Portugal rewards the curious traveler: centuries of maritime history, soulful food, and landscapes that swing from vineyard-clad valleys to volcanic lakes. In this 14-day backpacking itinerary, you’ll blend urban energy with island wilderness, surf a world-class break, and boat past storied shores.

Expect tiled facades in Porto, miradouros in Lisbon, laurel forests in Madeira, and hot springs in the Azores. You’ll hike levadas, taste port at the source, and chase Atlantic sunsets—without blowing the budget.

Practical notes: trains and intercity buses are frequent and affordable; flights connect Lisbon with Madeira and São Miguel (Azores). Portuguese cuisine runs hearty and coastal: grilled sardines, bifanas, francesinhas, cozido, and pastel de nata. Vegetarian options are improving, and casual yoga classes run €8–15 in bigger cities.

Porto

Days 1–3: River city vibes, Douro day trip, port lodges

Start in Porto, where granite lanes tumble to the Douro and ironwork bridges stitch both banks. Wander Ribeira, climb Clérigos Tower, and cross to Vila Nova de Gaia for storied port wine lodges.

• Top sights: Livraria Lello, São Bento’s azulejos, Palácio da Bolsa, sunset at Jardim do Morro, Foz do Douro promenade.
• Adventurous extras: Rent a bike along the riverside path to Foz; beginner surf lessons at Matosinhos; sunrise jog across Dom Luís I Bridge.

Recommended activities (Viator):

• Complete Douro Valley Wine Tour with Lunch, Wine Tastings and River Cruise

  

  
  Why go: UNESCO scenery by road and boat, two quintas, and traditional lunch—great value for a full day.
• Porto Walking Tour, Lello Bookshop, River Cruise and Cable Car

  

  
  Why go: Efficiently hits the icons and gets you on the water the first afternoon.
• Porto: Douro River Boat Cruise with Port Wine and Snacks

  

  
  Why go: Small-boat vibe plus a taste of port—perfect at golden hour.

Eat & drink like a local:

• Coffee/breakfast: Combi Coffee Roasters (light roasts, granola bowls); Café Progresso (since 1899, eggs on broa toast).
• Casual lunch: Casa Guedes (serra-cheese pork sandwich legend); Taberna Santo António (daily stews, vinho da casa).
• Dinner: Adega São Nicolau (bolinhas de bacalhau, arroz de polvo); Cantina 32 (modern Portuguese, shareable plates).
• After: Port lodges—Graham’s or Cálem—for a lodge tour; craft beer at Letraria with a leafy garden.

Stay (budget to splurge):

• VRBO Porto (great for shared apartments near Cedofeita or Bolhão).
• Moov Hotel Porto Centro (clean, central, wallet-friendly).
• HF Ipanema Park (pool and bikes; good value in Boavista).
• The Yeatman (iconic splurge with river views and wine cellar—treat night).
• Gallery Hostel (stylish hostel, art-filled common areas).

Getting in & onward:

• Fly into OPO (Porto): search Europe flights on Omio. Metro from airport to Trindade ~30 min, ~€2.20.
• Porto → Lisbon: Alfa Pendular or Intercidades trains 2h50–3h15, often $15–40 if booked early via Omio trains. Buses are 3.5–4h from ~$8 via Omio buses.

Lisbon

Days 4–6: Miradouros, Belém by bike, Sintra palaces, and a surf day to Baleal

Lisbon is layers: Moorish Alfama, grand Baixa, café-strewn Chiado, and riverside Belém. Ride the bike path to the Discoveries Monument, sip a bica, and watch the city glow from Portas do Sol.

• Don’t miss: Jerónimos Monastery, Belém Tower, LX Factory, Tram 28 viewpoints (go early), Time Out Market for a quick graze.
• Active: Gira bike-share along the Tagus to Belém; sunrise stairs up to Graça; drop-in yoga in Jardim da Estrela or studios around Intendente (typically €8–15).

