Our Alentejo vacations & tours
Our Alentejo vacations roam one of Portugal’s lesser-visited regions, yet one that spans an incredible third of the country. Walkers and cyclists can make excellent use of trails along the clifftops, and through Alentejo’s peaceful agricultural interior, with rustic farmhouses and orchards of olives and oranges dotting the undulating hillsides. Whether you opt for a small group tour or a self-guided trip, rest assured that routes have been crafted by people with years of experience who know the region well, and select lovely, locally run hotels and guest houses that provide a warm welcome. Families will find an equally enthusiastic reception on Alentejo’s wild Atlantic coast, where activities such as surfing and SUP are led by brilliant local guides.
Our top Alentejo vacations
Alentejo heritage bike tour, Portugal
From
€1170 to €1320
8 days
ex flights
Cycle through Alentejo’s historic scenery
Tailor made
Alentejo & Algarve self guided hiking vacation, Portugal
From
€585
8 days
ex flights
Independent coastal walking vacations in the Alentejo Coast
Tailor made
Coastal hiking vacation in Portugal
From
US $3105 to US $3825
8 days
ex flights
Portugal’s Rota Vicentina is the ultimate hikers paradise
Small group2026: 5 Sep, 19 Sep, 3 Oct, 17 Oct, 31 Oct, 2027: 6 Mar, 10 Apr, 8 May, 22 May, 12 Jun, 4 Sep, 18 Sep, 2 Oct, 16 Oct, 13 Nov, 2028: 4 Mar, 8 Apr, 6 May, 20 May, 10 Jun, 2 Sep, 16 Sep, 7 Oct, 21 Oct, 11 Nov
Vicentina coastal walking vacation, Portugal
From
€1295 to €1580
13 days
ex flights
Walk the Rota Vicentina through the Alentejo & Algarve
Tailor made
Guadiana River cycling vacation, Portugal
From
€1100 to €1275
8 days
ex flights
Cycle the majestic Guadiana River for a relaxing escape
Tailor made
Alentejo self guided hiking in Portugal
From
€1070
14 days
ex flights
walk Rota Vicentina historical and fishermen's trail
Tailor made
Alentejo self guided cycling vacation, Portugal
From
€1186 to €1336
8 days
ex flights
center-based vacation sw portugal with great hotels
Tailor made
Alentejo & Algarve self guided biking vacation, Portugal
From
€850 to €950
8 days
ex flights
touring bicycle vacations sw portugal - alentejo and algarve.
Tailor made
Alentejo self guided hiking vacation, Portugal
From
€469
6 days
ex flights
Walk the Fishermen's Trails along Rota Vicentina's landscape
Tailor made
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ALENTEJO MAP & HIGHLIGHTS
The warm and lovely Alentejo spreads from Lisbon to the Algarve, a little-changed landscape of fertile fields and shepherd’s trails, dotted with medieval villages. It’s a couple of hours’ drive from Faro or Lisbon – far enough to keep the stop-and-flop vacationmakers away – and once here, pick the beach for surfing and sunning, or choose a walking or cycling vacation. These typically focus on the Rota Vicentina trails, which stretch from Santiago do Cacém to Cabo De São Vicente in the Algarve. Trips tend to be self-guided, traveling point-to-point with luggage transferred, and provide a great overview of the region.
1.
Fishermans trail
2. Historical Way
3. Parque Natural do Sudoeste Alentejano e Costa Vicentina
4. Pego das Pias
5. Vila Nova de Milfontes
2. Historical Way
3. Parque Natural do Sudoeste Alentejano e Costa Vicentina
4. Pego das Pias
5. Vila Nova de Milfontes
Fishermans trail
1. Fishermans trail
Sitting within the Parque Natural do Sudoeste Alentejano e Costa Vicentina, this route was shaped by the daily trek fishermen made between villages and remote fishing spots. Some sections cross sand dunes or skirt cliff edges, so are better suited to walkers than cyclists, but however you travel there are superb views over empty beaches and the chance to see unique wildlife, including nesting storks at Cabo Sardão.
Historical Way
2. Historical Way
The Historical Way is an old pilgrims’ trail that threads inland, dotted with churches, old country houses and time-warp villages where locals love to chat. Sections such as San Luis to Odemira reveal a different, very verdant side to this region, where the River Torgal’s banks are choked with wild asparagus and oregano and you can swim in the clear waters.
Parque Natural do Sudoeste Alentejano e Costa Vicentina
3. Parque Natural do Sudoeste Alentejano e Costa Vicentina
This is the largest protected coastal natural park in Europe, a rolling landscape of verdant hills, river valleys, dramatically eroded cliffs and virgin beaches. This is the haunt of rare fishing eagles, the world’s only shore-living white storks who build their nests on the craggy cliffs and sea otters, while unique indigenous plants offer botanical treasure.
Pego das Pias
4. Pego das Pias
This secluded lagoon on the River Torgal northeast of Odemira nestles in a steep-sided valley and is one of the area’s little-known treasures. Flanked by rocks and oak trees, its waters are still and inviting. Family adventure vacations tackle raft building here, and it’s lovely for an anytime-of-year swim – this section of the river never dries up – or a picnic on its grassy banks.
Vila Nova de Milfontes
5. Vila Nova de Milfontes
This picturesque village makes a great base for a family activity vacation. It’s surrounded by beautiful, safe surfing beaches which are ideal for beginners, including Malhão, while the cleanest of all European rivers, the Mira, spills into the Atlantic here and can be explored by kayak. The Fishermen’s Trail passes through and eating’s a treat, too, with fresh, well-priced seafood in its many restaurants.
Our Alentejo vacations reviews
4.7
39Alentejo vacations reviews
Sandra Burke03 Jun 2026
Overall, we enjoyed the trip especially the first part through the Alentejo region. read more
andrea galpin15 Mar 2026
Easy walking. Good views. Dramatic coastal scenery.read more
Madeleine Stevens28 Oct 2025
Climbing down to deserted beaches - not often swimmable because of rocks, waves and currents, but beautiful, and great for a cooling dip. Seeing the changes in vegetation as we went South. We also enjoyed the interesting inland sections, and coming across Moorish ruins.read more
Jane Geeson28 Sep 2025
Beautiful scenery. Just do it!read more
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