Biking Southern Portugal: Alentejo to the Algarve

Depart from home and travel to Portugal. The particulars of your arrival overseas are detailed with your flight itinerary and airline tickets.

Upon arrival at Lisbon’s International Airport, proceed through immigration; claim your luggage and clear customs. If your luggage is delayed, fill in a PIR form before leaving the customs area; VBT representatives are not allowed into the customs area. Make certain that your VBT luggage tags are affixed to your bag so your VBT representative can identify you. After exiting customs, enter the arrival hall and look for your VBT representative holding a VBT sign. Transfer to your Lisbon hotel in the city center. Transfer time is approximately 30-45 minutes, depending on traffic.

VBT provides you with City Information that includes information and recommendations on what to see and do in Lisbon.

Hotel: Pousada de Lisboa
Alternate Hotel: Fontecruz Lisboa Autograph Collection

VBT-Bicycle-Vacation-only guests: Meet your VBT Representative at the Pousada de Lisboa at 9:00 a.m. The hotel is located at Praça do Comércio, 31-34, 1100-148 Lisbon and the phone number is +351 21 040 7640 (Alternate hotel – Fontecruz Lisboa Autograph Collection). Please be dressed in your riding attire. If you are so delayed that you will miss the morning transfer from here, then we suggest you take a train to Évora at your own expense. There are direct trains departing from Lisbon’s Estação do Oriente train station and the cost is approximately 13 euros – journey time is 1 hour and 30 minutes. From the Évora train station you may take a taxi (approximately 20 minutes) to your hotel outside of Évora. Cost of the taxi is approximately 20 euros. Please contact the Lisbon hotel to advise them of any travel delays or changes so the staff can pass the message on to your VBT Trip Leaders.

VBT Air Package & Pre-Trip Extension guests: Please have your luggage outside your room by 8:15 a.m. Make sure you have your VBT luggage tags on your bags. After breakfast, meet your VBT Representative in the lobby of your hotel at 9:00 a.m. Please be dressed in your riding attire.

Your VBT Representative will escort you by shuttle (approximately 1 hour and 15 minutes) to join your VBT Trip Leaders. You will depart Lisbon via the expansive Vasco de Gama Bridge, the longest bridge in Europe, spanning the mighty Tagus River. Heading east, you will arrive on the scenic plains of the Alentejo region, known for its stunning vistas and abundant cork and olive groves. You will meet your VBT Trip Leaders for a bike-fitting and safety session. Afterwards, get to know your fellow travelers over lunch before departing on a warm-up ride amidst this scenic region of rustic farmland and gentle hills to your hotel outside of the historic medieval town of Évora, a UNESCO World Heritage Site.

Your accommodation for the next two nights is in the Convento do Espinheiro, a Luxury Collection Hotel & Spa. The 15th-century convent is listed as a national monument for the many important noble figures who have met here throughout the centuries to shape Portugal’s history.

This evening, join the hotel’s sommelier in the Convent’s wine cellar to sample some of the region’s wines before enjoying a sumptuous welcome dinner in the hotel’s historic dining room.

Hotel: Convento do Espinheiro, a Luxury Collection Hotel & Spa
Meals: Breakfast, Lunch, Dinner
Daily Options: 10 miles (16.8km)

After breakfast, shuttle from your hotel to the white-washed town of Redondo, home to a 500-year-old Portuguese pottery tradition. From here you will begin cycling across the plains of Alentejo, following scenic country roads bordered by cork forests. Our destination looms in the distance: hilltop Monsaraz, one of Portugal’s oldest settlements, and its imposing castle. Enthusiastic riders may enjoy the climb into town; the VBT van will be available to shuttle you from Aldeia de Venda to Monsaraz if you need assistance or would like more time to explore Monsaraz.

With Monsaraz’s ideal hilltop location and endless vistas of the Alentejo and neighboring Spain, it has been occupied by various civilizations since pre-historic times. After the town’s Roman occupation, the Visigoths, Arabs, Mozarabs, Jews, and Christians settled here as well. As you explore its narrow warrens and admire it white-washed, red-roofed houses, you can marvel at the remarkable view of the Alqueva Dam and the second-largest artificial lake in Europe. Enjoy lunch at a local café before shuttling back to your hotel.

