Wine regions of Portugal: A tailor-made trip

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The wines of Portugal trip invites discerning travelers to a sensory celebration of Portuguese wine and culture. Designed for those who seek authentic, tailor-made experiences and lively entertainment, this journey turns evenings into memorable stories, pairs personalized tasting moments with local warmth, and crafts an itinerary that reflects your tastes.

Reserve your customized plan now and let local experts design a playful, private celebration that delights your palate and awakens curiosity. Create Portugal trips that will be remembered long after the last glass is raised.

The wines of Portugal trip highlights

  • Private vineyard tastings: Savor rare, estate bottlings during private tastings with passionate vintners.
  • Meet artisan winemakers: Connect directly with artisan winemakers, hear their stories, and customize tastings.
  • Scenic Douro River cruise: Drift along the Douro, absorbing vineyard panoramas between tastings.
  • Gastronomic pairings with local chefs: Enjoy bespoke menus pairing Portuguese wines with regional cuisine.
  • Customized cultural excursions: Explore historic cellars, charming villages, and markets.
DayMorningAfternoonEvening
Day 1 Afternoon tailored city tour: historic neighborhoods, viewpoints, cafésEvening city tour of viewpoints and intimate petiscos dining
Day 2Morning half-day: Liberty Avenue, Alfama, Cathedral, St George's Castle Fado show with dinner; stroll to Jerónimos and Belém Tower
Day 3Leisurely breakfast; explore Sintra palaces, gardens, wooded ravines Curated Michelin-starred dinner
Day 4Private transfer; winery tasting and cellar tour; Chapel of BonesRelax; explore local markets; savor personalized dining recommendationRelax, explore local markets, personalized dining recommendation
Day 5Sumptuous breakfastPoolside relaxation, spa, horse riding, private wine tastings 
Day 6Breakfast, transfer to Coimbra, curated tastings with producersScenic transfer to Douro Valley; vineyard visits 
Day 7Breakfast; travel Douro; Regua river cruise; Mateus tastingRiver cruise, Mateus palace wine tasting, Quinta Nova tastings 
Day 8Transfer to Porto, half-day private city tour (Mercado, Torre) Return to Porto hotel; overnight stay
Day 9Hotel breakfast; wander riverside streets; visit wine lodges  

Places you'll visit

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Alentejo
AlentejoPortugal
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Day01

Day 1: Arrival in Lisbon

Arrive at Lisbon Airport and meet your guide for a private transfer to your hotel. Refresh, then begin a tailored city tour highlighting Lisbon's historic neighborhoods, viewpoints, and lively cafés. Savor petiscos and local drinks during an intimate dining experience as your expert guide shares stories and insider tips.

This trip delivers authentic, tailor-made experiences to your Portugal travel, blending culture, flavors, and unforgettable moments.

Toast with sardines, olives and white wine served as appetizer or tapa.
Day02

Day 2: Cultural Lisbon tour

Begin your day with a private, tailor-made half-day tour of Lisbon. Walk through Liberty Avenue, Restauradores Square, Rossio Square, and the historic Alfama Quarter to Lisbon Cathedral. Visit St. George's Castle and Roman theatre ruins, then explore the delightful district of Belem with its monuments, museums, and charming cafes.

In the evening, enjoy a Fado Show with traditional music paired with local dishes, then stroll to see Jerónimos Monastery and the 16th-century Belem Tower. The rest of the evening is free.

Beautiful image of the Hieronymites Monastery (Jeronimos), a UNESCO world heritage site, in Lisbon, Portugal. HDR
Day03

Day 3: Sintra, Cabo da Roca, Cascais and Estoril

After a leisurely breakfast, enjoy a full day of exploring Sintra's palaces, wooded ravines, and springs linked to Lord Byron and royal retreats. Walk historic streets, visit palaces and gardens, then continue to sunlit Cabo da Roca, the westernmost point of continental Europe, for dramatic ocean views.

