Portugal

Days 1 – 5

Lisbon

Portugal's capital sits on seven hills above the Tagus, tiled in blue azulejos and lit in that particular golden Atlantic light. It's one of Europe's oldest cities and one of its most alive. Five days here will barely scratch the surface — and you'll never want to leave.

🏨 Where to Stay

Bairro Alto Hotel

Our top pick

The finest boutique hotel in Lisbon, sitting at the edge of the bohemian Chiado neighbourhood. Rooftop bar overlooking the city, Portuguese contemporary art throughout, and service that remembers your name after the first morning. From €350/night.

Memmo Alfama

Neighbourhood gem

Carved into the hillside of the ancient Alfama district, with a terrace and infinity pool hanging over the Tagus. More intimate than Bairro Alto. Wake up to the view that Lisboetas have painted for centuries. From €220/night.

Tivoli Avenida Liberdade

Grand boulevard classic

A grand 5-star on Lisbon's finest boulevard, the Champs-Élysées of Portugal. Rooftop pool with views across the whole city. If you want the classical Lisbon grand-hotel experience — this is it. From €280/night.

🍽 Where to Eat

Belcanto

✦ 2 Michelin Stars

Chef José Avillez is Portugal's most celebrated cook, and Belcanto in Chiado is his masterpiece. A 10-course tasting menu through the history and landscape of Portugal. Book months in advance and save it for your best night. Nick — this one is for you.

Cura — Four Seasons Ritz Lisbon

✦ 1 Michelin Star

Chef Pedro Pena Bastos in the iconic Ritz. Elegant, unhurried, flawlessly executed. The tasting menu is a portrait of modern Portugal — extraordinary Portuguese wine pairing available. A serious dinner.

Cervejaria Ramiro

Non-negotiable

Since 1956, the temple of Lisbon seafood. Queue before it opens. Order the garlic butter prawns, the percebes (gooseneck barnacles — strange-looking, tasting exactly like the ocean), the clams in white wine, and finish with a prego steak sandwich. Then consider returning tomorrow.

Tasca do Chico

30 seats · Live fado nightly

Thirty seats, a kitchen the size of a wardrobe, and the best fado dining room in Lisbon. Honest petiscos, house wine, and musicians who will make the hairs on the back of your neck stand up. Book weeks ahead. This is the Lisbon you came for.

Pastéis de Belém

Since 1837

Not a restaurant — a pilgrimage. The original pastel de nata, made from a recipe kept secret since 1837. Eat them warm from the oven, dusted with cinnamon, next to a bica (espresso). The single most important food experience in Portugal.

🗺 What to Do

Morning in Alfama

Lisbon's oldest quarter, built by the Moors a thousand years ago. Arrive before 9am — cobblestones, laundry drying between balconies, cats, a bakery at every corner. Climb to São Jorge Castle for the view across the city and the Tagus.

A Day in Belém

The grand historical quarter along the river. Jerónimos Monastery (UNESCO, breathtaking). Torre de Belém. The Monument to the Discoveries. Then pastéis de nata next door — eat two, then eat another.

Day Trip to Sintra

40 minutes by train. One of the most magical places in Europe — a forested mountain studded with 19th-century Romantic palaces. Pena Palace perched above the clouds. Quinta da Regaleira with its spiral initiation well descending underground. A completely different world.

Live Fado Evening

Fado is Lisbon's music — mournful, beautiful, born in the Alfama. Book a table at Tasca do Chico or Sr. Vinho for dinner with live performance. The singers are extraordinary. The emotion is untranslatable. This is something you carry home.

Westernmost European Vineyard

Adega de Colares — one of the few surviving wine estates near the Atlantic, growing ungrafted vines in sand. A completely unique Portuguese wine style. Worth a half-day trip to Sintra/Cascais combined with the coast.

Private Alfama & Belém Guided Tour

Book a private guide for your first full day. The context transforms everything — the history of the Moorish quarter, the meaning of the Manueline architecture in Belém, the story of the Age of Discoveries. You'll spend the rest of the trip noticing things you'd have walked past.

Days 6 – 10 · 1h10min flight from Lisbon

Madeira

A volcanic island in the middle of the Atlantic — dramatic cliffs, UNESCO ancient laurel forest, flowers everywhere year-round, and the most extraordinary wine in the world. Subtropical, wild, improbably beautiful. This is where the hiking, the views, and the adventure live.

🏨 Where to Stay

Belmond Reid's Palace, Funchal

Clifftop Atlantic grand hotel since 1891

THE hotel of Madeira. Opened in 1891 on a clifftop above the Atlantic. Churchill stayed here to paint. The terraced gardens cascade down to private sea pools, the afternoon tea ritual is a Madeira institution, and the light off the ocean at dusk is genuinely one of the most beautiful things you'll ever see. For a 50th birthday, there is no better address on this island. From €450/night.

