Portugal blends age-old maritime heritage with today’s creative energy. From Lisbon’s tiled facades and miradouros to Porto’s riverside cellars and the golden beaches of Cascais, this itinerary threads together history, food, and the Atlantic light that artists rave about. You’ll taste the Douro’s wines, wander palaces in Sintra, ride e‑bikes along the coast, and still make time for sunset cocktails.

Lisbon has been a global crossroad since the Age of Discovery; Porto has shipped its fortified wine down the Douro since the 18th century; Cascais evolved from royal retreat to elegant seaside playground. Expect cobblestones, azulejos, and soulful fado at night. Food ranges from seafood cataplana and charcoal-grilled sardines to modern Portuguese tasting menus—perfect for travelers who love nice restaurants.

Practical notes: English is widely spoken; currency is the euro; tap water is safe; tipping is appreciated but modest (round up or 5–10%). Pack layers and good walking shoes. You’ll arrive after an overnight transatlantic flight and depart mid-day on the last day. This plan assumes two travel days to get there and one to get back within the 10 days.

Lisbon

Lisbon is Europe’s sun-drenched amphitheater: seven hills, red roofs, river views. Ride a tuk‑tuk through Alfama’s medieval lanes, snack through Baixa and Mouraria on a food tour, and watch trams rattle by at golden hour. Belém’s monuments honor navigators; Bairro Alto and Cais do Sodré keep the music going late.

• Top sights: Alfama, São Jorge Castle, Belém Tower and Jerónimos Monastery, LX Factory, Time Out Market, viewpoints like Miradouro da Senhora do Monte.
• For foodies: Seafood temples like Cervejaria Ramiro; farm-to-table at Prado; petiscos at Taberna da Rua das Flores; pastel de nata in Belém. Not into coffee? Opt for fresh juices, herbal teas, and thick hot chocolate found at most pastelarias.
• Where to stay (Hotels.com/VRBO):
  • Upscale: Four Seasons Hotel Ritz Lisbon, Olissippo Lapa Palace Hotel, Martinhal Lisbon Chiado Family Suites.
  • Stylish value: Lisbon Destination Hostel.
  • Browse more: VRBO Lisbon | Hotels.com Lisbon
• Getting there and around: Book CLT–LIS flights via Omio. In the city, use metro, trams, tuk‑tuks, or e‑bikes (Gira has e‑stations). For day trips and onward trains, see Omio Trains and Omio Buses.

Day 1: Fly Charlotte to Lisbon (Overnight)

Morning: Depart Charlotte for Lisbon. Search one-stop or seasonal one‑stop options via Omio. Aim for an evening arrival on Day 2; pick aisle seats for easier rest and mobility.

Afternoon: In transit. Hydrate, walk the aisle, and set clocks to Lisbon time.

Evening: In transit. Try to sleep early; eye mask and a light snack help.

Day 2: Arrive in Lisbon, Golden-Hour Stroll and Dinner

Morning: Land in Lisbon and transfer to your hotel. Drop bags and freshen up. If your room isn’t ready, ask the front desk to store luggage.

Afternoon: Easy orientation walk: Baixa’s grid, Elevador de Santa Justa (view from Carmo terrace), and Chiado’s boutiques. Pause for a pastel de nata and fresh-squeezed orange juice at Manteigaria or a tea at Confeitaria Nacional.

Evening: Dinner at Time Out Market to sample multiple chefs under one roof—try Sea Me’s tuna tartare, Surf & Turf’s pica-pau, and Manteigaria’s warm custard tart for dessert. Post-dinner rooftop at PARK (top of a parking garage) for sunset views over the 25 de Abril Bridge.

Day 3: Tuk‑Tuk Highlights + Lisbon Food & Wine

Morning: See the hills the fun way on a private tuk‑tuk tour—great early in the trip to map the neighborhoods and viewpoints.

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

Afternoon: Join the city’s top-rated food experience to taste classic dishes, wines, and learn food history in lesser-known quarters.

Winner 2025 Undiscovered Lisbon Food & Wine Tour by Eating Europe

Evening: Reserve Cervejaria Ramiro for garlicky clams, scarlet prawns, and razor clams; end with the traditional prego steak sandwich. Nightcap in Bairro Alto at Red Frog Speakeasy (award‑winning cocktails) or Foxtrot (Art Deco lounge). Prefer live music? Try a fado set at Clube de Fado in Alfama—book ahead.

