Portugal: Lisbon, Évora & the Algarve

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Start off your first day in Lisbon right by having a VBT representative greet you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

After an included breakfast, meet your VBT representative in the hotel lobby at 8:30 a.m.

Your VBT representative will accompany you by shuttle (approximately one hour and 15 minutes) to Herdade do Barrocal for a tour and lunch. Depart Lisbon via the expansive Vasco da Gama Bridge—the longest bridge in Western Europe—spanning the mighty Tagus River. Heading east, you enter the scenic plains of the Alentejo region, known for its stunning vistas and abundant cork and olive groves. After lunch, continue to your hotel and change into your riding attire before meeting your VBT trip leaders for a bike-fitting and safety session.

Begin your bike tour from the hotel with a warm-up loop ride through the rustic farmland and gentle hills of this picturesque region, returning to your hotel outside the historic medieval town of Évora, a UNESCO World Heritage site.

Your accommodation for the next two nights is the Convento do Espinheiro Historic Hotel & Spa. This beautifully preserved 15th-century convent, once a meeting place for noble figures who shaped Portugal’s history, is today recognized as a national monument.

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

Today's Ride Choices

Afternoon: Warm-Up Ride — 9 km (5 miles)

What to Expect:

After meeting your VBT trip leaders for a bike-fitting and safety session, set out on an easy afternoon warm-up ride to become familiar with your bike. This scenic loop follows quiet, well-maintained two-lane roads, winding through charming neighborhoods and the rolling countryside surrounding your hotel.

Cumulative Distance Range: 9 km (5 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, shuttle from your hotel to the whitewashed town of Redondo, home to a 500-year-old Portuguese pottery tradition. From here, begin a picturesque ride across the plains of Alentejo, following scenic country roads bordered by cork forests. Your 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 support vehicle will be available to shuttle you from Aldeia de Venda to Monsaraz if you would like assistance or prefer more time to explore.

With its lofty locale, Monsaraz offers sweeping vistas of the Alentejo and neighboring Spain. Over the centuries, it has been occupied by Romans, Visigoths, Arabs, Mozarabs, Jews, and Christians. As you explore its narrow lanes and admire the whitewashed, red-roofed houses, take time to marvel at the views 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, venture into Évora to meet a local guide for an enriching walking tour of this magnificently preserved UNESCO World Heritage site. Visit São Francisco Church to view its eerie Chapel of Bones, constructed by 16th-century Franciscan monks. Wander atmospheric alleyways lined with patrician mansions and whitewashed houses trimmed in bright yellow. Dinner is on your own in Évora this evening.

Today's Ride Choices

Morning: Redondo to Aldeia de Venda and Monsaraz — 37 km (23 miles)

What to Expect:

Today’s ride begins in the town of Redondo, approximately a 45-minute shuttle from your hotel. From Redondo, ride toward the hilltop village of Monsaraz. The route features some short inclines and rolling hills, with the VBT support vehicle nearby should you wish to shuttle at any point. At the end of the short option in the town of Aldeia de Venda, the shuttle will transport you to the historic village of Monsaraz, where you will have ample time to explore before lunch. The long option continues from Aldeia de Pais through the scenic Alentejo countryside and finishes with a challenging 1.5 km (just under one mile) climb into Monsaraz.

Cumulative Distance Range: 37 km (23 miles)

Included Meals: Breakfast, Lunch

After breakfast, shuttle south to the small town of Castro Verde in the lower Alentejo region, or Baixo Alentejo. Today’s rides introduce you to the arid, beautiful landscapes of the Campo Branco, or White Plains. As you cycle, you may pass shepherds grazing their herds across the wide-open terrain. For lunch, stop at a typical Portuguese rural café for a farm-fresh meal with warm, welcoming hosts. Afterward, 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 rich history stretches back to the Phoenicians, Carthaginians, and Romans. Its most important remnant from the 500-year Moorish occupation is the medieval mosque—the only one from this period to have survived in Portugal. Today it serves as Mértola’s main church, still preserving many of its original Moorish features.

This evening, enjoy dinner at your leisure in one of the town’s inviting restaurants.

Today's Ride Choices

Morning: Geraldos to Mértola — 45 km (28 miles)

What to Expect:

After a two-hour morning shuttle south, begin today’s ride in Geraldos, pedaling into the arid and beautiful landscape of the Campo Branco, or White Plains. The route across the Campo Branco is mostly level and follows narrow, paved country roads with very little traffic, though it promises an excellent workout if there is a breeze. Stop for lunch at a farm café in São João dos Caldeireiros. After your meal, continue cycling onto the main road toward Mértola, where traffic increases as you approach town. The VBT support vehicle is available for anyone who would prefer to shuttle to the hotel after lunch.

