Itinerary
- Day 1
Lisbon to Estremoz
You arrive in Lisbon and then transfer to Estremoz, a charming old town where you'll be staying in a historic castle-turned-hotel. From your room, you'll have views overlooking the town and the Alentejo plain stretching out below. It's a great spot to get oriented and settle in for the week ahead.
Landmarks Estremoz Castle - Day 2
Estremoz
Time to get on the bike and cycle through the Alentejo countryside. The main sounds keeping you company are sheep bells as you pedal past whitewashed villages with blue and ochre borders. Later you'll pull into a local winery to sample red and white wines, then head back to your hotel for the evening.
- Meals
- Breakfast
Included Activities
- Winery visit and wine tasting
Landmarks Alentejo Region - Day 3
Estremoz to Vila Viçosa
After breakfast, you cycle through historic villages and rural landscapes, passing by old battle sites and charming communities along the way. By afternoon you'll roll into Vila Viçosa, Portugal's marble capital, and can spend time at the impressive Ducal Palace built between the 16th and 17th centuries. The rest of the day is yours to walk around the city center.
- Meals
- Breakfast
Optional Activities
- Visit to Ducal Palace
Landmarks Ducal Palace - Day 4
Vila Viçosa
Today's a loop ride taking you through cork oak and olive groves with views of the Guadiana River that separates Portugal from Spain. You'll stop at Juromenha village overlooking Spain, then face some climbs on the ride back. By evening you're back at the hotel enjoying dinner.
- Meals
- Breakfast
Optional Activities
- Stop at Juromenha village
Landmarks Guadiana River Juromenha - Day 5
Vila Viçosa to Monsaraz
Heading south past Alandroal, you ride through fragrant oleander flowers before arriving in Monsaraz, a medieval village with deep cultural roots and prehistoric history. Consider stopping to see the Outeiro menhir before checking into your accommodation for the night.
- Meals
- Breakfast, Dinner
Optional Activities
- Visit to Outeiro menhir
Landmarks Outeiro Menhir 
- Day 6
Monsaraz to Redondo
You cycle through golden landscapes toward Redondo and explore the Redondo Hotel-Museum, which has an impressive tile collection. The building is a former convent that's been hosting guests since 1500. Wrap up the day at the city's Wine Museum to learn about Portuguese wine production.
- Meals
- Breakfast, Dinner
Optional Activities
- Visit to Redondo Hotel-Museum with tile collection
- Wine Museum visit
Landmarks Redondo Hotel-Museum Wine Museum - Day 7
Redondo to Évora
Pedaling through beautiful golden and green hills dotted with cork oaks, unspoiled vineyards, and abandoned castles, you make your way to Évora. This historic city is a UNESCO World Heritage Site with 2,000 years of history layered throughout, and you'll have plenty to explore here.
- Meals
- Breakfast
Landmarks Évora Historic Center 
- Day 8
Évora
Starting with a late breakfast, you spend the morning exploring Évora and cycling to nearby Arraiolos, known for its colorful hand-embroidered wool carpets. On this final day of cycling, you'll have a chance to celebrate your journey with Portuguese wine from its birthplace region.
- Meals
- Breakfast
Optional Activities
- Cycling to Arraiolos
- Purchase hand-embroidered wool carpets
Landmarks Arraiolos - Day 9
Departure
Your cycling tour wraps up today. You'll depart with memories and experiences from your week riding through Portugal's nature trails and historic towns.
- Meals
- Breakfast
