Explore Portugal's iconic landscapes and colorful cities on this 16-day trip for culture and nature lovers. Kick things off in Porto with a food tour, then discover the city in style in a vintage car. With plenty of free time in between, you'll sample port wine and hop on a river cruise in the Douro Valley, dive into Lisbon's traditional fado music, cycle past the castles of Sintra, and relax on the golden beaches of the Algarve.


  • Find wild horses in Peneda-Gerês National Park
  • Cook regional delights on a local farm near Évora
  • Ride the Elevador de Santa Justa on a Lisbon Tour
  • See playful dolphins on a cruise to Benagil Cave
  • Watch the sunset over the Atlantic in the Algarve

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Porto, Food & Wine Tour  Porto
Day 2 Vintage Car Tour in Porto, Explore at Leisure Porto
Day 3 Hike in Peneda-Geres National Park Porto
Day 4 Transfer to the Douro Valley, Vineyard Tour Douro Valley
Day 5 Cruise the Douro River, Explore at Leisure Douro Valley
Day 6 Transfer to Evora via the Convento de Cristo & Almourol Castle Évora
Day 7 Regional Cooking Class, Explore Évora Évora
Day 8 Transfer to Lisbon, Fado Music & Dinner Lisbon
Day 9 Lisbon Walking Tour, Explore at Leisure Lisbon
Day 10 Discover Sintra by Bicycle Lisbon
Day 11 Transfer to Lagos, Explore the Algarve Region Algarve
Day 12 Algarve Beaches Day, 4WD Sunset Tour Algarve
Day 13 Regional Tour of the Algarve & Liqueur Tasting Algarve
Day 14 Benagil Cave Cruise, Dolphin-Watching Tour Algarve
Day 15 Visit Igreja de São Lourenço, Transfer to Lisbon Lisbon
Day 16 Depart Lisbon  

Detailed Itinerary

Day 1: Arrive in Porto, Food & Wine Tour 

Sample local delights in Porto, like pastel de nata and port wine

Welcome to Porto, the second-largest city in Portugal. Meet your driver at the airport for a transfer to your hotel. Refresh, then join a three-hour gastronomic tour with a local expert. Visit family-owned shops, restaurants, and cafés to learn about Porto's culinary culture and sample local dishes, such as bacalhau à brás—shredded cod fish with potatoes, or francesinha—Porto's traditional sandwich.

Wash everything down with the city's beloved drink, port wine, from the nearby Douro Valley—sample three different versions, including a vintage wine that will excite your taste buds. If you're not too full, end the tour with pastel de nata, a flaky pastry with creamy custard filling. Though commonly associated with Lisbon, you'll find delicious versions of it in Porto before returning to the hotel.

Day 2: Vintage Car Tour in Porto, Explore at Leisure

Head to the upscale district of Foz do Douro to explore the charming streets

Explore Porto in style today in a vintage 1920s car on a three-hour guided tour. Choose between the fishing village of São Pedro da Afurada, with its cobblestone streets and colorful houses adorned with fishing nets, or coastal Foz do Douro, with its trendy boutiques, elegant mansions, and inviting cafés. Whichever you choose, the tour ends at a port cellar for a guided tasting of the city's fortified wines.

After lunch, spend the afternoon exploring Porto at leisure. Marvel at views of the double-decked Dom Luís I Bridge from the UNESCO-listed Ribeira area with its colorful dockside houses on the Douro River. Wander the maze of windy streets behind, or immerse yourself in history at the Sé do Porto, an impressive cathedral showcasing a blend of Romanesque and Gothic architecture.

Day 3: Hike in Peneda-Geres National Park

Discover waterfalls and wild horses in Parque Nacional Peneda-Gerês

Lace up your hiking shoes and enjoy a hearty breakfast, ready for a full-day trek through Parque Nacional Peneda-Gerês. Transfer 1.5 hours north to the national park and follow your guide down one of the meandering trails through dense forest. Cross crystal-clear streams to cascading waterfalls for a refreshing swim if the weather is right. Lay on the rocks to dry off before continuing down the path.