Cumulative Distance Range: 45 km (28 miles)

Included Meals: Breakfast, Lunch

After breakfast, set out directly from your hotel. (Those preferring a shorter option may shuttle approximately 15 minutes to the starting point of their ride instead.) This morning’s cycling leads you into the Guadiana Valley Natural Park, one of 30 natural areas officially protected by the Portuguese government. Wind your way through small towns showcasing beautifully preserved traditional architecture, and coast down to the banks of the Guadiana River. The river’s small port village of Pomarão was specially constructed to support nearby mining operations. Here, you may straddle the Portugal–Spain border—standing with one foot in each country and half your body in Spain’s later time zone!

Savor lunch at a riverside café overlooking the marina. Then, embark a privately chartered boat for a relaxing afternoon cruise on the Guadiana River. Your cruise delivers you directly to the hotel’s private dock in Mértola. Those seeking a longer and more challenging option after lunch may forfeit the boat excursion and cycle back to the hotel.

This evening, enjoy dinner at your hotel.

Today's Ride Choices

Morning: Mértola to Pomarao — 24 km (15 miles)

Afternoon: Pomarao to Hotel Museu (No River Cruise) — 20 km (12 miles)

What to Expect:

Today’s ride starts from the hotel, beginning with a steady climb on a national road with some potentially fast-moving traffic and trucks. (If you prefer to avoid the climb and traffic, you may shuttle approximately 15 minutes from the hotel to where your trip leaders will have your bike ready.) The morning cycling route follows small, paved country roads through the less-traveled Guadiana Valley Natural Park. Although today’s ride is shorter than on other days, you will encounter some rolling hills and a steep descent over the final 1.2 miles (2 km) to the Guadiana River. After lunch, those who choose to ride back to the hotel instead of joining the boat excursion will begin with a challenging 1.2-mile (2-km) climb, rewarded by sweeping views and well-earned bragging rights. The final 3.1 miles (5 km) into Mértola are again on a national road shared with fast-moving traffic and trucks. The VBT support vehicle is available throughout the day.

Cumulative Distance Range: 24 – 44 km (15 – 27 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, shuttle southward into the Algarve, a region where the mountains meet the sea. Begin your morning ride in the beautiful village of Cachopo, tucked into the rolling foothills of the Serra do Caldeirão. Today’s routes reveal a changing landscape, with sweeping views of the Algarve’s rugged countryside and glimpses of the distant Atlantic shimmering on the horizon. Though the morning ride is short, the steady climbs offer a satisfying workout—and the perfect appetite for an included lunch featuring local flavors.

After lunch, continue cycling mostly downhill toward your next hotel. Along the way, you may wish to pause and explore the Algarve Costumes Museum in São Brás de Alportel, a charming celebration of the region’s rich cultural heritage.

Your ride concludes at Vila Monte Farm House, a serene hideaway set amid fragrant gardens and citrus groves. Settle into one of its breezy, elegant suites and savor the tranquility of the authentic Algarvian countryside—far from the crowds of the coast, yet infused with the true spirit of Portugal.

Today's Ride Choices

Morning: Cachopo to Montes Novos Lunch — 17 km (11 miles)

Afternoon: Montes Novos to Vila Monte — 33 km (21 miles)

What to Expect:

Today’s ride in the Algarve follows undulating hills, offering beautiful vistas of the Atlantic Ocean in the distance. Enjoy a brief stop for lunch in the port town of Monte Novos. In the afternoon, continue on quiet country roads, descending downhill to your hotel, the Vila Monte Farm House.

Cumulative Distance Range: 50 km (32 miles)

Included Meals: Breakfast, Lunch

After a sumptuous breakfast, enjoy a leisurely spin through the surrounding Algarve countryside, with vistas of the sea in the distance. Along the way, stop to visit the Monterosa olive groves for an olive oil tasting and to learn more about the production process. From here, cycle to the small Algarve city of Tavira, home to a medieval castle. Spend time exploring the site and enjoy lunch at your leisure in one of the many lively cafés.

After lunch, continue pedaling to the lovely whitewashed village of Cacela-a-Velha, perched atop a hill overlooking 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 before shuttling to your resort for a leisurely late afternoon, perhaps relaxing by the pools or visiting the spa.

This evening, join your fellow travelers and trip leaders for a fireside farewell reception, followed by a delightful dinner featuring regional Algarve cuisine made with the freshest ingredients and paired with local wines.

Today's Ride Choices

Morning: Vila Monte to Cacela-a-Velha with Monterosa — 41 km (25 miles)

What to Expect:

Today’s ride starts from your hotel, following less-traveled lanes through the Algarve countryside past groves of citrus, olive, and avocado trees. There will be some city riding with heavier traffic as you pass through Tavira. As you approach the Algarve coast, catch glimpses of the Atlantic Ocean in the distance before arriving at the seaside village of Cacela-a-Velha. Today’s ride is less challenging, featuring gently rolling hills.

