Call us: (910) 742-5324
Call us: (910) 742-5324
If you’ve ever dreamed of experiencing the magic of Portugal during the holidays, this is the trip for you. Portugal and Madeira 2026 is a festive, fun-filled women-only journey that combines the best of seasonal charm, cultural discovery, and connection, with beautiful weather and even better company.
From the sparkling Christmas markets of Porto and Lisbon to the sun-kissed shores of Madeira, you’ll enjoy temperate December days without the crowds. Portugal, just before winter sets in, is a true hidden gem, offering everything from historic villages dressed in holiday lights to joyful local traditions, artisan gifts, and warm hospitality.
This 16-day adventure is your chance to explore Portugal, the island of Madeira, and their Christmas markets in one unforgettable trip. Stroll cobblestone streets lined with decorations, sip hot chocolate or a glass of port, and take in the spirit of the season while traveling with a phenomenal group of women who will quickly become your new best friends.
If you want to visit Portugal and experience the festive magic of its Christmas markets, this is the perfect time and the perfect trip. Fun, festivities, and friendship await you in one of Europe’s most beautiful and welcoming destinations.
Welcome to Porto, a city where old-world charm and modern energy coexist along the banks of the Douro River. Upon arrival, your driver will meet you in the Arrivals Hall to whisk you away to our perfectly located hotel where you can rest, relax, and rejuvenate. This evening, join your Tour Manager and new Sisters for a welcome reception at our hotel to toast our adventure ahead. (Welcome Reception included tonight)
Hotel: Turim Porto Hotel
Today is all about diving into the heart of Porto. A local expert will guide us through the city’s cobblestone streets, sharing stories and insights as we pass landmarks like the São Bento Railway Station, famous for its stunning tilework. At the Palácio da Bolsa, the opulent Arab Room offers a glimpse into the city’s grand past.
Next, we’ll wander through the historic Ribeira District, a UNESCO World Heritage site filled with colorful facades and riverside charm. Then, we’ll cross the bridge into Vila Nova de Gaia to visit a traditional wine cellar and taste the vintages that put Porto on the map. We’ll end the day with a scenic cruise along the Douro River, soaking in views of the city’s striking skyline and iconic bridges. Tonight, gather with your fellow travelers for a welcome dinner as we toast to the journey ahead. (Breakfast and Dinner included)
Hotel: Turim Porto Hotel
Today begins with a scenic drive to Braga, where we’ll visit the iconic Bom Jesus do Monte Sanctuary. Ride the historic funicular to the top for sweeping views of the city below. Afterward, enjoy free time with your Sisters to explore Braga’s charming center and find a local spot for lunch.
Later, we’ll continue to Guimarães, often called the birthplace of Portugal. Step inside the Palace of the Dukes of Braganza, a restored 15th-century treasure filled with period furnishings and history. Then stroll through the cobbled streets of this UNESCO World Heritage site, where medieval charm meets modern life. We’ll return to Porto this evening with a deeper appreciation for northern Portugal’s rich cultural roots. (Breakfast included)
Hotel: Turim Porto Hotel
This morning, we say farewell to Porto and begin our journey south. Our first stop is Aveiro, often called the “Venice of Portugal,” known for its peaceful canals, colorful boats, and beloved egg-yolk sweets. Enjoy free time to explore and have lunch on your own. In the afternoon, we’ll visit Fátima, one of the most important pilgrimage sites in the world. You’ll have time to reflect or explore at the Chapel of the Apparitions, where the Virgin Mary is said to have appeared in 1917.