Day 4: Sintra Palaces and the Atlantic Coast (Day Tour)

Make a full day of fairy‑tale Sintra and the coastal town of Cascais with a small-group tour that handles tickets and lines—ideal for seeing Pena Palace, Quinta da Regaleira’s initiation well, Cabo da Roca (continental Europe’s westernmost point), and the marina of Cascais.

Sintra and Cascais Small-Group Day Trip from Lisbon

Dinner back in Lisbon at Prado (seasonal Portuguese ingredients; bright, modern plates) or Sea Me (modern fish market vibe). For dessert without coffee, try Ginginha (cherry liqueur) or a rich chocolate mousse at Landeau in LX Factory.

Porto

Porto is granite and azulejos, steep lanes dropping to the Douro, and the aroma of aging port wine. The Ribeira waterfront hums with boats; across the bridge in Vila Nova de Gaia, lodges offer tastings with river views. Food is hearty yet refined, from francesinha to Michelin-star kitchens.

• Top sights: Ribeira, Dom Luís I Bridge, Livraria Lello bookshop, São Bento station’s tile panels, Clerigos Tower, Gaia’s port lodges.
• Food & wine: Petiscos at Taberna dos Mercadores; octopus at Brasão Cervejaria; sandes de pernil at Casa Guedes; tastings at Graham’s or Taylor’s across the river.
• Where to stay (Hotels.com/VRBO):
  • Upscale: The Yeatman, HF Ipanema Park.
  • Great value: Moov Hotel Porto Centro, Gallery Hostel.
  • Browse more: VRBO Porto | Hotels.com Porto
• Getting there: Fast train from Lisbon Santa Apolónia/Oriente to Porto Campanhã takes ~2h50–3h; typical fares €25–40. Book via Omio Trains.

Day 5: Lisbon to Porto, Ribeira and Gaia at Sunset

Morning: Train Lisbon → Porto (~2h50–3h) via Omio Trains. Check in and grab a light lunch—try sandes de pernil with Serra cheese at Casa Guedes, paired with lemonade or a local craft soda.

Afternoon: Stroll São Bento station’s azulejo murals, climb Clerigos Tower for a 360° view, then descend to the Ribeira quays. Optional 50‑minute Six Bridges boat ride for an overview of Porto’s riverfront architecture.

Evening: Dinner at Adega São Nicolau (traditional northern dishes) or Taberna dos Mercadores (tiny, intimate petiscos). Cross the lower deck of the Dom Luís I Bridge at sunset to Gaia for a riverside drink; Capela Incomum is a romantic wine bar inside a former chapel.

Day 6: Full‑Day Douro Valley Wine Tour (Vineyards, Lunch, River Cruise)

Spend the day among terraced vines on the UNESCO-listed Douro. You’ll visit two quintas for tastings (table wines and ports), break for a regional lunch, and float past the slopes on a short cruise—easy logistics and top scenery for wine lovers.

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

Return to Porto for dinner at Brasão Cervejaria (shareable plates, wood‑grilled octopus, and their lighter take on francesinha). Nightlife clusters along Galerias de Paris; for something calmer, BASE is an open‑air garden bar by the Clerigos tower.

Day 7: Porto on Two Wheels, Markets, and Nightlife

Morning: Not coffee drinkers? Start with fresh juices and a warm bola de berlim pastry at Mercado do Bolhão. Pick up e‑bikes and follow the Douro downstream to Foz do Douro, then up the Atlantic promenade—flat miles, sea air, and wide bike paths.

Afternoon: Cross to Gaia for a self‑guided port lodge pairing of your choice (Graham’s, Taylor’s, and Sandeman are classics—book a timed tasting). For late lunch, Cantinho do Avillez serves modern Portuguese plates with great service.

Evening: Dinner at DOP by Rui Paula for a special night out, or at Taberna Santo António for rustic fare. Finish with cocktails at The Royal Cocktail Club or Bonaparte Downtown.

Cascais

Cascais is Lisbon’s elegant seaside escape—palm-lined promenades, sandy coves, and a glorious coastal bike path to windswept Guincho beach. The marina buzzes with sailing and boating; the old town mixes seafood restaurants with tiled villas.

