

Classic Lisbon & The Portuguese Islands
2 Nights in Lisbon + 3 in Madeira & 3 in São Miguel, The Azores


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Why We Love This Deal

Want to skip the tourist traps and dive straight into the heart of Portugal? This escape through Lisbon, Madeira, and São Miguel is exactly what you need!
We're not just offering you a trip; we're offering a local’s insider guide to Portugal’s must-see gems. From Lisbon’s vibrant charm to Madeira’s island bliss and São Miguel’s dramatic landscapes, every moment is tailored to give you the best of it all. Trust us—this is the Portugal you’ve been dreaming of.
Day By Day Itinerary
- Day 1Arrival in Lisbon

Welcome to Lisbon! Relax and unwind from the moment you arrive. We'll handle your airport transfers on arrival and departure, ensuring your adventure's seamless start and finish.
*Want to maximize your time in paradise? Consider pre-booking an early check-in during the booking process. This way, you can hit the ground running and start exploring sooner! Don't hesitate to contact our booking agents if you have any questions or need assistance setting this up.
Suggestion for the day: Stroll Around Downtown Lisbon
Lace up your walking shoes and embark on a journey through Lisbon's captivating historical neighborhoods. It’s time to explore Lisbon's vibrant neighborhoods on foot.
- Start in Chiado, a charming district with elegant shops and cafes. Don't miss Livraria Bertrand, a historic bookstore.
- Move to Baixa, the bustling downtown area with Praça do Comércio, a grand waterfront square. Climb the Arco da Rua Augusta for city views.
- Immerse yourself in Bairro Alto's lively nightlife scene. Wander its maze-like streets filled with bars, restaurants, and traditional Fado music venues.
Can't-Miss Sights:
- São Roque Church: Admire its opulent interior.
- São Pedro de Alcântara Garden: Relax and enjoy panoramic views.
- Ruins of Carmo Church: Reflect on Lisbon's history.
- Santa Catarina Viewpoint: Capture stunning cityscapes.
- Luís de Camões Square: Pay homage to Portugal's literary icon.
- Terreiro do Paço: Soak in the lively atmosphere of this vast waterfront square.
- Santa Justa Lift: Enjoy a unique perspective from this neo-Gothic elevator.
- Day 2Lisbon

Suggestion for the day: Day Trip to Fairytale Sintra
A short 28-kilometer drive whisks you away from the bustling capital and into a world of enchanting palaces, captivating gardens, and romantic charm. This UNESCO World Heritage Site boasts a mesmerizing cultural landscape, characterized by winding mountains, lush forests, and remarkable architectural wonders. In the 19th century, Sintra emerged as the epicenter of Romantic architecture in Europe, renowned for its distinctive palaces and whimsical designs that could easily inspire fairytales.
Don’t Miss:
- Early Start & Pena Palace: Start your exploration with the iconic Pena National Palace, a vibrant masterpiece perched atop a hill. Marvel at its eclectic architectural styles, ranging from Romanticism to Moorish Revival.
- Quinta da Regaleira: If you have time and a taste for adventure, delve into the mysteries of Quinta da Regaleira. This enigmatic estate features a labyrinth of hidden grottoes, tunnels, and secret passages waiting to be discovered.
- Moorish Castle: For history buffs, the Moorish Castle offers a glimpse into Sintra's medieval past.
- Sintra Village & Lunch: Head back to the charming village of Sintra. Wander through the narrow cobbled streets lined with colorful houses and quaint shops. Explore the Sintra National Palace, the former summer residence of the Portuguese royal family.
- Monserrate Palace: For those seeking a different architectural style, consider visiting Monserrate Palace. This 19th-century palace boasts a captivating blend of Gothic, Moorish, and Indian influences.
- There’s More of Sintra! Add Cabo da Roca to your itinerary. Experience the stunning views from the westernmost point of mainland Europe, where dramatic cliffs meet the Atlantic Ocean. This natural landmark, located within the Sintra-Cascais Natural Park, is perfect for breathtaking scenery, sunsets, and a touch of adventure.
Tips for Your Trip:
- Consider booking a guided tour to Sintra ahead of time to ensure you don’t miss out on the top sights—we can help arrange this for you.
- Purchase your tickets to Sintra attractions in advance, especially during peak season.
- Consider purchasing the Sintra Card for discounted entry to several attractions and public transportation within Sintra.
- Wear comfortable shoes as you'll be doing a fair amount of walking.
- Pack a light jacket or sweater as the weather in Sintra can be cooler than Lisbon, especially in the mornings and evenings.
- The drive from Lisbon to Sintra takes about 30 to 40 minutes, while the train journey takes approximately 40 minutes.
- Day 3Flight to Madeira Island (approx. 1.45 hours)
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Welcome to Madeira Island! Relax and unwind from the moment you arrive. We'll handle your airport transfers on arrival and departure, ensuring your adventure's seamless start and finish.
*Want to maximize your time in paradise? Consider pre-booking an early check-in during the booking process. This way, you can hit the ground running and start exploring sooner! Don't hesitate to contact our booking agents if you have any questions or need assistance setting this up.
Suggestion for the day: Explore Downtown Funchal
Step back in time and explore the vibrant tapestry of Funchal, the heart of Madeira Island! Nestled amidst lush hills and overlooking the vast Atlantic, this city boasts a rich history dating back to the early 15th century. Founded by Portuguese explorers, Funchal quickly blossomed into a cosmopolitan center, a vital stop on trade routes between Europe and the New World. Today, Funchal exudes Portuguese charm, offering a captivating blend of its historical legacy and lively modern spirit.
Don't Miss:
- Mercado dos Lavradores (Farmers' Market): Immerse yourself in the sights and smells of the bustling Mercado dos Lavradores (and taste delicious exotic fruit!)
- Sé Cathedral (Funchal Cathedral): Step into the magnificent Sé Cathedral, a landmark showcasing Gothic and Romanesque architectural styles.
- Santa Clara Convent: Admire the beautiful cloisters and learn about the convent's fascinating history.
- Museu de Arte Sacra (Museum of Sacred Art): Uncover a collection of religious art and artifacts at the Museu de Arte Sacra.
- Blandy's Wine Lodge: Embark on a journey through Madeira's renowned wine culture with a visit to Blandy's Wine Lodge. Sample the island's famous fortified wines and learn about the traditional production methods.
- Zona Velha (Old Town): Wander through the charming cobbled streets of Zona Velha, Funchal's historic center. Admire the colorful houses and discover hidden squares and fountains.
- Praça do Município (Municipal Square): Relax in the heart of Funchal at the Praça do Município, the main square. People watch, soak in the atmosphere and enjoy the lively street performers.
- Fortaleza de São Tiago (São Tiago Fort): Cap off your day with a visit to the Fortaleza de São Tiago, a 17th-century fort offering stunning ocean views. Explore the ramparts and learn about Funchal's maritime history.
- Day 4Madeira Island

