Italy: Southern Tuscany & Giglio Island

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

A VBT representative will greet you at the Rome airport to start your adventure off right. A complimentary car service will whisk you to your conveniently located hotel in Orvieto.

After an included breakfast, meet your VBT representative at the hotel in Orvieto at 10:00 a.m. Transportation by motorcoach (approximately two hours) will be provided to Antica Fattoria La Parrina. Note that you will walk approximately .5 mile from the hotel to the motorcoach, as large vehicles are not allowed to circulate in the old town. Arrive at La Parrina by approximately 1:00 p.m. There you can purchase your lunch (for €15), as the hotel will prepare a buffet meal with organic vegetables and cheese produced on the grounds. If you prefer, buy lunch in Orvieto before meeting the VBT representative, and eat it at La Parrina.

Your Tuscany bike tours begin at Antica Fattoria La Parrina, a welcoming, four-star agriturismo resort, featured in Condé Nast Traveler magazine. Surrounded by beautiful countryside, it produces its own wine, cheese, yogurt, vegetables, oil, balsamic vinegar and flowers. Organic pasta, delicious jams and sauces, and cosmetics are also partly prepared and available here. All products are made with natural and healthy ingredients. In the afternoon, you’ll join our trip leaders for a safety and bike-fitting session, followed by a short warm-up ride over the estate along quiet country roads. Later, gather with the group for a welcome cocktail reception on the terrace. Dinner is at the hotel.

Today’s Ride Choices

Afternoon Warm-up — 17 km (11 miles)

What to Expect:

An easy loop ride in the countryside past La Parrina’s orchards and working farmers and into the small village of Albinia. A short stretch is on an unpaved but well beaten track, otherwise the roads are paved and quiet.

Cumulative Distance Range: 17 km (11 miles)

Included Meals: Breakfast, Dinner

After breakfast, you’ll leave La Parrina and cycle to the coast and Talamone, where you’ll discover the many Greek legends linked to this little fortress village. There’ll be time during the morning’s ride to swim in the glittering blue sea. The medieval hilltop town of Talamone overlooks the Mediterranean and is set in the rolling countryside of the Maremma, one of the least-developed areas of central Italy. Its skyline is dominated by an ancient Sienese castle. This little town of fishermen originally stood on Talamonaccio Hill and served as an ancient Etruscan port. Currently, Talamone is set inside a World Wildlife Fund nature reserve known as Parco Regionale della Maremma (Maremma Park), which features an incredible variety of protected flora and fauna. Lunch today is a delicious picnic prepared by your trip leaders.

In the afternoon, you’ll cycle back to your hotel, where you can relax at the wonderful pool or take a walk on the mapped trails that weave through the estate. Or you may opt for horseback riding in the area, well known for its local breed of Maremma horses. Your tour leaders will facilitate your option and you will need to call in advance to book.

Today’s Tuscany bike tours culminates with a special treat. Tonight, join your hosts at La Parrina on the terrace for a hands-on cooking class. Learn how to prepare typical Tuscan cantucci—delicious almond cookies that are best when dipped in sweet Vin Santo wine. Enjoy dinner at the hotel.

Today’s Ride Choices

Morning Parrina to Talamone — 31 km (19 miles)

Afternoon Talamone to Parrina — 25 km (16 miles) OR Talamone to Parrina PLUS — 37 km (23 miles)

What to Expect:

Ride country roads in typical Tuscan landscape. After the initial 0.8 miles on unpaved terrain, today’s route is entirely on paved road with very limited car traffic. The route features a couple of easy short hills. The support vehicle is available back to the hotel if you prefer to pass on the afternoon ride.

Cumulative Distance Range: 25 — 68 km (15 — 42 miles)

Included Meals: Breakfast, Lunch, Dinner

This morning, ride through the countryside toward the coast and Ansedonia, passing elegant villas and gardens and enjoying splendid views of the sea and the old watchtower that once defended this coast. Enjoy a picnic lunch along the way at a typical Maremma family-run country farm that grows its own organic vegetables. This afternoon, you’ll cycle through a thick pine forest, and then roll alongside a sandy beach; if you wish, you can pause here for a refreshing swim. This is one of the most beautiful routes of the week.

Later, you’ll continue to the old town of Orbetello, traversing a cycling path built on the lagoon. Explore the lush byway around the lagoon, then rejoin your trip leaders and follow them to a great gelato spot. A short shuttle ride will take you back to your hotel.

Tonight, you’ll shuttle to Orbetello for a stroll and maybe some shopping before enjoying dinner on your own; you can opt to remain at your hotel if you prefer.

