Lisbon and the Island of Madeira: The Tapestry of Portugal

When you arrive in Lisbon, take a taxi from the airport, or we can arrange your transportation to Brown's Central Hotel, a charming and contemporary 5-star hotel in the heart of the city. 

After checking in, settle in and unwind after your journey. You might want to explore the hotel’s beautiful surroundings or relax in your room, soaking in the atmosphere of this 18th-century building where Kings and Queens once roamed the halls. 

We’ll meet for a welcome drink around sunset before dinner at Baía do Peixe, just a short walk from the hotel. This is our first opportunity to gather as a group, relax, and enjoy a warm introduction to Lisbon’s culinary scene. Savor expertly prepared dishes highlighting local flavors, including succulent steaks and Portuguese wines. 

We’ll begin with breakfast at the hotel, followed by a walking tour through Lisbon’s most iconic districts: Baixa, Chiado, and Bairro Alto. We’ll start at Praça do Comércio and stroll down Rua Augusta, learning about the 1755 earthquake and Lisbon’s reconstruction led by the Marquis of Pombal.

Along the way, we’ll visit the Santa Justa Elevator for sweeping views of the city, Rossio Square, and São Domingos Church. We’ll also stop to taste Ginjinha, a traditional cherry liquor. A ride on the Gloria Funicular will take us to São Pedro de Alcantara for a breathtaking lookout over the city. 

We’ll continue through Bairro Alto, touching on the history of Fado music, and Carmo Square, where we’ll discuss the Carnation Revolution. Our stroll through Chiado will include visits to Portuguese cotton and porcelain shops.

After savoring lunch at By the Wine, we’ll hop on the Bica Funicular and head to Belém for a panoramic tour. Highlights include the Belém Tower, the Monument to the Discoveries, and an exterior visit to Jeronimos Monastery. We’ll wrap up the day with a taste of Pastéis de Belém before heading back to the hotel. 

Take a moment to refresh and relax. We'll gather for dinner at the hotel's restaurant tonight. What could be better than savoring an authentic Portuguese meal with new friends? 

Following a slow morning and breakfast, we’ll head to the magnificent Palácio Marquês Fronteira, a true hidden 17th-century gem. This estate is a masterpiece of the Portuguese Baroque period, offering a glimpse into the aristocratic life of the time. 

Lunch today will be at Matte, a stunning Japanese restaurant serving some of the freshest fish and creative dishes in the neighborhood. 

Next, we’ll visit the Tile Museum to immerse ourselves in Portugal’s deep tradition of ceramic artistry. Here, we’ll discover how tiles have symbolized Portuguese identity for centuries as decoration and cultural expression. The museum is housed in a former convent, and as we walk through its historic corridors, we’ll see everything from the earliest Islamic-inspired tiles to vibrant modern pieces. 

To wrap up our day of sightseeing, we'll stop by Jerónimos Monastery, one of the most striking examples of the late Portuguese Gothic Manueline style, near the Tagus River. 

The afternoon is yours to enjoy – whether you want to shop in Lisbon’s charming streets or relax and take in the city at your own pace.

We’ll come together for dinner at A Severa, the oldest Fado House in Lisbon. Indulge in the delicately prepared Portuguese dishes in a candlelit dining room while we listen to an array of Fado performances throughout our meal. 

We’ll set off for a day of discovery in Sintra, one of Portugal’s most enchanting towns. Our first stop is the stunning Pena Palace, where we’ll enjoy fast-track access to this vibrant and whimsical UNESCO World Heritage site. We’ll spend the morning exploring the palace's eclectic architecture and the surrounding park. As we walk through the gardens, take a moment to soak in the diverse flora, hidden paths, and breathtaking views that transport us elsewhere.

For lunch, we’ll head to Tasca Boutique Das Tapas, a charming restaurant in the heart of Sintra, where we’ll enjoy a tapas-style meal that celebrates local flavors.

After lunch, you'll have free time to wander Sintra's historic center at your own pace. Browse local shops, visit quaint cafés, or simply admire the beauty of this fairy-tale town. Don’t miss the chance to try Sintra’s famous Travesseiros, a delicious puff pastry filled with almond cream, perfect for an afternoon treat.

We’ll return to Lisbon in the evening to freshen up before a special night. Dinner will be at SÁLA de João Sá, a Michelin-starred restaurant serving farm-to-table dishes that are heavily inspired by Asian cuisines. 

Enjoy a leisurely breakfast and a relaxed morning before we head to the airport at around 11 am for our flight to Madeira. A van will be waiting once we arrive to take us to Castanheiro Boutique Hotel in the heart of Funchal, where we’ll check in and get settled.

