Portugal packs a millennium of history into a country you can cross in half a day. Phoenicians traded here, Moors built hilltop castles, and the Age of Discoveries sailed from Lisbon’s shores. Today, tiled facades, soulful fado, and world-class wine live alongside a vibrant contemporary food scene.

This 14-day itinerary links the best of the country: Lisbon’s seven hills and palaces, Aljezur’s wind-brushed Atlantic coves on the Costa Vicentina, and Porto’s riverfront and Port wine lodges. You’ll day-trip to Sintra and the Douro Valley, hike coastal trails, and taste everything from pasteis de nata to cataplana.

Practical notes: trains and buses are reliable and bookable on Omio (trains/buses in Europe). Consider a car for the Aljezur segment (coastal villages are spread out). Sun and surf are strong on the west coast—bring reef-safe sunscreen, respect the Atlantic, and check local surf flags.

Lisbon

Lisbon is light and azulejos: sun flares over the Tagus, trams rattle through Alfama, and miradouros (viewpoints) turn sunsets into an evening sport. The city rebuilt itself after the 1755 earthquake, leaving a checkerboard Baixa, ornate convent ruins, and a taste for reinvention.

Between Belém’s monuments and the contemporary buzz of LX Factory, Lisbon is a feast: custard tarts born in a monastery, tinned fish elevated to art, seafood towers at old-school cervejarias, and new-wave natural wine bars. Fado spills from doorways in Mouraria and Alfama most nights.

Getting in + Where to Stay

Fly into LIS (Lisbon). For flights within or to/from Europe, compare options on Omio (flights in Europe). For long-haul fares, check Trip.com (flights) and Kiwi.com. Metro to the center takes ~25 minutes (~€2), taxi/ride-hail ~20–30 minutes (~€12–20).

• Hotels.com picks: Four Seasons Hotel Ritz Lisbon (classic views over Parque Eduardo VII), Olissippo Lapa Palace Hotel (resort feel in leafy Lapa), Martinhal Lisbon Chiado Family Suites (apartment-style for families), Lisbon Destination Hostel (budget, inside Rossio Station).
• Browse more stays: VRBO Lisbon apartments or Hotels.com Lisbon.

Days 1–3: Historic Lisbon, Belém, and Alfama

Start with Baixa and Chiado: sit at A Brasileira then wander to Largo do Carmo to see the roofless Carmo Convent—a haunting reminder of 1755. Ride Elevador de Santa Justa for skyline views, then glide down to Praça do Comércio and the Tagus.

In Belém, pair Jerónimos Monastery and the riverfront Discoveries Monument with a still-warm pastel de nata at Manteigaria or a rival pastry shop. Time your visit to the MAAT’s undulating rooftop for sunset over the 25 de Abril Bridge.

• Coffee/breakfast: Fábrica Coffee Roasters (single-origin flat whites), Hello, Kristof (Scandi-style toasts), or Copenhagen Coffee Lab (sourdough cinnamon buns).
• Lunch: Time Out Market’s best stands: O Prego da Peixaria (steak or tuna “prego” in bolo do caco), Marlene Vieira (modern Portuguese petiscos), and Manteigaria for dessert.
• Dinner: Taberna da Rua das Flores (creative small plates; arrive early), Cervejaria Ramiro (garlic shrimp, percebes, and a post-seafood prego), or Solar dos Presuntos (clams Bulhão Pato, arroz de marisco).
• Evening: Park Bar (rooftop over Bairro Alto’s garages) or Pavilhão Chinês (eclectic antiques and cocktails).

Featured experience (foodie intro to Lisbon):

Winner 2025 Undiscovered Lisbon Food & Wine Tour by Eating Europe – weave through hidden neighborhoods with four seated tastings and local wines.

Days 4–5: Sintra and the Riverfront

Devote a day to Sintra’s whimsical palaces and cool mountain air. You can DIY via the Rossio–Sintra train (~40 minutes, ~€2.30 each way; check Omio) but a guided small-group visit streamlines tickets and viewpoints.