Today’s Ride Choices

Morning Parrina to Orti di Capalbio — 32 km (20 miles) OR Parrina to Carige to Orti di Capalbio — 43 km (27 miles)

Afternoon Orti di Capalbio to Orbetello — 28 km (17 miles) | Orbetello WWF — 5 km (3 miles)

What to Expect:

Our morning route is easy, surrounded by vineyards and sunflower or wheat fields on paved roads with little car traffic.  A longer easy to moderate loop takes you on a panoramic route on the hills near Capalbio. In the afternoon, the ride is almost all flat, with the exception of a short steep climb to Ansedonia. It is followed by a 5-mile stretch in a nature reserve near the sea and beach where the terrain here is packed unpaved. After, a flat, well-paved bike path follows a shallow lagoon, leading to our final destination in Orbetello. You can take our support vehicle to avoid the climb to Ansedonia.

Cumulative Distance Range: 32 — 76 km (20 — 47 miles)

Included Meals: Breakfast, Lunch

Today, take a pedaling break from your Tuscany bike tours to enjoy the tranquility of the Giglio island. You’ll start this morning with a warm goodbye to your hosts at La Parrina before traveling to the bustling harbor and quaint village of Porto Santo Stefano. From this port town, board a ferry to Giglio Island, arriving in the village of Giglio Porto. With a local guide, you’ll shuttle to the walled hilltop town of Giglio Castello, where you’ll explore the imposing Rocca Pisana fortress. Giglio Castello is the oldest inhabited center on the island and still retains much of its medieval atmosphere.

After, continue westward to Campese Beach for an informal lunch in one of the restaurants. You have free time to swim or relax on the beach. If you prefer, opt for a hike along the Faraglione cliffs: Learn about the 700 different species of wildflowers and plants that grow in this remote corner of Tuscany. On your way back to Giglio Porto, stop for a gelato before ferrying back to the mainland.

This evening at Fattoria di Magliano, our small local country resort and your home for the next three nights, you’ll have time to relax by the pool and enjoy the sunset from the landscaped gardens. Dinner is at the hotel.

What to Expect:

Short hike on Giglio Island or relax at beach, guided tour of castle and along the sea on the cliffs.

Included Meals: Breakfast, Dinner

After breakfast, cycle to the medieval town of Capalbio. Dating to the 11th century, historic Capalbio is surrounded by massive walls. Stroll along these ancient ramparts above the city and take in the panoramic views of the surrounding countryside. Then enter the historic center through one of two gates—the Sienese or the Porticina—and visit the city’s Romanesque Castle of Saint Nicholas, with its dramatic bell tower. The tower features two rows of mullioned windows dating to the 12th century. Explore the town’s winding cobblestone streets, medieval churches, and shops. Finish your day with a rewarding ride all the way back to the hotel. If you prefer, you may hop our shuttle.

Back at the hotel this afternoon, relax or swim in the pool before sipping local wines—produced right on the farm—during an included wine tasting. Fattoria di Magliano is one of the region’s most renowned producers of the Tuscan wines that have changed the Italian wine industry. Dinner is at our agriturismo tonight.

Today’s Ride Choices

Morning Fattoria to Capalbio — 29 km (18 miles)

Afternoon Capalbio to La Sgrilla to Shuttle — 20 km (12 miles)

What to Expect:

After an exhilarating downhill from our hotel on a paved road with little car traffic, you cycle along a slightly rolling road before a gradual uphill to Capalbio. Loop back on a different route, mostly downhill on a very scenic road. You may take the support vehicle back to the hotel from La Sgrilla or continue on a rolling road with little traffic. Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 20 — 49 km (12 — 30 miles)

Included Meals: Breakfast, Dinner

After a leisurely breakfast, set off on quiet country roads, passing fields of poppies and sunflowers and vineyards gently sloping down to the sea. Tour the wine roads south of Scansano, famous for red Morellino wine. Then stop at the Magliano olive oil shop and former mill to indulge in an interesting olive-oil discussion and tasting. Continue cycling through Magliano and enjoy an included lunch on the medieval piazza. In the Middle Ages, this walled city was the winter home of the Aldobrandeschi court. Some of its 14th-century city walls are still intact.

From Magliano, those who wish to sample the hills of Tuscany on two wheels can join an optional, gentle-but-steady climb to the lovely villages of Pereta and Scansano.

Tonight, enjoy an aperitivo as the sun sets behind the Tuscan horizon one final time during your trip. Prepare to share stories of your Tuscany bike tours during a festive farewell dinner at a local osteria, featuring delicious specialties and local wines.

