Sometimes a journey begins not with a destination, but with a perfectly placed stopover. Milan, Italy’s stylish northern capital, makes an ideal gateway when heading further afield. Even with just one evening before an early flight, the city offers a taste of elegance, culture, and irresistible cuisine.
Having visited Milan before, we didn’t feel the need to rush between landmarks this time. Instead, we enjoyed a relaxed evening soaking up the atmosphere and revisiting the city in a slower way.
If it’s your first time in the city, it’s worth heading to the magnificent Milan Cathedral. The Gothic masterpiece dominates the main square and is one of the most impressive landmarks in Italy. Art lovers may also want to book ahead to see The Last Supper by Leonardo da Vinci, one of the world’s most famous paintings.
For those who prefer to explore neighborhoods, Milan offers endless charm. The picturesque canals of the Navigli District are particularly magical at sunset, when locals gather along the water and restaurants fill with evening energy. Meanwhile, the elegant streets of Brera invite leisurely wandering among boutique galleries, leafy squares, and cultural highlights such as the renowned Pinacoteca di Brera.
Of course, no evening in Milan would feel complete without experiencing aperitivo. This beloved local tradition is as much about socializing as it is about food and drink. Typically, you order a drink—often a spritz, negroni, or a glass of prosecco—and it comes with a generous spread of snacks and small bites. From olives and cheeses to cured meats and miniature sandwiches, it’s the perfect way to unwind and ease into the slower rhythm of the evening before the next leg of your journey.
For us, the evening was all about food. We headed to Mercato Centrale Milano, a lively food hall where you can sample a variety of Italian specialties under one roof. It was the perfect place for a relaxed dinner—choosing from fresh pasta, local dishes, and sweet treats—without the formality of a traditional restaurant.
After dinner, it was time to head to our airport hotel, ready for an early flight the next morning. It was a simple but enjoyable way to start the journey: one last taste of Milan before swapping city streets for the lush landscapes and ocean views of Madeira.
From City Buzz to Island Calm: Arriving in Madeira
After the energy and elegance of Milan, arriving in Madeira feels like stepping into a completely different rhythm of life. The lush volcanic island rising from the Atlantic is known for its dramatic cliffs, emerald mountains, and winding coastal roads.
Instead of staying in the busier areas, we chose the quieter north coast and based ourselves in the charming village of Arco de São Jorge. Surrounded by vineyards, banana plantations, and the deep blue ocean, it felt wonderfully peaceful and authentic.
Miradouros, Coastal Walks & Natural Pools
Our first full day began with a short drive to the spectacular viewpoint of Miradouro de São Cristóvão. Perched above rugged cliffs, it offers sweeping views of the dramatic northern coastline where the green mountains plunge straight into the Atlantic.
After taking in the scenery, we stopped for coffee at Restaurante As Pedras—a relaxed local spot perfect for a quick break before continuing our walk.
From there we headed toward the small and picturesque Capelinha de Nossa Senhora de Fátima, a charming hilltop chapel with postcard-worthy views across the coast.
Later we cooled off at the natural lava pools of Piscinas Naturais do Porto Moniz. These volcanic rock pools filled with crystal-clear ocean water are one of Madeira’s most iconic experiences.
On the way back, we grabbed a casual local meal at Take‑Away Armando’s—simple, delicious, and exactly what you want after a day outdoors.
Into Madeira’s Green Heart: Levada Walks
The following day was dedicated to one of Madeira’s most famous hikes: Levada do Caldeirão Verde. This magical trail follows one of the island’s historic irrigation channels through dense laurel forest, tunnels carved into the rock, and moss-covered cliffs, eventually leading to a beautiful waterfall cascading into a lush green amphitheater.
The next morning we opted for a shorter but equally rewarding walk at Levada dos Balcões. The path ends at a stunning balcony-like viewpoint overlooking the deep valleys and jagged peaks of Madeira’s interior.