Finish along the coast in Cascais and Estoril to sample seaside charm, local shops, and beaches. Cap the day with a curated dinner at a Michelin-starred restaurant.

most beautiful castles of Europe - Pena palace in Portugal
Day04

Day 4: Exploring Alentejo

After breakfast, your private transfer takes you through rolling plains to a splendid winery in southern Alentejo for a tasting and cellar tour, then visit the evocative Chapel of Bones in the city of Evora.

Arrive in Alentejo and check in. The afternoon and evening are yours to relax, explore local markets, or savor a personalized dining recommendation.

Olive Trees in a field of yellow Lupine flowers (Lupinus luteus) against cloudy sky in Alentejo, Portugal alentejofieldportugalagriculturebackgroundblossombluecampo maiorcloudscloudy skycopy spacedeltadelta coffeeflowerfreshnessgrassgreenhappinessherbsholidayidylliclandscapelupinlupin flowerlupinelupinusmeadownaturalnaturenature landscapeno peopleoakoutdoorsruralscenicscenic landscapeseasonskyspringspringtimesummertourismtranquiltraveltreevibrantviewwild flowerswildfloweryellowShow more
Joel

Tips from Joel

Portugal Travel Expert

quotes

In Alentejo, don’t rush through the small towns. Places like Vila Viçosa or Redondo may look quiet, but pop into a local tasca and ask about the pottery or wine. You’ll often end up with a homemade snack, a story, and a connection you won’t find on any itinerary.

Day05

Day 5: Around Alentejo

After a sumptuous breakfast, spend a leisurely day by the hotel pool or rejuvenate in the spa while enjoying tranquil views across Alentejo.

The hotel arranges horse riding, private wine tastings, and bespoke local experiences that bring this Portugal trip to life. If you're wondering about the best time to visit Portugal, spring and autumn are perfect for soaking up Alentejo’s calm without the summer heat. Relax or personalize your day with expert hosts and signature regional flavors.

typical portuguese dish Carne de Porco a Alentejana on dish and glass of red wine
Day06

Day 6: Coimbra Wine-Tasting Experience

After a sumptuous breakfast, a private transfer takes you to the historic wine town of Coimbra for curated tastings with local producers. Tailor-made experiences let you meet winemakers, sample rare varietals, and learn traditional methods.

Enjoy a leisurely lunch at a charming winery before continuing by scenic road to the Douro Valley.

The University of Coimbra is a university in Coimbra, Portugal. Established in 1290, it is one of the oldest universities in the world.
Day07

Day 7: Wines of the Douro Valley

Travel to the serene Douro Valley, home of Port wine. In Regua, enjoy a scenic river cruise through terraced vineyards, then visit the Mateus 18th-century palace for a guided wine tasting that reveals local traditions.

Continue to Quinta Nova Luxury Winery House, a renovated nineteenth-century manor with sweeping vineyard and river views. Relax in the garden, sip wines at the Wine Bar, and enjoy curated tastings and cuisine.

Facade of the Mateus Palace (Casa de Mateus), Portugal
Day08

Day 8: Porto

Transfer to Porto after breakfast for a half-day private city tour showcasing Mercado do Bolhão, Torre dos Clérigos, and other landmarks. Your private guide tailors the route for authentic, tailor-made travel that balances driving with walking to reveal Porto's mix of medieval and modern architecture.

Enhance the experience with the Douro Cruise of Six Bridges to admire Porto and Vila Nova de Gaia from the water amid scenic river and mountain views. Return to your Porto hotel for the night.

Cruise ship arrives to Porto by the river Douro. Portugal
Day09

Day 9: Porto departure

After a hotel breakfast, enjoy a free morning to wander Porto’s riverside streets, visit local wine lodges, and uncover hidden gems. Our team can arrange last-minute experiences to perfect your stay.

At the appointed time, transfer to the airport for your departure flight and carry home lasting memories of authentic, tailor-made travel and Portuguese wine culture.

Portuguese breakfast. Room service in hotel in Portugal. Black coffee, pasteis de nata, strawberries.