Madeira, Portugal’s subtropical “Floating Garden,” rises from the Atlantic in a quilt of cliffs, laurel forests, and terraced vineyards. Settled in the 15th century by Portuguese explorers, the island blends maritime history with a deep culinary heritage—think espetada skewers, black scabbardfish with banana, and centuries-old Madeira wine.

Beyond Funchal’s cafe-lined promenades, you’ll find easy levada walks to balcony-like viewpoints, volcanic sea pools, and quiet fishing villages where poncha (a citrus-rum-honey tipple) fuels spirited conversations. The climate is gentle year-round, though microclimates can switch from sun to mist—bring a light layer and good walking shoes.

With a rental car and a mid-range budget, this 8-day plan keeps you based in Funchal while day-tripping in every direction. You’ll taste, stroll, cruise, and hike without strenuous ascents—most walks are about 2 hours roundtrip or less—leaving time for oceanfront sunsets and memorable meals.

Funchal

Funchal is Madeira’s lively capital, a harbor city wrapped in jacaranda and tiled pavements. Its Old Town (Zona Velha) is a maze of painted doors and wine lodges; its hills lead to Monte’s gardens and the legendary wicker toboggans. Cafes, museums, and markets make it easy to balance culture with seaside downtime.

• Top sights: Mercado dos Lavradores, Sé Cathedral, Blandy’s Wine Lodge, CR7 Museum, Santa Catarina Park, Monte Palace Tropical Garden, Madeira Botanical Garden.
• Short scenic drives: Câmara de Lobos fishing village, Cabo Girão skywalk, Ribeiro Frio Balcões viewpoint, Ponta de São Lourenço peninsula, Santana’s thatched houses, Porto Moniz rock pools.
• Fun fact: Winston Churchill painted seascapes in Câmara de Lobos—still one of the island’s prettiest harbor scenes.

Where to stay (Hotels.com/VRBO): Base yourselves in central or Lido-area Funchal for easy parking and dining. Browse stays on Porto Mare Hotel (resort comforts and pools), the design-forward Belmond Reid's Palace (iconic clifftop classic), and value-friendly retro-modern Hotel do Carmo. Compare more options on Hotels.com Funchal or self-catering apartments via VRBO Funchal.

How to get here: Fly into Funchal (FNC). From Europe, compare routes on Omio flights (many nonstops; LIS–FNC ~1h45). From beyond Europe, check Trip.com flights and Kiwi.com for competitive fares with one-stop connections. A compact car suits Madeira’s narrow roads; many hotels have garages or nearby municipal car parks.

Day 1: Arrival in Funchal, Old Town Stroll, First Taste of Madeira

Afternoon: Land at FNC and drive 25–30 minutes to Funchal. Check in and stretch your legs along Avenida Arriaga and Santa Catarina Park for harbor views. Pop into Blandy’s Garden courtyard for a coffee or head to the Municipal Garden to see endemic flora.

Evening: Dinner at Armazém do Sal (creative Madeiran cuisine, excellent value tasting menus) or O Portão (old-town favorite for espada with banana and grilled limpets). Toast your first night with a poncha at Venda Velha—start classic (lemon) before venturing to passionfruit. Early night to shake off travel.

Day 2: Funchal Essentials, Market to Wine

Morning: Breakfast at Prima Caju (great coffee, fresh bowls, eggs) or a pastel de nata at a downtown pastelaria. Wander the Mercado dos Lavradores (go early; admire fruit and flowers, but verify prices before buying). Explore painted doors on Rua de Santa Maria and step inside the ochre Forte de São Tiago for sea views.

Afternoon: Join a guided tasting walk to dive into island flavors:

Madeira Food, Wine & Cultural Tour — sample bolo do caco, espetada, local cheeses, and Madeira wine while learning the island’s food history. If you prefer DIY, visit Blandy’s Wine Lodge for a guided lodge tour and tasting, then call at D’Oliveiras for older vintages.

Evening: Dine at Kampo by Chef Júlio Pereira (modern Madeira, grilled meats, local produce) or sister spot Akua (seafood-forward). Nightcap at a harbor bar or a scoop from an artisanal gelato stand around Praça do Povo.

Day 3: Monte by Cable Car, Tropical Garden, and the Toboggan

Morning: Park near the cable car station (Almirante Reis car park) and ride up to Monte for panoramic bay views. Stroll Monte Palace Tropical Garden—koi ponds, exotic flora, and a compelling African sculpture and mineral collection.

Optional, packaged experience: Tour Cable Car Toboggan and Tropical Garden bundles the cable car, the famous wicker toboggan ride down to Livramento, and a visit to the Botanical Garden.

Afternoon: Visit the Church of Nossa Senhora do Monte and stop for coffee at a viewpoint cafe. If you didn’t book the tour, descend by toboggan (2-person sleds; taxis wait at the bottom) or take the cable car and drive to the Botanical Garden for a quick loop.

Evening: Casual dinner at O Tasco (small plates, local wines) or go classic with Beef & Wines (picanha and Madeiran sides). Sunset stroll along the Lido promenade.

Day 4: The East – Ponta de São Lourenço and Machico

Morning: Drive 40 minutes to the Ponta de São Lourenço (PR8) trailhead. Do an easy out-and-back to the peninsula’s viewpoints—turn around at ~1 hour to keep the walk to roughly 2 hours total. Sea cliffs, lichen-red rocks, and wind-whipped heather make this one of Madeira’s most dramatic coastal hikes.

Afternoon: Snack or light lunch at the simple Casa do Sardinha cafe near the trail’s far end, or picnic with supermarket treats. Continue 15 minutes to Caniçal’s Whale Museum for a thoughtful look at the island’s whaling past and conservation present. Then stop in Machico for a coffee by the sandy bay.