As we arrive in the Portuguese Riviera, the charm of Cascais and Monte Estoril unfolds. Once a retreat for European royalty, this coastal haven welcomes us with elegant mansions and sea breezes. After we settle into our hotel, we’ll gather together for dinner at a local restaurant. (Breakfast and Dinner included)
Hotel: Hotel Baia Cascais
We’ll begin our day in the storybook village of Óbidos, where whitewashed homes, cobblestone streets, and medieval walls create a picture-perfect scene. Be sure to try a local favorite, ginjinha, served in a small chocolate cup. Next, we’ll travel to Sintra, a UNESCO World Heritage site that once served as the summer retreat for Portuguese royalty. This afternoon, you choose your adventure: stroll through the charming hilltop village at your own pace or join a guided visit to the National Palace of Sintra, one of Portugal’s best-preserved medieval palaces. This evening is free for you and your Sisters to explore and dine independently. (Breakfast included)
Hotel: Hotel Baia Cascais
Today, we’ll travel through the rolling countryside of Portugal as we head into the Alentejo region. We’ll stop at a family-owned cork factory to learn why Portugal leads the world in cork production and how this sustainable material shapes the local economy. Next, we continue on to Évora, a UNESCO World Heritage site, where a traditional Alentejo lunch awaits, paired with the soulful sounds of Cante Alentejano music. In the afternoon, we’ll explore this beautifully preserved medieval city with a local expert, including a visit to its iconic Roman temple. Tonight, enjoy free time with your Sisters. (Breakfast and Lunch included)
Hotel: Vila Gale Evora
This morning, we’ll journey south to the sun-kissed shores of the Algarve. Along the way, we’ll visit a local gin distillery where tradition and creativity come together in small-batch spirits crafted with regional botanicals. Sample the flavors that make this gin truly unique. Next, we’ll stop at a countryside winery for a tasting of rich Alentejo wines, paired with a light lunch amid the vineyards.
In the afternoon, we’ll continue to the Algarve and breathe in the salty ocean air. Explore Lagos, a historic port town where Moorish and Renaissance influences meet dramatic coastal cliffs. This is where Portugal’s great explorers once set sail and where your coastal adventure begins. (Breakfast and Lunch included)
Hotel: Vila Gale Lagos Algarve
After breakfast, we’ll set sail across the clear waters of the Bay of Lagos for a coastal experience you won’t forget. We’ll arrive at Ponta da Piedade, home to some of Portugal’s most iconic coastal scenery, where golden cliffs rise dramatically above hidden beaches. We will transfer to smaller boats to navigate through the magical grottoes. Marvel at the intricate rock formations, sea-carved caves, and quiet inlets that have been shaped by nature over thousands of years. It’s a peaceful, awe-inspiring way to witness the raw beauty of the Algarve. (Breakfast and Dinner included)
Hotel: Vila Gale Lagos Algarve
We’ll begin our day along the Algarve coast with a visit that highlights the region’s sardine canning legacy, a tradition that has shaped local life for generations. Then, we’ll head inland to Monchique, a charming mountain village surrounded by lush scenery. There, you’ll discover the secrets behind traditional Algarve bread and fruits, followed by a rustic picnic lunch featuring fresh, seasonal specialties. Return to Lagos in the afternoon and enjoy the evening at your own pace with your Sisters. (Breakfast and Lunch included)
Hotel: Vila Gale Lagos Algarve
As we journey toward Lisbon, we’ll stop in Setúbal, a colorful coastal city known for its working-class charm and incredible seafood. You’ll have time to enjoy our visit the Mercado do Livramento, one of the world’s top fish markets, brimming with fresh catch, local produce, and vibrant energy.
Arrive in Lisbon, Portugal’s capital of culture and character. Tonight, immerse yourself in the soulful sounds of fado during a three-course dinner at one of the city’s beloved fado restaurants. This traditional music, recognized by UNESCO, captures the heart of Portuguese life—raw, emotional, and unforgettable. (Breakfast and Dinner included)
Hotel: Lumen Lisboa Hotel Lisbon
Today, choose how you’d like to experience Lisbon. Join a locally guided walking tour that reveals the beauty and artistry of Portugal’s iconic mosaic sidewalks or explore the city’s deep connection to bacalhau (salted codfish) with your Tour Manager, uncovering stories behind this beloved national dish.
