Portugal is the perfect destination for a luxurious and laid-back adventure. This 14-day itinerary takes you across the nation, from Lisbon to Porto via the Algarve coast and Alentejo countryside. Start in the capital with private e-bike and Segway tours, then venture south to the Algarve, where you'll sail and kayak around rock formations and sea caves. Head inland to ancient Évora for an ancient aqueduct hike, tick off Porto with a bridge climb and river cruise, and finish in seaside Cascais.


  • Discover Portugal's seafaring history with a private segway tour of Belém
  • Take a private catamaran cruise along the dramatic Algarve coastline
  • Hike along a Roman aqueduct as you explore the Alentejo countryside near Évora
  • Venture into the Douro Valley to taste your way through the ancient wine region
  • Stay in top 5-star hotels, including a converted palace and a luxe beachside resort

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Dinner at Cervejaria Trindade Lisbon
Day 2 Lisbon E-Bike Tour, Dinner & Fado Performance Lisbon
Day 3 Belém's Age of Discovery Segway Tour, Free Time in Lisbon Lisbon
Day 4 Day Trip to Sintra: Palaces, Parks & Coastline Lisbon
Day 5 Transfer to Lagos & the Algarve, Dinner at Luca's Rooftop Restaurant Lagos
Day 6 Boat Trip to Benagil Cave, Discover the Algarve's Beaches Lagos
Day 7 Kayaking Tour to Ponta da Piedade, More Beach Time Lagos
Day 8 Transfer to Évora & the Alentejo, Dinner at Tábua do Naldo Évora
Day 9 Água de Prata Aqueduct Guided Hike, Free Time in Évora Évora
Day 10 Transfer to Porto via Coimbra, Dinner at Brasão Porto
Day 11 Porto Walking Tour & Bridge Climb, Douro River Cruise Porto
Day 12 Day Trip to the Douro Valley: Wine Tasting & River Cruise Porto
Day 13 Transfer to Cascais via Nazaré & Óbidos, Dinner at Baía do Peixe Cascais
Day 14 Transfer to Lisbon, Depart  

Detailed Itinerary

Day 1: Arrive in Lisbon, Dinner at Cervejaria Trindade

Head out to explore Lisbon or unwind by the pool this afternoon (photo courtesy of The One Palácio da Anunciada)

Olá and welcome to Lisbon, the colorful capital of Portugal. On arrival, a private driver will be waiting to transfer you to one of Lisbon's newest 5-star hotels, The One Palácio da Anunciada. Set within a 16th-century palace, you'll spend the next four nights soaking up the luxurious interiors, which emphasize the building's original beauty. Drop your bags and explore the 27,000-square-foot (2,500 sq m) garden and its hundred-year-old dragon tree, then don your walking shoes and head out to get your bearings in the city.

You'll step out of the hotel close to Avenida Liberdade, Lisbon's chic tree-lined avenue with top restaurants and luxury boutiques. Follow the flow to Baixa-Chiado, where you'll find souvenir shops, small markets, and centuries-old sweets. If you still have energy to burn, continue to Praça do Comercio and the Tejo River, where you can watch sailboats and the sunset. For dinner, you have a reservation at Cervejaria Trindade, the city's oldest and most beautiful seafood restaurant, where you'll dine on the finest fresh shellfish and prawns plucked from the icy Atlantic Ocean.

Day 2: Lisbon E-Bike Tour, Dinner & Fado Performance

Luxury Meta: Up the Hills Private E-Bike Tour in Lisbon
E-bikes make easy work of Lisbon's hilly landscape

Those who know Lisbon's geography may think a bike tour is something worthy of an Olympic feat. But today, you'll take to the streets in the form of electric bikes. E-bikes make it surprisingly easy to ride and explore a handful of the city's seven hills. Your private ride will take in some of the most iconic places and highlight the best historic architecture in town over 2.5 hours—as your local guide shares cheeky curiosities and hidden spots along the way.

Return to your hotel to refresh ahead of this evening's special dinner experience. A private driver will collect you for the transfer to a fado house, where you'll experience one of Portugal's greatest art forms. Everything stops when fado is performed. Silence rules the room, the lights dim, and only then the show begins. More than a traditional style of music, fado is an emotional experience that will be further enhanced with your creative and contemporary Portuguese meal. Enjoy a multicourse dinner with paired wines, then wait for the show to begin.

