Celebrate your milestone anniversary with a seamless six-day route connecting Lisbon, Sintra, historic central towns, Porto, and the Douro Valley.
Day 1: Arrival in Lisbon, Historic Belém and Riverside Vistas
Land at Lisbon Portela Airport and meet your dedicated driver to begin your anniversary journey without the stress of navigating unfamiliar streets. Start along the Tagus waterfront in historic Belém, viewing the intricate Manueline stonework of the Jerónimos Monastery and the fortified Belém Tower, both built during Portugal’s Age of Discovery. Stop at Pastéis de Belém to taste the warm custard tarts dusted with cinnamon, paired with Portuguese espresso. Take in a panoramic view from the Miradouro das Portas do Sol before heading to your hotel in central Lisbon for an evening exploring the cobbled streets of the Chiado district.
Day 2: Romantic Sintra, Cabo da Roca and the Cascais Shoreline
Ascend into the misty Serra de Sintra to explore the whimsical architecture of Pena Palace and the romantic gardens of Quinta da Regaleira with its subterranean Initiation Well. Having a professional driver handle the narrow mountain roads means avoiding Sintra’s challenging traffic and parking restrictions entirely. Continue west to Cabo da Roca, the rugged westernmost point of continental Europe, where sheer granite cliffs plummet into the Atlantic. Conclude the afternoon driving through the coastal hamlet of Cascais, stopping for fresh sea bass grilled over charcoal and a chilled glass of crisp Colares white wine before returning to Lisbon for the night.
Day 3: Northward Through Óbidos, Batalha and Medieval Coimbra
Depart Lisbon on a scenic journey northward, stopping first within the fourteenth-century defensive walls of Óbidos to stroll beneath whitewashed houses draped in vibrant bougainvillea. Further north, pause at the Monastery of Batalha, a masterpiece of late Gothic and Manueline architecture commissioned by King John I to commemorate the battle of Aljubarrota in 1385. Arrive in the ancient university city of Coimbra in late afternoon to explore the historic university campus and its Baroque Joanina Library. Dine on roasted suckling pig or regional duck rice paired with a robust Bairrada red wine, resting overnight in Coimbra.
Browse our travel inspiration for ideas, or tell us what kind of day you have in mind.
Day 4: Ancient Scholars, Aveiro Canals and Arrival in Porto
Spend the morning walking the medieval lanes of Coimbra down to the banks of the Mondego River, passing the Old Cathedral of Sé Velha. Travel north to the coastal town of Aveiro, known for its salt pans and colorful moliceiro boats that traditionally harvested seaweed in the lagoon. Taste the regional ovos moles, sweet egg pastries enclosed in delicate rice paper, before continuing to the granite city of Porto. End your day overlooking the dramatic Dom Luís I bridge as sun sets across the Douro, checking into your hotel in Porto.
Day 5: The Steep Vineyards and River Bends of the Douro Valley
Embark on a magnificent day excursion into the UNESCO-listed Alto Douro Wine Region, where terraces of schist rock carve dramatic lines down to the winding river. Having a local driver guide allows you to relax completely and enjoy the twisting, legendary bends of the N222 scenic road without worry. Visit a family-owned quinta near Pinhão for an unhurried tasting of Vintage Port and single-estate Douro reds paired with local sheep milk cheese and olive oil. Return along the river valley in the evening for a second peaceful night in Porto.
Day 6: Historic Porto, Riverside Cellars and Evening Departure
Dedicate your final morning to the cultural treasures of Porto, beginning with the vibrant azulejo tile murals inside São Bento Railway Station. Stroll past the baroque Clérigos Tower and downward through the UNESCO-listed Ribeira district along the water’s edge. Cross the river into Vila Nova de Gaia to visit historic port wine lodges that have aged fortified wines in French oak casks for centuries. Enjoy an anniversary lunch of salted cod bacalhau à Gomes de Sá and a glass of aged Tawny Port before your driver delivers you smoothly to Porto Airport for your flight home.
Plan your own day
Share your dates, group size and interests, and we will suggest a tailored plan with a local driver/guide.
