Portugal was once considered the "end of the world" and still feels like the earth's edge with its wild landscapes and expansive ocean views. It also reflects life beyond its borders with its mix of histories, cultures, and cuisines. Explore the mainland and island of Madeira, beginning with a tour of historic Lisbon. Sip port wine by the Douro River in Porto, then fly to Madeira to experience its pristine scenery, and finally return to the mainland and the seaside resort of Cascais for some relaxing beach time.


  • Go off-roading with a Jeep tour in Madeira National Park
  • Sample some of Portugal's best wines in the Douro Valley
  • Take a surf lesson in the seaside town of Cascais
  • Learn about Lisbon's epic history on a walking tour

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon & See the City by Tuk-Tuk Lisbon
Day 2 Explore Lisbon with a Private Walking Tour Lisbon
Day 3 Encounter History in Fátima, Batalha, Nazaré & Óbidos Lisbon
Day 4 Transfer to Porto via Aveiro Porto
Day 5 Enjoy a Private Walking Tour of Porto Porto
Day 6 Wine Tour & River Cruise in the Douro Valley Porto
Day 7 Fly from Porto to Funchal Funchal
Day 8 Off-Road Jeep Trip & Wine Tour in Madeira Funchal
Days 9-10 Explore the History & Nature of Madeira Funchal
Day 11 Fly from Funchal to Cascais Cascais
Day 12 Sunbath or Surf at Cascais Cascais
Day 13 Transfer to Lisbon & Depart  

Detailed Itinerary

Day 1: Arrive in Lisbon & See the City by Tuk-Tuk

The sun shines over Lisbon
The sun shines over Lisbon

Welcome to Portugal! A private driver will pick you up at the airport to bring you to your accommodations in Lisbon, a city whose history goes back to 1200 BCE. After getting settled, head out on a late afternoon tour with an eco-friendly tuk-tuk. The tour passes through Baixa, Lisbon's old center filled with 18th-century Pombaline buildings. This Portuguese style of architecture emerged after the Great Lisbon Earthquake of 1755 and can be seen all around the capital.

Discover this history and more with your guide as the tour hits the best viewpoints in town, like São Pedro de Alcântara and Senhora do Monte, which offer breathtaking panoramic views of Lisbon. At the end of the tour, your driver will return you to your hotel or can drop you off at a great local place for dinner.

Day 2: Explore Lisbon with a Private Walking Tour

Statue at Praca do Comercio in Alfama
Statue at Praça do Comercio in Alfama

There's no better way to feel the heart of a historic city like Lisbon than by exploring it on foot. In the morning, head out on a walking tour led by an expert local guide. The guide will point out the major sights and recount anecdotes about local lore to paint a picture of this fascinating city. 

The tour includes stops at many highlights, including the upscale shopping area around Chiado Square and the 12th-century Lisbon Cathedral, which is the oldest church in the city. Visit the old town of Baixa and its historic Rossio Square. Stand under the Arco da Rua Augusta, a magnificent 18th-century arch located in the Praça do Comércio on the banks of the Tagus River. End the tour with a tasting of ginjinha, Portugal's famous liqueur made from sour cherries.

Day 3: Encounter History in Fátima, Batalha, Nazaré & Óbidos

The ornate Batalha Monastery
The ornate Batalha Monastery

Today is centered around some of the best cultural and historical sites near Lisbon. A guide will bring you north through the agricultural lands of the Ribatejo province to the Sanctuary of Fátima, which was built after three children experienced visitations by the Virgin Mary in 1917. Next is a visit to the stunning 14th-century Batalha Monastery, Portugal's finest example of Flamboyant Gothic architecture. Continue to the fishing town of Nazaré and enjoy lunch in this area known for its delicious seafood.

Soak in more panoramic views and picturesque villages such as Foz do Arelho and São Martinho do Porto, which you'll pass on the way to today's final destination: the charming medieval town of Óbidos. Explore the narrow streets and impressive medieval castle on your own time or peruse some of the traditional handicraft and souvenir shops for gifts. End the day with a tipple of the potent local ginja liqueur (an aguardiente made with sour cherries and spices) before returning to Lisbon.

Day 4: Transfer to Porto via Aveiro

Costa Nova striped houses
Colorful striped houses in Aveiro

Travel to Porto today, but first make a stop in the intriguing port city of Aveiro. With its decorative boats, elaborate architecture, and intricate canal system, this city is known as the "Portuguese Venice." Explore Aveiro on your own by strolling its center or taking a ride on one of the traditional moliceiro boats.

Continue to Porto, and take the day to enjoy this 2,000-year-old city in your own time. One of the best places to begin is the medieval Ribeira district, whose narrow and cobblestoned streets wind past merchants' houses and cafés along the Douro River. It includes landmarks like the São Francisco Church, known for its lavish Baroque interior and ornate gilded carvings. In the evening, sample some of the staples of Porto's culinary scene: fresh seafood, local organic produce, wines produced in the Douro Valley, and of course, a glass of port.

Day 5: Enjoy a Private Walking Tour of Porto

Porto, a UNESCO World Heritage Site
Porto at the magic hour

Start this morning with a guided tour of this UNESCO World Heritage city. Porto has been a key locale throughout Portugal's rich history—the site of Celtic, Roman, and Moorish occupations, an invasion by Napoleon and Spanish troops, and even a civil war, all of which can be seen in its architecture and landmarks. Learn about this past while touring Porto's historic center, including the Praça da Liberdade, the most impressive plaza in the city. Visit the shopping thoroughfare of Rua Santa Catarina and the Baroque church of Igreja dos Clérigos, which dates back to 1750.

