Self-Guided Tours & Trips in Alentejo
Explore a wide diversity of self-guided tours through Alentejo. We have 17 adventures that vary from 7 days to 9 days. With the greatest number of departures in October, this is also the most popular time of the year.
10 best self-guided Alentejo tours
Compiled by

MelissaAlentejo travel expert at TourRadar
- The walk of the historical Alentejo (7 days)
- Alentejo Vineyards & Alqueva Lake Road 9 Days
- Portugal - Along the Vicentina Coast 8 Days
- Portugal - Castles and Wine 8 Days
- Alentejo Vineyards Road 7 Days
- Rota Vicentina & Alentejo 8 Days
- The Fishermen's Trail - Rota Vicentina 7 Days
- Lisbon - Sagres: Along the Atlantic Coast 7 Days
- Portugal's diversity - 3-Region Tour 8 Days
- Costa Vicentina Natural Park Hike Tour 8 Days
Walk the 13th-century castle walls of Marvão on your own, taking in views across Serra de São Mamede from this medieval hilltop fortress. Trek through cork and chestnut forests from Castelo de Vide to Portagem, passing megalithic sites and traditional Alentejo villages along the way.
Duration 7 days Destinations Faro, Castelo De Vide, Marvao, Portagem, Lisbon Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$1,549
Duration 9 days Destinations Estremoz, Vila Vicosa, Monsaraz, Redondo, Evora, Arraiolos Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$2,054
Navigate independently through Portugal's southwestern coast, cycling from Sesimbra through Santiago do Cacém to Vila Nova de Milfontes with comprehensive navigation app guidance. Ride through the Lagoas de Santo André wetlands and along the Costa Vicentina cliffs, with luggage transported daily between accommodations. This self-guided cycling trip includes 7 breakfasts, basic tools, 24-hour telephone support, and opportunities to see fishing villages and sample regional wines at your leisure.
Duration 8 days Destinations Sesimbra, Arrabida Natural Park, Setubal, Santiago do Cacém, Porto Covo, Vila Nova de Milfontes Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$1,914
Pedal through Évora's UNESCO-listed historic center, checking out the 13th-century bone chapel and Europe's largest dolmen near Nossa Srª de Machede. Quiet back roads guide you through olive groves as you cycle 30-60 km daily, and there's a stop at Fita Preta winery in a 14th-century estate.
Duration 8 days Destinations Arraiolos, Evora, Monsaraz, Vila Vicosa, Estremoz Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$1,543
Duration 7 days Destinations Lisbon, Estremoz, Vila Vicosa, Redondo, Evora, Arraiolos Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$1,659
Walk the Fishermen's Trail independently from Vila Nova de Milfontes to secluded beaches near Almograve and Zambujeira do Mar, following the Rota Vicentina coastal path. Trek through ancient cork oak forests from Odeceixe to São Teotónio, following historic shepherd paths inland.
Duration 8 days Destinations Vila Nova de Milfontes, Almograve, Zambujeira, Odeceixe, São Teotónio, Odemira, São Luís, Beja Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$869
Navigate the wild Alentejo coastline on your own with luggage transfers and a navigation app guiding you through Porto Covo's Pessegueiro island fortress and Aivados dunes to Malhão beach. Stay in comfortable spots including the Touril guesthouse while having regional sea bass dinners.
Duration 7 days Destinations Lisbon, Vila Nova de Milfontes, Porto Covo, Almograve, Touril, Brejão, Odeceixe Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$1,682
Navigate on your own using GPS data and a navigation app as you cycle through Arrábida Nature Park's rock formations and Costa Vicentina's beaches. The route has ferry trips across the Tagus River and Sado estuary, with luggage transfers between 3- and 4-star hotels as you cover 40 to 70 km daily.
Duration 7 days Destinations Lisbon, Setubal, Sines, Vila Nova de Milfontes, Algarve, Sagres Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$1,136
Check out Alvados, Évora, and Vila Nova de Milfontes at your own pace with detailed route instructions and a navigation app. Cycle independently through the famous carpet-making town of Arraiolos and along Alentejo's wine and cork routes. Stay in comfortable accommodations with luggage transported between each stop, plus a basic tool kit and 24-hour telephone support throughout.
Duration 8 days Destinations Alvados, Evora, Santiago do Cacém, Vila Nova de Milfontes Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$3,017
Use digitized routes via app from Vila Nova de Milfontes to Arrifana Beach, independently seeing the Atlantic coast's cliffs and hidden coves. Daily luggage transfers support your trip through Porto Covo, Zambujeira do Mar, and Odeceixe's river confluence at your own rhythm.
Duration 8 days Destinations Vila Nova de Milfontes, Porto Covo, Almograve, Zambujeira, Odeceixe, Aljezur, Arrifana Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
- US$870





















