Portugal layers Roman ruins, Moorish castles, Age of Discovery swagger, and Atlantic drama into a country sized perfectly for adventurous travelers. From Lisbon’s hilltop viewpoints and azulejo-lined alleys to Nazaré’s record-breaking waves and Madeira’s jagged ridgelines, you’ll pack a lot of wow into six days.

Expect hearty flavors—grilled sardines, caldo verde, pastéis de nata—and excellent value wines, from Douro reds to Madeira’s fortified styles. Coffee culture thrives; Lisbon’s third-wave cafés fuel early starts, while poncha (citrus-rum-honey) warms mountain evenings on Madeira.

Practical notes: Lisbon is walkable but hilly; trams and metro help. Nazaré is a painless bus ride away. Madeira is best explored by car or guided tours; weather shifts quickly at altitude. Tipping is appreciated but modest (round up or 5–10%). Always carry water, sun protection, and layers for high-altitude hikes.

Lisbon

Lisbon is a city of light and viewpoints—miradouros perched over terracotta rooftops and the shimmering Tagus. It marries maritime history (Belém) with a creative present (street art at LX Factory), and its neighborhoods reward wandering: Fado-echoing Alfama, café-hopping Chiado, and the tiled lanes of Mouraria.

Top sights: Jerónimos Monastery, Belém Tower, MAAT, the azulejo-rich National Tile Museum, and the Elevador da Bica. Secret favorites for photographers include Miradouro da Senhora do Monte at sunset and the pastel-hued Rua da Bica funicular first thing in the morning.

• Stay via Hotels.com (Lisbon) or VRBO (Lisbon). Specific picks: Lisbon Destination Hostel (budget, inside Rossio Station), Martinhal Lisbon Chiado Family Suites (mid-range suites), splurge-worthy Four Seasons Hotel Ritz Lisbon or Olissippo Lapa Palace Hotel.
• Getting in: Fly into Lisbon with Omio (flights in Europe). If you’re arriving from outside Europe, compare on Trip.com or Kiwi.com. Metro Red Line connects the airport to the center in ~30 minutes. A 24-hour transit pass (~€6.80) covers metro, trams, and funiculars.

Day 1: Arrival, Alfama sunsets, and a tuk-tuk orientation

Afternoon: Arrive and drop bags. Shake off jet lag at Fábrica Coffee Roasters (beans roasted in-house) or Hello, Kristof (Scandi-minimalist, great filter coffee). Stroll Baixa to Chiado; pop into Manteigaria for a warm pastel de nata. Climb to the Castelo de S. Jorge quarter and aim for Miradouro da Graça.

Evening: Kick off with a private tuk-tuk overview—perfect on day one to map the hills with a local’s commentary.

Recommended activity: Welcome Tour to Lisbon in Private Eco Tuk Tuk

Dinner in Baixa/Chiado: Taberna da Rua das Flores (blackboard of seasonal petiscos; go early), or Zé da Mouraria (no-frills, huge portions of grilled fish and pork). Nightcap in Alfama at a small Fado house; mind cover charges and minimums.

Day 2: Sintra palaces, Atlantic cliffs, and Cascais (full-day tour)

Trade the city for fairy-tale peaks and coast. This is a full-day small-group tour—no need to split into morning/afternoon/evening.

Recommended activity: Sintra, Pena, Regaleira, Cabo da Roca & Cascais from Lisbon

Expect colorful Pena Palace, the mystic wells of Quinta da Regaleira, windblown Cabo da Roca (Europe’s westernmost point), and time for gelato in Cascais. Pack layers; Sintra’s microclimate runs cooler than Lisbon.

Optional evening in Lisbon: If you still have energy, join a food tour to meet cooks and taste regional specialties.

Recommended activity: Winner 2025 Undiscovered Lisbon Food & Wine Tour by Eating Europe

Day 3: Belém icons, street art, and an LX Factory evening

Morning: Tram or rideshare to Belém. Tour Jerónimos Monastery (Manueline carving masterwork) and stroll to Belém Tower. Refuel with still-warm tarts at Pastéis de Belém. Coffee lovers can grab a flat white at Comoba or Monte Mar Coffee nearby.

Afternoon: Walk the riverfront to MAAT for bold contemporary architecture and exhibits. Then head to LX Factory for street art, indie shops, and a photo stop at Ler Devagar bookstore’s soaring presses. Casual lunch: Ni Michi (birria tacos) or P’razeres da Picanha (Brazilian grill).

Evening: Graça or Senhora do Monte viewpoints for golden hour. Dinner at Cervejaria Ramiro (garlic clams, scarlet shrimp—go early or expect a wait) or small-plate fun at Pharmácia in a former apothecary. Nightcap ginjinha near Rossio.

Day 4: Nazaré big waves and medieval Óbidos (day trip)

Morning: Depart Lisbon for Nazaré. By bus via Omio (buses) from Sete Rios, it’s ~1h45–2h each way, ~€12–16. On arrival, walk or funicular up to Sítio for sweeping views and the lighthouse at Forte de São Miguel Arcanjo, overlooking the monster swells of Praia do Norte (peak season: roughly Oct–Mar). Photographers: bring a long lens and windbreaker.

Afternoon: Seafood feast: A Tasquinha (cataplana), Taberna d’Adélia (golden bream), or Maria do Mar (octopus rice). Optional add-on: bus or taxi to the walled town of Óbidos for a shot of cherry ginja and wall walks. Return to Lisbon by evening bus.