Head to the iconic São Bento Railway Station, built in 1900 on the site of a former convent. Discover the history of Porto's emblematic Dom Luís I Bridge, a double-decked iron-arched feat of engineering that stands 279 feet (85 m) over the Douro River. On this waterway, colorful wooden rabelo boats line up in front of the old port wine cellars. End the tour with lunch at a local café, then enjoy the rest of your day in the city.

Day 6: Wine Tour & River Cruise in the Douro Valley

A bird's eye view of the Douro Valley
A view above the Douro Valley

In the morning, journey to the Douro Valley, a fertile grape-growing region that produces some of Portugal's best wines. This full-day guided tour begins with a visit to a quinta (winery) to see the vineyards and production facilities and enjoy a wine tasting. The next activity is a leisurely lunch of traditional Portuguese cuisine in a nearby town, followed by another wine tasting.

In the afternoon, hop aboard a riverboat for a cruise down the tranquil Douro River. Relax and admire the beautiful scenery of the valley and the rolling hills along the riverbanks. After the cruise, return to Porto and have the evening to yourself to explore the city.

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

Day 7: Fly from Porto to Funchal

Fly to the "Island of Eternal Spring" today 
Your driver will take you to Porto Airport this morning to catch your flight to the small city of Funchal on the island of Madeira. Madeira is part of an archipelago located in the North Atlantic, uninhabited until the arrival of Portuguese sailors in the 15th century. Known for its wild beauty, wine production, and pre-historic laurel forests, Madeira has long been a favorite destination for travelers looking for beauty and adventure off the mainland. After landing, a driver will pick you up and whisk you off to your accommodation on this idyllic island, where you'll have the rest of the day to rest.

Day 8: Off-Road Jeep Trip & Wine Tour in Madeira

A lookout spot in Madeira's Chão dos louros Park
A lookout spot in Madeira's Chão dos Louros Park

Today begins with a drive in a Jeep up to the viewpoint of Serra d'Agua, a lush valley at the center of the island. The next stop is Encumeada, which offers epic mountain views and serves as a crossroads to connect the different directions of Madeira: Ribeira Brava (south), São Vicente (north), and Paúl da Serra (west). The off-road adventure heads deeper into the Chão dos Louros Forest Park, which gets its name from its abundance of laurel trees, and includes fantastic views of the north side of Madeira.

This nature-filled morning will become a wine-centered afternoon with a guided tour through Madeira's vineyards. Meet the leading wine producers of the island, enjoy a tasting, and learn about the traditions, culture, and production of this island's wine. End the tour with a drive to Cabo Girão, the highest sea cliff in Europe and the second highest in the world at 1,866 feet (589 m). This death-defying drop has a suspended glass floor viewpoint for those without a fear of heights, offering a spectacular view over the Atlantic Ocean, Câmara de Lobos, and Funchal.

Days 9-10: Explore the History & Nature of Madeira

The rainbow colors of Madeira
The rainbow colors of Madeira

Enjoy two days to explore Madeira at your leisure. This small island is packed with things to do, whether you're in the mood for nature, culture, adventure, or all of the above. For those looking to get a deeper knowledge of Funchal, there's the remarkably intact 15th-century Gothic-style Cathedral of Sé, the charming Old Town that features an open art gallery on Rua da Santa Maria, and the Mercado dos Lavradores or Farmers' Market, filled with fresh produce and even fresher flowers.

Nature lovers can spot thousands of plants at the Monte Palace Tropical Garden, Palheiro Gardens, or the Madeira Botanical Garden. There are also a number of hiking trails and viewpoints around the island, all of which go directly into the heart of Madeira's beautiful landscape. Recreational activities around Madeira include whale and dolphin-watching boat tours, scuba diving, and mountain biking.

Day 11: Fly from Funchal to Cascais

The sandy beaches of Cascais
The sandy beaches of Cascais

Your driver will transfer you to Funchal Airport this morning for your flight back to Portugal's mainland. After landing in Lisbon, a driver will meet you from the airport to take you west to the nearby beach town of Cascais, once the favorite vacation spot for Portuguese royalty. Its proximity to Lisbon made it the perfect choice as a summer resort for the royal family and other aristocrats, and remnants of this history are still visible in its stunning mansions and estates.

Day 12: Sunbath or Surf at Cascais

A 19th-century seafront mansion in Cascais

Today is all yours to enjoy the seaside town of Cascais and its spectacular beaches. Praia da Conceição and Praia da Duquesa form the main coast of Cascais, where you can find a beautiful stretch of sand with calm, clean sea waters and recreational activities. If you're looking for a nice walk, follow the scenic coastal promenade to Praia do Tamariz, which has an old fort overlooking the water.

If you're feeling adventurous, check out Praia do Guincho, a wild and rugged beach in the Serra de Sintra Natural Park. This is one of the best surfing spots in the Lisbon region, and whether you get on a board or not, you're sure to be thrilled by this landscape's incredible beauty.

Day 13: Transfer to Lisbon & Depart

Lisbon's colorful streets and street cars 
After getting in some last-minute sun and beach time in Cascais, return to Lisbon Airport with a private driver. Continue to the next destination, and safe travels!

More Great Portugal Itineraries

Looking for more inspiration for your trip to Portugal? Check out these other Portugal itineraries, explore different ways to spend 13 days in Portugal, or discover the best time of year to visit Portugal.


Map of Discover Mainland Portugal & Madeira - 13 Days
Map of Discover Mainland Portugal & Madeira - 13 Days