Learn about the diverse flora and fauna, and keep an eye out for wild horses or grazing herds of endangered garrano ponies. Trek to the park's best observation decks for panoramic views of the expansive valleys, lush landscapes, and granite mountain peaks, stopping for a picnic lunch on the way. After a full day, rest at your hotel before dining at a local tasca (traditional restaurant). 

Day 4: Transfer to the Douro Valley, Vineyard Tour

Sample the Douro Valley's variety of port wines at a local vineyard

Trade the bustling city for a lush natural landscape on today's 1.5-hour transfer to the Douro Valley—a fertile grape-growing region renowned for its wines. Settle into your hotel, then set off on a nearby winery tour. 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 used 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 skill of the winemaker. After lunch, enjoy a stroll among the vines and the view of the Douro River before returning to your hotel. 

Day 5: Cruise the Douro River, Explore at Leisure

Admire the terraced landscape on a cruise down the Douro River

After breakfast, spend your morning at leisure exploring the area. Hop aboard the historic Douro Railway, which winds its way through the valley's picturesque scenery. Sit back and relax as you pass by terraced vineyards, quaint villages, and ancient landmarks. Or, visit the Douro Museum to browse the artifacts, interactive displays, and multimedia presentations detailing the region's history.

After lunch, explore the valley from the water on a boat trip down the meandering Douro River. Jump on board and cruise down the tranquil waterway surrounded by terraced hills adorned with rows of grapevines. Look out for charming villages and historic estates showcasing the region's rich winemaking history. After the two-hour cruise, the rest of the day is yours to spend as you wish.

Day 6: Transfer to Evora via the Convento de Cristo & Almourol Castle

Wander through the 12th-century Convento de Cristo on your way to Évora

Say goodbye to the Douro Valley this morning as you set off on a full-day transfer south to the UNESCO-listed city of Évora, nestled in the lush Alentejo region. Break up the 4.5-hour drive with a two-hour self-guided visit to the Convento de Cristo, a 12th-century Knights Templar stronghold in Tomar. Explore the sprawling complex and wander the vast cloisters, chapels, and courtyards.

Visit the round church in the center to admire its Roman and Gothic-style architecture, then continue to Almourol Castle, perched atop a small rocky island in the Tagus River. Hop in a boat across the river and discover the castle's well-preserved battlements, stone walls, and square towers that blend Moorish and Templar architectural influences.

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Enjoy panoramic views of the surrounding river and undulating countryside from the towers before completing the drive to your hotel in Évora. After refreshing, the rest of the evening is yours to spend as you wish. You can head to the city's main square, Praça do Giraldo, to browse the collection of shops and enjoy the lively atmosphere as you dine in an outdoor restaurant.

Day 7: Regional Cooking Class, Explore Évora

Admire the Templo Romano Évora's Corinthian columns

Delve into the rich culinary traditions of the Alentejo region today by taking a 2.5-hour cooking class at a nearby farm nestled in the countryside. Handpick fresh, seasonal produce and herbs, then follow your host to the kitchen to learn how to prepare regional appetizers, fish and meat dishes, and a dessert. You can sit down to enjoy lunch as a group before you return to the city to explore on your own.

Begin at the Templo Romano Évora, also known as the Temple of Diana, with its well-preserved Corinthian columns dating back to the first century CE. Wander the historic center's cobblestone streets to discover the ornate Igreja de São Francisco and marvel at its intricate gold-covered woodwork. Don't miss the eerie yet fascinating 16th-century Capela dos Ossos, adorned with human bones and skulls.

Outside of Évora, you'll find fascinating megalithic monuments dating back thousands of years when early hunter-gatherer communities thrived on the vast Alentejo Plains. Choose from over 10 sites scattered across Alentejo—a hotspot of ancient history. In the evening, wander down Rua João de Deus and pick from the authentic local restaurants for dinner.