Cumulative Distance Range: 41 km (25 miles)

Included Meals: Breakfast, Dinner

Enjoy breakfast before departing on a scenic drive to Cascais (approximately four hours). Your tour concludes at approximately 1:00 p.m. at your Post-Tour hotel, the Pestana Cidadela Cascais, an elegant historic property overlooking the marina and the Atlantic Ocean. You have the remainder of the afternoon and evening at leisure to explore the enchanting seaside town of Cascais, known for its vibrant waterfront, golden beaches, boutique shops, and refined cafés.

Spend the evening soaking in the relaxed coastal atmosphere, with easy access to a variety of restaurants and cultural sites. City information is provided, offering curated recommendations for transportation, museums, dining, and local experiences to help you make the most of your stay.

Included Meals: Breakfast

Begin your day with a Portuguese breakfast and perhaps a final sip of coffee at a nearby café.

After breakfast, complimentary transportation will be provided to Lisbon International Airport—an approximately 45- to 60-minute drive, depending on traffic—for your departing flight.

Included Meals: Breakfast

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Start off your first day in Lisbon right by having a VBT representative greet you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

After an included breakfast, meet your VBT representative in the lobby of your hotel.

Your VBT representative will accompany you by shuttle (approximately one hour and 15 minutes) to Herdade do Barrocal for a tour and lunch. You depart Lisbon via the expansive Vasco de Gama Bridge, the longest bridge in Western Europe, spanning the mighty Tagus River. Heading east, you arrive on the scenic plains of the Alentejo region, known for its stunning vistas and abundant cork and olive groves. After lunch, continue to your hotel where you meet your VBT trip leaders for a safety session. After the session, check in to your rooms and change into your riding attire before your bike fitting.

Begin your bike tour from the hotel with a warm-up loop ride traversing this scenic region of rustic farmland and gentle hills, returning you 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 historic Convento do Espinheiro Historic Hotel & Spa. Many important noble figures have met here throughout the centuries to shape Portugal’s history, earning this 15th-century convent a place as a national monument.

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 historic dining room.

Today's Ride Choices

Afternoon: Warm-up to Évora — 9 km (5 miles)

What to Expect:

After meeting your VBT trip leaders for a bike-fitting and safety session, you become accustomed to riding your bike on an easy afternoon warm-up ride. The scenic ride on quiet, well-maintained two-lane roads winds through the neighborhoods and countryside surrounding your hotel.

Cumulative Distance Range: 9 km (5 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, shuttle from your hotel to the whitewashed town of Redondo, home to a 500-year-old Portuguese pottery tradition. From here, you begin with a picturesque ride 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 support vehicle 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 its lofty locale, Monsaraz enjoys endless vistas of the Alentejo and neighboring Spain. It has been occupied by various civilizations from Romans, Visigoths, and Arabs to Mozarabs, Jews, and Christians. As you explore its narrow warrens and admire its whitewashed, red-roofed houses, you’ll have time to 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 venture into Évora to meet a local guide for an enriching walking tour of this magnificently preserved UNESCO World Heritage site. Stop by the São Francisco Church to view its eerie Chapel of Bones, constructed by 16th-century Franciscan monks. Wander atmospheric alleyways past old patrician mansions and whitewashed houses with bright yellow trim. Enjoy dinner on your own in Évora this evening.

Today's Ride Choices

Morning: Redondo to Aldeia de Venda and Monsaraz — 37 km (23 miles)

What to Expect:

Today’s ride begins in the town of Redondo, a 45-minute shuttle from your hotel. From Redondo, begin riding toward the hilltop village of Monsaraz. Your ride consists of some short inclines and rolling hills, but the VBT support vehicle will be nearby if you opt to shuttle at any point. At the end of the short option in the town of Aldeia de Venda, our shuttle provides transportation to the historic village of Monsaraz, where you have ample time to explore prior to lunch. Today’s long option continues from Aldeia de Pais through the scenic Alentejo countryside and finishes with a challenging 1.5 km (just under a mile) climb into Monsaraz.

Cumulative Distance Range: 37 km (23 miles)

Included Meals: Breakfast, Lunch

After breakfast, shuttle south to the small town of Castro Verde in the lower Alentejo region, or Baixo Alentejo. Today’s rides introduce you to the arid, beautiful 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, you 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 rich history dates all the way back to the Phoenicians, Carthaginians, and Romans. Its most important remnant from the 500-year Moorish occupation is the medieval mosque, the only mosque from this period to have survived 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 inviting restaurants.

