Arrive in Portugal’s capital and take an evening walk through Alfama’s winding lanes. Enjoy the views from São Jorge Castle and stop for a riverside dinner.
Overnight: Lisbon

Ride Tram 28 through the historic quarters, then head to Sintra for the fairytale Pena Palace, Moorish Castle, and a stroll through Quinta da Regaleira’s gardens. Return to Lisbon in the evening.
Overnight: Lisbon

Travel inland to Évora, where you can explore its Roman Temple, cathedral, and peaceful squares. Evening stroll through the medieval walls.
Overnight: Évora

Discover the surrounding Alentejo region — rolling plains, cork oak forests, and fortified hilltop towns like Monsaraz with castle views over the Guadiana River.
Overnight: Évora

Head south to the western Algarve and settle into Odeceixe, a whitewashed village near a wide sandy beach backed by cliffs and dunes. Evening coastal walk at Odeceixe Beach.
Overnight: Odeceixe

Spend the day exploring the wild Vicentine Coast — golden beaches, turquoise coves, and dramatic sea stacks. Walk part of the Rota Vicentina trail for panoramic views.
Overnight: Odeceixe

Relax on the beach or venture west toward Sagres and Cape St. Vincent, Europe’s southwestern tip, for rugged cliffs and sweeping Atlantic horizons.
Overnight: Odeceixe

Travel north via Lisbon or Porto and continue into the Douro Valley. Stay in Tabuaço, a quiet hillside town surrounded by terraced vineyards and dramatic river scenery.
Overnight: Tabuaço

Take a river cruise along the Douro, with views of vine-covered slopes and quaint riverside villages. Pause at panoramic viewpoints around Tabuaço.
Overnight: Tabuaço

Drive or cycle through the valley, stopping at small hamlets and miradouros such as São Leonardo da Galafura. Evening at leisure among the vineyards.
Overnight: Tabuaço

Fly to Pico in the Azores, famous for its volcanic peak and stone-walled vineyards. Explore coastal villages and watch sunset over the Atlantic.
Overnight: Pico

Climb part of Mount Pico or hike gentler trails through lava fields and vineyards. Swim in natural ocean pools along the coast.
Overnight: Pico

Take a whale-watching excursion, then ferry across to nearby Faial to see Horta’s harbor and the lunar-like Capelinhos volcanic landscape before returning to Pico.
Overnight: Pico

Fly back to Lisbon for your final night. Take a relaxed evening riverside walk along the Tagus and enjoy a farewell dinner.
Overnight: Lisbon

Bid farewell to Portugal after a memorable 14-day journey. Airport transfer for your flight home, filled with rich stories and unforgettable experiences.