Evening: Low-key dinner back in Lisbon at Time Out Market—try Henrique Sá Pessoa – Cozinha and Marisqueira Azul for fast, quality bites. Early night before your island hop.

Prefer a guided day: Consider a small-group excursion that combines Fátima, Nazaré, and Óbidos for logistics-free travel. Fátima, Nazaré and Óbidos Small-Group Day Trip from Lisbon

Funchal (Madeira)

Welcome to Madeira, the “Floating Garden” of the Atlantic—steep vineyards, knife-edge ridgelines, and deep-blue ocean. The capital, Funchal, mixes historic lanes with a modern food scene and cable cars linking the harbor to tropical gardens in Monte.

Highlights: sunrise at Pico do Arieiro, the PR1 ridge hike to Pico Ruivo, the PR8 trail along the lunar peninsula of Ponta de São Lourenço, the glass skywalk at Cabo Girão, and Câmara de Lobos for poncha at day’s end. Weather shifts fast: pack layers and check mountain forecasts.

• Stay via Hotels.com (Funchal) or VRBO (Funchal). Specific picks: Hotel do Carmo (retro, budget-friendly, central), Porto Mare Hotel (mid-range resort with pools and gardens), or iconic Belmond Reid's Palace (historic cliffside).
• Getting there from Lisbon: Fly to Funchal (FNC) in ~1h45 with TAP/EasyJet/Ryanair; typical fares ~€60–120 if booked ahead via Omio (flights). On arrival, rideshare/taxi to Funchal center is ~20 minutes (~€20–30).

Day 5: Fly to Madeira, Funchal old town, cable car, and garden vistas

Morning: Morning flight Lisbon → Funchal via Omio. Check in, then brunch at Prima Caju (excellent coffee, bowls, pancakes). Wander Mercado dos Lavradores—browse produce and flowers but confirm prices before buying exotic fruit.

Afternoon: Ride the harbor cable car up to Monte (~€18–22 round trip). Explore Monte Palace Tropical Garden and the koi-filled lakes, then descend partway by the traditional wicker toboggan (about 2 km; ~€25–30 per person, cash). Walk or taxi the rest.

Evening: Sunset aperitivo on the Three House rooftop or at the marina. Dinner at Armazém do Sal (contemporary Madeiran plates), O Portão (grilled limpets, espada with banana), or O Tasco (rustic petiscos, book ahead). Nightcap poncha at Rei da Poncha.

Day 6: Mountains and sea — PR1 ridge or PR8 peninsula, then depart

Morning: For a signature hike, choose one:

• PR1 Pico do Arieiro → Pico Ruivo (out-and-back or shuttle): 7–11 km depending on route; 3.5–6 hours; tunnels and steep stairways. Sunrise at Arieiro is spectacular for photography. Bring headlamp, layers, and water.
• PR8 Ponta de São Lourenço: ~7.5 km out-and-back; 3–4 hours; little shade; windswept volcanic scenery and turquoise coves. Great if you prefer sea-level views and need a shorter drive to the airport.

Afternoon: Late lunch in Caniçal (try O Muralhas for grilled catch) or in Câmara de Lobos (Vila do Peixe for charcoal-grilled seafood). Quick stop at Cabo Girão Skywalk (glass platform; ~€2) if time allows. Transfer to FNC for your afternoon departure.

Evening: Fly onward; if staying one more night, consider a short levada walk near Funchal (Levada dos Tornos section) and dinner on the Lido promenade.

Logistics at a glance

• Lisbon ⇄ Sintra: CP suburban train from Rossio ~40 min, ~€2.30 each way via Omio (trains) if you extend time there independently.
• Lisbon ⇄ Nazaré: Buses from Sete Rios ~1h45–2h, ~€12–16 via Omio (buses).
• Lisbon ⇄ Funchal (Madeira): Flights ~1h45; fares often €60–120 on Omio.
• Traveling to/from Europe: Compare flight deals on Omio. From outside Europe, also check Trip.com and Kiwi.com.

Coffee shop short list (for your route): Lisbon: Fábrica Coffee Roasters, The Mill, Hello, Kristof, Heim Cafe. Funchal: Prima Caju, The Ritz Madeira (historic terrace), Art Food Corner.

Dining short list (budget to moderate focus): Lisbon: Zé da Mouraria, Taberna da Rua das Flores, Pharmácia, Cervejaria Ramiro, Time Out Market stalls. Nazaré: A Tasquinha, Taberna d’Adélia, Maria do Mar. Funchal/Câmara de Lobos: O Portão, O Tasco, Armazém do Sal, Vila do Peixe, Vila da Carne.

Safety and trail notes: Check mountain forecasts before Madeira hikes; trails can close for wind or fog. Start early to secure parking at Pico do Arieiro. Carry cash for the Monte toboggan. In Lisbon’s trams and busy viewpoints, mind pockets and bags.

Optional Lisbon add-ons: If you prefer an open-air overview instead of day 1’s tour, consider: Private Lisbon Sightseeing Tuk-Tuk Tour: Alfama, Belém & More

In six days you’ll sip espresso in tile-clad Lisbon, watch thundering surf at Nazaré’s lighthouse, and hike Madeira’s otherworldly spines—an adventurous loop tailor-made for photographers. With mid-range stays and smart transit, it’s big on experience and easy on the wallet.