Today's Ride Choices

Morning: Geraldos to Mértola — 45 km (28 miles)

What to Expect:

After a two-hour morning shuttle south, begin today’s ride in Geraldos, pedaling into the arid and beautiful landscape of the Campo Branco, or White Plains. The ride across the Campo Branco is mostly level, easy riding on narrow, paved country roads with very little traffic, but it promises an excellent workout if there is a breeze. Stop to enjoy lunch at a farm café in Sao João dos Caldeiros. Following your meal, continue your cycling onto the main road to Mértola, where the traffic increases as we near our destination. The VBT support vehicle is also available for anyone who would prefer to shuttle to the hotel after lunch.

Cumulative Distance Range: 45 km (28 miles)

Included Meals: Breakfast, Lunch

After breakfast, set out directly from your hotel. (Those preferring a shorter option shuttle 15 minutes to the starting point of their ride instead.) Your morning cycling leads you into the Guadiana Valley Natural Park, one of 30 natural areas in Portugal officially protected by the government. Wind your way through small towns of beautifully preserved traditional architecture, and coast down to the banks of the Guadiana River. The river’s small port village of Pomarão was specially constructed for 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 Guadiana River. Your cruise delivers you right to your hotel dock in Mértola. Those seeking a longer ride and more challenging option after lunch may forfeit the boat excursion and cycle back to the hotel.

This evening, enjoy dinner at your hotel.

Today's Ride Choices

Morning: Mértola to Pomarao — 24 km (15 miles)

Afternoon: Pomarao to Hotel Museu (no river cruise) — 20 km (12 miles)

What to Expect:

Today’s ride starts from the hotel. It begins with a steady climb on a national road with some potentially fast-moving traffic and trucks. (If the climb and traffic are an issue, you may take the shuttle from the hotel to where your trip leaders will have your bike ready, an approximately 15-minute ride.) The morning cycling takes you on small paved country roads through the less-traveled Guadiana Valley Natural Park. Although this morning’s ride is shorter than those of other days, you will have some rolling hills to challenge you and a rather steep descent for the last 1.2 miles (2 km) to the Guadiana River.

After lunch, if you opt to ride back to the hotel and forfeit the boat excursion, the ride begins with a challenging 1.2-mile (2-km) climb that will reward you with bragging rights and stunning views. The last 3.1 miles (5 km) into Mértola are on a national road that you share with fast-moving traffic and trucks. The VBT support vehicle is available throughout the day.

Cumulative Distance Range: 24 – 44 km (15 – 27 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, shuttle southward into the Algarve. We begin our morning ride at a viewpoint overlooking the dragon shaped Lake Albufeira.  Today’s rides will introduce you to a different landscape with views of the scenic Algarve regions and the distant Atlantic Ocean.  The morning ride is short but the vertical gain will ensure a good workout and build up your appetite for your included lunch. Once you have finished lunch, continue cycling mostly downhill towards your next hotel.

You will end today’s ride at your lovely accommodations in the Algarve, the Praia Verde Boutique Hotel, and settle in to one of its breezy, elegant rooms. Enjoy an evening at leisure either enjoying what the hotel has to offer or take a short stroll to the beach before dining at a restaurant in the neighborhood.

Today's Ride Choices

Morning: Odeleite to Praia Verde Boutique Hotel — 35.7 km (22 miles)

What to Expect:

Our ride in the Algarve follows undulating hills that offer beautiful vistas of the Atlantic Ocean in the distance. Enjoy a brief stop in the border town of Vila de Real Santo Antonio for lunch. In the afternoon continue to your hotel, the Praia Verde Boutique Hotel.

Cumulative Distance Range: 35.7 km (22 miles)

Included Meals: Breakfast, Lunch

After a sumptuous breakfast, enjoy a leisurely spin through the surrounding Algarve countryside with vistas of the sea in the distance. Cycle to the small Algarve city of Tavira with its medieval castle.  Spend time exploring the site, and enjoy lunch in one of the many lively cafés at your leisure.

After lunch, continue pedaling to 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 cycling to your resort for a late 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 Portugal bike tour and adventures during an al fresco (weather permitting) farewell reception, followed by a delightful dinner of regional Algarve cuisine made with the freshest of ingredients paired with local wines.

Today's Ride Choices

Morning: Praia Verde Boutique Hotel to Tavira Loop Ride — 37 km (28 miles)

What to Expect:

Today’s ride starts from your hotel. You will cycle on less-traveled lanes through the Algarve countryside past lovely citrus, olive, and avocado groves. You will have free time in the town of Tavira for lunch on your own. In the afternoon enjoy a scenic ride back to your hotel with a stop enroute at the lovely seaside village of Cacela Velha. Today’s ride is less challenging with slightly rolling hills.

Cumulative Distance Range: 37 km (28 miles)

Included Meals: Breakfast, Dinner

Your morning journey to Cascais will take approximately four hours. You have the remainder of the afternoon and evening to explore this delightful seaside town. Spend tonight at the Cidadela Cascais Pousada & Art District Hotel, overlooking the marina and Atlantic Ocean. The city is a pleasure to explore by foot. City information is provided with recommendations for transportation options, cafés, museums, and restaurants.

