Experience the laid-back luxury of Portugal with this 10-day trip that takes you from Lisbon to the coast and countryside. Start in the capital, where you'll explore the city with private e-bike and Segway tours. Take a day trip to mystical Sintra, then venture south to the Algarve to sail through the stunning Benagil Caves and paddle around Ponta da Piedade. Finally, head inland to Évora and cap off the adventure with a hike along an ancient Roman aqueduct.


  • Stay exclusively at luxurious 5-star hotels, including an adults-only golf retreat
  • Discover Portugal's seafaring history with a private Segway tour of Belém
  • Spend a day exploring UNESCO-listed Pena Palace in Sintra
  • Charter a private boat to Benagil Caves and kayak at Ponta da Piedade
  • Go on an evocative hike around the Água de Prata Aqueduct in Évora

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 Lisbon, Depart  

Detailed Itinerary

Day 1: Arrive in Lisbon, Dinner at Cervejaria Trindade

Wander down to Praça do Comércio, the gateway to Lisbon
Wander down to Praça do Comércio, the gateway to Lisbon

Olá and welcome to Lisbon, the colorful capital of Portugal. On arrival, a private driver will be waiting to transfer you to one of the city's most prestigious 5-star hotels, the Tivoli Avenida Liberdade. This landmark hotel has seen celebrities, heads of state and royalty walk through its doors since opening in 1933, and over the next four nights, you'll enjoy its exceptional hospitality (and views) too. Drop your bags and wander down to the oasis swimming pool and tropical garden, then go explore Lisbon.

You'll step out of the hotel and onto 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 have your walking shoes on, 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 can taste 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 famous 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. Your active local guide will share some 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 memorable dishes with paired wines, then wait for the show to begin.

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

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 sailboat.

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

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 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

Views over the coast from the 5-star Palmares Beach House terrace

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 just 20 rooms and its own golf course located only 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
Benagil Cave is sometimes called a cathedral because of its huge size and arches

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 rugged 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

Devote this afternoon to choosing your favorite of the Algarve's golden beaches

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 catamaran, 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

Charming streets of Evora
Évora's whitewashed streets with yellow trim hide countless landmarks

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

Discover the Past and Present on a Guided Hike Tour Over the Água de Prata Aqueduct in Évora!
The past collides with the present at the Água de Prata Aqueduct in Évora

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 Lisbon, Depart

Beautiful and compact Évora is filled with landmarks and surrounded by gorgeous countryside
Beautiful and compact Évora is filled with landmarks and surrounded by gorgeous countryside
Your luxurious 10-day adventure in Portugal comes to an end today. Depending on the time of your flight, you may be able to squeeze in one last swim before your return 90-minute transfer to Lisbon's airport. At the designated time, you'll be collected from your hotel by a private driver and transferred to the airport for your departing flight. Safe travels!

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Map of Luxury Adventure in Portugal: Lisbon, Lagos & Évora- 10 Days
Map of Luxury Adventure in Portugal: Lisbon, Lagos & Évora- 10 Days