Day 3: Belém's Age of Discovery Segway Tour, Free Time in Lisbon

Luxury Meta: Private 3H Segway Sailor Tour in Belém - Portuguese Discoveries
Glide through history and heritage in the shadow of Jerónimos Monastery

Rev up your adventure engines and roll through Lisbon's vibrant streets on an electrifying Segway tour. This morning you'll explore Belém's famous monuments with a private guide, who will share stories of how great Portuguese explorers embarked on dangerous and ambitious voyages. You'll start in Praça do Comercio and cruise along the riverside, soaking up beautiful landscapes and good vibes as you pass under the Abril de 25 Bridge. Then, continue past the Monument to the Discoveries and the Jerónimos Monastery, and finish with the original Portuguese custard tart.

The rest of the day is yours to explore Lisbon as you wish. This afternoon you might like to catch the number 28 tram to the top of Graça, then walk down through the twisting and cobbled streets of Alfama, pausing at the São Jorge Castle, Santa Luzia, and Portas do Sol lookouts, and the Sé Cathedral. Closer to sunset, return to the water and enjoy a drink by the river or join a sunset sailing tour.

Day 4: Day Trip to Sintra: Palaces, Parks & Coastline

Sintra's hilltop setting near Lisbon
Palácio da Pena (Pena Palace) sits on top of Sintra's highest peak near Lisbon

Today you'll experience the magic of Sintra and its crown jewel, Pena Palace, in the lap of luxury. A private driver will collect you for a full-day tour through the area's enchanting landscapes and historic wonders. Journey from Lisbon to the picturesque mountain town, starting with a visit to the fairy-tale Palácio da Pena (Pena Palace). After exploring the famous red-and-yellow Disney-like palace and Pena Park, venture into the historic Sintra village for lunch and delicious local pastries. Continue exploring winding roads through the verdant Sintra-Cascais Natural Park, then head to the coast.

On the return journey to Lisbon, your private driver will stop at the towering cliffs of Cape Roca, the westernmost point of continental Europe, and then follow the coast south. Cruise past the beautiful Guincho Beach, a paradise for surfers and windsurfers, and stroll through Cascais, an upmarket resort town made popular in the 19th century. For dinner, you might like to try SEEN by Olivier at your hotel or take in the sunset with a drink at Sky Bar.

Day 5: Transfer to Lagos & the Algarve, Dinner at Luca's Rooftop Restaurant

Check into your 5-star beach resort just steps from the Algarve coast (photo courtesy of Palmares Beach House)

After breakfast this morning, a private driver will transfer you to the Algarve, a three-hour drive south. Your final destination is Lagos, a charming coastal destination with a walled Old Town, a pretty harbor, dramatic sandstone cliffs, beautiful beaches, authentic restaurants, and buzzing nightlife. While the Algarve is a popular destination for summer holidays, Lagos still retains its distinctive character and laid-back charm. Check into the Palmares Beach House, an adults-only 5-star hotel with only 20 rooms and its own golf course, located just 2,300 feet (700 m) from the beach.

Use the rest of the afternoon to laze on the nearby beach at Meia Praia or play a round of golf. For dinner, take a taxi to the other side of town. Luca's Rooftop Restaurant offers some of the best Portuguese food in Lagos with unmatched ocean views.

Day 6: Boat Trip to Benagil Cave, Discover the Algarve's Beaches

Luxury Meta: Private Boat Trip to the Timeless View of the Benagil Caves
Take your pick of the Algarve's golden beaches this afternoon
Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

Explore the Algarve's iconic soaring cliffs and curious coastal formations today with a private boat cruise. Depart Lagos destined for the world-famous Benagil Cave. Along the way, you'll pass the beaches of Carvoeiro and Algar Seco, as well as the Alfanzina Lighthouse and Praia da Marinha's stunning views. Relax on the catamaran's twin sunbathing nets and enjoy the gentle breeze as you cruise along this dramatic coastline, exploring secret spots only accessible by sea. Anchor in the coves of João de Arens to swim and snorkel before returning to shore.

The rest of the day is yours to relax and soak up the Algarve's warm Mediterranean climate. The 96-mile-long (155 km) coastline has dozens of beaches, big and small, where you can enjoy the soft sand and sun's rays and take a refreshing dip in crystal-clear waters. From secluded coves nestled between towering cliffs to vibrant stretches with beachside bars and water sports, there's the type of beach for every traveler—perhaps you spotted one you'd like to explore from the boat this morning.

