Portugal packs centuries of maritime history into a country that’s easy to traverse by train and rich in culture. From Lisbon’s Moorish alleys and miradouros to Porto’s azulejo-clad stations and wine lodges, every day brings vivid color and flavor. Down south, the Algarve’s limestone cliffs and calm coves invite you to slow down, swim, and linger over grilled fish at sunset.

Expect a cuisine of simple excellence—grilled sardines, pork and clam cataplana, creamy bacalhau, and pastries like pastel de nata, perfected by monks. Pair it with vinho verde and Douro reds, or sip tawny Port while watching the river glow at dusk. Museums often close Mondays, dinner starts later than in North America, and comfortable shoes are essential for cobblestones and hills.

In 14 days you’ll savor Lisbon, Porto, and Lagos on the Algarve with logical rail connections, morning departures, and time to breathe. This itinerary prioritizes neighborhood wanders, local favorites, and a Douro Valley day, with a dedicated Sintra excursion and relaxed beach days to end the journey.

Lisbon

Lisbon dazzles with seven hills, terracotta rooftops, and the broad Tagus River. Alfama’s lanes recall Moorish days; Belém’s Manueline monuments salute Portugal’s Age of Discovery. Streetcar bells, fado in tiny taverns, and the aroma of cinnamon custard tarts set the rhythm.

Start in Baixa and Chiado for grand squares and cafés, then climb to Miradouro da Senhora do Monte for citywide views. In Belém, the Jerónimos Monastery and the 16th‑century Belém Tower tell stories of caravels and cartographers. Contemporary Lisbon thrives, too—LX Factory’s creative spaces and the MAAT’s swooping curves face the river.

Days 1–5: Classic Lisbon, Belém, Alfama, and a Sintra Day Trip

• Orientation and neighborhoods: Stroll Praça do Comércio to Rossio, browse Livraria Bertrand in Chiado, then weave into Alfama for the Sé Cathedral and Castelo de São Jorge ramparts. Go slow—the joy here is in tiled façades, azulejo street shrines, and viewpoints at every corner.
• Belém morning: Visit Jerónimos’ cloister and the waterfront Belém Tower; stop at Pastéis de Belém for still-warm custard tarts dusted with cinnamon. Nearby, explore the Discoveries Monument and riverside promenade.
• Modern culture: Head to LX Factory for indie shops and galleries; catch sunset at Miradouro de Santa Catarina or Portas do Sol with a glass of vinho verde.
• Sintra day trip (from Lisbon): Palaces nestled in misty hills feel plucked from a fairytale. Consider a small-group tour to see more without logistics headaches (see tours below) and add Cabo da Roca cliffs and the seaside town of Cascais.

Recommended activities (Viator picks):

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

  

  Ideal on Day 1 to get the lay of the land and conquer the hills with ease.

• Lisbon Small-Group Portuguese Food and Wine Tour

  

  A guided tasting walk through Baixa and Mouraria with petiscos, local wines, and culinary history.

• Sintra and Cascais Small-Group Day Trip from Lisbon

  

  Hit Pena Palace, Sintra’s historic center, windswept Cabo da Roca, and seaside Cascais in a single day.

Where to eat and drink:

• Breakfast/coffee: Fábrica Coffee Roasters (third-wave espresso and pour-overs); Dear Breakfast (fluffy pancakes, eggs Benedict, and juices); Manteigaria (grab a still-warm pastel de nata with your espresso).
• Lunch: O Trevo de Carmo (Bourdain-approved bifana pork sandwich); Time Out Market (sample Marisqueira Azul’s seafood rice or O Prego da Peixaria’s steak-on-bolo-do-caco); Zé da Mouraria (home-style cod and grilled fish—arrive early).
• Dinner: Cervejaria Ramiro (plateaus of clams, scarlet prawns, and garlic butter); Taberna da Rua das Flores (ever-changing chalkboard of seasonal Portuguese plates); Solar dos Presuntos (classic seafood and Minho dishes).
• Nightcap: Listen to fado at tiny taverns in Alfama; for cocktails, try Red Frog (speakeasy-style) or Foxtrot (art deco ambiance).

How to get to Lisbon: Fly into LIS; compare options on Omio (flights). From many European hubs it’s 2–3 hours, often €40–€150 on low-cost carriers. Metro and rideshares connect the airport to the center in ~20–30 minutes.

Lisbon stays (affiliate picks): Browse citywide deals on VRBO Lisbon or Hotels.com Lisbon. Standouts: Four Seasons Hotel Ritz Lisbon (classic city views), Lisbon Destination Hostel (great for social travelers), Martinhal Lisbon Chiado Family Suites (family-friendly), and Olissippo Lapa Palace Hotel (resort-like calm above the river).

Travel to Porto (morning of Day 6): Take the Alfa Pendular or Intercidades from Lisboa Santa Apolónia or Oriente to Porto Campanhã in ~2h50–3h15. Typical fares €25–€40; book on Omio (trains). Buses take ~3.5 hours via Omio (buses).

Porto

Porto pairs baroque spires with workaday grit, spilling down to the UNESCO-listed Ribeira. São Bento Station’s blue-and-white tile panels tell a country’s story in ceramic; the iron Dom Luís I Bridge frames river sunsets like a stage.

This is the cradle of Port wine—rabelo boats once ferried barrels down the Douro. Today, Gaia’s lodges pour tawnies and vintages beside sleek tasting rooms. Up the coast, Matosinhos’ grills char the day’s catch over fragrant coals.