Later, we’ll head to Belém to view two of Lisbon’s most iconic landmarks: the Belém Tower and the stunning façade of the Jerónimos Monastery, both UNESCO World Heritage sites that reflect Portugal’s Age of Discovery. This evening, gather with your Sisters for a celebratory dinner, toasting the memories we’ve made across Portugal. (Breakfast and Dinner included)
Hotel: Lumen Lisboa Hotel Lisbon
Today, we’ll fly to Madeira, the “Pearl of the Atlantic,” where subtropical beauty meets rugged volcanic landscapes. After arriving in the early afternoon, enjoy free time for lunch in Funchal’s vibrant Santa Maria district. Later, we’ll join a guided walking tour through the old town’s narrow streets, visiting landmarks like the 15th-century cathedral. Then explore the stunning Botanical Garden of Madeira, home to over 2,500 plant species from around the world. This evening is yours to explore and dine independently with your Sisters. (Breakfast included)
Hotel: Pestana Casino Park Hotel
We’ll start our day in Câmara de Lobos, a picturesque fishing village that once inspired Winston Churchill’s paintings of Madeira. Continue along scenic mountain roads lined with banana plantations and vineyards as we head to Cabo Girão, one of the world’s highest sea cliffs, with sweeping views of the Atlantic. Next, we visit a unique, artistic center dedicated to Madeira’s beloved banana before continuing to the coastal village of Porto Moniz. Enjoy free time to explore before returning to Funchal for the evening. (Breakfast included)
Hotel: Pestana Casino Park Hotel
Today is yours to enjoy as you wish with your Sisters. You might explore the Sacred Art Museum, where centuries-old Flemish paintings reflect Madeira’s sugar trade legacy, or simply unwind and take full advantage of your hotel’s amenities. Tonight, we’ll celebrate our adventure with a traditional espetada dinner, featuring skewered meats cooked over an open fire. Local folk dancers and live music bring the culture of Madeira to life as you dine. (Breakfast and Dinner included)
Hotel: Pestana Casino Park Hotel
This morning, we’ll board our group return flight to Lisbon where you’ll have the rest of the day and evening to do that last minute shopping, grab a pastry at a local café, rest and relax, or simply have a lot of laughs with your Sisters as you prepare for your return flights home tomorrow. (Breakfast included)
Hotel: Pestana Casino Park Hotel
Today, we’ll be transferred to the Lisbon airport for our return flights home. As your unforgettable adventure draws to a close, carry with you the laughter, stories, and Sisterhood connections that made this experience truly extraordinary. Until next time, Sisters. (Breakfast included)
PLEASE READ THIS INFORMATION CAREFULLY
This vibrant journey through Portugal and Madeira is ideal for women who are comfortable walking and standing for moderate periods and participating in full days of cultural exploration and discovery. In true Sisterhood Travels fashion, this itinerary is thoughtfully paced for engagement, connection, and meaningful experiences, with time for spontaneity and rest along the way.
Walking & Standing:
Expect moderate walking most days, especially during guided walking tours through historic cities, villages, and cultural landmarks. Terrain includes cobblestone streets, uneven sidewalks, inclines, and occasional stairs, particularly in towns like Óbidos, Évora, and Lisbon. Some free exploration time is included, and participation in optional experiences may involve additional walking or standing.
Terrain, Transport & Accommodations:
You’ll travel comfortably by private coach and enjoy centrally located hotels with modern amenities and access to elevators. Scenic boat rides in the Algarve and small-boat transfers during the Ponta da Piedade grotto tour may require balance and steady footing. Roads in rural areas and along coastal or mountainous routes can be winding but are taken at a relaxed pace.
Cultural Experiences and Christmas Markets:
This tour includes immersive and enriching experiences such as wine and gin tastings, traditional music performances, food and artisan demonstrations, and UNESCO World Heritage site visits, as well as the Christmas Markets. While culturally rewarding, these experiences are not physically strenuous and can be enjoyed at a comfortable pace.