Day 8: Transfer to Lisbon, Fado Music & Dinner

Spend some time exploring Lisbon on your own, stopping at the Torre de Belém

This morning, exchange one iconic city for another with a 1.5-hour transfer west to Portugal's capital, Lisbon. After settling into your hotel, venture down to Belém, a historic district on the banks of the Tagus River. Stroll along the waterfront to the 16th-century fortress, Torre de Belém (Belém Tower), with its intricate Manueline details. Explore the interior's maritime exhibits, then climb to the top for panoramic views.

Continue to the UNESCO-listed Jerónimos Monastery, whose facade features maritime motifs, celestial imagery, and botanical elements. In the evening, meet your guide in the bohemian Bairro Alto district for dinner at one of the city's best fado restaurants, where emotive fado performers serenade you with melancholic music and haunting melodies accompanied by traditional Portuguese guitars.

Day 9: Lisbon Walking Tour, Explore at Leisure

Ascend to the Bairro Alto district on the Elevador de Santa Justa

Spend the morning on a three-hour guided walking tour visiting Lisbon's iconic sites. Start at the Elevador de Santa Justa, a wrought-iron elevator that ascends from the Baixa district to the elevated Bairro Alto. Soak in the views of the cityscape and the distant Tagus River, then stroll the cobblestone streets lined with colorful buildings, eclectic boutiques, and traditional houses.

Continue to the cultural and artistic Chiado neighborhood, where historic charm blends seamlessly with modern sophistication. Admire the vibrant tapestry of shops, theaters, and literary cafés as you pass through picturesque squares like Largo do Chiado. After the tour, enjoy lunch in one of the squares (try a bifana pork sandwich) and spend the rest of the day as you wish.

You can visit the city's oldest district, Alfama. Follow the labyrinthine alleyways to the 12th-century São Jorge Castle, perched atop one of the highest hills in the city. Explore the ancient courtyards and battlements, then take in the spectacular view below. In the evening, visit one of the many taverns or restaurants in the neighborhood and listen as it comes alive with traditional fado music. 

Day 10: Discover Sintra by Bicycle

Cycle past the winding walls of Sintra's Castelo dos Mouros

Get ready for an active full-day guided cycling adventure in the UNESCO-listed town of Sintra today, just 30 minutes outside of Lisbon. Beginning at the Palácio Nacional de Sintra, a medieval palace that blends Moorish, Gothic, and Manueline styles, you'll cycle past lush gardens, enchanting palaces, and ancient ruins. Continue pedaling along the cobblestone streets, past vibrant markets and cafés.

When you reach Parque Natural de Sintra-Cascais, take in the vistas of hidden beaches and dramatic cliffs. Then, head to an observation deck for unobstructed views of the colorful Palácio da Pena (Pena Palace) and the historic Castelo dos Mouros. Conclude your ride at the tranquil Sanctuary of Peninha, nestled atop a hill with far-reaching Atlantic views. Explore the charming chapel before returning to Lisbon.

Day 11: Transfer to Lagos, Explore the Algarve Region

Sample four distinctive Algarve wines at Morgado do Quintão

Bid farewell to Lisbon today as you head three hours south by private transfer to Lagos, a seaside town nestled in the Algarve region. On the way, stop at Morgado do Quintão to stroll through the vineyard and discover the art of winemaking. Enjoy a delightful lunch under a 2,000-year-old olive tree, savoring a flight of the estate's distinctive Algarve wines. Then, continue to your hotel in Lagos.

Once refreshed, head to a local beach, like Praia do Pinhão, or lace up your shoes and explore the coastline on an 8-mile (12 km) hike down the Seven Hanging Valleys Trail. Follow the scenic clifftop path through seven beautiful valleys and watch as mesmerizing rock formations, natural arches, and sea caves unveil themselves below you. In the evening, check out a waterfront restaurant for dinner. 

Day 12: Algarve Beaches Leisure Day, 4WD Sunset Tour

Spend a day relaxing on the golden sands of Praia Dona Ana

Discover the Algarve's picturesque coastline, dramatic cliffs, hidden caves, and golden sand beaches at your leisure today. Start with a 20-minute walk to Praia Dona Ana, a postcard-perfect beach surrounded by limestone cliffs and turquoise waters. Relax on the fine sand, take a dip in the calm shallow waters, snorkel, or, if adventurous, rent a kayak or standup paddleboard to see the nearby sea caves.

