Highlights
- Stay in a succession of historic 5-star hotels, palaces, and forts
- Experience the haunting notes of fado music with a dinner show
- Access premium port wines with an exclusive cellar and tasting experience
- Go wine tasting and river cruising in the UNESCO-listed Douro Valley
- Sample elevated Portuguese favorites at Michelin-starred restaurants
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Lisbon, Free Time to Explore | Lisbon |
| Day 2 | Lisbon Walking & Tasting Tour, Dinner & Fado Performance | Lisbon |
| Day 3 | Day Trip to Sintra's Palace & Parks, Dinner at Fifty Seconds Restaurant | Lisbon |
| Day 4 | Transfer to Porto via Óbidos & Nazaré | Porto |
| Day 5 | Gastronomy & Culture Tour, Port Cellar Tasting, The Yeatman Restaurant | Porto |
| Day 6 | Day Trip to the Douro Valley, Wine Tasting & River Cruise | Porto |
| Day 7 | Transfer to Évora & the Alentejo via Coimbra | Évora |
| Day 8 | Historic Walking Tour of Évora, Dinner at Divinus | Évora |
| Day 9 | Transfer to Cascais, Dinner at Fortaleza do Guincho | Cascais |
| Day 10 | Transfer to Lisbon, Depart |
Detailed Itinerary
Day 1: Arrive in Lisbon, Free Time to Explore
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 has seen celebrities, heads of state, and royalty walk through its doors since opening in 1933, and over the next three 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 step out to explore.
Lisbon is one of Europe's most charming capitals, with friendly locals, delicious cuisine, and gorgeous terracotta-roofed buildings that cling haphazardly to its famous seven hills. You'll step out of the hotel and onto Avenida Liberdade, Lisbon's chic tree-lined avenue that houses top restaurants and luxury boutiques. Follow the flow toward Baixa-Chiado, where you'll find souvenir shops, small markets, and centuries-old delicacies. If you have your walking shoes on, continue down to Praça do Comercio and the Tejo River, where you can watch sailboats and the sunset.Day 2: Lisbon Walking & Tasting Tour, Dinner & Fado Performance
Today you'll experience the best of Lisbon with a private gastronomic walking tour. As you explore the historic neighborhoods with a knowledgeable guide, you'll pause to taste gourmet delights. Wear good walking shoes to traverse the hilly streets as you visit iconic landmarks and learn about the city's history and culture. You'll explore Baixa-Chiado, where the great 20th-century writers and philosophers used to gather, and Alfama, one of the oldest districts in Lisbon. You'll end at a beautiful winery where you'll taste a range of wines paired with Portuguese delicacies.
After lunch, 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 elevated classics with paired wines, then wait for the show to begin.
Day 3: Day Trip to Sintra's Palace & Parks, Dinner at Fifty Seconds Restaurant
Today you'll experience the magic of Sintra and its crown jewel, Pena Palace, in a 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. Cruise past the beautiful Guincho Beach, a paradise for surfers and windsurfers. Back in Lisbon this evening, you have a reservation at Fifty Seconds, a Michelin-starred restaurant with breathtaking panoramic views and exquisite food. The chef marries Portuguese flavors with international influences, resulting in a memorable meal.
Day 4: Transfer to Porto via Óbidos & Nazaré
After breakfast at your hotel, it's time to make the journey to Porto, Portugal's second-largest city. A private driver will make a day of the three-hour drive by stopping at the medieval village of Óbidos and the fishing town of Nazaré. An hour north of Lisbon, Óbidos is a charming medieval walled village where the historic center is a small maze of cobblestoned streets and flowerbeds, and the whitewashed houses are livened up with dashes of vivid yellow and blue paint. Try the local liqueur—ginjinha—a sweet, sour cherry drink often served in a small chocolate cup.
Continue north to Nazaré, where you'll stop for lunch. The coastal town is famous for its long, sandy half-moon-shaped beach and some of the biggest waves in the world. Admire the beautiful wooden fishing boats and the local women who still wear the traditional seven skirts. If you're lucky, the world-record-breaking waves might be pumping, attracting top surfers from all over the world. Finally, continue to Porto, where you'll check into The Yeatman, a timeless and elegant 5-star hotel with spellbinding views over Porto's Old Town from its location across the river in Gaia.
Day 5: Gastronomy & Culture Tour, Port Cellar Tasting, The Yeatman Restaurant
Chat with a local specialist who can help organize your trip.
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. From bustling central squares to treasured secret corners, you'll quickly see why Portugal's "capital of the north" is worthy of its UNESCO World Heritage Site designation. Best of all, as you explore, you'll get a taste of the city as you pause to try traditional jams and jellies, port wines, cheeses and sausages, salt cod, and rojões (fried pork).
No visit to Porto is complete without sampling the local wines. Port wine is born in the Douro Valley, but the wine ages at cellars in Gaia, across the river from Porto. This afternoon you'll take a private tour of a wine cellar to learn about the famous export, then taste special port wines that have aged for 10, 20, 30, and 40 years. After, return to your opulent hotel for a gastronomic journey. With two Michelin stars and panoramic views of Porto, enjoy a romantic meal as the sun sets at The Yeatman Restaurant.
Day 6: Day Trip to the Douro Valley, Wine Tasting & River Cruise
Explore the picturesque Douro Valley on a full-day 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. A private driver will take you from the city streets to the vineyards and valleys of this 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 wines.
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 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 7: Transfer to Évora & the Alentejo via Coimbra
It's time to head south again, making the journey to Évora, the capital of the Alentejo. During the four-hour transfer, you'll stop at the charming student city of Coimbra. At the very top of Portugal's medieval capital sits one of the most important monuments—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, then continue to Évora.
The Alentejo region is a place where time stands still, life moves slower, and the people are the warmest. Switch off when you enter the ancient town walls of Évora. Soon you'll discover the rich treasures and gastronomic heritage that lie between the whitewashed, yellow-trimmed houses, including the Templo Romano and the Chapel of Bones, but for now, 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.
Day 8: Historic Walking Tour of Évora, Dinner at Divinus
Évora is a UNESCO World Heritage site and the cultural and gastronomic capital of the Alentejo region. After breakfast today, you'll explore this ancient, compact city with a local expert. Wander past the well-preserved ruins of the Templo Romano, proof of Évora's Roman past, and witness the golden age of Portuguese maritime discoveries. Discover the hauntingly beautiful Chapel of Bones, an eerie yet fascinating ossuary adorned with human bones; delight in the architecture of the Sé de Évora (Évora Cathedral); and enjoy the grandeur of Praça do Giraldo, the city's lively plaza.
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 relax by the hotel pool, which overlooks the 16th-century aqueduct that circles Évora. Tonight you'll dine at Divinus, an upmarket restaurant at the Convento do Espinheiro, a 15th-century convent turned 5-star hotel. Born and raised in the Alentejo, chef Jorge Peças reinterprets regional dishes in a fine dining setting.
Day 9: Transfer to Cascais, Dinner at Fortaleza do Guincho
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 two-hour drive to the elegant beach town right next to Lisbon. Cascais attracted a summer-dwelling artistic community in the 1930s and has continued to charm locals and visitors since. 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 a late lunch. This evening you'll dine at Fortaleza do Guincho, a Michelin-starred restaurant set within a historic fortress with breathtaking views of the ocean and Guincho Beach. Chef Gil Fernandes puts an emphasis on seafood and Portuguese gastronomy, showcasing the freshest catches from the Atlantic Ocean.
Day 10: Transfer to Lisbon, Depart
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