Arrive Lisbon, Penha Longa, The Moorish Castle

Your Portuguese journey begins with a private transfer to the luxurious Penha Longa Resort, a Ritz-Carlton property in the UNESCO world heritage town of Sintra. From there, the choice is yours on how to begin your Portuguese adventure: explore the dramatic Moorish Castle with our expert guide, wander through the surrounding 545-acre National Park, or ease into your vacation with a dip in the pool followed by a massage. This evening, we’ll indulge in an extraordinary culinary experience at LAB Restaurant, where Michelin-starred Chef Sergi Arola presents an artisanal tasting menu paired with exceptional wines. 

Penha Longa
Dinner (D) Wine (W)

Quinta da Regaleira, Pena Palace

After breakfast, we’ll discover the historic palace and gardens of Quinta da Regaleira, known for its legendary spiral well symbolizing the journey of initiation. After lunch at your leisure in the charming town of Sintra, we’ll tour Pena Palace, a colorful, fairy tale castle considered one of the world’s best examples of 19th century romanticism. This evening, we’ll savor a contemporary, creative twist to Portuguese cuisine at Arola, Penha Longa's celebrated restaurant.

Penha Longa
Breakfast (B), D/W

Cascais, National Palace of Sintra

After breakfast, we’ll enjoy a guided tour of Cascais, a lively seaside town on the stunning Portuguese Riviera. We’ll have lunch in a beautiful historic villa in the heart of Cascais Bay, then return to Penha Longa, where you can choose from a range of activities: relaxing at the 1500-meter spa and wellness center, a dip in the pool or a round of golf. Or, if you feel like a cultural excursion, you can visit the National Palace of Sintra. Dinner this evening is at your leisure, and fortunately, Penha Longa has a range of exceptional dining options.

Penha Longa (B,L)

Costa Nova, Aveiro, Porto

Today, we’ll head north to the romantic city of Porto. On the way, we'll stop in the picturesque fishing village of Costa Nova, known for its iconic striped houses. Then we'll continue on to Aveiro, the "Venice of Portugal," where we'll admire the canal views on our guided tour and have lunch. Upon arrival in Porto, we’ll check in to The Yeatman Hotel, with its world-class wine cellar, 2 Michelin star restaurant, and stunning views. Dinner will be at Olivier da Costa’s Yakuza, offering the best in East/West fusion.

The Yeatman Hotel (B,D)

The Douro Valley, Six Senses

After breakfast, we'll venture into the Douro Valley, a UNESCO-protected wine region and one of the world's oldest. We'll tour the vineyards and enjoy a tasting at Quinta da Vacaria, a historic estate dating back to 1616. For lunch, we'll indulge in a seasonal tasting menu at The Vale de Abraao, the flagship restaurant at the ultra-luxurious Six Senses Douro Valley resort. In the evening, you'll choose from several dining options in Porto: the 2 Michelin-starred Yeatman Gastronomique, the restaurants in the World of Wine Cultural District, or your pick from TCNT’s curated Porto restaurant list.

The Yeatman Hotel
(B,L/W)

Porto

Today, we'll discover the romantic charms of Porto with our brilliant local guide.  In addition to many beautiful and iconic sites throughout the city, we'll visit the Harry Potter-esque Livraria Lello bookshop, with its iconic wooden staircase and stained glass windows, and explore the vibrant Mercado do Bolhao, filled with merchants selling fresh produce, aromatic cheeses, baked breads, and more. In the afternoon, we'll visit Graham's Port Lodge overlooking the Douro River, where we'll taste and compare different port vintages with food pairings. As the sun sets, we'll board a luxury yacht on the Douro for a Six Bridges tour, complete with wine and appetizers.

The Yeatman Hotel (B,D/W)

Obidos, Lisbon

After breakfast, we'll tour the walled, hilltop medieval town of Obidos, known for its castles and winding streets. Following a relaxing lunch there, we'll continue on to Lisbon, where we'll check into the stylish Barrio Alto Hotel in the city's historic district. After enjoying drinks and views from one of Lisbon’s breathtaking rooftop bars, we will head to Jose Avillez’s posh, gourmet Mini Bar for a gastronomic treat.

Barrio Alto Hotel (B,D)

Lisbon

After breakfast, we'll head to the historic Belem neighborhood for a Pastéis de Belém Workshop & City Tour. We'll visit landmarks like the Belem Tower and Jerónimos Monastery, then learn to make the famous Portuguese egg custard tarts. The afternoon is yours to explore Lisbon at your own pace - you could ride the iconic Tram 28 or the Elevador do Santa Justa, visit the Castelo de São Jorge, or–my personal recommendation–check out the National Museum of Ancient Art. For dinner, we'll dine at Rocco Restaurant, known for its warm, authentic ambiance.

Barrio Alto Hotel (B,D)

Lisbon

The morning is at your leisure. But, if you'd like to discover some of Lisbon's best shops for Portuguese textiles, ceramics, perfumes, and specialty foods, join me on a guided shopping tour using TNCT's insider shopping guide, followed by lunch at the iconic, stylish JNcQUOI restaurant. This evening, we'll embark on a Fado & Food Tour in the charming Alfama neighborhood. Known for its cobblestone streets, bohemian atmosphere, and views of the Tagus River, Alfama is the perfect setting to indulge in tapas, local wines, and a traditional fado music performance. Fado is a beloved Portuguese genre celebrated for its expressive, melancholic style and heartfelt lyrics, and it is a must-see while in Lisbon.

Barrio Alto Hotel (B,D/W)

Transfer to Lisbon airport for flights to the US