After your beach day, meet your guide at the hotel for a 40-minute drive in a 4WD to Cabo de São Vicente—the most southwesterly point in continental Europe. Discover the history of Sagres and enjoy a spectacular Atlantic Ocean sunset as you sit back in a local restaurant, sampling Portuguese wine and nibbling on fresh bread with chouriço (smoked pork sausage) before driving back to Lagos.

Day 13: Regional Tour of the Algarve & Liqueur Tasting

Sample a delicious glass of fruit brandy paired with local desserts

Go off the beaten track today on a guided tour to discover the picturesque landscape, charming villages, and slower pace of life in the Algarve countryside. Drive past vast orchards of citrus and almond trees, learn about the Algarve's rural traditions, and stop at small streetside markets to sample fresh local honey and homemade medronho, a strong fruit brandy made using traditional methods.

Head up Mount Fóia, the Algarve's highest peak at 2,959 feet (902 m). At the summit, enjoy 360-degree views of lush forests, terraced hillsides, and coastal plains, then stop for lunch at a mountain restaurant, where you'll finish with a sampling of local desserts and a cup of medronho and melosa (honey liqueur). On the way back to your Lagos hotel, stop to swim at a hidden beach to relax on the golden sand.

Day 14: Benagil Cave Cruise, Dolphin-Watching Tour

Cruise to the Benagil Cave carved into the golden limestone cliffs

Don your bathing suit for a catamaran cruise to the famed Benagil Cave, accessible only by sea. En route, soak in the beauty of Praia da Marinha and the Farol de Alfanzina lighthouse. Marvel at the cave's golden limestone cliffs from the boat or swim ashore and bask under the natural skylight. Then, cruise on to set anchor in the coves of Praia João de Arens to swim, snorkel, or paddleboard.

This afternoon, spot resident dolphin pods on a guided marine-wildlife boat tour out in the open sea. With your expert captain at the helm, you'll most likely see common and occasional bottlenose dolphins, but keep your eyes peeled for minke whales, sea turtles, and even orcas, depending on the time of year you visit. After a day on the water, cruise back to shore and return to the hotel to relax.

Day 15: Visit Igreja de São Lourenço, Transfer to Lisbon

Discover the ominous Capela dos Ossos within the Igreja de São Lourenço

Delve into the Algarve's history and culture in the town of Almancil this morning. Catch the train 1.5 hours east and visit Igreja de São Lourenço. This 18th-century Baroque church showcases blue handpainted azulejos—traditional Portuguese tiles, and inside, you'll discover the eerie Capela dos Ossos, a chapel adorned with human bones and skulls arranged in decorative patterns.

Afterward, take a 10-minute taxi to Cerro da Vila, the well-preserved ruins of a Roman villa. Wander the archaeological site, looking for remnants of intricate mosaics, thermal baths, and a fish-salting factory. Browse the museum's collection of pottery and decorative artifacts before returning to your hotel for a transfer to the train station, a 3.5-hour train to Lisbon, and then a transfer to your hotel.

Day 16: Depart Lisbon

Wander through the Time Out Market for souvenirs on your last day

After 16 days of exploring some of Portugal's best landmarks and natural landscapes, your journey comes to a close today. If you have time before your flight, explore more of the city on your own. Visit the Mercado da Ribeira, better known as the Time Out Market, to search for some last-minute souvenirs or sample local delights, like bifana, a sandwich filled with marinated pork cutlets.

Then, return to your hotel and meet your driver for a transfer to the airport in time for your flight. Safe travels!

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Map of Portugal Cities & Landscapes: Porto, Douro Valley, Evora, Lisbon & the Algarve - 16 Days
Map of Portugal Cities & Landscapes: Porto, Douro Valley, Evora, Lisbon & the Algarve - 16 Days