Included Meals: Breakfast

Begin your day with a Portuguese breakfast and perhaps a sip of coffee at a nearby café.

After breakfast, complimentary transportation will be provided to Lisbon’s international airport (an approximately 45- to 60-minute drive, depending on traffic) for your departing flight.

Included Meals: Breakfast

Meet your VBT representative at the Pousada de Lisboa, our Pre-Tour hotel in Lisbon, at 8:30 a.m.

Your VBT representative will accompany you by shuttle (approximately one hour and 15 minutes) to Herdade do Barrocal for a tour and lunch. Depart Lisbon via the expansive Vasco da Gama Bridge—the longest bridge in Western Europe—spanning the mighty Tagus River. Heading east, you enter the scenic plains of the Alentejo region, known for its stunning vistas and abundant cork and olive groves. After lunch, continue to your hotel and change into your riding attire before meeting your VBT trip leaders for a bike-fitting and safety session.

Begin your bike tour from the hotel with a warm-up loop ride through the rustic farmland and gentle hills of this picturesque region, returning to your hotel outside the historic medieval town of Évora, a UNESCO World Heritage site.

Your accommodation for the next two nights is the Convento do Espinheiro Historic Hotel & Spa. This beautifully preserved 15th-century convent, once a meeting place for noble figures who shaped Portugal’s history, is today recognized as a national monument.

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

Today's Ride Choices

Afternoon: Warm-Up Ride — 9 km (5 miles)

What to Expect:

After meeting your VBT trip leaders for a bike-fitting and safety session, set out on an easy afternoon warm-up ride to become familiar with your bike. This scenic loop follows quiet, well-maintained two-lane roads, winding through charming neighborhoods and the rolling countryside surrounding your hotel.

Cumulative Distance Range: 9 km (5 miles)

Included Meals: Lunch, Dinner

After breakfast, shuttle from your hotel to the whitewashed town of Redondo, home to a 500-year-old Portuguese pottery tradition. From here, begin a picturesque ride across the plains of Alentejo, following scenic country roads bordered by cork forests. Your 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 support vehicle will be available to shuttle you from Aldeia de Venda to Monsaraz if you would like assistance or prefer more time to explore.

With its lofty locale, Monsaraz offers sweeping vistas of the Alentejo and neighboring Spain. Over the centuries, it has been occupied by Romans, Visigoths, Arabs, Mozarabs, Jews, and Christians. As you explore its narrow lanes and admire the whitewashed, red-roofed houses, take time to marvel at the views 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, venture into Évora to meet a local guide for an enriching walking tour of this magnificently preserved UNESCO World Heritage site. Visit São Francisco Church to view its eerie Chapel of Bones, constructed by 16th-century Franciscan monks. Wander atmospheric alleyways lined with patrician mansions and whitewashed houses trimmed in bright yellow. Dinner is on your own in Évora this evening.

Today's Ride Choices

Morning: Redondo to Aldeia de Venda and Monsaraz — 37 km (23 miles)

What to Expect:

Today’s ride begins in the town of Redondo, approximately a 45-minute shuttle from your hotel. From Redondo, ride toward the hilltop village of Monsaraz. The route features some short inclines and rolling hills, with the VBT support vehicle nearby should you wish to shuttle at any point. At the end of the short option in the town of Aldeia de Venda, the shuttle will transport you to the historic village of Monsaraz, where you will have ample time to explore before lunch. The long option continues from Aldeia de Pais through the scenic Alentejo countryside and finishes with a challenging 1.5 km (just under one mile) climb into Monsaraz.

Cumulative Distance Range: 37 km (23 miles)

Included Meals: Breakfast, Lunch

After breakfast, shuttle south to the small town of Castro Verde in the lower Alentejo region, or Baixo Alentejo. Today’s rides introduce you to the arid, beautiful landscapes of the Campo Branco, or White Plains. As you cycle, you may pass shepherds grazing their herds across the wide-open terrain. For lunch, stop at a typical Portuguese rural café for a farm-fresh meal with warm, welcoming hosts. Afterward, 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 rich history stretches back to the Phoenicians, Carthaginians, and Romans. Its most important remnant from the 500-year Moorish occupation is the medieval mosque—the only one from this period to have survived in Portugal. Today it serves as Mértola’s main church, still preserving many of its original Moorish features.

This evening, enjoy dinner at your leisure in one of the town’s inviting restaurants.

Today's Ride Choices

Morning: Geraldos to Mértola — 45 km (28 miles)

What to Expect:

After a two-hour morning shuttle south, begin today’s ride in Geraldos, pedaling into the arid and beautiful landscape of the Campo Branco, or White Plains. The route across the Campo Branco is mostly level and follows narrow, paved country roads with very little traffic, though it promises an excellent workout if there is a breeze. Stop for lunch at a farm café in São João dos Caldeireiros. After your meal, continue cycling onto the main road toward Mértola, where traffic increases as you approach town. The VBT support vehicle is available for anyone who would prefer to shuttle to the hotel after lunch.