Later, you will venture into Évora for a visit to the São Francisco and its eerie Chapel of Bones, constructed by 16th-century Franciscan monks. Your local guide will then take you on a walking tour of the UNESCO World Heritage Site of Évora, wandering atmospheric alleyways past old patrician mansions and white-washed houses with bright yellow trim. Enjoy dinner on your own in Évora this evening.

Hotel: Convento do Espinheiro, a Luxury Collection Hotel & Spa
Meals: Breakfast, Lunch
Daily Options: 23 miles (36.5 km)

After breakfast, shuttle south to the small town of Castro Verde and other small villages for the start of your rides in the lower Alentejo region. Today’s rides introduce you to the arid landscapes of the Campo Branco, or White Plains territory. As you cycle, you may pass shepherds grazing their herds on wide-open spaces. For lunch, we will stop at a typical Portuguese rural café for a farm-fresh meal with warm, welcoming hosts. After, shuttle or ride to the remarkable fortified hilltop town of Mértola and your hotel.

After settling into your accommodations, join a local guide for a fascinating exploration of Mértola. This town’s history dates back to the Phoenicians, Carthaginians and Romans. The most important remnant from the 500-year Moorish occupation is the medieval mosque, the only mosque to have survived the period in Portugal. Today it is Mértola’s main church, though it boasts many of its original Moorish features. This evening dine at your leisure in one of the town’s restaurants.

Hotel: Hotel Museu
Meals: Breakfast, Lunch
Daily Options: 13 or 27 miles (21.1 or 45 km)

This morning begin your ride cycling from your hotel. If you prefer a shorter option, you may shuttle 15 minutes to the starting point of today’s ride. Enjoy your morning cycling through the Guadiana Valley Natural Park, one of 30 areas in Portugal officially protected by the government. You will wind your way through small towns of well-preserved traditional architecture and coast to the banks of the Guadiana River. The river’s small port village of Pomarão was specially constructed for the nearby mining operations. Here you may straddle the Portugal / Spain border with a foot in each country and half your body in Spain’s later time zone! Savor lunch in a riverside café overlooking the marina. Then embark a privately chartered boat for a relaxing afternoon on the River Guadiana. Your cruise delivers you right to our hotel dock in Mértola. Those seeking a longer ride and challenging option after lunch may forfeit the boat excursion and cycle back to the hotel.

This evening enjoy dinner at your hotel overlooking the Guadiana River.

Hotel: Hotel Museu
Meals: Breakfast, Lunch, Dinner
Daily Options: 10, 15 or 26 miles (15.9, 24.5 or 44.1 km)

After breakfast, shuttle southward to the Algarve and the banks of the Guadiana River. The Guadiana is the fourth longest river on the Iberian Peninsula and serves as the natural border between Spain’s Andalucía region and Portugal’s Alentejo and Algarve regions. Today’s lovely ride traces the scenic banks on the Portugal side while providing distant views across the river towards Spain. Those looking for more mileage today may extend their morning ride. At the end of your ride, savor a tasty picnic lunch served by your Trip Leaders.

After, we shuttle (approximately 1 hour) to our lovely accommodations in the Algarve, the Vila Monte Farm House, and settle in to one of breezy, elegant suites. Enjoy an authentic Algarvian countryside experience, removed from the bustle of coastal resorts and embraced by a distinctly Portuguese beauty and tranquility.

Enjoy delicious regional Algarve cuisine made with the freshest of ingredients during your dinner here this evening.

Hotel: Vila Monte Farm House
Meals: Breakfast, Lunch, Dinner
Daily Options: 14 or 27 miles (22.2 or 44.4 km)

After a sumptuous breakfast, enjoy a leisurely reel through the surrounding Algarve countryside with vistas of the sea in the distance. Our destination is the lovely whitewashed village of Cacela-a-Velha, perched on top of a hill with a view to the easternmost lagoon of the Formosa River. The village is home to the Fortaleza de Cacela located on the site of the original castle constructed during the Muslim period. Spend time exploring the village before enjoying lunch at one of the lively cafés. Alternately, you may have the hotel pack a picnic for you so as to enjoy lunch on the beach. In the afternoon cycle back or shuttle to your resort for an afternoon at leisure, taking advantage of the property’s pools or spa.