Day trip: Sintra & Cascais

• Sintra and Cascais Small-Group Day Trip from Lisbon

  

  
  Fairytale Pena, Quinta da Regaleira’s initiatic well, Cape Roca cliffs, and beachy Cascais in a single efficient day.

Lisbon city experiences (Viator):

• True 4Hour Private Tuk Tuk Tour: Discover Lisbon with a Local!

  

  
  Great primer to neighborhoods and viewpoints without steep hills.
• Winner 2025 Undiscovered Lisbon Food & Wine Tour by Eating Europe

  

  
  Hearty tastings in lesser-visited quarters—ideal for “live like a local” vibes.

Surf day from Lisbon: Baleal (Peniche)

One of Europe’s most consistent and beginner-friendly surf zones. Buses run Lisbon → Peniche in ~1h45–2h; a 10-minute taxi connects you to Baleal beach breaks.

• Getting there: Lisbon Sete Rios → Peniche buses from ~$10 via Omio buses. First bus ~7:00, last back ~19:00–21:00 (check seasonal timetables).
• Lessons (Viator):
  • Baleal Exclusive Surfing Private Adventure

    

    
    Small ratios, flexible to forecast.
  • Surf Experience in Peniche

    

    
    Personalized coaching; boards and wetsuits included.
• Fuel: Breakfast wraps and espresso at The Base; post-surf petiscos at Taberna do Ganha; seafood rice in nearby Peniche at Tasca do Joel.

Eat & drink in Lisbon:

• Coffee/breakfast: Fábrica Coffee Roasters (roastery vibes); Dear Breakfast (egg-forward plates).
• Lunch: Zé da Mouraria (daily fish/grill, generous portions); Mercado de Campo de Ourique (casual stalls, great for groups).
• Dinner: Taberna da Rua das Flores (blackboard menu; arrive early); Ramiro (shellfish feast; split plates to save).
• Night: Fado at Tasca do Chico (Alfama/Bairro Alto), then a ginjinha nightcap.

Stay:

• VRBO Lisbon (Chiado/Baixa for walkability; Graça for views).
• Lisbon Destination Hostel (inside Rossio Station; social and central).
• Martinhal Lisbon Chiado Family Suites (aparthotel with kitchenettes—budget control).
• Four Seasons Hotel Ritz Lisbon or Olissippo Lapa Palace Hotel if you plan one memorable splurge night.

Optional Algarve swap:

If you crave sea caves over surf, swap the Baleal day for 1–2 nights in the Algarve near Carvoeiro. Lisbon → Lagoa/Portimão buses ~3–3.5h via Omio buses. Hike the Seven Hanging Valleys (Algar Seco to Praia da Marinha), paddle at sunrise into Benagil Cave, and dine on cataplana at O Pescador.

Next leg:

• Lisbon → Madeira (Funchal): Frequent flights ~1h45. Typical fares $35–120 on Omio flights. Morning departure keeps your island day intact.

Funchal (Madeira)

Days 7–9: Ridgeline sunrises, levada hikes, and ocean safaris

Madeira is dramatic: cloud-brushed peaks, terraced bananas, and laurel forests that look prehistoric. Base in Funchal for markets and cable cars, then roam by jeep or on foot.

• Active highlights: Pico do Arieiro sunrise, PR1 ridge hike toward Pico Ruivo (fit hikers), Cabo Girão skywalk, Levada do Caldeirão Verde (lush and misty).
• Unique: Monte cable car + traditional wicker toboggan ride down steep lanes—only in Madeira.

Recommended activities (Viator):

• Madeira Pico do Arieiro Sunrise Tour

  

  
  Beat the crowds and watch the Atlantic light up from above the clouds.
• Madeira Dolphin and Whale Watching on an Ecological Catamaran

  

  
  Hybrid-electric cat, marine-life focus—great boating day.
• Madeira Highlights: Toboggan, Garden & Cable Car (All-Inclusive)

  

  
  Efficient combo for a full Funchal day with minimal planning.