Back in Lisbon, stroll Alfama’s alleys and viewpoints (Portas do Sol, Santa Luzia), visit the National Tile Museum, and end riverside at Cais do Sodré/LX Factory for boutiques and craft beer.

Featured day trip (Sintra + Coast): Sintra and Cascais Small-Group Day Trip from Lisbon – Pena Palace, fairy-tale gardens, Cabo da Roca cliffs, and Cascais’s seaside.

• Food focus: In Sintra, try travesseiros (flaky almond pillows) and queijadas (cheese tarts). Back in Lisbon, book Bairro do Avillez for a modern spin on classics or Zé da Mouraria for bacalhau straight from a grandmother’s cookbook.

Aljezur (Vicentina Coast)

Aljezur is the antidote to rushing: a whitewashed village split by a river, crowned by a 10th–11th-century Moorish castle. Around it, the Southwest Alentejo and Vicentina Coast Natural Park protects dunes, cliffs, and broad beaches where the Atlantic booms.

Surfers ride Arrifana, families wade the Amoreira river mouth, and hikers trace the Rota Vicentina across thyme-scented headlands. The local star is the Aljezur sweet potato (PGI)—you’ll find it roasted, in soups, even in custard tarts.

Getting to Aljezur + Where to Stay

Lisbon → Aljezur: Morning Rede Expressos bus from Sete Rios is ~3.5–4 hours, ~€15–25 (search times and fares on Omio (buses)). Driving the A2/IC4 takes ~3–3.5 hours plus tolls—recommended for beach hopping.

• Browse stays: VRBO Aljezur villas and cottages (Vale da Telha pools, Monte Clérigo sea views) and Hotels.com Aljezur.

Days 6–8: Beaches, Surf, and Castle Views

Ease in at Praia da Amoreira: a wide beach where a river meets the sea—great for families at low tide and mellow swims upriver. Monte Clérigo next door offers rock pools at low tide and cliff-top views.

Climb to Aljezur Castle for a panorama over the valley and whitewashed town. In the late afternoon, head to Praia da Arrifana—dramatic cliffs, consistent surf, and one of the best sunsets in Portugal.

• Surf and lessons: Book a morning with a local surf school at Arrifana or Amoreira; conditions are typically best earlier in the day. Wetsuits are needed year-round.
• Coffee/breakfast: Start at Mercado Municipal for fresh fruit and tostas, or drive to Rogil for batata-doce pastries at Padaria e Pastelaria Pão do Rogil.
• Lunch: O Sargo (Monte Clérigo) for grilled fish and seaweed butter potatoes; picnic from the market for clifftop miradouros.
• Dinner: O Paulo (Arrifana cliffs; book ahead) for percebes and arroz de polvo; Gulli Bistrot (Aljezur old town) for handmade pasta and local produce; Arte Bianca (Vale da Telha) for sourdough pizza post-sunset.

Days 9–10: Rota Vicentina, Coves, and Coastal Villages

Walk a section of the Rota Vicentina’s Fishermen’s Trail—try Arrifana → Monte Clérigo or the circular loop around Carrapateira’s boardwalks. Expect storks nesting on sea stacks in spring and endless Atlantic drama.

Day trip north to Praia de Odeceixe Mar (a river-meets-sea gem) or south to Praia do Amado for surfing and dunes. The small Museu do Mar e da Terra in Carrapateira adds context to this coast’s fishing heritage.

• Lunch/dinner: Sítio do Forno (near Amado) for seafood with cliffside views; in Odeceixe, look for grilled dourada and cataplana on menus along the village lanes.
• Drinks: Watch the sky go pink from Arrifana’s viewpoints; bring a light jacket—Atlantic winds can be brisk even in summer nights.

Optional Algarve boat day (departing Albufeira; 1h30 drive each way): Explore sea caves and look for dolphins on this photogenic cruise.