This evening, join your fellow travelers and Trip Leaders to reminisce about your Portuguese adventures during a fireside farewell reception, followed by a delightful dinner with local wines.

Hotel: Vila Monte Farm House
Meals: Breakfast, Dinner
Daily Options: 20 or 40 miles (33 or 66.4 km)

VBT-Bicycle-Vacation-only guests: Enjoy breakfast before your transfer to Cascais (approximately 4 hours). Your tour concludes at approximately 1:00 p.m. at the Cidadela Cascais Pousada & Art District hotel in Cascais or the alternate hotel Grande Real Villa Italia. Taxis are available at the Cascais hotel to take you to central Lisbon hotels, the Lisbon train station, or to the Lisbon airport – approximately 30-45 minutes depending upon traffic.

Important: Flight departures from Lisbon prior to 4:00 p.m. are not recommended. If you depart earlier, you are responsible for your own transfer arrangements from the last hotel in the Algarve to Lisbon’s airport.

VBT Air Package guests: Our morning journey to Cascais will take approximately 4 hours arriving to your Cascais hotel at approximately 1:00 p.m. You will have the remainder of the afternoon and evening to explore the seaside town of Cascais. You will spend tonight at the Cidadela Cascais Pousada & Art District overlooking the marina and Atlantic Ocean or the alternate hotel Grande Real Villa Italia. The city is a pleasure to explore by foot. You will receive City Information in your Final Travel Booklet, with recommendations for transportation options, cafés, museums and restaurants.

VBT Post-trip Extension guests: Our morning journey to Cascais will take approximately 4 hours arriving to your Cascais hotel at approximately 1:00 p.m. You will have the remainder of the afternoon and evening to explore the seaside town of Cascais. You will spend tonight at the Cidadela Cascais Pousada & Art District overlooking the marina and Atlantic Ocean or the alternate hotel Grande Real Villa Italia. The city is a pleasure to explore by foot. You will receive City Information in your Final Travel Booklet, with recommendations for transportation options, cafés, museums and restaurants.

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Air Package Hotel: Cidadela Cascais Pousada & Art District
Alternate Hotel: Grande Real Villa Italia
Meals: Breakfast

After breakfast,* transfer to the Lisbon International airport (approximately 45-60 minutes) for your departing flight.** Please note: Ensure that you are ready in the hotel reception area at the designated time.

* Please note: For guests with early-morning departures, breakfast at the hotel may not be available. Please check with the Front Desk to verify the times that breakfast is served.

** Please note: VBT transfer times and departure points are finalized in advance and cannot be modified for individual guests. If you extend your stay beyond the scheduled program dates, return transportation to the airport will be at your own expense.

Meals: Breakfast

VBT-Bicycle-Vacation-only guests: Meet your VBT Representative at the Pousada de Lisboa at 9:00 a.m. The hotel is located at Praça do Comércio, 31-34, 1100-148 Lisbon and the phone number is +351 21 040 7640 (Alternate hotel – Fontecruz Lisboa Autograph Collection). Please be dressed in your riding attire. If you are so delayed that you will miss the morning transfer from here, then we suggest you take a train to Évora at your own expense. There are direct trains departing from Lisbon’s Estação do Oriente train station and the cost is approximately 13 euros – journey time is 1 hour and 30 minutes. From the Évora train station you may take a taxi (approximately 20 minutes) to your hotel outside of Évora. Cost of the taxi is approximately 20 euros. Please contact the Lisbon hotel to advise them of any travel delays or changes so the staff can pass the message on to your VBT Trip Leaders.

VBT Air Package & Pre-Trip Extension guests: Please have your luggage outside your room by 8:15 a.m. Make sure you have your VBT luggage tags on your bags. After breakfast, meet your VBT Representative in the lobby of your hotel at 9:00 a.m. Please be dressed in your riding attire.

