This epic Portugal tour highlights two cosmopolitan cities and a stunning mid-Atlantic island—part of an autonomous region—known for its tropical foliage and eternal spring-like weather. You'll kick off in Porto, home of centuries-old wine production and colorful architecture along the Douro River. Then fly to Madeira Island for secluded beaches and untouristed villages waiting to be discovered. Last but not least is Lisbon's friendly, up-and-coming capital—a striking city built on seven hills.


  • Explore Porto's UNESCO-listed city center, followed by a gastronomy tour
  • Spend two nights surrounded by vineyards in the oldest wine region in the world
  • Hike to a steep village on Madeira Island that was once a hiding place from pirates
  • Walk and tram through Lisbon's cobbled streets and trendy dining options
  • Visit the fairy-tale village of Sintra for glorious views and pastel-hued architecture

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Porto, Culinary Excursion Porto
Day 2 Get to Know Porto Porto
Day 3 Transfer to the Douro Valley Douro Valley
Days 4-5 Wine Tasting in the Douro Valley Douro Valley
Day 6 Transfer to Lisbon, Fly to Madeira Island Funchal
Day 7-9 Explore Madeira Island Funchal
Day 10 Fly from Funchal to Lisbon Lisbon
Day 11 Half-Day Tour of Lisbon Lisbon
Day 12 Day-Trip to Sintra, Cascais & Estoril Lisbon
Day 13 Free Day in Lisbon Lisbon
Day 14 Depart Lisbon  

Detailed Itinerary

Day 1: Arrive in Porto, Culinary Excursion

Porto's Old Town of Foz
Porto's Old Town of Foz

Welcome to Portugal! Upon arrival at Porto's airport, you will be met by a driver who will transfer you to your hotel. Take some time to rest before you start exploring. In the late afternoon, you will learn more about Porto and its cuisine with a 3.5-hour walking tour of the historic downtown. Guided by a friendly English-speaking native, this excursion offers a first-hand look at the culinary renaissance that the city is experiencing, including the rebirth of specialty food shops and new restaurants that are adopting old methods.

You'll take part in several distinct tasting locations that harken back to an era of simple, quality products and recipes created by people who love what they do. Learn about these family-owned businesses and why they are integral to what makes gastronomy in Porto so unique. Furthermore, you'll witness the revival of Portuguese cuisine while you explore local restaurants, cafés, and stores offering the best of Porto.

The evening, of course, would not be complete without an introduction to the famous drink of Porto: Port wine. As you taste three different versions, including one vintage, you will learn about the history of this drink and why it is a timeless favorite.

Day 2: Get to Know Porto

Porto's scenic skyline
Porto's scenic skyline

Today is a great introduction to Porto! After breakfast at the hotel, you'll join a half-day tour of the city with a local guide. This excursion will lead you through the most important landmarks of Portugal’s second most populous city as you travel from place to place in a comfortable private vehicle. Your guide will explain the rich history of this city, also called Invicta (the Unbeaten City), with stories of heroes and battles as you make your way to the trendiest and most cultural area of the city. Here you'll explore Boavista Avenue, one of the city's most important streets, and Foz, home to some of the most important museums and modern local treasures.

Next, you'll head to the city center—a UNESCO World Heritage Site—to admire the most renowned Romanesque, Gothic, Baroque and Neo-Classical monuments and sites, including the São Bento Railway StationClerigos TowerChurch of St. FrancisLello Bookshop, Sta. Catarina Street, Majestic Café, and Bolhão Market, to name a few. After visiting the imposing Porto Cathedral with its superb silver altarpiece, you will finish the tour along the banks of the immense Douro River with views of Ribeira Plaza and the D. Luís Bridge

But that's not all: In the evening (after some time to rest), it's time for another tour—this time centered on the city's exciting food scene. This is your chance to get off the well-worn tourist path for a side of Porto that travelers rarely see. You'll be welcomed by local families in their small, authentic restaurants, cafés, and bars as you taste a range of traditional dishes, local pastries, and, of course, Portuguese wines.

Day 3: Transfer to the Douro Valley

Douro Valley
Douro Valley

After breakfast at your hotel, a driver will pick you up for the transfer to the Douro Valley—a scenic journey that takes about two hours. Keep your camera close as you make your way toward green, hilly landscapes where fantastic wines (both Port and table varietals) are produced. The valley is actually listed as a UNESCO World Heritage Site, and you'll easily see why as you encounter various viewpoints, towns, and villages, allowing you to admire breathtaking landscapes on both sides of the river.