Evening: Back in Funchal, try Casa Madeirense (hearty espetada skewers, milho frito, and salads) or seafood at Gavião Novo in the Old Town. If you fancy dessert, hunt down a slice of bolo de mel (sticky honey cake) from Fábrica Santo António’s shop earlier in the day.

Day 5: The West – Câmara de Lobos, Cabo Girão, Fanal Forest, and Porto Moniz

Morning: Drive 15 minutes to Câmara de Lobos for a harbor stroll and perhaps a pre-lunch poncha. Continue 10 minutes to the Cabo Girão Skywalk (580 m glass platform; breathtaking). Carry on to the north via Encumeada; plan a short, gentle wander among ancient laurel trees in the Fanal Forest (there are easy loop paths near the picnic area).

Afternoon: Reach Seixal for a quick look at its black-sand beach, then on to Porto Moniz for a swim in the natural lava pools (bring towels; small fee for the main complex, free pools also exist). The drive back to Funchal via the south coast takes ~1h30 with viewpoint stops.

Prefer a guide and no driving? Consider Madeira West - Enchanted Terraces & Fanal (open-top jeep) for an all-day route to waterfalls, Fanal, and Porto Moniz with insider stops.

Evening: Dine casual in Funchal after the big day—Restaurante dos Combatentes is a reliable, good-value pick near the Municipal Garden. If you’re staying near Lido, promenade eateries offer easy options for groups.

Day 6: North & Santana – Balcões Viewpoint and Thatched Houses

Morning: Drive 30 minutes to Ribeiro Frio and walk the Vereda dos Balcões (PR11), a super-easy, mostly flat 1.5 km path (about 30–40 minutes each way). On clear days, it frames the central massif like a theater stage—look for chaffinches near the miradouro.

Afternoon: Continue 25 minutes to Santana to see the colorful palheiros (traditional thatched houses). Lunch on hearty northern fare—trout, corn bread, and soups—at a local tasca in town. If skies are clear, detour to the Guindaste viewpoint above Faial for gorgeous coastline, then meander back to Funchal via the scenic road past Pico do Areeiro viewpoints.

Evening: Back in the capital, enjoy a Madeira wine flight at D’Oliveiras, then dinner at Restaurante do Forte (romantic, set inside the old fort) or keep it low-key with petiscos in the Old Town. Nightcap along the marina.

Day 7: Ocean Day – Dolphin Watching and Sunset at Sea

Morning: Slow start with coffee at Café do Teatro by the flower-lined avenue. Browse the Sé Cathedral area and pop into the CR7 Museum if you’re a football fan. Light lunch—try a prego sandwich on bolo do caco from a snack bar.

Afternoon & Evening: Head to the marina for a golden-hour sail: Catamaran Sunset Cruise from Funchal. With luck you’ll spot dolphins (and in season, whales) as the sun colors the cliffs. After docking, dinner at Taberna Ruel in the Old Town, known for friendly service and a broad Madeiran menu.

Day 8: Lazy Funchal Morning, Gardens & Goodbyes

Morning: Squeeze in a final garden—Quinta das Cruzes (decorative arts and a serene orchid-filled yard)—or a promenade walk in the Lido area if you prefer sea air. Stop by Fábrica Santo António for edible souvenirs (bolo de mel and honey cookies pack well). Check out and transfer to the airport for your afternoon flight.

Extra Easy Hikes (swap into any free morning):

• Levada do Alecrim (Rabaçal): Do the shorter out-and-back to Lagoa do Vento viewpoint or to the plateau lagoons; turn around at the 1-hour mark for a gentle 2-hour total. Drive ~55 minutes from Funchal; paid parking near Rabaçal entrance and shuttle available seasonally.
• Short Fanal Strolls: Near the Fanal picnic area, multiple very easy paths let you wander the UNESCO-listed laurisilva among atmospheric junipers—perfect if clouds roll in.

Dining Cheat Sheet (mix-and-match all week)

• Breakfast/Coffee: Prima Caju (healthy brunch plates), Café do Teatro (classic spot), bakery counters around Avenida Arriaga for natas.
• Lunch: Mercado dos Lavradores area snack bars (prego and soups), casual espetada in Câmara de Lobos, light bites at Casa do Sardinha after São Lourenço hike.
• Dinner: Armazém do Sal (modern Madeiran), Kampo or Akua (chef-driven), Gavião Novo (seafood), Restaurante do Forte (special occasion), O Tasco (petiscos), Casa Madeirense (grilled skewers).
• Drinks: Poncha at Venda Velha (Funchal) or Rei da Poncha (Câmara de Lobos), Madeira wine flights at Blandy’s or D’Oliveiras.

Optional Add-Ons You Might Love

If you want a small-group, upscale ocean experience, consider VipDolphins Luxury Whale Watching (sparkling wine included) or the eco-friendly catamarans that focus on wildlife ethics. For sunrise lovers who don’t want to drive pre-dawn, a guided Pico do Areeiro Sunrise Tour is unforgettable on clear mornings.

Practical Tips: Madeira’s roads are steep—use low gear downhill and favor paid garages in Funchal’s center. Weather swings quickly; pack a light rain shell even on sunny days. For popular restaurants and tours, reserve 24–48 hours ahead (especially for a group of four).

With Funchal as your home base, this 8-day Madeira itinerary layers easy hikes, day trips, and sea time without rushed drives. You’ll taste the island’s soul—from poncha bars and wine lodges to laurel forests and sunset sails—and head home with a camera full of cliffs and gardens.