Days 6–9: Ribeira, Wine Lodges, and a Douro Valley Day

• City essentials: Climb Clérigos Tower, browse Livraria Lello’s carved staircase, and wander the Ribeira quays. Cross to Vila Nova de Gaia for tastings at Graham’s, Taylor’s, or Sandeman and river views from the terraces.
• Douro Valley day trip: Terraced vineyards ripple along a river first demarcated in 1756—the world’s oldest regulated wine region. Combine estate visits, a local lunch, and a short river cruise (see tours below).
• Coastal afternoon: Tram or rideshare to Foz do Douro’s seaside promenade; continue to Matosinhos for grilled sardines, turbot, or sea bream straight off the boats.

Recommended activities (Viator picks):

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

  

  Two estates, a regional lunch, and a gentle rabelo-style cruise showcase the valley’s best in one day.

• Authentic Small Group Douro Wine Tour with Lunch & River Cruise

  

  Small-group pacing and knowledgeable guides—great for first-time Douro explorers.

Where to eat and drink:

• Breakfast/coffee: Época Porto (seasonal brunch, superb sourdough); Combi Coffee Roasters (single-origin espresso); 7g Roaster (over the bridge in Gaia, with riverside seating).
• Lunch: Casa Guedes (slow-roasted pork sandwich with Serra cheese); Mercado do Bolhão (browse produce then try a quick petisco plate); Gazela (ultra-crispy hot dogs “cachorrinhos” with fiery sauce).
• Dinner: Brasão Cervejaria Aliados (francesinha with proper beer sauce and excellent rissóis); Cantinho do Avillez (creative Portuguese plates); O Gaveto in Matosinhos (spot-on grilled fish and shellfish rice).
• Sweets: Café Majestic for Belle Époque atmosphere and a pastel de nata; grab a chocolate truffle at Chocolataria Equador.

Porto stays (affiliate picks): Check options on VRBO Porto or Hotels.com Porto. Favorites include The Yeatman (iconic wine hotel with panoramic views), Gallery Hostel, HF Ipanema Park, and Moov Hotel Porto Centro.

Travel to Lagos, Algarve (morning of Day 10): Fastest rail route is Porto Campanhã → Tunes/Faro → Lagos in ~6–7 hours, €40–€55 on Omio (trains). Direct buses take ~7 hours via Omio (buses). If you prefer to break the trip, stop for lunch in Faro before the regional hop to Lagos.

Lagos (Algarve)

Lagos mixes whitewashed lanes, Moorish walls, and a working marina with some of Portugal’s most photogenic coastline. Ponta da Piedade’s honeycomb cliffs hide grottoes where the Atlantic turns emerald, and Praia do Camilo’s wooden steps descend to scalloped coves.

Days fall into a happy rhythm here: beach-hop, kayak beneath golden arches, nibble on grilled sardines, and toast the sunset as lighthouse beams sweep the horizon. Nearby day trips include windswept Sagres and the red-stone castle of Silves.

Days 10–14: Clifftop Trails, Coves, and Seafood Feasts

• Beaches and views: Start with the clifftop path from Ponta da Piedade to Praia do Camilo for sunrise light. Spend lazy afternoons at Meia Praia’s broad sands or Dona Ana’s sheltered cove.
• On the water: Book a small-boat grotto tour from Lagos Marina to thread sea caves at low tide, or join a kayak outing along Ponta da Piedade’s arches. Early departures mean calmer seas and fewer boats.
• Day trips: Drive or bus to Sagres for the fortress and Cabo de São Vicente, Europe’s southwestern tip—raw cliffs and big Atlantic skies. Inland, Silves’ castle and citrus groves offer a slower Algarve.
• Market morning: Browse Lagos Municipal Market for figs, almonds, and local cheeses; assemble a picnic for sunset at Praia do Canavial.

Where to eat and drink:

• Breakfast/coffee: Coffee & Waves (specialty brews, smoothie bowls, and a surf vibe); Goji Lounge Café (hearty brunch plates, veggie-friendly); Padaria Central (old-school bakes for a quick galão and croissant).
• Lunch: Adega da Marina (big portions, grilled chicken, and piri‑piri prawns); Casa do Prego (petiscos and octopus in garlic butter on the rooftop); Odiáxere’s snack bars for rustic daily specials if you’re out by Meia Praia.
• Dinner: O Camilo (book ahead for cliffside seafood and cataplana); A Forja (“The Bell” to locals—no-frills grill turning out superb sardines and dourada); Don Sebastião (traditional fare and a strong Algarve wine list).
• Drinks: Bon Vivant (multi-level rooftop for sundowners); Three Monkeys (casual pub atmosphere after dinner).

Lagos stays (affiliate picks): See broad choices on VRBO Lagos and Hotels.com Lagos. Top picks: Cascade Wellness & Lifestyle Resort (clifftop pools and spa), Lagos Avenida Hotel (marina views, adults-friendly), and Vila Galé Lagos (resort-style stay steps from Meia Praia).

Return travel (Day 14): Lagos → Lisbon by train via Tunes in ~4h (from ~€20–€30) on Omio (trains) or bus in ~3.5–4h via Omio (buses). If flying out of Faro, it’s ~1h15 by regional train/bus to the airport; compare fares on Omio (flights).

Insider tips: Reserve popular restaurants (Ramiro, O Camilo, Brasão) several days ahead. Watch for pickpockets on Tram 28 and in crowded miradouros. In summer, hit beaches early or late for mellow winds and golden light; in off-season, pack a light jacket for cool evenings.

This two-week Portugal itinerary balances capital-city culture, a wine-country escape, and slow days by the sea. You’ll leave with a camera full of tilework, cliff paths, and sunset rivers—and a new appreciation for the simple perfection of grilled fish and custard tarts.