When you get to your hotel, take the rest of the afternoon and evening and relax on the property while enjoying the views.

Days 4-5: Wine Tasting in the Douro Valley

Tour some vineyards known for Port wine production
Tour some vineyards known for Port wine production

After breakfast, you'll be picked for a full-day wine experience in the Douro Valley. The excursion begins at a family-owned winery in the picturesque town of S. João da Pesqueira, located in a small subregion called Douro Superior. Upon arrival, one of the family members will lead you on a walking tour of their undulating vineyards over the Douro River, followed by an intimate wine tasting. This winery is part of a new generation of small family wineries based in the Douro with over a century of Port wine experience.

For lunch, you can take your pick between several options, including a charming restaurant in the mountainous town of Ervedosa serving traditional recipes that have been made in households across the region for centuries. Your driver will then take you through the picturesque vineyards of a winery in the heart of Douro's Pinhão Valley. This innovative yet rustic winery was founded by Jorge Serôdio Borges and his wife Sandra Tavares da Silva—two of the most celebrated winemakers in Portugal. Initially, the winery included a lone vineyard called Pintas, but it has gradually expanded to include additional properties, such as the magnificent Quinta da Manoella.

At the end of the afternoon, your driver will take you back to the hotel.

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

Day 6: Transfer to Lisbon, Fly to Madeira Island

Cape Girao in Funchal
Cape Girão in Funchal

Today you'll depart Portugal's mainland and fly to Madeira Island—part of a tiny archipelago (four islands) in the mid-Atlantic, just northwest of Africa. You'll be picked up from your hotel and transferred to the airport for your flight to the capital city, Funchal, located on the main island (Madeira). Make sure to snag a window seat and take advantage of the stunning views as you land.

Upon arrival, you'll pick up your rental car and drive to the hotel, where you'll have the rest of the day to explore Funchal on your own. With stunning green mountains facing the vivid blue ocean—and colorful flowers that bloom all year round—a good place to start is simply taking a walk around the city, where you'll find a relaxed urban atmosphere. For dinner, check out the range of café and restaurant options near the attractive harbor, along with sunset views.

Day 7-9: Explore Madeira Island

Madeira island's scenic landscape
Madeira island's scenic landscape

Today, you'll have the entire day to enjoy the tiny volcanic island of Madeira at your leisure. Known for its subtropical climate—and eternal spring-like weather—Madeira offers an enchanting mix of green mountains, rugged cliffs, pebbly beaches, and interesting settlements along the Fajã River. If you prefer to stay in town, the hilly capital of Funchal offers botanical gardens and the centuries-old Funchal Cathedral, notable for its carved wooden ceiling. Along the harbor is São Tiago Fortress which now houses the Contemporary Art Museum with a large collection of Portuguese works.

For an active day trip, you can head downhill to the village of Curral das Freiras (Nun's Valley) by foot. The steeply-situated village—once the sanctuary for a convent of nuns hiding from pirates—offers a network of foot and mule trails with scenic overlooks and local delicacies to sample, like chestnut cakes and a cherry-infused liqueur.

Day 10: Fly from Funchal to Lisbon

Aerial view over Lisbon
Aerial view over Lisbon

This morning, you'll transfer to the airport for your flight to Lisbon, one of Europe's fastest-changing and trendiest capitals. Upon arrival, check into your hotel and take the remainder of the day to either rest or explore your neighborhood surroundings.

A good place to start is the charismatic Alfama district, with twisting streets that wind up to an imposing castle on one of the city’s highest hills. Alfama is a perfect mix of historical landmarks and charming residences with whitewashed houses, flower-laden balconies, and red-tiles roofs. You will also discover one of the most important squares in the city and the famous Liberdade Avenue. Make sure to look for and taste the delicious Pastel de Belém, a traditional pastry found here.

In the evening, after sampling some of the city's best seafood, be sure to visit one of the many Fado houses and experience a unique genre of Portuguese music.

Day 11: Half-Day Tour of Lisbon

Statue at Praca do Comercio
Statue at Praca do Comercio

Today you'll get to discover Lisbon on a half-day tour visiting key sites and some well-kept secrets, exposing the city's unique atmosphere and authenticity. This will be a fun adventure as you travel around the city using the yellow tram system broken up with relaxed strolls. Make sure to wear a good pair of walking shoes.