Your VBT Representative will escort you by shuttle (approximately 1 hour and 15 minutes) to join your VBT Trip Leaders. You will depart Lisbon via the expansive Vasco de Gama Bridge, the longest bridge in Europe, spanning the mighty Tagus River. Heading east, you will arrive on the scenic plains of the Alentejo region, known for its stunning vistas and abundant cork and olive groves. You will meet your VBT Trip Leaders for a bike-fitting and safety session. Afterwards, get to know your fellow travelers over lunch before departing on a warm-up ride amidst this scenic region of rustic farmland and gentle hills to your hotel outside of the historic medieval town of Évora, a UNESCO World Heritage Site.

Your accommodation for the next two nights is in the Convento do Espinheiro, a Luxury Collection Hotel & Spa. The 15th-century convent is listed as a national monument for the many important noble figures who have met here throughout the centuries to shape Portugal’s history.

This evening, join the hotel’s sommelier in the Convent’s wine cellar to sample some of the region’s wines before enjoying a sumptuous welcome dinner in the hotel’s historic dining room.

Hotel: Convento do Espinheiro, a Luxury Collection Hotel & Spa
Meals: Breakfast, Lunch, Dinner
Daily Options: 10 miles (16.8km)

After breakfast, shuttle from your hotel to the white-washed town of Redondo, home to a 500-year-old Portuguese pottery tradition. From here you will begin cycling across the plains of Alentejo, following scenic country roads bordered by cork forests. Our destination looms in the distance: hilltop Monsaraz, one of Portugal’s oldest settlements, and its imposing castle. Enthusiastic riders may enjoy the climb into town; the VBT van will be available to shuttle you from Aldeia de Venda to Monsaraz if you need assistance or would like more time to explore Monsaraz.

With Monsaraz’s ideal hilltop location and endless vistas of the Alentejo and neighboring Spain, it has been occupied by various civilizations since pre-historic times. After the town’s Roman occupation, the Visigoths, Arabs, Mozarabs, Jews, and Christians settled here as well. As you explore its narrow warrens and admire it white-washed, red-roofed houses, you can marvel at the remarkable view of the Alqueva Dam and the second-largest artificial lake in Europe. Enjoy lunch at a local café before shuttling back to your hotel.

Later, you will venture into Évora for a visit to the São Francisco and its eerie Chapel of Bones, constructed by 16th-century Franciscan monks. Your local guide will then take you on a walking tour of the UNESCO World Heritage Site of Évora, wandering atmospheric alleyways past old patrician mansions and white-washed houses with bright yellow trim. Enjoy dinner on your own in Évora this evening.

Hotel: Convento do Espinheiro, a Luxury Collection Hotel & Spa
Meals: Breakfast, Lunch
Daily Options: 23 miles (36.5 km)

After breakfast, shuttle south to the small town of Castro Verde and other small villages for the start of your rides in the lower Alentejo region. Today’s rides introduce you to the arid landscapes of the Campo Branco, or White Plains territory. As you cycle, you may pass shepherds grazing their herds on wide-open spaces. For lunch, we will stop at a typical Portuguese rural café for a farm-fresh meal with warm, welcoming hosts. After, shuttle or ride to the remarkable fortified hilltop town of Mértola and your hotel.

After settling into your accommodations, join a local guide for a fascinating exploration of Mértola. This town’s history dates back to the Phoenicians, Carthaginians and Romans. The most important remnant from the 500-year Moorish occupation is the medieval mosque, the only mosque to have survived the period in Portugal. Today it is Mértola’s main church, though it boasts many of its original Moorish features. This evening dine at your leisure in one of the town’s restaurants.

Hotel: Hotel Museu
Meals: Breakfast, Lunch
Daily Options: 13 or 27 miles (21.1 or 45 km)

This morning begin your ride cycling from your hotel. If you prefer a shorter option, you may shuttle 15 minutes to the starting point of today’s ride. Enjoy your morning cycling through the Guadiana Valley Natural Park, one of 30 areas in Portugal officially protected by the government. You will wind your way through small towns of well-preserved traditional architecture and coast to the banks of the Guadiana River. The river’s small port village of Pomarão was specially constructed for the nearby mining operations. Here you may straddle the Portugal / Spain border with a foot in each country and half your body in Spain’s later time zone! Savor lunch in a riverside café overlooking the marina. Then embark a privately chartered boat for a relaxing afternoon on the River Guadiana. Your cruise delivers you right to our hotel dock in Mértola. Those seeking a longer ride and challenging option after lunch may forfeit the boat excursion and cycle back to the hotel.