Day 7: Kayaking Tour to Ponta da Piedade, More Beach Time

Ponta da Piedade
Kayak around a maze of unique sea caves at Ponta da Piedade

The sea caves around Ponta da Piedade in Lagos are among the most popular and unmissable attractions on the Algarve coast. In this area, you'll find a wide variety of rock formations resembling familiar figures, such as the Titanic, the Elephant, and the Cathedral. This morning you'll board a private, which will take you to the place where the kayaking begins. Then an experienced guide will navigate through the labyrinths of caves, grottoes, and rock formations as you paddle along this remarkable piece of coast, learning its secrets, culture, and history.

After kayaking, the rest of the day is yours to enjoy at your pace. Keep exploring the Algarve's famous beaches, return to the green for another round of golf, or seek out an alternative adventure. You could organize a private tour to Sagres, where you can watch the sun sink into the Atlantic Ocean while enjoying a glass of Portuguese wine with bread and chorizo from the clifftop, or visit a traditional winery to taste native grape varietals beneath a 2,000-year-old olive tree.

Day 8: Transfer to Évora & the Alentejo, Dinner at Tábua do Naldo

Enjoy your pool time with a backdrop of Roman history in Évora (photo courtesy of M'ar de Ar Aqueduto)

After a final morning on the Algarve, it's time to make the journey north to Évora, the capital of the Alentejo. In this region, time stands still, life moves slower, and the people are the warmest. Switch off when you enter the ancient town walls of Évora, a three-hour transfer from Lagos, and check into the luxurious 5-star M'ar de Ar Aqueduto. Your room sits within a restored 16th-century palace, complete with the original chapel, vaulted ceilings, and Manueline windows. Take your time to refresh and relax by the hotel pool, which overlooks the 16th-century aqueduct that circles the city.

Évora is a UNESCO World Heritage Site and the cultural and gastronomic heart of the Alentejo. It's easy to explore the ancient, compact city on foot, so venture out to explore. Wander past the well-preserved ruins of the Templo Romano, proof of Évora's Roman past; discover the hauntingly beautiful Chapel of Bones, an eerie ossuary adorned with human bones; delight in the grand Sé de Évora (Évora Cathedral); and enjoy the lively Praça do Giraldo square. For dinner, Tábua do Naldo serves up great cocktails and Portuguese petiscos (tapas).

Day 9: Água de Prata Aqueduct Guided Hike, Free Time in Évora

See more of Évora with a hike through the surrounding Alentejo countryside

Today you'll embark on a journey back in time with an evocative guided hike along the Évora's Água de Prata Aqueduct. Led by a passionate local guide, you'll traverse this historic engineering marvel, which was started by King João III in 1532, and take in sweeping vistas of Évora and the picturesque Alentejo countryside. Discover the aqueduct's ancient roots and uncover hidden archaeological gems as you follow the lengthy water channel across the city and countryside through oak and cork forest. This hike blends nature, history, and local culture.

Back in the city, find a local tavern or tasca for a casual lunch and the chance to try hearty Alentejo dishes, such as grilled black pork and seracaia (a flan-like dessert). Spend the rest of the afternoon wandering between whitewashed houses and shopping for artisan goods, or kick by beside the hotel pool, where you can continue your admiration of the aqueduct from a sun lounger.

Day 10: Transfer to Porto via Coimbra, Dinner at Brasão

Views across the rooftops of Porto from your historic base (photo courtesy of Le Monumental Palace)

It's time to leave the tranquil Alentejo behind and make the journey north to Porto, Portugal's second-largest city. During the 3.5-hour transfer south you'll stop at the charming student city of Coimbra. At the very top of Portugal's medieval capital sits its most important monument—the University of Coimbra, one of the oldest in the world. When it opened in 1290, the first intellectuals arrived and made this the knowledge center of the country. Tour the still-functioning historic university, which has the UNESCO World Heritage seal and is housed within a former royal palace.

Continue to Porto, where you'll check into Le Monumental Palace, a 5-star hotel set within a gorgeous historic building from 1923. Drop your bags in your elegant, 1930s-inspired room, then set out to explore the capital of the north and the "Cidade Invicta" (Undefeated City) at sunset. You could slip into Rooftop Flores, a secret garden bar with views of the city, or venture down to the banks of the Douro River at Ribeira. For dinner, try Brasão, one of the best spots in the city to try a francesinha, Porto's famous meat-heavy sandwich. 

