Portugal’s Finest: Lisbon and Madeira

Upon arrival in Lisbon, you can take a taxi from the airport, or we can arrange transportation for you to Hotel Pousada Lisboa, a charming hotel located in the heart of the city. After checking in, take some time to settle in and unwind after your journey. You might want to explore the hotel’s beautiful surroundings or simply relax in your room, soaking in the atmosphere of this historic building, which was once the headquarters of the Portuguese Ministry of Internal Affairs.

Around sunset, we will meet for a welcome drink. Afterward, we’ll have dinner at RIB Beef & Wine, the hotel’s signature restaurant. This will be our first opportunity to gather as a group, relax, and enjoy a warm introduction to Lisbon’s culinary scene. Savor expertly prepared dishes that highlight 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 for a taste of 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. A stroll through Chiado will include visits to Portuguese cotton and porcelain shops.

Lunch will be at By the Wine, after which 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. 

Dinner will be at Suba Restaurant where we'll experience Michelin Star dining at a historic Lisbon palace with rooftop bar & stunning 360º views.

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

Next, we’ll immerse ourselves in Portugal’s deep tradition of ceramic artistry at the Tile Museum. Here, we’ll discover how tiles have been a symbol of Portuguese identity for centuries, not only as decoration but as cultural expression. The museum itself is housed in a former convent, and as we walk through its historical corridors, we’ll see everything from the earliest Islamic-inspired tiles to vibrant modern pieces. 

For lunch, we’ll head to Zambeze, where Portuguese cuisine meets African influences, offering us a unique dining experience with stunning panoramic views of Lisbon and the Tagus River. 

Afterward, the afternoon is yours to enjoy – whether you want to dive into some shopping in Lisbon’s charming streets or simply relax and take in the city at your own pace.

We’ll come together again in the evening for dinner at SÁLA de João Sá, a  one star Michelin experience. This is an intimate and stylish restaurant that blends tradition and innovation. With a focus on modern Portuguese flavors, this is the perfect place to savor creative dishes, each one an exciting interpretation of the local culinary scene. 

Today, 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 dedicate the entire morning to exploring both the palace, with its eclectic mix of architectural styles, and the expansive park that surrounds it. As we make our way down through the gardens, you’ll be captivated by the diverse flora, hidden pathways, and stunning views that seem to transport you to another world.

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

After lunch, there will be some free time to wander the historical center of Sintra at your own pace. You’ll have the opportunity to browse local shops, visit quaint cafés, or simply soak in 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.

In the evening, we’ll return to Lisbon to freshen up before a special night. Dinner will be at A Severa, a traditional Fado restaurant where the soulful sounds of this beloved Portuguese music will accompany our meal. It’s the perfect way to end a day filled with history, beauty, and unforgettable experiences.

We will enjoy a leisurely breakfast and a relaxed morning before heading to the airport around 11 a.m. for our flight to Madeira. Upon arrival, a van will be waiting to take us to Castanheiro Boutique Hotel in the heart of Funchal, where we’ll check in and get settled.

Once refreshed, we’ll embark on a walking tour of Funchal, exploring the city’s charming old town. Our guide will take us through the vibrant streets, sharing insights into the local culture and history. Along the way, you’ll have the opportunity to admire Funchal’s colorful doors and murals that have become a hallmark of the city’s artistic revival.

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

In the evening, we’ll gather for dinner at the hotel, where we can enjoy a relaxing meal before resting up for the adventures to come.

After breakfast, we’ll set off by coach for a scenic drive to Ribeiro Frio, a beautiful area known for its lush forests and tranquil atmosphere. The drive takes approximately one hour, offering lovely views of the Madeira countryside along the way. Once we arrive, we’ll embark on the Levada dos Balcões walk, a must-do in Madeira. This easy and picturesque trail follows along one of Madeira’s famous levadas (irrigation channels), providing stunning panoramic views of the island’s verdant landscapes.

From there, we’ll continue on 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 Restaurante, where we’ll dine with breathtaking views of the Atlantic Ocean. The combination of 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, allowing us to capture one of Madeira’s most picturesque spots. 

We’ll end the day with a visit to Blandy’s Wine Lodge, where we’ll enjoy a guided tasting of Madeira wines paired with a selection of local cheeses. This tasting will serve as a light dinner, offering a perfect introduction to 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 followed, by a visit to the Funchal Farmer’s Market. There you can explore the vibrant local produce and 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’ll have the opportunity to visit the Monte Public Garden, Quinta do Monte, and the stunning Monte Palace Tropical Garden.

For lunch, we’ll have free time to choose from local spots and enjoy a relaxed meal with beautiful views.

Afterward, there’s the exciting option of experiencing the Monte sledges (carros de cesto), an exhilarating ride down to the city center. If you’d like to try it, the option is available at an additional cost.

The afternoon and evening are free for you to explore or relax at your own pace.

Our morning starts with a whale and dolphin tour, where we’ll experience the beauty of Madeira’s coastal waters. Afterward, we’ll head by coach to Fajã dos Padres, where a cable car descent offers breathtaking panoramic views of the island. Once there, we’ll have time to explore, swim, and enjoy a fresh, local lunch by the ocean.

In the afternoon, we’ll stop at Cabo Girão, known for its spectacular skywalk and breathtaking cliff views. We’ll return to Funchal for a special farewell dinner at Quinta Jardins do Lago, where we’ll toast to the memories we’ve made on this incredible journey.

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 back to Lisbon and to beyond. As we take one last look at the stunning beauty of Madeira, 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.