Cumulative Distance Range: 45 km (28 miles)

Included Meals: Breakfast, Lunch

After breakfast, set out directly from your hotel. (Those preferring a shorter option may shuttle approximately 15 minutes to the starting point of their ride instead.) This morning’s cycling leads you into the Guadiana Valley Natural Park, one of 30 natural areas officially protected by the Portuguese government. Wind your way through small towns showcasing beautifully preserved traditional architecture, and coast down to the banks of the Guadiana River. The river’s small port village of Pomarão was specially constructed to support nearby mining operations. Here, you may straddle the Portugal–Spain border—standing with one foot in each country and half your body in Spain’s later time zone!

Savor lunch at a riverside café overlooking the marina. Then, embark a privately chartered boat for a relaxing afternoon cruise on the Guadiana River. Your cruise delivers you directly to the hotel’s private dock in Mértola. Those seeking a longer and more challenging option after lunch may forfeit the boat excursion and cycle back to the hotel.

This evening, enjoy dinner at your hotel.

Today's Ride Choices

Morning: Mértola to Pomarao — 24 km (15 miles)

Afternoon: Pomarao to Hotel Museu (No River Cruise) — 20 km (12 miles)

What to Expect:

Today’s ride starts from the hotel, beginning with a steady climb on a national road with some potentially fast-moving traffic and trucks. (If you prefer to avoid the climb and traffic, you may shuttle approximately 15 minutes from the hotel to where your trip leaders will have your bike ready.) The morning cycling route follows small, paved country roads through the less-traveled Guadiana Valley Natural Park. Although today’s ride is shorter than on other days, you will encounter some rolling hills and a steep descent over the final 1.2 miles (2 km) to the Guadiana River. After lunch, those who choose to ride back to the hotel instead of joining the boat excursion will begin with a challenging 1.2-mile (2-km) climb, rewarded by sweeping views and well-earned bragging rights. The final 3.1 miles (5 km) into Mértola are again on a national road shared with fast-moving traffic and trucks. The VBT support vehicle is available throughout the day.

Cumulative Distance Range: 24 – 44 km (15 – 27 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, shuttle southward into the Algarve, a region where the mountains meet the sea. Begin your morning ride in the beautiful village of Cachopo, tucked into the rolling foothills of the Serra do Caldeirão. Today’s routes reveal a changing landscape, with sweeping views of the Algarve’s rugged countryside and glimpses of the distant Atlantic shimmering on the horizon. Though the morning ride is short, the steady climbs offer a satisfying workout—and the perfect appetite for an included lunch featuring local flavors.

After lunch, continue cycling mostly downhill toward your next hotel. Along the way, you may wish to pause and explore the Algarve Costumes Museum in São Brás de Alportel, a charming celebration of the region’s rich cultural heritage.

Your ride concludes at Vila Monte Farm House, a serene hideaway set amid fragrant gardens and citrus groves. Settle into one of its breezy, elegant suites and savor the tranquility of the authentic Algarvian countryside—far from the crowds of the coast, yet infused with the true spirit of Portugal.

Today's Ride Choices

Morning: Cachopo to Montes Novos Lunch — 17 km (11 miles)

Afternoon: Montes Novos to Vila Monte — 33 km (21 miles)

What to Expect:

Today’s ride in the Algarve follows undulating hills, offering beautiful vistas of the Atlantic Ocean in the distance. Enjoy a brief stop for lunch in the port town of Monte Novos. In the afternoon, continue on quiet country roads, descending downhill to your hotel, the Vila Monte Farm House.

Cumulative Distance Range: 50 km (32 miles)

Included Meals: Breakfast, Lunch

After a sumptuous breakfast, enjoy a leisurely spin through the surrounding Algarve countryside, with vistas of the sea in the distance. Along the way, stop to visit the Monterosa olive groves for an olive oil tasting and to learn more about the production process. From here, cycle to the small Algarve city of Tavira, home to a medieval castle. Spend time exploring the site and enjoy lunch at your leisure in one of the many lively cafés.

After lunch, continue pedaling to the lovely whitewashed village of Cacela-a-Velha, perched atop a hill overlooking 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 before shuttling to your resort for a leisurely late afternoon, perhaps relaxing by the pools or visiting the spa.

This evening, join your fellow travelers and trip leaders for a fireside farewell reception, followed by a delightful dinner featuring regional Algarve cuisine made with the freshest ingredients and paired with local wines.

