Planning a road trip around Madeira? The island might be small, but it’s packed with postcard-perfect towns that each offer something special. If you’re heading to the eastern side of the island, this guide is for you.
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I’m Hazel – a British travel blogger, beach lover, and lifelong island-chaser. I’ve explored every nook of Madeira, from the lush forests of Santana to the cliffside viewpoints in Caniço. I’ve packed this guide with honest tips, local highlights, and practical info.
Here are the best towns to visit in East Madeira – and where to stay for the ultimate experience.
👉 Don’t miss my companion post on Best Towns in West Madeira for the full island lowdown.
1. Funchal – The Big One 🌆
Madeira’s unique capital is the gateway to the island, and it’s so much more than just a stopover.
You’ve got tropical gardens, cable cars, buzzing markets and ridiculously good restaurants, all with a salty sea breeze on the side.
Start with a cable car ride to Monte for sweeping views of the bay, then wander back down through the painted doors of Santa Maria Street. If you’re feeling brave, zoom downhill on a traditional wicker toboggan ride – weird, wonderful, and a Funchal must-do.
Don’t miss the Mercado dos Lavradores for tropical fruit and colourful local crafts, or the serene paths of Monte Palace Tropical Gardens. This city has layers, and you’ll want at least a couple of days to peel them back.
👉 Check out my full guide to Things to Do in Funchal for even more ideas.
Where to stay in Funchal:
- Boutique vibes at Castanheiro Boutique Hotel.
- Historic glam at Belmond Reid’s Palace.
- Seafront luxury at Hotel Baia Azul.
- 🏨 Check out more Funchal hotels.
2. Santana – Triangle Houses & Forest Walks 🏡
Santana is all about tradition. Cute A-frame thatched houses (“palheiros”) and lush green landscapes that make you feel like you’ve stepped into a fairytale.
Quaint and green, Santana is most famous for its traditional palheiros – those postcard-perfect A-frame thatched houses. But there’s more here than a photo stop. It’s also a gateway to stunning forest walks, like those starting in the Queimadas Forest, where misty trails wind through laurel woods and moss-covered stones.
If you’re curious about Madeira’s culture and traditions, the Madeira Theme Park offers a surprisingly interesting look into island life (it’s better than it sounds!)
Where to stay in Santana:
- Lush retreat at Hotel Quinta Do Furão.
- Central comfort at Hotel O Colmo.
- Nature and sea views at Sao Jorge cottages.
- 🏨 Check out Santana stays here.
3. Machico – Where History Begins 🏖️
As the site of Madeira’s first Portuguese landing, Machico has plenty of history – but today it’s more about peace and sea views. The town has one of the island’s few sandy beaches, ideal for a dip or a nap under the sun, and the vibe here is refreshingly low-key.
Climb up to Pico do Facho for dramatic views over the bay, or pay a visit to the João Gonçalves Zarco statue for a quick history lesson with your beach day. Be sure to dip your toes at the sandy beach (a rarity in Madeira!)
Where to stay in Machico:
- Boutique style at White Waters Hotel.
- Beachfront ease at Dom Pedro Madeira.
- 🏨 Browse Machico hotels here.
4. Porto da Cruz – Rum & Rugged Coastlines 🥃
A small village with big energy, Porto da Cruz clings to the dramatic north coast and oozes old-school charm. There’s a sugar cane mill, dramatic cliffs, and one of the island’s coolest surf beaches.
You can still visit the Engenho do Norte distillery to see rum made the old-fashioned way, with steam-powered machinery and a whole lot of sugarcane.
The local beach at Prainha is a hidden gem (tiny but stunning) and the Vereda do Larano trail runs along the cliffs here, offering jaw-dropping Atlantic views with almost zero crowds. Wild, beautiful, and deeply relaxing.
Where to stay in Porto da Cruz:
- Yoga vibes and sea views at Nature Madeira Guest House.
- Modern comfort at Quinta da Vila.
- 🏨 Find Porto da Cruz spots.
5. Caniçal – Boats, Beaches & Whales 🐬
Caniçal used to be a sleepy fishing village – now it’s a go-to for boat tours and marine life spotting.
You can learn about the area’s past at the surprisingly engaging Whale Museum, or jump straight into the action with a whale and dolphin watching tour from the marina.
The beaches here are calm and picturesque, including the much-loved Prainha do Caniçal, and nearby Ponta de São Lourenço offers one of the island’s most iconic hikes – all cliffs, sea spray, and cinematic landscapes.
Where to stay in Caniçal:
- Beachfront bliss at Home Away From Home.
- Big group luxury at FLH Villa Mar with Sea Access.
- 🏨 Look at Caniçal accommodation.
6. Santa Cruz – Easy Breezy Stopover 🌴
Santa Cruz is the closest town to Madeira’s airport, which makes it a popular first or last night stop – but it’s more than just convenient. There is a pretty promenade, palm-lined streets, and a very chill atmosphere. Perfect for a night before or after your flight.
