks like the wetlands of the Tagus Estuary Natural Reserve, the sandy shores and fossil-rich cliffs of Costa da Caparica, and Santuario de Cristo Rei, a towering statue of Jesus Christ inspired by Christ the Redeemer in Rio de Janeiro. After the 30-minute flight, the rest of the day is yours to explore the city at your leisure.

You can visit some of the sites you may have viewed from above, like Mosteiro dos Jerónimos ( Jerónimos Monastery). This 16th-century monastery, classified as a UNESCO World Heritage Site, was built to commemorate the explorer Vasco da Gama's world-first ocean voyage to India. When you arrive, admire the intricate facade adorned with maritime motifs before stepping inside to discover the church within that holds the tombs of notable figures, such as Vasco da Gama and Luís de Camões, considered Portugal's greatest poet. In the evening, wander to the waterfront to enjoy fresh seafood overlooking the river. 

Day 4: Drive to Nazaré, Explore the Coastal Town

Say goodbye to Lisbon today as you pick up your rental car and drive 1.5 hours north to the fishing village of Nazaré, nestled along Portugal's Silver Coast. With just one day to explore the area, head to Praia da Nazaré, a golden-sand beach renowned for its impressive waves. Here, you'll see local women in traditional "seven skirts" regional dress tending to salted fish drying on racks in the sun. And if you're not into surfing, grab a sunbed, soak up the sun, and watch the surfers in action. Afterward, visit Forte de São Miguel Arcanjo, a 17th-century fortress overlooking the Atlantic Ocean.

Wander through the fort to discover its cannons, military structures, and a maritime museum, which delves into the town's seafaring heritage. Continue to the nearby century-old funicular and ride it to the town's highest point, where the Sítio district awaits. Stroll through the historic district and browse various souvenir shops, boutiques, and cafés. In the evening, sit down at one of the many restaurants in the neighborhood to sample local delights, like arroz de marisco, rice with an array of seafood, tomatoes, and white wine, or arroz de polvo, rice with octopus and squid.

Day 5: Drive to Porto, Tour the City on a Tuk-Tuk

After breakfast, continue your road trip by driving two hours up the coast to Porto, the second-largest city in the country. On your way, stop in Avéiro, often called the "Venice of Portugal," thanks to its extensive canal network, where colorful boats navigate the waterways. You can jump on one of these boats, moliceiros, to explore the town's picturesque canals or wander along the cobblestone streets of the historic center. Whichever you choose, you're sure to see elegant Art Nouveau buildings, beautiful gardens, and picturesque squares.

Day 6: Boat Cruise Down the Douro River, Explore the Ribeira Neighborhood

Experience the city from the water today with a 50-minute cruise down the Douro River on a tourist version of a rabelo boat, originally used to carry wine barrels from Vila Nova de Gaia. From Ribeira Quay, you'll follow the journey of the wine merchants down the tranquil waterway, passing beneath six iconic bridges. At the last bridge, look out at Foz do Douro, a waterfront district known for its scenic promenades, pristine beaches, and elegant mansions. Don't miss Farolim de Felgueiras, a towering lighthouse from 1886. Following the cruise, the rest of the day is yours to spend as you wish.

Perhaps head to the Ribeira neighborhood, nestled along the riverbanks. Wander down the winding streets lined with colorful tiled buildings to discover local shops or savor traditional dishes, such as francesinha, a hearty sandwich with layers of cured ham, linguiça (smoked sausage), and fresh sausage, all smothered in a thick, spicy tomato and beer sauce. Step back in time at the nearby Palácio da Bolsa, a 19th-century palace. Admire the neoclassical and Gothic facade before entering to discover the intricate halls and lavish chambers within.

Day 7: Local Market Visit & Private Cooking Class

Skip breakfast this morning so you're ready for today's four-hour cooking class, which begins with a visit to a local market. Follow the chef down the narrow alleys and learn how to pick the freshest ingredients for today's recipes. When you have everything you need, head to the kitchen for a hands-on lesson. You may prepare local delights like francesinha or bacalhau à brás, a salted codfish dish with potatoes and eggs, then end with a sweet treat of pastel de nata, the beloved egg custard tart. When everything is ready, sit down to enjoy the fruits of your labor paired with local wines and spirits.

