With just over two weeks to spare, you can combine the best of mainland Portugal with the lush valleys and volcanic beaches of "the Island of Eternal Spring." Start with cycling and culinary tours of Lisbon, wine tasting in the Douro Valley, and a deep dive into the history of colorful Porto. Then it's time to jet off into the North Atlantic for four days on Madeira, before returning to the mainland for some downtime at the chic coastal resort of Cascais.


  • Zip through Lisbon's steep streets on a tuk-tuk tour
  • Take a river cruise through the heart of the Douro Valley wine country
  • Watch history come alive in Porto's medieval Ribeira district
  • Take an off-road adventure into the verdant valleys and mountains of Madeira
  • Explore romantic palaces and white sand beaches around Cascais

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, See the Capital by Tuk-Tuk  Lisbon
Day 2 Explore Lisbon with a Private Walking Tour Lisbon
Day 3 Cycle Lisbon's Riverside, Evening Food Tour Lisbon
Day 4 Transfer to Coimbra via Nazaré & Alcobaça  Coimbra
Day 5 Transfer to the Douro Valley Douro Valley
Day 6 Douro Valley Wine Tour & River Cruise Douro Valley
Day 7 Transfer to Porto, Portugal's Second City Porto
Day 8 Enjoy a Private Walking Tour of Porto Porto
Day 9 Fly to Funchal & the Island of Eternal Spring Funchal
Day 10 Madeira Off-Road Jeep Trip & Wine Tour  Funchal
Day 11-12 Explore the History & Nature of Madeira Funchal
Day 13 Fly to Lisbon & Transfer to Cascais Cascais
Day 14 Day Trip to Sintra & the Estoril Coast Cascais
Day 15 Depart Portugal  

Detailed Itinerary

Day 1: Arrive in Lisbon, See the Capital by Tuk-Tuk 

Trams climb Lisbon's hilly streets
Welcome to Lisbon! Upon arrival, you'll be greeted by your driver and transferred to your hotel in the city center. After checking in, you can unwind after your long journey or head out for a quick stroll. You'll find Lisbon to be an unheralded gem of a European capital. Hilly waterfront neighborhoods are dotted with grand plazas and pastel-colored buildings, many dating back hundreds of years. Old cable cars lurch up winding cobbled roads, and medieval castles sit perched atop the city's highest points. 
In the late afternoon, you'll hop in an eco-friendly tuk-tuk to explore Lisbon's famously steep streets in style. Your driver/guide will share fascinating details about the capital as they take you to some fabulous lesser-known areas and stop at the best viewpoints to soak in breathtaking panoramic views. 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

Lisbon's grand Rossio Square

There's no better way to get to the heart of historic Lisbon than by exploring it on foot. In the morning, head out on a walking tour led by an expert local guide, who will paint a vivid picture of the city as they point out major sights and share anecdotes about the colorful local lore. 

The tour includes stops at the upscale shopping area around Chiado Square and the 12th-century Lisbon Cathedral, 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: Cycle Lisbon's Riverside, Evening Food Tour

Cycle along the scenic riverfront to Belém
See more of Lisbon today as you venture out on a guided cycling tour to explore lesser-known neighborhoods and cross the mouth of the Tagus River to Cacilhas. Starting at the cosmopolitan city center, experience the buzz of this beautiful European capital as you pedal along atmospheric avenues and alleys, following the tranquil riverside toward Belém
After working up an appetite, acquaint yourself with Lisbon's culture through its traditional cuisine this evening with a gourmet food tour. Discover flavors and dishes created by a blend of Mediterranean traditions and exotic influences from all corners of the world. Try local specialties like pastéis de bacalhau (cod fritters) alongside glasses of refreshing Vinho Verde wine as you get to know the city's authentic neighborhoods and historic center, home to some of Lisbon's best restaurants, fado-houses, bars, and nightclubs.

Day 4: Transfer to Coimbra via Nazaré & Alcobaça 

The beautiful view of Nazaré's beach from above
Views across Nazaré's sweeping beaches
Today, your driver will take you north toward Coimbra, stopping at some of the region's best cultural and historical sites en route. Your first port of call is the fishing town of Nazaré, where you'll meet a local guide for an introduction to this charming coastal spot. Explore the 14th-century Sanctuary of Nossa Senhora da Nazaré, then ride the funicular up to the 12th-century Chapel of the Memory for spectacular views of the area. Scope out the epic breakers beneath the lighthouse of Farol da Nazaré, where the largest wave in the world was surfed in 2020.

After a fantastic seafood lunch and stroll through town, you'll meet your driver and continue on your way. The next stop is Alcobaça, where you can stand in awe of the ornate stonework and impressive architecture of the magnificent 12th-century Monastery of Alcobaça, the first Gothic building in Portugal. You'll have time to linger at this UNESCO World Heritage site before meeting your driver to continue north to riverside Coimbra, the country's former medieval capital and home to one of Europe's oldest universities.

