September is one of the most magical times to experience Madeira. The island seems to glow under softer sunlight, the ocean is still warm enough for long swims and the mountain trails open up to crisp, clear views. With the peak summer season behind, villages feel more authentic, roads are quieter, and there’s space to enjoy Madeira at your own pace. From sunrise above the clouds to the cool shade of ancient laurel forests, every corner of the island feels like an invitation to explore.
To make the most of your stay, you can start your journey stress-free with Transfers Madeira and enjoy total freedom with Funchal Car Hire.

1. Pico do Arieiro – Sunrise Above the Clouds
Rising to 1,818 meters, Pico do Arieiro is Madeira’s third-highest peak and one of its most awe-inspiring. Arrive early to catch the sunrise — a breathtaking moment when golden light spills over jagged mountain ridges while clouds swirl below your feet. From here, adventurous hikers can follow the spectacular trail toward Pico Ruivo, Madeira’s highest summit. Even if you’re not up for a full trek, simply driving up in the early morning is an unforgettable experience, and having your own hire car means you won’t be tied to bus schedules.

2. Levada Walks and the Laurissilva Forest
No trip to Madeira is complete without exploring its levadas — the centuries-old irrigation channels that now double as scenic walking paths. September is ideal for these hikes: the air is cooler, waterfalls are flowing, and the Laurissilva Forest, a UNESCO World Heritage site, is at its lushest. Trails like Levada do Caldeirão Verde guide you through moss-covered tunnels, while the 25 Fontes walk rewards you with dozens of cascading springs. Along the way, you’ll hear birdsong, breathe in fresh mountain air and glimpse untouched valleys — a side of Madeira that feels truly timeless.

3. Porto Moniz Natural Pools
Tucked away on Madeira’s north-west coast, Porto Moniz is famous for its volcanic rock pools filled naturally with Atlantic seawater. The pools are safe for swimming and perfect for cooling off after a scenic coastal drive. Spend the afternoon relaxing by the ocean, watch waves crash dramatically against black lava formations and sample freshly grilled limpets at a local restaurant. With a hire car, you can also stop at hidden viewpoints along the dramatic north coast on the way, making the journey just as rewarding as the destination.

4. Santana – Tradition and Charm
Santana is a charming village best known for its triangular thatched houses painted in bright primary colors. These traditional homes offer a glimpse into Madeira’s past, but the area is more than just photogenic architecture. Santana also serves as a gateway to the island’s mountainous interior, with access to some of the best trails in Madeira, including hikes around Pico das Pedras and Queimadas. Driving here gives you the chance to discover smaller villages en route, where you can stop for homemade poncha (a traditional Madeiran drink) and enjoy warm local hospitality.

5. Funchal – The Heart of Madeira
The island’s capital is a vibrant blend of culture, cuisine and gardens. Wander through the cobbled streets of the Old Town, discover street art along Rua de Santa Maria, and don’t miss the Mercado dos Lavradores, where stalls overflow with tropical fruit, flowers and local specialties. In September, the grape harvest brings lively wine festivals, complete with tastings, music and traditional dancing. Take the cable car up to Monte for panoramic views, then stroll back down through the famous Monte Palace Tropical Garden. Funchal is the perfect place to slow down and soak up Madeira’s atmosphere after a day of road-tripping.

Madeira in September is all about freedom — freedom to watch the sun rise above the clouds, to wander through laurel forests, to pause at a quiet village café or dive into volcanic rock pools. The island invites you to slow down, explore and let each day unfold in its own rhythm.
To make the journey effortless, many travelers choose Transfers Madeira for a smooth start, and Funchal Car Hire to unlock the freedom of the open road. With these comforts in place, Madeira becomes not just a destination but an experience you can fully embrace — one breathtaking view, one winding road, one unforgettable moment at a time.