There’s a relaxed seafront promenade, a little square for ice cream or espresso, and plenty of palm trees swaying in the breeze.
It’s not packed with sights, but that’s kind of the point. It’s the perfect place to decompress before or after a big trip, and nearby Santo da Serra Golf Course adds a bonus if you fancy a round.
Where to stay in Santa Cruz:
- Stylish stays at Hotel Solar Bom Jesus.
- Relaxed resort vibes at Vila Galé Santa Cruz.
- 🏨 Explore Santa Cruz stays.
7. Caniço – Clifftop Views & Christ the King ✝️
Caniço is dramatic. Clifftop homes, a giant statue of Jesus, and underwater marine reserves make it a hot pick for divers, snorkellers, and romantics alike.
On one trip, my taxi driver actually stopped here to show it to me, insisting I stay there on my next visit!
The giant Christ the King statue stands watch over the ocean here, and the nearby Garajau Nature Reserve is a diver’s dream, with clear waters and colourful marine life. Even if you’re not a diver, take the cable car to Garajau Beach – the ride is scenic, and the cove at the bottom is a lovely place to swim or snorkel.
Where to stay in Caniço:
- Adults-only luxury at Sentido Galomar.
- Wellness retreat at Galo Resort Galosol.
- 🏨 Discover Caniço hotels.
8. Câmara de Lobos – Boats, Poncha & Churchill Vibes 🎨
Possibly the most photogenic fishing village in Madeira, Câmara de Lobos is all cobbled lanes, bright boats bobbing in the harbour, and the hum of poncha-fuelled conversation.
It’s easy to see why Winston Churchill set up his easel here – the views are pure poetry, especially from the Churchill viewpoint, which looks out over the sea and the colourful little bay below.
Stop at one of the waterfront bars for a glass of poncha (my fave is the passion fruit one), then stroll through the narrow backstreets where murals and mosaic benches add even more character. It’s lively, local, and effortlessly charming – definitely worth a detour (or an overnight stay if you want to soak in the atmosphere after the day-trippers leave).
Where to stay in Câmara de Lobos:
- Boutique comfort at Pestana Churchill Bay.
- Great value at Hotel Do Campo.
- 🏨 Check out Câmara de Lobos stays.
👉 Want the full island experience? Check out my guide to Best Towns in West Madeira – packed with forest hikes, food markets and cable car views!
Madeira Road Trip Itineraries 🚗
Here’s how to turn these towns into unforgettable island road trips:
🏝️ 7 Days East: Spend a week exploring the island’s eastern side, with coastal hikes, traditional villages, and one or two levada walks.
🌄 7 Days West: Focus on the dramatic cliffs, natural pools, and relaxed fishing towns of the island’s western half.
🚗 12-Day Coastal Route: The full island loop – from Funchal to Seixal via hidden beaches, dramatic cliffs, forest trails and sleepy fishing villages.
Map of East Madeira Towns 🗺️
Use this map to visualise your route and plan your stops around the island’s eastern gems.
FAQs About East Madeira Towns 💡
Planning a trip and still got questions? Here are the things people most often ask me about exploring this beautiful part of Madeira:
A: Spring (April–June) and autumn (September–November) are ideal. Expect mild temps, blooming landscapes and fewer crowds.
A: Not essential – but very helpful. Buses connect major towns, but a car gives you freedom to reach trails, viewpoints and hidden gems. I recommend Discover Cars for car rentals in Madeira.
A: Funchal for city vibes, Santana for tradition, and Machico for an easy beach stay with history.
A: Machico and Santa Cruz are great for kids with easy beaches and laid-back feels. Funchal has a cable car, gardens and even a toboggan ride.
A: Layers, hiking shoes, sunscreen, a swimsuit, and a rain jacket just in case. Oh, and extra camera storage – it’s ridiculously scenic everywhere on the island. Tips for taking unbelievable travel photos.
A: I travelled solo and felt safe the entire time. The locals are friendly, and there’s a welcoming vibe everywhere you go. If you are worried, check out my tips and advice for solo travel first.
A: Cards are widely accepted, especially in hotels and restaurants. But bring some cash for smaller shops, local markets, and rural spots.
A: Funchal’s Flower Festival in spring is a stunner, and summer brings lively music events and food fairs across the island
Enjoy your Eastern wanderings!
Hazel ☀️
Related Reading 📚
Want to keep exploring Madeira? Here are a few more guides you might love:
🌅 Best Towns in West Madeira: Sunsets, Surf & Seriously Good Views
🚐 20 of the Best Day Trips from Funchal, Madeira
🛣️ 12-Day Madeira Road Trip: Coastal Itinerary
🌆 15 Unmissable Things to Do in Funchal, Madeira.
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👉 Looking for practical travel tools? Check out my Travel Resources page.
Tags: Europe, Islands, Madeira, Portugal
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