The tour includes the following:

  • Praça do Comércio: the largest of Lisbon’s plazas
  • Baixa: the 'new city,' built after the devastating 1755 earthquake
  • Praça da Figueira: Lisbon’s traditional market square
  • Rossio: the heart of downtown Lisbon
  • Iron Lift Viewpoint: a stellar 360º view over the downtown district
  • Largo do Carmo: the setting for the democratic revolution of 1974
  • Carmo ruins: the only Gothic monument of the city
  • St. Roque Church: a Baroque extravaganza
  • Bairro Alto: the lively bohemian district
  • Chiado: the city's most elegant shopping area
  • Portas do Sol: a breathtaking view over Alfama (the Old Town)

In the evening, you'll dine at one of the best Fado restaurants in Lisbon for traditional Portuguese cuisine interspersed with authentic singing and music.

Day 12: Day-Trip to Sintra, Cascais & Estoril

Sintra's fairytale setting near Lisbon
Sintra's fairy-tale setting near Lisbon

The area surrounding Lisbon offers an incredible variety of architecture and scenery, from fairytale palaces to romantic towns and breathtaking viewpoints. Today's guided excursion is the ideal way to experience some of these attractions.

After breakfast at your hotel, your guide will deliver you to the first stop on the tour: Sintra. This village—about 30 minutes by car from the capital—is a harmonic combination of history and fantasy, described as a “glorious Eden” by the British poet Lord Byron in the 18th century. You will have free time to explore on your own and have lunch, and your guide can recommend some imposing monuments and wonderful palaces worth visiting.

Your next stop will be the Cabo da Roca, the westernmost point of Portugal and mainland Europe. Enjoy the gorgeous views across the Atlantic Ocean as waves crash onto the shore. On the return trip to Lisbon, you will have time to appreciate the fishing harbor and tourist center of Cascais, the former summer residence of the Portuguese royal family, and nowadays an excellent spot for surfing. You'll also be able to visit the luxury entertainment town of Estoril, known for its casino (the largest in Europe) and attractive gardens.

After the excursion, you'll have the remainder of the day to enjoy Lisbon any way you'd like.

Day 13: Free Day in Lisbon

You can kayak in the calm waters of Arrábida Natural Park
You can kayak in the calm waters of Arrábida Natural Park

Today, you'll have a free day in Lisbon to enjoy the city any way you'd like! If you've seen enough of the city and are anxious to explore other areas, here are some excellent day-trip ideas:

  • Fátima & Nazaré: Religiously significant, Fatimá is the site of an important Catholic shrine, Our Lady of Fatima. From there you'll continue to the coastal town of Nazaré for a completely different type of sightseeing: the site of the biggest wave ever surfed.
  • Jeronimos Monastery: This glorious example of ancient architecture was listed as a UNESCO World Heritage Site in 1983. Located near the Tagus River, King Manuel I commissioned the monastery in the late 15th century to honor Our Lady and Saint Jerome.
  • Sesimbra: This is a great village to stroll along the beach and just watch the world go by. You can also pay a visit to Sesimbra's beautifully-restored central church or head uphill to Sesimbra Castle. If you have time on the way back, you can also make a stop in Almada for spectacular views over Lisbon.
  • Óbidos: The historical medieval village of Óbidos definitely merits its own day trip. Surely one of the best-preserved old towns in Portugal, visitors will be delighted by its cobbled streets and sunnily painted houses.
  • Arrábida Natural Park: For something more active, take a kayaking trip in Arrábida Natural Park and admire the gorgeous views from the water as you paddle through its tranquil river systems. You’ll have the chance to discover numerous hidden caves and secluded beaches; pack a picnic lunch. 
  • Knights Templar: Visit the villages of Constância and Tomar and learn about the intriguing story of the holy order of warrior monks. 
  • Évora: One of Portugal’s most beautifully preserved medieval towns, Évora is an enchanting place to delve into the past. Inside the 14th-century walls, you'll find narrow, winding lanes leading to an impressive number of important architectural works. Évora's also a lively university town with great restaurants. 

Day 14: Depart Lisbon

Goodbye, Lisbon!
Goodbye, Lisbon!

It's time to say goodbye to Portugal! Depending on the time of your flight, squeeze in one more walk through the streets of Lisbon, perhaps picking up some last-minute souvenirs. At the designated time, you will be picked up at your hotel and transferred to the airport for your departure onward. Safe travels!

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Map of Explore Portugal: Porto, Lisbon, & Madeira Island - 14 Days
Map of Explore Portugal: Porto, Lisbon, & Madeira Island - 14 Days