Today's Ride Choices

Morning: Vila Monte to Cacela-a-Velha with Monterosa — 41 km (25 miles)

What to Expect:

Today’s ride starts from your hotel, following less-traveled lanes through the Algarve countryside past groves of citrus, olive, and avocado trees. There will be some city riding with heavier traffic as you pass through Tavira. As you approach the Algarve coast, catch glimpses of the Atlantic Ocean in the distance before arriving at the seaside village of Cacela-a-Velha. Today’s ride is less challenging, featuring gently rolling hills.

Cumulative Distance Range: 41 km (25 miles)

Included Meals: Breakfast, Dinner

Enjoy breakfast before departing on a scenic drive to Cascais (approximately four hours). Your tour concludes at approximately 1:00 p.m. at our Post-Tour hotel, the Pestana Cidadela Cascais. Taxis are readily available at the hotel to take you to central Lisbon hotels, the Lisbon train station, or Lisbon Airport—a drive of approximately 30–45 minutes, depending on traffic.

Important: For a smooth departure, we recommend booking flights from Lisbon after 4:00 p.m. If you are departing earlier, you will need to arrange your own transportation from the last hotel in the Algarve to Lisbon Airport.

Included Meals: Breakfast

Meet your VBT representative at the Pousada de Lisboa. Please refer to your final day-to-day itinerary for the exact time and place of the meeting.

Your VBT representative will accompany you by shuttle (approximately one hour and 15 minutes) to Herdade do Barrocal for a tour and lunch. You depart Lisbon via the expansive Vasco de Gama Bridge, the longest bridge in Western Europe, spanning the mighty Tagus River. Heading east, you arrive on the scenic plains of the Alentejo region, known for its stunning vistas and abundant cork and olive groves. After lunch, continue to your hotel where you meet your VBT trip leaders for a safety session. After the session, check in to your rooms and change into your riding attire before your bike fitting.

Begin your bike tour from the hotel with a warm-up loop ride traversing this scenic region of rustic farmland and gentle hills, returning you 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 historic Convento do Espinheiro Historic Hotel & Spa. Many important noble figures have met here throughout the centuries to shape Portugal’s history, earning this 15th-century convent a place as a national monument.

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 historic dining room.

Today's Ride Choices

Afternoon: Warm-up to Évora — 9 km (5 miles)

What to Expect:

After meeting your VBT trip leaders for a bike-fitting and safety session, you become accustomed to riding your bike on an easy afternoon warm-up ride. The scenic ride on quiet, well-maintained, two-lane roads winds through the neighborhoods and countryside surrounding your hotel.

Cumulative Distance Range: 9 km (5 miles)

Included Meals: Lunch, Dinner

After breakfast, shuttle from your hotel to the whitewashed town of Redondo, home to a 500-year-old Portuguese pottery tradition. From here, you begin with a picturesque ride 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 support vehicle 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 its lofty locale, Monsaraz enjoys endless vistas of the Alentejo and neighboring Spain. It has been occupied by various civilizations from Romans, Visigoths, and Arabs to Mozarabs, Jews, and Christians. As you explore its narrow warrens and admire its whitewashed, red-roofed houses, you’ll have time to 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 venture into Évora to meet a local guide for an enriching walking tour of this magnificently preserved UNESCO World Heritage site. Stop by the São Francisco Church to view its eerie Chapel of Bones, constructed by 16th-century Franciscan monks. Wander atmospheric alleyways past old patrician mansions and whitewashed houses with bright yellow trim. Enjoy dinner on your own in Évora this evening.

Today's Ride Choices

Morning: Redondo to Aldeia de Venda and Monsaraz — 37 km (23 miles)

What to Expect:

Today’s ride begins in the town of Redondo, a 45-minute shuttle from your hotel. From Redondo, begin riding toward the hilltop village of Monsaraz. Your ride consists of some short inclines and rolling hills, but the VBT support vehicle will be nearby if you opt to shuttle at any point. At the end of the short option in the town of Aldeia de Venda, our shuttle provides transportation to the historic village of Monsaraz, where you have ample time to explore prior to lunch. Today’s long option continues from Aldeia de Pais through the scenic Alentejo countryside and finishes with a challenging 1.5 km (just under a mile) climb into Monsaraz.

Cumulative Distance Range: 37 km (23 miles)

Included Meals: Breakfast, Lunch

After breakfast, shuttle south to the small town of Castro Verde in the lower Alentejo region, or Baixo Alentejo. Today’s rides introduce you to the arid, beautiful 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, you 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 rich history dates all the way back to the Phoenicians, Carthaginians, and Romans. Its most important remnant from the 500-year Moorish occupation is the medieval mosque, the only mosque from this period to have survived 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 inviting restaurants.