Day 11: Porto Walking Tour & Bridge Climb, Douro River Cruise

Porto's cityscape
See the city from different vantage points with a bridge climb and river cruise in Porto

Get to know the city of Porto and its most famous monuments on a three-hour private walking tour this morning. Your local guide will lead you past the Cathedral, Torre dos Clérigos, and the São Bento train station, famed for its elegant azulejo tiles. Along the way, hear stories of Porto's fascinating past, including its connections to the Knights Templar and Jewish history. From bustling, central squares to treasured secret corners, you'll quickly see why Portugal's second city is worthy of its UNESCO World Heritage Site designation

Later, get ready to experience some serious thrills when you ascend over the magnificent Arrábida Bridge. Whether you're an adrenaline junkie or simply after incredible panoramic views, this unusual climbing adventure takes you 213 feet (65 m) above the river on what was once the largest concrete arch in the world. After, you'll experience the bridge from another perspective when you board a private river cruise. For one hour, you'll sail along the Douro River, navigating the city's history and sights while enjoying local wine and traditional snacks.

Day 12: Day Trip to the Douro Valley: Wine Tasting & River Cruise

Douro Valley
Take an exclusive day trip to the beautiful Douro Valley and explore its famous wines

Explore the picturesque Douro Valley on a full-day private tour from Porto, where you'll explore elegant wineries, savor a delicious lunch at a renowned quinta (a country estate), and unwind on a scenic river cruise. Your driver will take you from the city streets to the vineyards and valleys of the famous wine country, which is the oldest demarcated wine region of the world, dating back to 1756. You'll spend the day visiting wineries and learning about the region's fascinating UNESCO-protected wine heritage as you walk through the vineyards and taste local varietals.

At lunch, you'll dive deeper into the region's winemaking heritage with a special tasting and sumptuous lunch at a local estate. Then it's time to hop aboard a boat for an hourlong private cruise down the tranquil Douro River. Relax and soak up the lush scenery of the valley, where the vines roll down to the riverbank while sipping on a glass of port wine. At the end of the day, return to Porto.

Day 13: Transfer to Cascais via Nazaré & Óbidos, Dinner at Baía do Peixe

Settle into 5-star luxury in a renovated 16th-century fortress (photo courtesy of Pestana Cidadela Cascais)

Today's final destination is Cascais, a former fishing village and 19th-century royal summer playground. A private driver will collect you from the hotel for the three-hour drive to the elegant beach town right next to Lisbon. En route, you'll stop by the fishing town of Nazaré, a coastal town famous for its long, sandy half-moon-shaped beach and some of the biggest waves in the world. Continue to the charming medieval walled village of Óbidos. Wander the maze of cobblestoned streets and try the local liqueur—ginjinha—a sweet, sour cherry drink often served in a chocolate cup.

Finally, check into your hotel, the 5-star Pestana Cidadela Cascais. Set in a 16th-century seafront fortress, the artsy hotel combines contemporary comforts and creativity within an unusual and luxurious historic setting. Freshen up, then step outside the hotel and into the Cascais Citadel. These 500-year-old fortifications were built to protect Lisbon from pirates and corsairs. Explore the Art District within the walls, then wander over to the historic center of Cascais for dinner. For an indulgent all-you-can-eat seafood affair, try Baía do Peixe and enjoy the waterfront views.

Day 14: Transfer to Lisbon, Depart

Wave goodbye to the blissful bays of Cascais
Wave goodbye to the blissful bays of Cascais

Your two weeks of luxury and adventure in Portugal come to an end today. Depending on the time of your flight, you may be able to squeeze in one more walk along the coastline of Cascais or perhaps pick up some last-minute souvenirs. At the designated time, you'll be collected from your hotel by a private driver and transferred to Lisbon's airport for your departing flight. 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 two weeks in Portugal in luxury, or discover the best time to visit Portugal.


Map of Luxury Adventure in Portugal: Lisbon, Lagos, Évora, Porto & Cascais - 14 Days
Map of Luxury Adventure in Portugal: Lisbon, Lagos, Évora, Porto & Cascais - 14 Days