Eat & drink:

• Breakfast: Art Corner Café (pão de casa, great coffee) or Ottavia (pastries near the market).
• Lunch: Mercado dos Lavradores for fruit tastings (ask for prices first), prego sandwiches at snack bars.
• Dinner: Espada com banana (black scabbardfish with banana) at Restaurante Viola; espetada skewers in Câmara de Lobos.
• Night: Try a tart poncha (traditional sugar-cane spirit) in an old-town tasca.

Stay:

• VRBO Funchal (balconies with ocean views are common).
• Hotel do Carmo (retro style, central, good value).
• Porto Mare Hotel (pools and seaside promenade access).
• Belmond Reid's Palace (historic splurge for a special night).

Next leg:

• Madeira → São Miguel (Azores): Direct flights exist seasonally (~2h) or connect via Lisbon (total 3.5–5h). Typical fares $60–180 on Omio flights.

Ponta Delgada (Azores)

Days 10–13: Crater lakes, hot springs, and ocean wildlife

São Miguel is wild and green: twin lakes at Sete Cidades, steam vents in Furnas, and tea fields rolling to the sea. Base in Ponta Delgada for easy day trips by car or guided tour.

• Active: Hike around Lagoa do Fogo (go early for clear views), soak in Terra Nostra or Poça da Dona Beija, and ride an ATV along volcanic rims.
• Local: Taste cozido das Furnas—slow-cooked in geothermal soil—and sip green tea at century-old Gorreana.

Recommended activities (Viator):

• Azores Whale Watching Tour – Ponta Delgada

  

  
  Biologist-guided spotting of dolphins and, in season, sperm whales and blue whales.
• Quad Biking – Sete Cidades (Half Day)

  

  
  Adrenaline with crater-rim views—adventurous and unforgettable.
• Full Day Guided Tour to Furnas with Lunch Included

  

  
  Geothermal fields, botanical gardens, and that classic cozido lunch.

Eat & drink:

• Coffee/breakfast: Louvre Michaelense (retro café for pastries and espresso); pastelarias along Rua dos Mercadores for affordable starts.
• Lunch: A Tasca (petiscos Azorean-style), Associação Agrícola (marbled steaks; share one and sides).
• Dinner: Otaka-inspired Japanese-Azorean takes pop up around town; for traditional, try lapas (limpets) and grilled chicharros.
• Night: Craft beer at Moby Dick Brewery; stroll the marina promenade.

Stay:

• VRBO Ponta Delgada (park off-street if you rent a car).
• Hotels.com Ponta Delgada (compare central stays around Campo de São Francisco).

Flight out:

• São Miguel → Lisbon: ~2h20 nonstop; fares often $50–140 on Omio flights. Aim for a late afternoon flight for a relaxed last morning.

How the 14 days stack up (multi-day blocks)

• Days 1–3: Porto (historic core, Douro tour, port lodges, optional Matosinhos surf).
• Days 4–6: Lisbon (city cycling, food tour or tuk-tuk; Day 5 Sintra; Day 6 Baleal surf day). Optional: replace Baleal with 1–2 nights in Carvoeiro/Algarve.
• Days 7–9: Madeira (Funchal, cable car + toboggan; sunrise at Pico do Arieiro; whale watching).
• Days 10–13: Azores – São Miguel (whales/dolphins, Sete Cidades ATV, Furnas hot springs, Lagoa do Fogo hike).
• Day 14: Fly to Lisbon and depart.

Money-saving & “adventurous” tips

• Use Omio trains and Omio buses to snag early fares; intercity buses can be half the price of trains.
• Self-cater breakfasts via VRBO kitchens; enjoy tasca lunches and split mains at dinner.
• Yoga on a budget: community and drop-in classes in Lisbon/Porto typically €8–15—ask hostels for the latest schedules.

Where city stories meet Atlantic wilds, this backpacking route gives you surfing in Baleal, levada horizons in Madeira, and crater-lake drama in the Azores—bookended by Porto’s tiles and Lisbon’s sunsets. With smart train, bus, and flight choices, it stays friendly to a mid-range budget while keeping the vibe adventurous.