Choupana Hills

Forest retreat above Funchal

Up in the ancient laurisilva forest above the city — complete privacy, no sounds except birds and wind, an infinity pool facing the Atlantic. More intimate than Reid's, with an extraordinary spa. If you want to fully disconnect, this is where you come. From €220/night.

Casa Velha do Palheiro

Private estate manor

A 200-year-old manor house on a private estate with its own gardens, golf course, and winery. Five-star but feels like staying at a friend's extraordinary countryside estate. The restaurant serves produce from the estate garden. From €300/night.

🍽 Where to Eat

William — Belmond Reid's Palace

✦ 1 Michelin Star

Even if you don't stay at Reid's, you dine here. A terrace above the Atlantic, impeccable service, and a tasting menu that reads like a portrait of the island — Madeiran goat cheese, grilled black scabbardfish, local passion fruit and honey. The wine pairing includes a flight through the great styles of Madeira wine. Book on arrival in Madeira.

Armazém do Sal

Best traditional fine dining

An 18th-century salt warehouse in old Funchal, beautifully restored with exposed stone walls and candlelight. The best traditional Madeiran fine dining — espetada, bacalhau à lagareiro, outstanding wine list. Warm, unhurried, exceptional.

Doca do Cavacas

Essential experience

Rocky coastline west of Funchal, Atlantic waves, natural pools cut into volcanic rock — and a small restaurant where they grill lapas (limpets) directly on the rock with garlic butter. You eat them looking at the ocean. Simple, perfect, completely unforgettable. Lunch only.

AKUA by Octopus

Best contemporary seafood

The island's finest contemporary seafood restaurant, in the marina. The freshest Atlantic fish handled with intelligence — black scabbard, clams, an extraordinary limpet risotto. The wine list is one of the best on the island.

O Jango

Local soul food

No tourists, all locals. Order the espetada (beef on a bay laurel skewer over charcoal — the smoke and the bay leaf together are extraordinary), bolo do caco (Madeiran garlic flatbread), and milho frito (fried cornmeal). Loud, warm, exceptional.

🗺 What to Do

25 Fontes Trail — Levada Hike

Built for you, Nick. A stunning levada (ancient irrigation channel) trail through UNESCO laurisilva forest to 25 natural springs and a 100m waterfall hidden in a volcanic crater. 8km round trip, dramatic landscapes, no crowds on weekday mornings. One of the great hikes of Europe.

Sunrise at Pico do Arieiro

4:30am. Drive to 1,818 metres. Watch the sun rise above a sea of clouds while the peaks catch the first gold light. Then hike the ridge to Pico Ruivo — Madeira's highest peak — above the clouds the whole way. Surreal, breathtaking, and a proper physical challenge.

Cabo Girão

The second highest sea cliff in Europe. A glass-floored viewing platform extends out over the 590-metre drop to the Atlantic. Stand on it. Look down. Nick — you've definitely done scarier things at CrossFit.

Private Sunset Catamaran Cruise

A private evening catamaran along the dramatic south coast sea cliffs — dramatic basalt formations, sea caves, the city of Funchal lit up at dusk from the water. Champagne included. Book through the Belmond concierge.

Whale & Dolphin Watching

Sperm whales are resident year-round off the coast of Madeira — not migratory, resident. Pilot whales, bottlenose dolphins, and blue whales pass through. A half-day boat from Funchal marina. One of the best wildlife experiences in Europe, full stop.

Porto Moniz Natural Pools

Natural lava rock pools on the wild northwestern tip of the island. Swimming in Atlantic seawater in volcanic pools, with waves crashing around you. Drive the north coast road to get there — the most dramatic road in Portugal the whole way.

Blandy's Wine Lodge

The most historic Madeira wine lodge in Funchal, operating since 1811. Tour the old lodges where pipes are stacked floor to ceiling, then taste through all four styles — Sercial (bone dry), Verdelho (medium dry), Bual (medium rich), Malmsey (luscious sweet). Some bottles in the lodge are older than the USA.

The Monte Toboggan

A Madeiran tradition since the 1850s: wicker basket toboggans on runners, racing down the steep cobblestone streets from Monte, steered by two men in white linen suits and straw hats. Completely absurd. Deeply joyful. Utterly Madeiran.

Eat Your Way Through Portugal

The Table

Portugal has one of the great culinary traditions in the world — simple ingredients, ancient techniques, extraordinary produce from the Atlantic, the Douro, and the south. Here's what you must eat.