Savor lunch at the hotel's rooftop restaurant, Pretas, while soaking in the stunning coastal views that will enchant us over the next few days. 

Once we're feeling refreshed, we’ll take a walking tour of Funchal, exploring the city’s charming old town. Our guide will lead us through the spirited streets, sharing insights about local culture and history. Along the way, we’ll admire Funchal’s colorful doors and murals, a hallmark of the city’s artistic revival.

To round out the tour, our guide will introduce us to Poncha, Madeira’s famous local drink. Poncha is a blend of aguardente, honey, and citrus, offering a sweet, tangy taste of the local culture. We’ll then stop at a traditional spot to toast our arrival on the island. 

We’ll gather for dinner at the hotel's other restaurant, Tipografia, where we can enjoy a relaxing meal before getting some rest for the upcoming adventures.

After breakfast, we’ll take a scenic coach ride to Ribeiro Frio, a beautiful area known for its lush forests and tranquil atmosphere. The drive takes approximately one hour and offers lovely views of the Madeira countryside along the way. 

Once we arrive, we’ll set off on the Levada dos Balcões walk, a must-do in Madeira. This easy and picturesque trail follows one of Madeira’s famous levadas (irrigation channels), providing stunning panoramic views of the island’s verdant landscapes.

We’ll continue to Santana Village, known for its traditional thatched houses, for a brief stop to soak in the charming atmosphere and unique architecture. 

Lunch will be a delightful affair at Quinta do Furão, where we can enjoy breathtaking views of the Atlantic Ocean. Combining fresh local ingredients and spectacular scenery makes for a memorable experience.

On the way back to Funchal, we’ll make a quick photo stop at São Lourenço. Take the time to capture one of Madeira’s most picturesque spots. 

We’ll end the day with a visit to Blandy’s Wine Lodge for a guided tasting of Madeira wines paired with a selection of local cheeses. The snacks will serve as a light dinner. The tasting perfectly introduces Madeira’s winemaking heritage in one of the island’s oldest and most famous wine lodges.

We’ll start our day with a delicious breakfast and a visit to Bordal, a traditional needlework shop in town. The store features over 60,000 embroidery designs using only the best materials.

Continuing on, we'll stroll through the Funchal Farmer’s Market. We can explore the local produce and vibrant flowers on our way to the Teleférico Funchal-Monte Cable Car. From there, we’ll take the first cable car ride up to Monte, where you can visit the Monte Public Garden, Quinta do Monte, and the stunning Monte Palace Tropical Garden.

We’ll sit down at Pátio das Babosas for lunch overlooking the lush, rolling hills of Madeira.

Afterward, you have the opportunity to experience the Monte Sledges (carros de cesto), an exhilarating ride down to the city center. If you’d like to try it, the option is included in the trip. If you're not feeling up for the experience, you can always ride the cable car back down. 

The afternoon and evening are free to explore or relax at your own pace. We'll gather for dinner later this evening at Olivia, a chic Mediterranean restaurant with fantastic seafood options. 

Our final day in the captivating archipelago of Madeira begins with an unforgettable encounter with its vibrant marine life. A dedicated whale and dolphin tour will immerse us in the beauty of the island's coastal waters, offering the chance to witness these magnificent creatures in their natural habitat. 

Following this aquatic adventure, we'll journey by coach towards the unique and secluded Fajã dos Padres. Here, a thrilling cable car descent will unveil breathtaking panoramic vistas of Madeira's dramatic landscape, showcasing its lush slopes plunging towards the azure Atlantic. 

Upon reaching this hidden gem at sea level, we'll explore its tranquil shores, perhaps swim in the clear waters, and enjoy a lunch of fresh local delicacies while the ocean breeze blows.

This afternoon, we'll head to Cabo Girão, known for its glass skywalk on Europe's second-highest sea cliff. From there, we can enjoy stunning views of the coastline and ocean, showcasing Madeira's volcanic roots. 

As our journey comes to an end, we'll return to Funchal for a farewell dinner at Quinta Jardins do Lago. Surrounded by flourishing gardens and elegance, we'll toast to memories made in the unique beauty of Madeira Island, a truly distinctive destination.

It’s our final day, and while it’s hard to say goodbye, the friendships and connections we’ve made will stay with us long after we leave. After a leisurely breakfast at the hotel, we’ll pack up and head to the airport for our flight back to Lisbon. 

As we take one last look at Madeira’s stunning beauty, let’s not forget the incredible women we’ve met along the way—each one bringing something special to this journey. From shared laughter to quiet moments of awe, we’ve built memories and bonds that will last far beyond this trip.