Madeira rose from the Atlantic as a volcanic sanctuary, and you feel it the moment you step into its terraced hills, laurel forests, and surf-laced coves. The island’s lifeblood—its levadas, or irrigation channels—cut emerald paths through a UNESCO-listed Laurissilva Forest. Coconut-frond sunsets, sea-to-table plates, and cozy taverns complete the picture.

Estreito da Calheta, on the sun-drenched southwest coast, is a countryside-meets-coast base: banana groves and vineyards on top, sandy Calheta Beach and a sleek marina below. Across the island, Funchal—Madeira’s capital—mixes historic lanes, tropical gardens, and a lively dining scene.

Practical notes: Madeira’s microclimates reward layers and good hiking shoes. Renting a car is useful for coastal loops, though tours cover the island handily. Try local staples like espada (black scabbardfish) with banana, espetada skewers on laurel wood, bolo do caco garlic bread, and a post-hike poncha (punchy sugar-cane spirit with honey and lemon).

Estreito da Calheta

Estreito da Calheta is terrace country—quiet lanes winding through vineyards and sugarcane, dropping to Calheta’s golden-sand beach (imported but irresistible) and a tidy marina with cafés. It’s minutes from Paúl da Serra and Rabaçal, the gateway to iconic levada walks.

Top nearby highlights include the MUDAS Contemporary Art Museum perched on a cliff, the Engenho da Calheta sugar mill and rum distillery (spring harvest is especially atmospheric), and sunset jaunts to Paul do Mar and Jardim do Mar—two surf-lapped villages with chilled bars.

• Where to stay: Browse coastal apartments and hillside villas on VRBO Calheta or hotels/resorts via Hotels.com Calheta. Look at Calheta Beach/Marina for sea access, or Arco da Calheta for bigger views.
• Eating & drinking: Onda Azul (grilled limpets, espada with banana) and A Poita at the marina; Alambique or Calhau (inside the Saccharum complex) for a polished dinner; sunset mojitos and poke at Maktub Pub (Paul do Mar); coffee and bolo do caco from beachfront kiosks.

Getting in: Fly into Funchal (FNC). From Lisbon ~1h45–2h; from London ~3h45–4h. Compare fares on Omio Flights (Europe) or Kiwi.com/Trip.com Flights. Transfer to Calheta by car (~45–55 min), taxi (~€60–75), or bus (~1h15–1h30).

Funchal

Funchal is the island’s handsome heart: 16th-century lanes and patterned calçada paving, jacarandas and banana trees, food markets, and seafront promenades. The cable car to Monte lifts you to tropical gardens and a basket-sledge ride that’s pure Madeira joy.

Spend time in Old Town’s painted-door streets (Rua de Santa Maria), taste Madeira wine at Blandy’s, and linger at viewpoints like Fortaleza de São Tiago. The dining scene is excellent—from creative small-plate kitchens to traditional tascas.

• Where to stay: Center yourself in Old Town or the Sé district via VRBO Funchal or check hotels on Hotels.com Funchal. Look near the cable car/Old Town for walkability.
• Eating & drinking: Kampo by Júlio Pereira (fire-kissed local produce), Akua (sea-inspired small plates), Armazém do Sal (Madeiran classics in a salt warehouse), O Tasco (rustic, generous grills), Barreirinha Bar Café (sunset drinks over the fort).

Day 1: Arrival in Madeira, settle into Estreito da Calheta

Morning: Fly into Funchal (FNC). For fares and times, compare on Omio Flights or internationally via Kiwi.com and Trip.com. Pick up a rental car at the airport or arrange a taxi.

Afternoon: Check in around Calheta/Estreito. Stretch your legs on Calheta Beach—calm water and golden sand make it ideal after a flight. Visit MUDAS Contemporary Art Museum for ocean-lapped architecture and rotating exhibitions.

Evening: Dinner at Onda Azul: start with lapas (grilled limpets with garlic and lemon), then espada with banana and passion fruit sauce. Nightcap with a poncha at the marina—classic fisherman’s fuel made with sugar-cane aguardente, honey, and citrus.

Day 2: Rabaçal and the 25 Fountains Levada (PR6)

Morning: Lace up for Madeira’s signature levada through the Laurissilva. Join this guided walk for context, transport, and trail timing:

25 Fountains Levada: Hiking Tour in Madeira Rabaçal Valley (PR6)

Afternoon: The route weaves from Paúl da Serra into Rabaçal’s mossy canyons, past weeping walls and fern tunnels to the 25 springs amphitheater. Expect 3–4 hours walking, moderate grade; bring a light rain shell and traction.

Evening: Reward yourself at Alambique (book terrace). Share tuna tataki with Madeiran spices, then espetada—beef skewers grilled on laurel branches—plus milho frito (crispy cornmeal cubes). Finish with passion fruit pudim.