Pastel de Nata

The custard tart. Eat them warm from Pastéis de Belém — recipe secret since 1837. Dusted with cinnamon next to a bica. The single most important food experience in Portugal.

Bacalhau

Salt cod. The national obsession — 365 recipes, one for every day of the year. Try bacalhau à Brás (shredded with eggs), bacalhau com natas (baked in cream), and à lagareiro (whole-roasted with olive oil).

Amêijoas à Bulhão Pato

Clams with garlic, white wine, butter and cilantro. One of the simplest and most perfect things you'll eat in your life. Order them at every opportunity.

Polvo à Lagareiro

Whole roasted octopus, tentacles crisped in olive oil, over crushed potatoes and garlic. A revelation. Order it every time you see it on the menu — and it will be on every menu.

Percebes

Gooseneck barnacles, harvested off Atlantic rocks. They look prehistoric. They taste exactly like the ocean. Order them at Cervejaria Ramiro and eat with your hands.

Espetada

Madeira's great dish: beef on a bay laurel skewer, over charcoal. The smoke and the bay leaf perfume the meat in a way nothing else does. Eat at O Jango with bolo do caco.

Lapas

Madeiran limpets grilled on volcanic rock with garlic butter. Eat them at Doca do Cavacas with your feet near the ocean. One of the most elemental food experiences on earth.

Ginjinha

Lisbon's sour cherry liqueur, sold from street kiosks. Served in a chocolate cup — you eat the cup. €1.50. The best €1.50 you will spend in Portugal.

Poncha

Madeira's drink: sugarcane spirit, wild flower honey, lemon. Mixed at a poncha bar with a wooden pestle. The real version is something else entirely. Dangerous in the best way.

Madeira Wine

One of the world's great fortified wines. Four styles from bone dry (Sercial) to lusciously sweet (Malmsey). Some bottles predate the American Revolution. Taste them all at Blandy's.

Vinho Verde

Portugal's fresh young wine — light, slightly effervescent, low alcohol. Perfect for Lisbon lunches in the sun. Ask for Alvarinho from the Minho — the finest expression.

Bolo de Mel

Madeira's dense, dark honey cake made with sugarcane molasses and spices. Break it apart with your hands — never cut it. A piece of the island to take home.

10 Days · Lisbon then Madeira

The Journey

Day 1

Arrive Lisbon

Check in. Evening walk through Chiado — Livraria Bertrand (the world's oldest bookshop), a glass of Vinho Verde at a terrace café. Dinner at Solar dos Presuntos. Early night — the next nine days are full.

Day 2

Alfama & Private Guided Tour

Walk Alfama before 9am. Guided tour of the quarter and São Jorge Castle. Afternoon free. Sunset at Miradouro da Graça. Fado dinner at Tasca do Chico. Ginjinha on the way home.

Day 3

Belém Day

Jerónimos Monastery (arrive at opening). Pastéis de Belém next door — eat three. Torre de Belém. Lunch at Time Out Market. Dinner: Cura at the Ritz, full tasting menu.

Day 4

Sintra & Cascais

Train to Sintra. Pena Palace at opening. Quinta da Regaleira. Lunch in the village. Drive to Cascais for the afternoon. Dinner: Cervejaria Ramiro. Order everything.

Day 5

Lisbon Free + Belcanto

Morning at LX Factory Sunday market (if Sunday). Afternoon: Museu Nacional do Azulejo. Evening: Belcanto. The full tasting menu. This is the dinner of the trip. This is the dinner of the year.

Day 6

Fly to Madeira

Morning flight from Lisbon (1h10min). Check into Reid's Palace. Afternoon: explore Funchal old town, Mercado dos Lavradores. Dinner: Armazém do Sal. First poncha of the trip.

Day 7

25 Fontes Levada Hike

Full day in the ancient forest. Levada to 25 Fontes waterfall. Pack lunch. Return to Funchal in late afternoon. Swim at Reid's pool. Sundowner on the terrace with a glass of Sercial Madeira. Dinner at the hotel.

Day 8

Above the Clouds

4:30am: drive to Pico do Arieiro for sunrise — yes it's worth it. Hike to Pico Ruivo. Back by noon. Monte toboggan. Blandy's wine tasting. Dinner: William at Reid's. The dinner of Madeira.

Day 9

The Wild North

Drive the north coast road to Porto Moniz. Swim in the natural lava pools. Lunch: grilled fish at the pools. Cabo Girão on the way back. Dinner: AKUA in the marina. Sunset catamaran cruise.

Day 10

Whale Watching + Fly Home

Morning whale watching boat from Funchal marina. Return to hotel. Last swim at Reid's pool. Afternoon flight home. Nick — you are a different person from the one who landed ten days ago. Portugal does that.