Arrive in Madrid, where you'll be met at the airport and transferred to your hotel. Settle in and take the rest of the afternoon at your own pace. This evening, Chelsea Blake welcomes the group at a private dinner, the first of many shared tables on this Journey and your introduction to the travelers you'll spend the week with.

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Note: If you'd like more time in Madrid, ask your Personal Vacation Manager about the optional hotel extension, which adds a night to your Madrid stay before the Journey begins.

Madrid opens at the Royal Palace, where you'll walk the grand halls and take in the art, armor, and centuries of royal heritage held inside the largest working royal palace in Western Europe. From there the day turns to the table: join Chelsea at a traditional market for the flavors and local products Madrileños actually shop for, then a tapas tasting paired with Spanish wine. Madrid is a city she has come back to over the years, and the first of two on this Journey she already knows well.

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The evening belongs to flamenco. Dinner and a performance at one of Madrid's most celebrated venues, as renowned for its kitchen as for its dancers.

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Leave Madrid for Toledo, the UNESCO World Heritage city known as the "City of Three Cultures" for the Christian, Muslim, and Jewish communities that shaped it. A panoramic tour takes in the viewpoints above the Tagus River, where the whole skyline rises in front of you at once. Inside the walls, a guided visit to Toledo Cathedral, one of the three great Gothic cathedrals of thirteenth-century Spain, where El Greco's work still hangs in the sacristy it was painted for.
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Lunch is at a traditional estate in the hills above the city. Then the road carries you west to Cáceres, whose old town is among the best-preserved medieval quarters in Europe, a UNESCO site of stone towers and quiet squares that most travelers never see. The evening is yours to wander.

The morning is a private half-day tour of Cáceres' Monumental City, a UNESCO World Heritage Site, walking medieval streets where the stories and legends are as well preserved as the stone.
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Then the Journey crosses the border into Portugal, the country Chelsea has spent years returning to, and the landscape opens into the Alentejo. Lunch is at a traditional estate along the way, followed by a stop at the Coffee Museum, an interactive look at how the bean becomes the cup and the rituals that have grown up around coffee in cultures around the world. Arrive by evening in Évora, the walled capital of the Alentejo, and check in to your hotel.

The morning and early afternoon are for getting properly acquainted with Évora, one of Portugal's best-preserved medieval towns and a UNESCO World Heritage Site. The Roman Temple anchors the old center, standing in the same square for nearly two thousand years, a short walk from the Cathedral and the famous Chapel of Bones, its walls and columns lined floor to ceiling with human bones.
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From there, Praça do Giraldo, the arcaded main square that has been the heart of civic life here since the 1500s, then lunch in the historic center among restaurants serving Alentejo cooking at its most traditional.

The afternoon is yours: cobblestone streets to wander, the cork and ceramics shops Évora is known for, or join Chelsea for a stroll through the town.

Leave Évora and cross the Alentejo countryside toward Setúbal, arriving at one of Portugal's oldest and most celebrated wine estates. A guided tour of the historic cellars leads into a tasting of three wines: a white, a red, and the Moscatel de Setúbal the region is known for. Then a long lunch at the estate, regional cooking paired with the wines you've just tasted.
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This is the afternoon Chelsea has been looking forward to most, and the reason she wanted to host this Journey herself. Over lunch she'll raise a glass to you and share a first look at where Enrichment Journeys is headed next, including departures that haven't been announced to anyone.

From there, on to Lisbon. The evening is yours, in the city Chelsea calls her second home, and she'll have no shortage of suggestions for how to spend it.

Lisbon's maritime history lives in Belém. There, you'll visit the Jerónimos Monastery and the Belém Tower, together a UNESCO World Heritage Site, with the Monument to the Discoveries standing over the water nearby. Plus, enjoy a tasting of the traditional Portuguese custard tart Belém is famous for.
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Lunch is on your own back in the city center. Ask Chelsea for her recommendations, and lunch like a local! The group will gather again afterward at Castelo de São Jorge, the hilltop fortress with the Tagus River and the whole of Lisbon laid out below.
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This evening is the farewell before the cruise. Dine at one of Lisbon's great fado houses, with a performance of the music built on the Portuguese word for longing for what isn't there. UNESCO recognizes it as Intangible Cultural Heritage. It's Chelsea's last night with the group and the last of the shared tables that began in Madrid.

After breakfast, check out of the hotel and transfer to the port, where you'll board the Oceania Allura.

Ports of call include Malaga, Melilla, Alicante, Valencia and Barcelona, Spain; Provence (Marseille), France; Genoa, Florence/Pisa/Tuscany, Rome, Salerno, Palermo and Syracuse, Italy;  Tunis, Tunisia; Valletta, Malta; Katakolon, Heraklion, Rhodes and Athens, Greece.

The Allura entered service in 2025 and is also built around the table, which makes her a natural continuation of this Journey. Specialty dining carries no surcharge. Ask how to add hands-on classes at the Culinary Center, sommelier-led wine pairings, or Privée, an eight-seat room for wine experiences by La Reserve.

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Enjoy breakfast onboard, then disembark the Oceania Allura and transfer to the airport for your return flight home.

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Note: If you wish to spend more time in Athens, ask your Personal Vacation Manager about the optional hotel extension.