Today's Ride Choices

Morning: Geraldos to Mértola — 45 km (28 miles)

What to Expect:

After a two-hour morning shuttle south, begin today’s ride in Geraldos, pedaling into the arid and beautiful landscape of the Campo Branco, or White Plains. The ride across the Campo Branco is mostly level, easy riding on narrow, paved country roads with very little traffic, but it promises an excellent workout if there is a breeze. Stop to enjoy lunch at a farm café in Sao João dos Caldeiros. Following your meal, continue your cycling onto the main road to Mértola, where the traffic increases as we near our destination. The VBT support vehicle is also available for anyone who would prefer to shuttle to the hotel after lunch.

Cumulative Distance Range: 45 km (28 miles)

Included Meals: Breakfast, Lunch

After breakfast, set out directly from your hotel. (Those preferring a shorter option shuttle 15 minutes to the starting point of their ride instead.) Your morning cycling leads you into the Guadiana Valley Natural Park, one of 30 natural areas in Portugal officially protected by the government. Wind your way through small towns of beautifully preserved traditional architecture, and coast down to the banks of the Guadiana River. The river’s small port village of Pomarão was specially constructed for 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 Guadiana River. Your cruise delivers you right to your hotel dock in Mértola. Those seeking a longer ride and more challenging option after lunch may forfeit the boat excursion and cycle back to the hotel.

This evening, enjoy dinner at your hotel.

Today's Ride Choices

Morning: Mértola to Pomarao — 24 km (15 miles)

Afternoon: Pomarao to Hotel Museu (no river cruise) — 20 km (12 miles)

What to Expect:

Today’s ride starts from the hotel. It begins with a steady climb on a national road with some potentially fast-moving traffic and trucks. (If the climb and traffic are an issue, you may take the shuttle from the hotel to where your trip leaders will have your bike ready, an approximately 15-minute ride.) The morning cycling takes you on small paved country roads through the less-traveled Guadiana Valley Natural Park. Although this morning’s ride is shorter than those of other days, you will have some rolling hills to challenge you and a rather steep descent for the last 1.2 miles (2 km) to the Guadiana River.

After lunch, if you opt to ride back to the hotel and forfeit the boat excursion, the ride begins with a challenging 1.2-mile (2-km) climb that will reward you with bragging rights and stunning views. The last 3.1 miles (5 km) into Mértola are on a national road that you share with fast-moving traffic and trucks. The VBT support vehicle is available throughout the day.

Cumulative Distance Range: 24 – 44 km (15 – 27 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, shuttle southward into the Algarve. We begin our morning ride at a viewpoint overlooking the dragon shaped Lake Albufeira.  Today’s rides will introduce you to a different landscape with views of the scenic Algarve regions and the distant Atlantic Ocean.  The morning ride is short but the vertical gain will ensure a good workout and build up your appetite for your included lunch. Once you have finished lunch, continue cycling mostly downhill towards your next hotel.

You will end today’s ride at your lovely accommodations in the Algarve, the Praia Verde Boutique Hotel, and settle in to one of its breezy, elegant rooms. Enjoy an evening at leisure either enjoying what the hotel has to offer or take a short stroll to the beach before dining at a restaurant in the neighborhood.

Today's Ride Choices

Morning: Odeleite to Praia Verde Boutique Hotel — 35.7 km (22 miles)

What to Expect:

Our ride in the Algarve follows undulating hills that offer beautiful vistas of the Atlantic Ocean in the distance. Enjoy a brief stop in the border town of Vila de Real Santo Antonio for lunch. In the afternoon continue to your hotel, the Praia Verde Boutique Hotel.

Cumulative Distance Range: 35.7 km (22 miles)

Included Meals: Breakfast, Lunch

After a sumptuous breakfast, enjoy a leisurely spin through the surrounding Algarve countryside with vistas of the sea in the distance. Cycle to the small Algarve city of Tavira with its medieval castle.  Spend time exploring the site, and enjoy lunch in one of the many lively cafés at your leisure.

After lunch, continue pedaling to 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 cycling to your resort for a late 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 Portugal bike tour and adventures during an al fresco (weather permitting) farewell reception, followed by a delightful dinner of regional Algarve cuisine made with the freshest of ingredients paired with local wines.

Today's Ride Choices

Morning: Praia Verde Boutique Hotel to Tavira Loop Ride — 37 km (28 miles)

What to Expect:

Today’s ride starts from your hotel. You will cycle on less-traveled lanes through the Algarve countryside past lovely citrus, olive, and avocado groves. You will have free time in the town of Tavira for lunch on your own. In the afternoon enjoy a scenic ride back to your hotel with a stop enroute at the lovely seaside village of Cacela Velha. Today’s ride is less challenging with slightly rolling hills.

Cumulative Distance Range: 37 km (28 miles)

Included Meals: Breakfast, Dinner

Enjoy breakfast before your drive to Cascais (approximately four hours). Your tour concludes at approximately 1:00 p.m. at the Cidadela Cascais Pousada & Art District Hotel in Cascais. 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 on traffic.

Included Meals: Breakfast