In the afternoon we explored the quiet surroundings of São Jorge, including the atmospheric ruins of the old sugar mill—reminders of the island’s agricultural past. As the day wound down, we found a small bar overlooking the ocean and simply relaxed with a drink while the sun dipped toward the Atlantic.
Clifftop Views and the East Coast
The next day started with one of the most dramatic viewpoints on the island: Miradouro do Guindaste. Standing on glass platforms suspended above the cliffs, you can look straight down to the crashing waves below—an unforgettable perspective of Madeira’s wild coastline.
We continued on to the seaside town of Machico, one of the island’s oldest settlements. Here we enjoyed a relaxed lunch at Minho Velho, known for hearty Portuguese dishes and a welcoming atmosphere.
Funchal & Coastal Icons
No visit to Madeira would be complete without exploring its capital, Funchal. Wandering through the historic center reveals colorful streets, lively markets, and charming squares framed by subtropical gardens.
Just outside the city we stopped at the famous Cristo Rei in nearby Caniço. The statue stands high above the ocean with sweeping coastal views—one of the island’s most photogenic spots.
Exploring the Sunny South Coast
Our final days were dedicated to exploring the warmer southern side of the island. We began in the fishing village of Câmara de Lobos, famous for its colorful boats and relaxed harbor atmosphere. A quick coffee break here was the perfect start to the morning.
Next stop was Ponta do Sol, known for having some of the best weather on the island. Its small waterfront and golden light made it a lovely place to pause and soak in the scenery.
For some beach time we headed to Calheta, home to one of Madeira’s few sandy beaches. The calm marina and golden sand—imported from Morocco—make it ideal for a relaxing afternoon by the sea.
Before the day ended, we drove along the coast to the dramatic cliffs of Ponta do Pargo, where the island seems to drop off into the endless Atlantic.
Rum, Roots & Remarkable Flavours
Let’s talk about some of the island’s highlights:
One of the standout experience was visiting a traditional rum distillery, which gave us a fascinating glimpse into the island’s centuries-old sugarcane heritage. Another memorable moment was passing through the terraced banana plantations — draped across dramatic cliffsides — a sight we won’t soon forget. The island’s tropical abundance meant endless opportunities to sample exotic fruits: papaya, passion fruit, custard apple, tamarind, and the famously sweet Madeiran banana. For drinks, nothing beats the national favourite poncha — a punchy blend of aguardente, honey, and citrus that locals have been sipping for generations. At the table, we were equally spoiled: a beautifully fresh fish fillet espada bathed in a tangy maracujá (passion fruit) sauce, succulent meat skewers (espetada) grilled over laurel wood with some bolo do caco (sweet flatbread served with garlic butter), fiery piri piri chicken, and a deeply comforting tomato and onion soup (sopa de tomate e cebola) that tasted like it had been simmering on someone’s grandmother’s stove all day. Madeira doesn’t just show you paradise — it lets you taste it.
Where we stayed
During our trip, we stayed in accommodations that were both comfortable and conveniently located, all booked through Booking.com, where we found great rates and have always been happy with their service. In Milan, we slept near the airport at the Moxy Marriott Hotel Malpensa, which was super modern, clean, and made traveling in and out of the city hassle-free. In Madeira, we spent five nights at the Pestana Quinta do Arco, a beautiful property with lush gardens and a fantastic pool—perfect for relaxing and enjoying the island’s natural beauty. For the final two nights, we stayed in Caniço near Funchal at the Infinito Azul apartment, which had a great location close to the city, making it easy to explore local restaurants, shops, and the coast.
From Milan’s elegant boulevards and aperitivo culture to Madeira’s rugged cliffs, quiet villages, and lush levada trails, the journey offered the perfect balance of city sophistication and island adventure—two completely different worlds, both unforgettable in their own way.
If you’re planning your own escape, this pairing offers a perfect balance of city and island experiences. If you’d like help creating a similar itinerary, feel free to get in touch.