Dolphins Search and Benagil Caves from Albufeira – 2.5 hours by semi-rigid boat, skimming past secret coves and the famous Benagil dome.

Porto

Porto is granite and gold-leaf baroque, azulejo-clad stations, and the Douro River bending under graceful bridges. The Ribeira district is a UNESCO World Heritage postcard, while across the water, Vila Nova de Gaia shelters venerable Port wine lodges.

Beyond wine, Porto is soulful and inventive. You’ll graze petiscos at tavernas, tuck into a decadent francesinha, and find contemporary art tucked inside 19th-century mansions.

Getting to Porto + Where to Stay

Aljezur → Porto options:

• Fastest: Drive (~1h15) or bus to Faro, then fly FAO→OPO (~1 hour; often €30–120 if booked early). Compare routes on Omio (flights in Europe).
• Overland: Bus to Lagos or Tunes, then Alfa Pendular/Intercidades train to Porto – ~6.5–7.5 hours, ~€30–50 with 1–2 changes. Check schedules/prices on Omio (trains) and Omio (buses).

• Hotels.com picks: The Yeatman (wine hotel with Douro views), HF Ipanema Park (pool and roomy quarters), Moov Hotel Porto Centro (budget in an Art Deco cinema). For hostels, see Gallery Hostel.
• Browse more stays: VRBO Porto apartments or Hotels.com Porto.

Days 11–12: Ribeira, Gaia Lodges, and Tiles

Wander from São Bento Station’s blue-and-white tile panels to the cathedral terrace, then down to Ribeira’s riverfront arcades. Cross Dom Luís I Bridge (upper deck for views, lower for cafés) into Gaia and choose a Port lodge for a guided tasting—Graham’s, Taylor’s, or Sandeman are classics.

Balance sweetness with savory: snack on bolinhos de bacalhau and octopus salad at a tasca, then ride the Gaia cable car for sunset. If you have energy, Livraria Lello’s neo-Gothic staircase glows after the crowds thin.

• Coffee/breakfast: Combi Coffee Roasters (pour-overs and pastries), 7g Roaster in Gaia (espresso with river views), or brunch at Zenith (pancakes to shakshuka).
• Lunch: Adega São Nicolau (slow-cooked tripe alheira, codfish rice), Casa Guedes (pork sandes with Serra cheese).
• Dinner: Brasão Cervejaria Aliados (francesinha with craft beer), Taberna dos Mercadores (tiny, book ahead; cod and clams).

Days 13–14: Douro Valley Day Trip + Contemporary Porto

Dedicate a day to the Douro Valley. Terrace vineyards plunge to the river, and cellar doors pour touriga-based reds and tawny Ports. A small-group day tour removes the logistics and pairs wine with a short river cruise.

Back in Porto, explore Rua de Miguel Bombarda’s galleries and the Serralves Museum’s art-deco park. Finish with sunset at Jardim do Morro, a final toast to the Douro.

Featured Douro experience: Complete Douro Valley Wine Tour with Lunch, Wine Tastings and River Cruise – two estates, a regional lunch, and a scenic boat ride.

Getting onward

Porto Airport (OPO) is ~25 minutes from the center by metro or taxi. For onward flights in Europe, compare on Omio; for long-haul options, check Trip.com and Kiwi.com.

Optional Lisbon add-on by train

If you prefer to finish in Lisbon, the Alfa Pendular train from Porto Campanhã takes ~2h50–3h15, usually €15–35 when booked ahead on Omio.

Extra Lisbon experiences (if you have a spare half-day)

Short on time but want a fun overview? Try a tuktuk circuit that hits hilltop viewpoints, Alfama, and Chiado with a local driver-guide.

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

Trip summary: Two weeks in Portugal carries you from Lisbon’s azulejos and Sintra’s palaces to Aljezur’s wild surf beaches and Porto’s wine-soaked riverbanks. With reliable trains and buses, plus a car for the coast, you’ll taste, hike, and sip your way through the country’s most evocative landscapes.