Portugal & Madeira Island in 10 Days: The Ultimate Wine, Food & Culture Journey

Portugal & Madeira Island in 10 Days

Some journeys feel like holidays, and others feel like stories you’ll tell for the rest of your life. This carefully curated 10-day experience across mainland Portugal and Madeira Island belongs firmly to the second category.

From historic cities and family-owned wine estates to dramatic Atlantic landscapes and private moments at sea, this itinerary is designed for travelers who seek authenticity, depth, and meaningful connections with the places they visit.

Why Portugal is One of Europe’s Most Desirable Destinations Right Now

Portugal continues to rank among the world’s most sought-after destinations, not only for its beauty, but for the quality of experiences it offers. Exceptional gastronomy, centuries-old wine traditions, diverse landscapes, safety, authenticity, and understated elegance make it uniquely appealing to discerning travelers.

This journey combines the very best of the country in one seamless itinerary:

• Lisbon’s culture and gastronomy

• Porto’s heritage and wine legacy

• The Douro Valley’s breathtaking vineyard landscapes

• Madeira’s wild nature and Atlantic soul

The Itinerary: A Day-by-Day Journey Through Portugal & Madeira

Day 1 - Welcome to Lisbon

Your journey begins in Lisbon, staying near Avenida da Liberdade allows you to experience Lisbon as locals do, elegant, central, and effortlessly connected to the city’s cultural life. The evening sets the tone with a traditional dinner at Solar dos Presuntos, a long-established restaurant celebrated for preserving the soul of Portuguese cuisine. It’s a warm, authentic introduction to the country, not staged, but real.

Day 2 - Lisbon Highlights

With a private guide, you explore the atmospheric streets of Alfama and walk through Baixa and Chiado, districts filled with architectural elegance and literary history. Along the way, the city reveals itself through taste: the famous bifana, reinvented pastel de bacalhau, a traditional ginjinha, and the iconic pastel de nata. These are not just tastings, but cultural rituals that connect you to everyday Portuguese life.

Torre de Belém

The afternoon takes you to Belém, birthplace of Portugal’s Age of Discovery. Landmarks such as Jerónimos Monastery, Belém Tower, and the Monument to the Discoveries provide historical depth and a powerful sense of place.

Day 3 - Sintra

Few places in Europe feel as dreamlike as Sintra. Surrounded by lush hills, palaces rise from the mist like scenes from a novel. You explore the colorful Pena Palace, the symbolic and mysterious Quinta da Regaleira, and historic gardens that feel suspended in time.

Palácio da Pena

The afternoon unfolds along the coast: Cascais, once a royal retreat, offers relaxed elegance by the sea, while Cabo da Roca, the westernmost point of mainland Europe, delivers dramatic Atlantic views that stay with you long after you leave. 

Day 4 - Óbidos

The morning introduces the Lisbon wine region with a visit to Quinta do Gradil, an estate whose history dates back to the 15th century. A guided tasting and vineyard picnic offer a peaceful immersion into Portugal’s wine culture. Later, you explore the medieval village of Óbidos, where whitewashed houses, cobbled streets, and castle walls create a timeless atmosphere.

The Yeatman Hotel

By the end of the day, you arrive in Porto and check in at The Yeatman, a hotel deeply connected to Portugal’s wine identity, overlooking the Douro River and the city’s historic skyline.

Day 5 - Porto 

With a private guide, you discover Porto’s most emblematic landmarks: Clérigos Tower, São Bento Station’s azulejos, Lello Bookstore, the Cathedral, and the Stock Exchange Palace. Each tells part of the city’s layered story. Lunch at Vinum, overlooking the Douro, introduces the strong connection between gastronomy and wine that defines this region.

The afternoon includes a visit to one of Porto’s most respected Port wine cellars, where you learn about the aging process and enjoy a guided tasting. 

Day 6 - Douro Valley

A scenic drive leads you into the heart of the Douro Valley, one of the world’s oldest demarcated wine regions. Terraced vineyards cascade toward the river, creating one of Europe’s most striking landscapes. You enjoy a private river cruise, followed by lunch at a vineyard restaurant overlooking the Douro. In the afternoon, a visit to a family-owned estate such as Quinta do Bomfim offers insight into generations of winemaking tradition, with tastings enjoyed in an intimate setting.

Day 7 - Madeira Island

Madeira, a destination that feels completely different in energy and landscape. Lush mountains rise from the Atlantic, cliffs drop dramatically into the ocean, and nature feels raw and untouched. This transition marks a new chapter in the journey: slower, more connected to nature, and deeply restorative.

Day 8 - Madeira Experiences

Explore Madeira by private jeep, reaching viewpoints and corners inaccessible to most visitors. Cabo Girão offers sweeping views from one of Europe’s highest sea cliffs, while Boca dos Namorados overlooks the dramatic valley of Curral das Freiras.

A visit to a local vineyard, followed by a traditional lunch with regional flavors and Madeira wine, creates a connection to the island’s culinary identity. The afternoon ends at the natural volcanic pools of Porto Moniz, a peaceful moment to simply enjoy the Atlantic and the surrounding landscape.

Day 9 - Private Day at Sea

A private sailboat cruise along Madeira’s rugged coastline. Over six unhurried hours, you sail across clear Atlantic waters, with the chance to spot dolphins and whales in their natural habitat.

There is time to swim, relax on deck, enjoy lunch on board, and experience the rare sensation of complete disconnection, surrounded only by ocean, cliffs, and sky.

Day 10 - Farewell

You leave Portugal not only with beautiful photographs, but with lived experiences: flavors remembered, conversations shared, landscapes that altered your perspective. This is the difference between visiting a destination and truly immersing yourself in it.

Who This Journey Is For

This itinerary is ideal for travelers who:

• Value meaningful experiences over fast-paced tourism

• Appreciate wine, gastronomy, and culture

• Seek authenticity and depth

• Prefer private guides and personalized service

• Want to discover Portugal beyond the obvious

It appeals equally to couples, friends traveling together, and sophisticated explorers looking for something thoughtfully designed. 

Why Book This Tour with Wine Tourism in Portugal

What distinguishes this journey is not simply the itinerary, but the way it is curated. Every hotel, estate, guide, and experience is carefully selected for its authenticity, quality, and consistency.

Wine Tourism in Portugal specializes in crafting journeys that feel personal rather than generic, designed by locals who have a deep understanding of the regions, producers, culture, and the country's rhythm. They can tailor each itinerary, adjust any detail, or create a completely bespoke journey based on your preferences.

This is the kind of journey that doesn’t feel staged. It feels real, effortless, and deeply memorable.