Day 3: Whale & dolphin watching, beach time, and sunset village-hopping

Morning: Head to Calheta Marina for a marine-life safari on stable RIBs or a catamaran. Spring to autumn sees resident dolphins, pilot whales, and seasonal visitors like sperm whales.

Whale and Dolphin Watching in Calheta, Madeira Island

Afternoon: Lunch at A Poita (octopus salad, grilled espada, tomato-and-onion bolo do caco). Then relax at Calheta Beach—rent loungers/umbrella, or try SUP/kayak rentals from the marina.

Evening: Drive 15 minutes to Paul do Mar for sunset at Maktub Pub (famed mojitos, poke bowls) or continue to Jardim do Mar for a stroll along the cobbled seafront and a casual seafood dinner. The west coast sunsets are spectacular on clear days.

Day 4: West coast road-trip—Cabo Girão, Seixal, and Porto Moniz

Morning: Set out north via the old coastal roads. First stop: Cabo Girão Skywalk, a glass platform 580 meters above the sea—bring a camera; entry is just a few euros. Continue to Câmara de Lobos’ cove for a quick poncha if you didn’t sip one yet.

Afternoon: Aim for Seixal’s velvet-black sand beach and the roadside “Veu da Noiva” waterfall viewpoint. Carry on to Porto Moniz to swim in the volcanic lava pools (natural and complex pools; small entry fee, changing rooms available). Lunch on grilled limpets and scabbard at a poolside restaurant.

Evening: Return to Calheta (about 50 minutes). Dinner at Calhau by the beach for charcoal-grilled fish, or keep it low-key with a pizzeria slice and gelato along the marina promenade.

Day 5: Transfer to Funchal, Old Town wander, Monte cable car and toboggan

Morning: Check out and travel to Funchal (45–60 minutes by car; ~€5–7 by bus, ~1h15). For bus and ferry search tools in Europe, compare on Omio Buses and Omio Ferries (for Porto Santo day trips). Drop bags at your hotel/apartment near the Sé or Old Town.

Afternoon: Explore Mercado dos Lavradores (fruit, flowers, fish market—go for the bustle, not just tastings). Ride the cable car to Monte (about €12 one-way/€18 return), visit Monte Palace Tropical Garden’s koi ponds and tile collections, then take the wicker toboggan ride down to Livramento—an only-in-Madeira tradition.

Evening: Dinner at Kampo by Júlio Pereira (open kitchen, Madeiran beef and seasonal sides) or Armazém do Sal (elegant takes on classics). Post-dinner, grab drinks at Barreirinha Bar Café overlooking Forte de São Tiago.

Day 6: Santana’s thatched houses and the high peaks (guided)

Morning: Venture to Madeira’s northeast for a full-day exploration—storybook A-frame casas de colmo in Santana and the island’s third-highest peak, Pico do Areeiro, weather permitting. A guided tour keeps timings tight on mountain roads:

East Tour Santana

Afternoon: Expect coastal viewpoints, laurel-forest stops, and time in Santana to peek inside the thatched houses. Layer up—the weather shifts quickly on the ridgelines.

Evening: Back in Funchal, keep it sea-forward at Akua (ceviches, local catch, clever sauces) or go traditional at O Tasco (espada, picado platters). Night stroll along the marina for gelato or a Madeira wine nightcap.

Day 7: Ponta de São Lourenço and Madeira wine send-off

Morning: Head to the island’s eastern tip for a volcanic peninsula walk—windswept, treeless, and cinematic. Join a guided outing for transport and geology insight:

Ponta de São Lourenço Tour

Afternoon: Return to Funchal for a guided tasting at Blandy’s Wine Lodge (intro tours from ~€13; book on arrival in town). Learn about sercial-to-malmsey styles, estufagem aging, and why Madeira wines circled the globe in the Age of Sail.

Evening: Farewell dinner in the Old Town—try Restaurante do Forte inside the yellow São Tiago fortress for a romantic finale, or keep it casual at O Portão near the cathedral. Toast your week with a glass of medium-dry verdelho.

Where to book and compare:

• Flights: Omio Flights (Europe) | Kiwi.com | Trip.com Flights
• Trains/Buses/Ferries in Europe: Omio Trains | Omio Buses | Omio Ferries
• Stays in Calheta: VRBO | Hotels.com
• Stays in Funchal: VRBO | Hotels.com

In one week, you’ll taste both sides of Madeira: the serene, sun-bathed southwest around Estreito da Calheta and the cultural heartbeat of Funchal. Between Laurissilva levadas, ocean wildlife, and cliff-hugging roads, this itinerary balances adventure, flavor, and the island’s timeless Atlantic views.