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 transportation to Brown's Central Hotel, a charming, 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 Essencial, 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. 

After breakfast at the hotel, we'll set out to discover the historic riverside district of Belém, where Portugal's Age of Discovery comes to life. Our morning begins at the magnificent Jerónimos Monastery, a UNESCO World Heritage Site and one of the finest examples of Manueline architecture, built to commemorate Vasco da Gama's legendary voyage to India. 

We'll then indulge in warm, freshly baked Pastéis de Belém, the famous custard tart crafted from a closely guarded recipe for nearly two centuries. 

Afterward, we'll visit the National Coach Museum, home to one of the world's most remarkable collections of royal carriages, offering a fascinating glimpse into Portugal's royal history.

After lunch at MAAT Kitchen, we'll continue exploring with a scenic ride aboard the iconic Bica Funicular before enjoying a panoramic tour of Belém. Along the way, we'll admire landmarks including the elegant Belém Tower, which once guarded the entrance to Lisbon's harbor, and the Monument to the Discoveries, honoring the explorers who helped shape Portugal's maritime legacy. 

Returning to the hotel, you'll have time to unwind before we gather for dinner at By The Wine, where seasonal Portuguese cuisine and exceptional regional wines provide a perfect setting to savor an authentic 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 Can the Can, a contemporary eatery that highlights Portuguese tradition while enriching it with global influences. 

Next, we’ll visit Cerâmica S. Vicente for a tile-painting workshop 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 and create our own to take home.

We're in for a real treat: a private experience aboard one of Lisbon's iconic red trams. As one of the most time-honored and well-loved forms of public transportation in the city, we'll board our very own vintage car for a sightseeing loop around Alfama, Graça, and Baixa. 

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 O Tasco do Strauss, 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 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 Barceló Funchal Oldtown in the heart of Funchal, where we’ll check in and get settled.

Savor lunch at the hotel's terrace restaurant, Noz, 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 Olivia, a chic, cozy restaurant serving delicious, hearty meals with a fantastic cocktail list to accompany.

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 Tipografia, a cozy Mediterranean restaurant with fantastic seafood options and a lovely terrace.

Our final day in the captivating archipelago of Madeira begins with an unforgettable encounter with its vibrant marine life. Enjoy an exclusive catamaran cruise along Madeira's spectacular coastline, taking in breathtaking views of the island from the sea while relaxing on board and experiencing the beauty of the Atlantic.

After this aquatic adventure, we'll travel by coach to the unique and secluded Fajã dos Padres. Here, a thrilling cable car descent will reveal breathtaking panoramic vistas of Madeira's dramatic landscape, with lush slopes plunging toward 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 Madeira's unique beauty.

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, pack up, check out, and head to the airport for onward travel at a time that suits best for you. 

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. 

You'll find plenty of direct flights out of Funchal to Newark, London, Paris, and Lisbon, to name a few.