• Top sights: Praia da Rainha and Conceição beaches, Boca do Inferno sea arch, Santa Marta Lighthouse, Guincho dunes, coastal path toward Cabo Raso.
• Why base here: Easy 40‑minute train from Lisbon, instant beach time, fantastic e‑biking, and boating opportunities without long Algarve transfers.
• Where to stay (Hotels.com/VRBO):
  • Resort living: Vila Bicuda Resort. Budget/social: Cascais Bay Hostel.
  • Browse more: VRBO Cascais | Hotels.com Cascais
• Getting there: Train Porto → Lisbon (~3h), connect to the Lisbon–Cascais coastal line from Cais do Sodré (~40 min). Book long leg via Omio Trains.

Day 8: Porto to Cascais, Beach Time and Old-Town Dining

Morning: Train from Porto Campanhã to Lisbon, then connect to the coastal train to Cascais (every ~20 minutes). Total travel ~3h + 40 minutes. Settle into your hotel.

Afternoon: Relax at Praia da Rainha or Praia da Conceição—calm, central beaches ideal after travel. If you’d like a leg-stretcher, walk the seaside path to Boca do Inferno for crashing-surf drama.

Evening: Dinner at Mar do Inferno (family-run seafood; try arroz de marisco) or Hifen (creative small plates with ocean views). Gelato at Santini—order fruit flavors if you’re skipping coffee-based options.

Day 9: E‑Bikes to Guincho + Boating the Cascais Coast

Morning: Pick up e‑bikes and cruise the oceanfront cycleway to Praia do Guincho (about 10 km each way). It’s one of Portugal’s most scenic rides: dunes, fortresses, and wind-swept surf. Hikers can add a short trail near Cresmina Dune Boardwalk.

Afternoon: Boating time: arrange a small RIB or sailboat from Cascais Marina to see the lighthouse, Guia cliffs, and the Boca do Inferno from the water. On calmer days you can swim off the boat. Late lunch near the marina at Hemingway or Terrazza for seafood risotto and salads.

Evening: Farewell dinner at Furnas do Guincho (oceanfront, classic seafood) or Taberna da Praça (petiscos in a historic house). Nightcap along Rua Frederico Arouca or a quiet seaside stroll.

Day 10: Cascais to Lisbon Airport, Fly Home

Morning: Easy breakfast—fresh juice, yogurt, and a warm pão de deus from a pastelaria. Train back to Lisbon Cais do Sodré and transfer to the airport. Pad extra time for security.

Afternoon: Fly Lisbon → Charlotte via your preferred connection; search or manage tickets with Omio.

Evening: Arrive home with a phone full of sunsets, vineyard views, and palace photos.

Optional swaps and add‑ons

• Lisbon tuk‑tuk alternatives: If you prefer an eco vehicle, consider this shorter overview:

  

  Welcome Tour to Lisbon in Private Eco Tuk Tuk
• Sintra ticket‑focused variant:

  

  Sintra, Regaleira, Pena, Cabo Roca (All Tickets Included)

Dining short list (reservations recommended)

• Lisbon: Prado (seasonal tasting), Taberna da Rua das Flores (petiscos; walk-in), Cervejaria Ramiro (seafood), Sea Me (modern fish), Alma (two‑star splurge). Sweets and drinks: Manteigaria (nata + hot chocolate), Landeau (chocolate cake).
• Porto: Adega São Nicolau (classic), Brasão Cervejaria (octopus and snacks), DOP (fine dining), Cantinho do Avillez (modern), Casa Guedes (pork and Serra cheese sandwich).
• Cascais: Mar do Inferno (seafood), Hifen (creative plates), Furnas do Guincho (oceanfront), Taberna da Praça (petiscos), Santini (gelato).

Getting around and budgets

• Trains: Lisbon ⇄ Porto ~2h50–3h; Porto → Lisbon → Cascais adds ~3h + 40m. Book on Omio Trains. Lisbon ⇄ Cascais commuter trains run every ~20 minutes.
• Transit passes: Lisbon’s zapping card works on metro/trams; taxis and ride‑hailing are affordable for hills and evenings.
• Budget level (68/100): Expect mid‑upscale restaurants most nights, select splurge dinners, and guided tours on two days. Portugal remains excellent value for quality.

From tuk‑tuks and tile-lined alleys to vineyard lunches and Atlantic bike rides, this 10-day Portugal plan balances big sights with authentic flavors. You’ll land in Lisbon, sip the Douro in Porto, and sign off with salt air in Cascais—an elegant arc that fits your love of food, wine, beaches, boating, and e‑bikes.