Madeira & Alentejo Tour: Portuguese Charm
⁍ Journeys ◦ Europe ◦ Portugal ◦ Nature ◦ Culture ◦ Beach ◦ Gastronomy ◦ Couples ◦ Families ◦ Private Driver
Highlights
Madeira & Alentejo: Discover Two Sides of Portugal
✓ A mix of Madeira’s mountainous landscapes and the unspoiled coastlines of the Alentejo.
✓ Private guidance and a driver when they truly add value, without disrupting the flow.
✓ Stay in charming luxury hotels with a strong connection to their surroundings
✓ Culinary moments that are always connected to the place where you are.
Self-guided tour of Madeira & Alentejo
On this self-guided tour, you’ll discover two Portuguese regions that complement each other perfectly. You’ll start on the lush island of Madeira, where mountains, gardens, and levadas set the pace. From there, you’ll travel to the mainland to explore the Alentejo, a region of open landscapes, historic towns, and secluded beaches. The trip combines nature, culture, and gastronomy, with comfortable transportation and carefully selected hotels. Everything proceeds at a leisurely pace, allowing you to truly experience each place.
Itinerary
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Your journey begins in Madeira, an island where the landscape sets the pace. From your accommodation above Funchal, you’ll explore both the lush interior and the city itself. A private jeep tour takes you off-road through volcanic mountain landscapes, deep valleys, and viewpoints high above the clouds. This exploration offers insight into the island’s geology and diversity, far from the hustle and bustle of the coast.
You’ll also explore Funchal with a local guide. You’ll stroll through the historic center, visit the market, and learn how wine, embroidery, and trade have shaped daily life on the island. A tasting session puts these traditions into their modern-day context. In Monte, you’ll enjoy tropical gardens and—for those who dare—the iconic toboggan ride with panoramic views of the bay.
Another highlight is the levada walk to Caldeirão Verde. You’ll follow narrow irrigation channels through laurel forests and along steep rock faces, ending at a waterfall deep within a lush valley. Afternoons and evenings offer time for relaxation, culinary delights, and refined moments such as the iconic afternoon tea at Belmond Reid’s Palace, with views over Funchal Bay.
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After your flight to Lisbon, your private driver will take you to the heart of the Alentejo. The landscape opens up before you: cork oaks, vineyards, and rolling hills dominate the view. In the charming UNESCO city of Évora, you’ll stroll with a local guide past Roman ruins, whitewashed facades, and quiet squares.
Next, you’ll continue toward the coast, where the pace noticeably slows down. In Comporta and Melides, you’ll alternate beach time with short explorations of the surrounding area. You’ll walk through dunes, along wide beaches, and through villages where simplicity and open space take center stage. Spend the day at the exclusive Sublime Comporta Beach Club. Imagine: soft lounge chairs in the sand, a fresh sea breeze, sophisticated cocktails… The sunset at Palafítico da Carrasqueira, where a wooden pier stretches out over the tide, provides a golden finale to this journey.
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After a final breakfast amidst pine trees and sand dunes, you’ll be taken to Lisbon Airport by private transfer. You’ll return home with memories of two unique regions, each with its own rhythm, scent, and beauty.
Practical Information
Duration 8 days, 7 nights
Indicative price: on request
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This price is subject to change. The estimated price includes a private driver and accommodations but excludes flights.
With Pegase Tailored, we bring your travel dreams to life, fully tailored to your wishes. No standard package—just a unique journey so you can discover the world on your own terms. Best time to visit
Our highlight of the trip
“The levada hike to Caldeirão on Madeira. You walk along narrow irrigation channels through dense laurel forest, with steep rock faces on one side and open ravines on the other. The endpoint, a waterfall deep within a green crater, feels secluded and untouched. This is Madeira at its purest, far from roads and buildings”
Maïté Quijo, Luxury Travel Advisor
Featured hotels
Casa Velha do Palheiro, Madeira
You'll stay in a historic country house above Funchal, surrounded by expansive gardens. The location offers peace and quiet along with stunning views, without being isolated. The hotel serves as an elegant base from which to explore the island.
Belmond Reid’s Palace, Madeira
A classic on the coast of Funchal, with a view of the sea. The gardens are lush, the service is unparalleled, and the history is palpable in every detail. Afternoon tea is a regular highlight of the itinerary.
Spatia Comporta, Alentejo
A small boutique hotel nestled among the dunes and pine trees in the enchanting coastal region of Comporta. The architecture is simple and natural, with a strong emphasis on space and light. The perfect place to unwind after an active day
Featured experiences
Private Jeep Tour in Madeira
You’ll explore the countryside via dirt roads and scenic overlooks. The route will be tailored to your interests and fitness level. The focus is on nature, not speed.
Caldeirão Verde Levada Walk
An active half-day out in nature. The hike is mostly flat but offers a wide variety of scenery. Ideal for those who want to experience nature up close.
Melides & Carrasqueira
An exploration of a coastal village and its surroundings, culminating at the wooden pier in Carrasqueira at sunset. A simple yet striking landscape, unadorned.
Discover even more travel experiences
Madeira Tour: Counting the Stars
Experience Madeira in style: luxurious quintas, refined cuisine, and landscapes that surprise you anew every day.