Suggestion for the day: Unveiling Madeira's Eastern Delights
Eastern Madeira offers a captivating blend of charming villages, dramatic landscapes, and historical significance. Join us on a journey of discovery as we explore traditional thatched houses, volcanic peaks, and a peninsula known for its lunar-like beauty.
Don’t Miss:
- Santana (Highlight): Our adventure begins in Santana, a village renowned for its iconic triangular thatched-roof houses. These colorful dwellings, known as "palheiros," are a symbol of Madeira's traditional architecture. Wander through the village, admiring these unique houses and soaking in the peaceful atmosphere.
- Machico: Continue your journey to Machico, the first capital of Madeira Island. Explore the historic city center, visit the Captain's House Museum to learn about the island's early settlers, and relax on the golden sands of Machico Bay.
- Pico do Arieiro: Ascend to breathtaking heights at Pico do Arieiro, Madeira's third-highest peak. On a clear day, witness stunning panoramic views of the island's dramatic landscapes, including the Curral das Freiras Valley.
- Ponta de São Lourenço: Your final stop is Ponta de São Lourenço, a nature reserve at the easternmost tip of the island. This peninsula boasts a unique lunar-like landscape with volcanic rock formations and sparse vegetation. Explore the network of hiking trails, take in the dramatic ocean views, and witness the beauty of this natural wonder.
- Day 5Madeira Island

Suggestion for the day: A Day Trip to the West Coast
Madeira Island boasts a dramatic coastline, and the west coast offers some of its most breathtaking scenery. Join us on a journey of discovery as we explore charming villages, volcanic wonders, and natural pools sculpted by the Atlantic Ocean.
Don’t Miss:
- Ribeira Brava: Ribeira Brava is known for its rum production, so consider a visit to a local distillery for a taste of this Madeiran specialty.
- São Vicente Caves: Venture into the depths of the earth at the São Vicente Caves, a volcanic wonder formed millions of years ago. Marvel at the caverns adorned with stalactites and stalagmites, and learn about the island's geological history.
- Seixal: Continue along the scenic route to Seixal, a charming village known for its black sand beach and natural rock pools. Take a refreshing dip in the crystal-clear waters or simply relax on the shore, basking in the beauty of the surroundings.
- Porto Moniz: Our suggested itinerary leads you to Porto Moniz, a highlight of the west coast. This seaside town is famous for its volcanic rock pools, natural formations filled with refreshing seawater.
- Calheta: As the day winds down, head to Calheta, a town known for its beach and laid-back atmosphere.
- Ponta do Sol: Your final stop is Ponta do Sol, a village named for its sunny disposition. Take a leisurely stroll along the promenade, enjoying the ocean views and the peaceful ambiance.
- Day 6Flight to São Miguel Island, The Azores (approx. 2 hours)