Day 5: Transfer to the Douro Valley

Coimbra's idyllic riverside setting

Take some time this morning to discover more of Coimbra. Located on a hilltop overlooking the Mondego River, you'll find impressive views, beautiful monuments, and charming streets around every corner of this medieval city. If time permits, pay a visit to the UNESCO-listed University of Coimbra and its Joanine Library—a Baroque spectacle that houses over 56,000 rare and important works.

Then it's time to meet your driver and get back on the road, traveling north out of the city for two hours to reach the rolling hills and winding rivers of the Douro Valley. Considered the world's oldest demarcated wine region, the steep, terraced vineyards here are famous for producing some of Portugal's finest wines. Upon arrival at your hotel, settle in for an evening of peaceful nature and fresh air among the vines.

Day 6: Douro Valley Wine Tour & River Cruise

Terraced vineyards overlooking the winding Douro River
Get under the skin of the Douro Valley today, a fertile grape-growing region that produces some of Portugal's best wines. Meet your guide and start the full-day excursion with a visit to a quinta (winery), where you'll tour the vineyards and production facilities and taste a selection of the valley's finest whites and reds. Continue to a nearby country town, where your guide will recommend the perfect restaurant for a leisurely lunch of traditional Portuguese cuisine, followed by another wine tasting.
Then it's time to hop aboard a riverboat for an hour-long 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, your guide will return you to your hotel to spend the evening at your leisure.

Day 7: Transfer to Porto, Portugal's Second City

Porto's riverfront Ribeira district

Meet your driver this morning and set off west toward Porto. Along the two-hour journey, you'll enjoy more of the spectacular scenery of the Douro Valley region before reaching Portugal's second-largest city. After settling into your hotel, take the rest of the day to enjoy this 2,000-year-old metropolis 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 8: Enjoy a Private Walking Tour of Porto

The intricately-tiled facade of Porto's Igreja do Carmo

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. 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 as you please.

Day 9: Fly to Funchal & the Island of Eternal Spring

Fly to the lush volcanic landscapes of Madeira
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. Known as the "Island of Eternal Spring," 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 transfer you to your accommodation on this idyllic island, where you'll have the rest of the day to rest.

Day 10: Madeira Off-Road Jeep Trip & Wine Tour 

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 up to the Serra d'Agua viewpoint, located in a lush valley at the center of the island. The next stop is Encumeada, which offers epic mountain views, and is a crossroads that connects the different directions of the island: Ribeira Brava (south), São Vicente (north), and Paúl da Serra (west). An off-road adventure begins as you journey deeper into the Chão dos Louros Forest Park, which gets its name from its abundance of bay trees and fantastic views of Madeira's north side.

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 Madeira's wine traditions, culture, and production. End the tour with a drive to Cabo Girão, the highest cliff in Europe and the second highest in the world at 1,866 feet (589 m). This death-defying precipice has a suspended glass floor viewpoint for those without a fear of heights, which offers a spectacular panoramic view over the Atlantic Ocean, Câmara de Lobos, and Funchal.

Days 11-12: Explore the History & Nature of Madeira

Ocean views from the Monte Palace Tropical Gardens

The next two days are free 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. Spend some more time getting to know Funchal with visits to 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 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 nearby include whale and dolphin-watching boat tours, scuba diving, and mountain biking.

Day 13: Fly to Lisbon & Transfer to Cascais

 Cascais' Praia da Ribeira beach
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.
Spend your afternoon settling in and exploring the area's spectacular beaches. Praia da Conceição and Praia da Duquesa form the central 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 pleasant stroll, follow the scenic coastal promenade to Praia do Tamariz, which has an atmospheric old fort overlooking the water.

Day 14: Day Trip to Sintra & the Estoril Coast

Palacio Nacional da Pena
 The colorful turrets of Palacio Nacional da Pena
Meet your guide this morning for a day trip to Sintra, a magical and memorable must-see on any visit to Portugal. Located just half an hour east of Lisbon, this resort town is known for its forested hills, upscale villas, and Moorish palaces. Start at the Palacio Nacional da Pena (Pena Palace), a 19th-century romanticist castle that blends Moorish and Portuguese late-Gothic architectural styles. Its canary-yellow towers perch above the pine forests of the Parque de Pena, where you'll stop next for a pleasant stroll around the abundant gardens.

You'll then have a break for lunch, at which point you can explore the historic village of Sintra and do some shopping and sightseeing. Then it's off to Sintra Cascais Natural Park. Some can't-miss spots in this area include the dramatic coastal cliffs of the Cabo de Roca, the Boca do Infierno, the long and inviting Guincho Beach, a popular surf spot, and the glamorous town of Estoril.

Day 15: Depart Portugal

Sunset over the Cabo Raso Lighthouse in Caiscais
After getting in some last-minute sun and beach time in Cascais, it's time to transfer to the Lisbon Airport for your departing flight. Safe travels and bon viagem!

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Map of Mainland Portugal & Madeira - 15 Days
Map of Mainland Portugal & Madeira - 15 Days