This evening enjoy dinner at your hotel overlooking the Guadiana River.

Hotel: Hotel Museu
Meals: Breakfast, Lunch, Dinner
Daily Options: 10, 15 or 26 miles (15.9, 24.5 or 44.1 km)

After breakfast, shuttle southward to the Algarve and the banks of the Guadiana River. The Guadiana is the fourth longest river on the Iberian Peninsula and serves as the natural border between Spain’s Andalucía region and Portugal’s Alentejo and Algarve regions. Today’s lovely ride traces the scenic banks on the Portugal side while providing distant views across the river towards Spain. Those looking for more mileage today may extend their morning ride. At the end of your ride, savor a tasty picnic lunch served by your Trip Leaders.

After, we shuttle (approximately 1 hour) to our lovely accommodations in the Algarve, the Vila Monte Farm House, and settle in to one of breezy, elegant suites. Enjoy an authentic Algarvian countryside experience, removed from the bustle of coastal resorts and embraced by a distinctly Portuguese beauty and tranquility.

Enjoy delicious regional Algarve cuisine made with the freshest of ingredients during your dinner here this evening.

Hotel: Vila Monte Farm House
Meals: Breakfast, Lunch, Dinner
Daily Options: 14 or 27 miles (22.2 or 44.4 km)

After a sumptuous breakfast, enjoy a leisurely reel through the surrounding Algarve countryside with vistas of the sea in the distance. Our destination is the lovely whitewashed village of Cacela-a-Velha, perched on top of a hill with a view to the easternmost lagoon of the Formosa River. The village is home to the Fortaleza de Cacela located on the site of the original castle constructed during the Muslim period. Spend time exploring the village before enjoying lunch at one of the lively cafés. Alternately, you may have the hotel pack a picnic for you so as to enjoy lunch on the beach. In the afternoon cycle back or shuttle to your resort for an afternoon at leisure, taking advantage of the property’s pools or spa.

This evening, join your fellow travelers and Trip Leaders to reminisce about your Portuguese adventures during a fireside farewell reception, followed by a delightful dinner with local wines.

Hotel: Vila Monte Farm House
Meals: Breakfast, Dinner
Daily Options: 20 or 40 miles (33 or 66.4 km)

VBT-Bicycle-Vacation-only guests: Enjoy breakfast before your transfer to Cascais (approximately 4 hours). Your tour concludes at approximately 1:00 p.m. at the Cidadela Cascais Pousada & Art District hotel in Cascais or the alternate hotel Grande Real Villa Italia. Taxis are available at the Cascais hotel to take you to central Lisbon hotels, the Lisbon train station, or to the Lisbon airport – approximately 30-45 minutes depending upon traffic.

Important: Flight departures from Lisbon prior to 4:00 p.m. are not recommended. If you depart earlier, you are responsible for your own transfer arrangements from the last hotel in the Algarve to Lisbon’s airport.

VBT Air Package guests: Our morning journey to Cascais will take approximately 4 hours arriving to your Cascais hotel at approximately 1:00 p.m. You will have the remainder of the afternoon and evening to explore the seaside town of Cascais. You will spend tonight at the Cidadela Cascais Pousada & Art District overlooking the marina and Atlantic Ocean or the alternate hotel Grande Real Villa Italia. The city is a pleasure to explore by foot. You will receive City Information in your Final Travel Booklet, with recommendations for transportation options, cafés, museums and restaurants.

VBT Post-trip Extension guests: Our morning journey to Cascais will take approximately 4 hours arriving to your Cascais hotel at approximately 1:00 p.m. You will have the remainder of the afternoon and evening to explore the seaside town of Cascais. You will spend tonight at the Cidadela Cascais Pousada & Art District overlooking the marina and Atlantic Ocean or the alternate hotel Grande Real Villa Italia. The city is a pleasure to explore by foot. You will receive City Information in your Final Travel Booklet, with recommendations for transportation options, cafés, museums and restaurants.

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Air Package Hotel: Cidadela Cascais Pousada & Art District
Alternate Hotel: Grande Real Villa Italia
Meals: Breakfast