In the late afternoon, we’ll gather at our hotel for a welcome drink and begin getting to know our fellow travelers for the week. Afterward, we’ll take to the water: soaking in stunning vistas in a private cruise down the Tagus, getting a fuller sense of the local geography and history as we sail past palaces, monasteries and monumental squares.

After the cruise, we’ll walk to dinner at Taberna Albricoque, a restored historic tavern known for its seasonal, Algarve-inspired cooking. Here, the focus is on simple, ingredient-driven dishes, especially seafood and vegetables, prepared with a refined but unfussy approach. Expect a meal built around what’s fresh and in season, meant for sharing, with flavors that reflect the chef’s southern Portuguese roots.

Our first full day in Lisbon explores the country’s deep connection to the sea. We begin at Mercado da Ribeira, where Lisbon’s most discerning shoppers come for fish and seafood. Here, we’ll check in with a trusted fishmonger to talk through the day’s catch and, if we’re lucky, spot seasonal delicacies like percebes, or gooseneck barnacles. From there, we’ll move through the city’s backstreets, stopping along the way to taste as we go before sitting down for seafood starters and classic cod cakes at a beloved family-run restaurant. We’ll then visit the atelier of renowned Portuguese artist Joana Vasconcelos, offering a glimpse into one of the country’s most distinctive creative voices. Before heading to the port, we’ll stop at a local wine shop, where the owner will guide us through Portugal’s wine regions, glass by glass. The day ends by the water with a late lunch of simply grilled fish at a no-frills spot long favored by port workers and locals in the know.

The evening is free to relax back at the hotel or explore Lisbon on your own.

We head north along the Atlantic to coastal Sintra, a dramatic stretch of wild beaches, cliffs, and lighthouses, home to one of Europe’s most distinctive wine regions. The day begins with a hike along the coastal cliffs, led by a local ethnobotanist who introduces us to the flora of this rugged landscape, shaped by wind, salt, and sea. From there, we make our way to a beachside restaurant for a long, relaxed lunch by the water, where the table fills with seafood drawn straight from the surrounding coast. In the afternoon, we visit a family-run winery to taste wines from vines that remarkably survived phylloxera, the 19th-century blight that devastated much of Europe’s vineyards. The focus here is on the wines themselves, along with the story of this rare and resilient terroir. 

We return to Lisbon in the early evening, with the night free to explore or unwind back at the hotel.

Today we say goodbye to the surf of Lisbon and Sintra and hello to the rich turf of eastern Portugal’s Alentejo, an inland region of rolling hills and vast farmlands famed for its earthy wines and black pigs, a domestic breed that produces a prized ham. Our welcome to this fertile region will begin with a visit to a local farm to learn about Alentejo agricultural life and some of its finest products. We’ll meet some of the farm’s free range black pigs, whose diet mostly consists of wild acorns, walk the fields and have a classic farm-style lunch of cozido à portuguesa – a hearty meat and vegetable stew – cooked in clay vessels on an open fire. After lunch we’ll head to Estremoz, a historical fortified village nestled in the rolling hills, where we’ll check into our hotel – a renovated palace. After a short rest, we’ll gather for a light dinner at the hotel’s excellent restaurant.

We dive even deeper into the Alentejo’s rural and agricultural heritage, with a day spent together with one of the region’s – and Portugal’s – most celebrated winemakers, Hamilton Reis. Working using regenerative practices and ancient techniques, such as clay vessel aging, Reis has made a name for himself by working with the Alentejo’s indigenous grape varieties and also for thinking creatively about how to adapt to climate change. He’ll lead us on a tour of his vineyards, followed by a wine tasting and big country-style late lunch. As the sun starts to set, we’ll be joined by a group of singers who will perform the classic Cante Alentejano, a polyphonic singing style unique to this area. The eveninToday is devoted to Alentejo’s ancient talha wine tradition, a method of winemaking that dates back to Roman times and still defines the region’s identity. We begin in Vila de Frades with a visit to the Talha Wine Interpretive Center, offering a brief introduction to this centuries-old practice. From there, we continue to Gerações da Talha, a family estate dating back to the mid-18th century, where generations have preserved and refined the art of fermenting and aging wine in clay amphorae. Here, we’ll meet the people behind the process, walk through the cellar, and see firsthand how these ancestral techniques have endured. The visit is followed by a long, relaxed lunch at the winery, with each course paired to highlight the rustic, soulful flavors of Alentejo. As the afternoon fades, we’ll be joined by local singers performing Cante Alentejano, the region’s traditional polyphonic style, recognized by UNESCO for its cultural significance.

The evening is free to relax at the hotel or wander the quiet streets of Estremoz.

Our final full day in Alentejo focuses on the ingredients that shape the region’s cooking and daily life. In the hilltop village of Monsaraz, we’ll explore the landscape with a local guide, getting a closer look at the rhythms of rural life and the role of olive oil, one of the area’s defining products.

We’ll visit a small-scale olive oil producer to learn about the process from grove to bottle, followed by a tasting that highlights the range and character of the region’s oils. For lunch, we’ll settle into a traditional village tavern for a meal rooted in Alentejo’s rustic, farm-driven cuisine.

After some time back at the hotel in Estremoz, we’ll gather again for a presunto tasting at a local restaurant. Led by a master presunto cutter, we’ll learn the art of slicing and taste this prized dry-cured ham, known for its delicate texture and depth of flavor.

After breakfast in Estremoz, we’ll check out of our palace and begin the journey back to Lisbon. Once back in the city, there will be some free time to relax or explore a bit more before our farewell dinner.

This evening, we’ll dine at one of Lisbon’s standout contemporary restaurants. Here, chef Vincent Farges offers a refined and creative tasting menu that highlights seasonal ingredients with a modern, minimalist approach. The experience is intimate and ingredient-driven, with thoughtful wine pairings that complement the precision and elegance of each dish.

Our pilgrimage to Portugal now complete, we'll say our final goodbyes over breakfast at the hotel. Our guide will be happy to provide additional recommendations, if you’d like. Until our next adventure!