In the afternoon, explore on your own by first hopping on the Funicular dos Guindais. This steep railway connects the Ribeira district to Batalha, offering spectacular views of the cityscape and the river below. Or, head to one of the numerous wine cellars in Vila Nova de Gaia, just across the river, for a guided tour and tasting session. While there, enjoy the sunset at Jardim do Morro, a scenic hilltop park in Vila Nova de Gaia, and then choose from the array of restaurants for dinner before heading back to your hotel for your last night in Porto. 

Day 8: Drive to the Douro Valley, Enjoy a Two-Hour River Cruise

Trade the city for the countryside this morning as you drive 1.5 hours inland to the lush Douro Valley—a fertile grape-growing region historically renowned for its fortified wines and, more recently, its fine table wines. On the way, stop in the quaint town of Amarante to wander along the cobblestone streets lined with traditional houses and inviting shops. Visit Igreja de São Gonçalo, an 18th-century Baroque church dedicated to the town's patron saint, to admire the ornate altars, gilded woodwork, and intricate azulejos.

Once you've explored the town, continue the drive to the Douro Valley. Upon arrival, check into your hotel and choose a hillside restaurant or a riverside eatery for lunch. Afterward, jump on board a riverboat for a cruise down another portion of the Douro River. Admire the terraced hills adorned with rows of grapevines echoing back to antiquity when the Romans made wine on these very banks. Spot charming villages and historic estates showcasing the region's rich winemaking history. Then, after the two-hour cruise, the rest of the day is yours to spend at your leisure.

Day 9: Guided Vineyard Tour, Drive to the Riverfront City of Coimbra

Time spent in the famous wine-growing Douro Valley requires a visit to a local winery. Follow your guide through the terraced vineyards and traditional aging cellars, where you'll learn about the winemaking process, from grape cultivation to fermentation and aging. After gaining insights into the traditional techniques to craft each wine, sit down for a delicious meal at a traditional quinta (wine estate). Savor a selection of the estate's finest wines and, with each sip, experience the nuances of the region's terroir and the winemaker's skill.

After lunch, enjoy a stroll among the vines and the view of the Douro River before grabbing your bags and driving 1.5 hours south to Coimbra, the former capital of Portugal, nestled on the Mondego River. When you arrive, take a self-guided tour of the UNESCO-listed historic center, where you can wander the narrow alleys and medieval churches like Sé Velha. Dating back to the 12th century, this Romanesque cathedral is perched atop the city's highest point, offering panoramic views of the cityscape below. 

Enter to see the vaulted ceilings, Gothic chapels, and the tombs of notable figures, such as Queen Isabel and King Afonso Henriques, Portugal's first monarch. When you get hungry, visit one of the charming eateries or traditional tavernas in the historic center to sample local delights, like chanfana, a hearty stew made with slow-cooked lamb or goat, or leitão à bairrada, a crispy-skinned spit-roasted suckling pig. End the night with one of the traditional pastries the city is famous for, like sweet buns called arrufadas or bolos de chila, a sponge cake prepared with fig-leaf squash.

Day 10: Explore the Buçaco National Forest, Drive to Lisbon

Lace up your hiking shoes and drive 40 minutes outside the city to the wall-enclosed Buçaco National Forest, home to 250 species of trees and shrubs. Trek through one of its 11 gateways into enchanting woodland renowned for its biodiversity. Keep an eye out for native and exotic trees as you follow one of the four main trails, which can take between two to three hours to complete. Whichever trail you pick, you're sure to stumble upon scenic viewpoints and historic monuments.

At the highest point of the forest, you'll encounter Cruz Alta, a stone cross, and enjoy wide-ranging views of the lush canopy below. Before you leave, stop at the Palace Hotel Bussaco, an opulent palace built as a royal residence for monarchs in the early 20th century. Nowadays, it's a luxury hotel surrounded by green woodland. Admire the exterior's intricate detailing, turrets, and medieval-inspired design before your two-hour drive south back to Lisbon, where you'll settle into your hotel for the night.