Welcome to the Azores! Relax and unwind from the moment you arrive. We'll handle your airport transfers on arrival and departure, ensuring your adventure's seamless start and finish.
*Want to maximize your time in paradise? Consider pre-booking an early check-in during the booking process. This way, you can hit the ground running and start exploring sooner! Don't hesitate to contact our booking agents if you have any questions or need assistance setting this up.
Suggestion for the day: Explore Downtown Ponta Delgada
It’s time to explore Ponta Delgada, the main city, that beckons not only with its charming streets and vibrant atmosphere but also with its status as the economic heart of the archipelago. Ponta Delgada evokes all the charms of Europe with cobbled streets, sidewalk cafes, and a thriving culinary scene.
Don’t Miss:
- Simply Stroll Through Ponta Delgada’s Cobblestone Streets: Start your São Miguel discovery with a stroll along Ponta Delgada's charming city streets. Admire the architecture, from historical buildings to colorful houses. Peek into local shops and soak in the atmosphere.
- Portas da Cidade: Standing proudly at the entrance to Ponta Delgada, the Portas da Cidade (City Gates) serves as a symbolic gateway to the city's rich history and vibrant culture.
- Matriz Church: Visit the impressive Matriz Church, a beautiful example of Azorean religious architecture right in the city center.
- Pineapple Paradise: Embark on a unique adventure to a nearby pineapple plantation. Learn about the island's pineapple production, witness these fascinating plants, and perhaps even enjoy a refreshing pineapple treat.
- Day 7São Miguel Island, The Azores

Suggestion for the day: Sete Cidades Lake
São Miguel Island, the largest in the Azores archipelago, is a treasure trove of natural beauty, and Sete Cidades is one of the most captivating gems. Today, embark on a journey through volcanic landscapes, serene lakes, and charming villages, and discover the essence of this enchanting island.
- Sete Cidades (A Realm of Twin Lakes): Begin your adventure in Sete Cidades, a village nestled within a vast volcanic crater. As you descend into the caldera, prepare to be awestruck by the sight of Lagoa das Sete Cidades a mesmerizing twin-lake complex. One of the 7 Natural Wonders of Portugal, this show-stopping crater full of lakes has become one of the signature and most famous images of the Azores.
- Mosteiros & Ferraria: Venture to the neighboring village of Mosteiros, a photographer's paradise known for its breathtaking sunsets. As you explore the western region, don't miss the chance to rejuvenate at Ferraria's unique ocean thermal baths. Remember, these thermal pools are best enjoyed during low tide when warm spring water mixes with the ocean for a truly luxurious experience.
- Day 8São Miguel Island, The Azores

Suggestion for the day: Lagoa do Fogo Lake
Explore the stunning Lagoa do Fogo, one of the most breathtaking lakes in the Azores. For the best experience, visit on a clear day, as the views are most spectacular when the skies are cloud-free. Be sure to check the weather forecast before heading up the mountain.
- Lagoa do Fogo (A Crater Lake of Tranquility): Lagoa do Fogo, which translates roughly into "Lagoon of Fire", is a crater lake at the center of São Miguel Island. This Protected Natural Reserve sits tucked away atop the impressive Pico da Barrosa, far from the whir, hum, and hurry of civilization below.
- Caldeira Velha Hot Springs: Caldeira Velha is an official natural monument, and the best thing about this lovely locale is not even the thermal pools (although they are divine), but rather the verdant vegetation. Visitors will find that Caldeira Velha is so lush and tropical, that you’ll almost find it hard to believe you are even in Portugal.
- Ribeira Grande: Discover the charm of Ribeira Grande, a vibrant town nestled on the north part of São Miguel Island. Explore its historic center, relax on the stunning Santa Bárbara Beach, known for its black sand and impressive waves, or embark on a hiking adventure through the lush countryside. Immerse yourself in the local culture, savor fresh seafood, and enjoy the laid-back atmosphere of this coastal paradise.
- Day 9Return Flight Home

We've arranged your hotel transfer to ensure a smooth journey to the airport.
Thank you for choosing us to be your travel companions on this adventure! It's been a pleasure assisting you in creating unforgettable memories. We wish you happy travels and until next time!
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