Day 11: Fly to Funchal & Madeira, Explore the Island

Leave mainland Portugal behind today as you drive to the airport for a flight to Funchal in Madeira, an archipelago in the Atlantic comprising four islands. Drop your rental car off, then head inside the airport for your two-hour flight. After settling into your hotel, venture out to explore the area on your own. Ride the cable car to Monte for magnificent views of Funchal Bay, then wander the charming Old Town, where you can follow narrow cobblestone streets to historic sites, such as the 15th-century Funchal Cathedral, which blends Gothic and Moorish architectural styles. 

Step inside the elegant interior to admire the wooden ceiling, religious artifacts, and the museum's vast collection of paintings, sculptures, and ecclesiastical vestments. Continue to Palácio de São Lourenço for a glimpse into the island's colonial past. Wander through the well-preserved rooms, hallways, and courtyards of this 16th-century palace until you work up an appetite. When hunger sets in, visit one of the many restaurants lining Rua de Santa Maria in the old town to savor local dishes, like espetada, skewers of marinated meat seasoned with garlic, herbs, and spices. 

Day 12: 4WD Tour to the West Side of the Island

Today's adventure is a full-day 4WD tour across the island, starting in the picturesque fishing village of Câmara de Lobos, just 16 minutes west of Funchal. Look out at Cabo Girão, one of the highest sea cliffs in Europe, and the colorful boats bobbing in the harbor before continuing to Canhas on the island's southern shore, Ponta do Sol. Wander through the small village to see the traditional Madeira houses (palheiros), colorful flowers, and banana plantations.

From here, your guide will drive off-road to the next village, Calheta, surrounded by lush green hills and terraced vineyards. Get ready for an uphill drive as your guide takes you to the only plateau on the island, Paul da Serra, situated at an altitude of 4,600 feet (1,400 m). Enjoy the panorama of lush greenery, colorful flora, and vast valleys from the top. Then, get back in the vehicle to drive to Porto Moniz, a captivating village renowned for its natural pools and dramatic landscapes.

Sit down for lunch at one of the nearby restaurants, then enjoy a relaxing swim in the Porto Moniz Natural Pools, a series of volcanic rock pools filled with crystal-clear ocean water. When ready, drive back to Funchal, stopping in the coastal village of Seixal on the way to relax on the black sand beach, Praia Formosa. If you get too hot, swim in the Atlantic Ocean's deep blue waters and admire the towering cliffs surrounding the village. After a full day exploring the island, return to your hotel to relax.

Day 13: 4WD Tour to the Northwest Side of the Island

Set off on another full-day 4WD tour across the island this morning to the northwest coast, stopping at the picturesque village of Serra de Água on the way. Translating to "Water Mountains," Serra de Água is a haven for nature lovers as towering mountains and lush greenery surround the village. Continue north to the nearby Miradouro da Encumeada, where you can set off down a short trail through the dense vegetation for spectacular views of the surrounding mountains and valleys.

Day 14: 4WD Tour to Chão dos Louros Forest Park & Local Vineyard

Spend your last day in Madeira on a 4WD tour to some hotspots you may have missed, like another portion of the Laurissilva Forest—Chão dos Louros Forest Park. Follow one of the well-maintained trails through the greenery and immerse yourself in the distinct microclimate that supports and preserves an ancient, endemic ecosystem. Watch out for the forest's various bird species, such as the Madeira firecrest or trocaz pigeon (Madeira laurel), up in the trees.

After exploring the forest, continue to a nearby winery to experience more of the island's rich wine culture. Learn about the winemaking process, discover the history behind this beloved beverage, and tour the cellars to see where the wine is aged. Before you leave, sample different varieties of Madeira wines paired with traditional tapas. End the tour at the top of Cabo Girão with a walk across the suspended glass-floor balcony 1,980 feet (580 m) above sea level. Enjoy panoramic views of the terraced hillside, vineyards, and picturesque coastal landscape before returning to your hotel in Funchal. 

Day 16: Portuguese Ceramic Tile-Painting Workshop, Depart Lisbon

Spend your last morning in Lisbon immersing yourself in the city's rich culture by painting your own azulejos. Learn about the rich history and intricate painting process of these traditional Portuguese tiles, then try creating your own colorful design. Whether a novice or an experienced artist, you can use the two-hour workshop to express your creativity and craft a personalized souvenir to take home. When it's time, return to your hotel to grab your bags and meet your driver for a transfer to the airport and your onward flight. Safe travels!

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