Today’s Ride Choices

Morning Fattoria to Magliano — 27 km (17 miles)

Afternoon Magliano to Fattoria — 5 km (3 miles) | Magliano to Scansano and Fattoria — 36 km (22 miles)

What to Expect:

The entirety of today’s route follows rolling terrain as we cycle toward the walled city of Magliano—our lunch stop. In the afternoon you can opt for a short ride to your hotel or choose a wider and hillier route by Scansano. While it is only a few miles back to the hotel, the shorter route includes a very challenging climb, but a five-minute shuttle will allow you to bypass it. The longer loop to Scansano features a long but moderate climb and rewards riders with breathtaking Tuscan vistas

Cumulative Distance Range: 27 — 63 km (17 — 39 miles)

Included Meals: Breakfast, Lunch, Dinner

After an included breakfast, complimentary transportation is provided by private motorcoach (approximately three hours) to our centrally located Rome hotel for a final overnight stay. You’ll arrive at approximately 11:30 a.m. and have the rest of the day to shop or relax in one of the city’s outdoor cafés.

Included Meals: Breakfast

After an included breakfast this morning, complimentary transportation to the Rome airport will be provided (an approximately 40 to 60 minute drive, depending on traffic) for your departing flight.

Included Meals: Breakfast

Meet your VBT trip leaders in the Orbetello-Monte Argentario train station at 2:15 p.m. Your trip leaders will be wearing VBT staff garments. Please plan to buy some lunch on your own before this meeting.

If you prefer, you can meet your group at the hotel in Orvieto at 10:00 a.m. You will travel by motorcoach (approximately two hours) to Antica Fattoria La Parrina.

Your Tuscany bike tours begin at Antica Fattoria La Parrina, a welcoming, four-star agriturismo resort, featured in Condé Nast Traveler magazine. Surrounded by beautiful countryside, it produces its own wine, cheese, yogurt, vegetables, oil, balsamic vinegar and flowers. Organic pasta, delicious jams and sauces, and cosmetics are also partly prepared and available here. All products are made with natural and healthy ingredients. In the afternoon, you’ll join our trip leaders for a safety and bike-fitting session, followed by a short warm-up ride over the estate along quiet country roads. Later, gather with the group for a welcome cocktail reception on the terrace. Dinner is at the hotel.

Today’s Ride Choices

Afternoon Warm-up — 17 km (11 miles)

What to Expect:

An easy loop ride in the countryside past La Parrina’s orchards and working farmers and into the small village of Albinia. A short stretch is on an unpaved but well beaten track, otherwise the roads are paved and quiet.

Cumulative Distance Range: 17 km (11 miles)

Included Meals: Dinner

After breakfast, you’ll leave La Parrina and cycle to the coast and Talamone, where you’ll discover the many Greek legends linked to this little fortress village. There’ll be time during the morning’s ride to swim in the glittering blue sea. The medieval hilltop town of Talamone overlooks the Mediterranean and is set in the rolling countryside of the Maremma, one of the least-developed areas of central Italy. Its skyline is dominated by an ancient Sienese castle. This little town of fishermen originally stood on Talamonaccio Hill and served as an ancient Etruscan port. Currently, Talamone is set inside a World Wildlife Fund nature reserve known as Parco Regionale della Maremma (Maremma Park), which features an incredible variety of protected flora and fauna. Lunch today is a delicious picnic prepared by your trip leaders.

In the afternoon, you’ll cycle back to your hotel, where you can relax at the wonderful pool or take a walk on the mapped trails that weave through the estate. Or you may opt for horseback riding in the area, well known for its local breed of Maremma horses. Your tour leaders will facilitate your option and you will need to call in advance to book.

Today’s Tuscany bike tours culminates with a special treat. Tonight, join your hosts at La Parrina on the terrace for a hands-on cooking class. Learn how to prepare typical Tuscan cantucci—delicious almond cookies that are best when dipped in sweet Vin Santo wine. Enjoy dinner at the hotel.

Today’s Ride Choices

Morning Parrina to Talamone — 31 km (19 miles)

Afternoon Talamone to Parrina — 25 km (16 miles) OR Talamone to Parrina PLUS — 37 km (23 miles)

What to Expect:

Ride country roads in typical Tuscan landscape. After the initial 0.8 miles on unpaved terrain, today’s route is entirely on paved road with very limited car traffic. The route features a couple of easy short hills. The support vehicle is available back to the hotel if you prefer to pass on the afternoon ride.

Cumulative Distance Range: 25 — 68 km (15 — 42 miles)

Included Meals: Breakfast, Lunch, Dinner

This morning, ride through the countryside toward the coast and Ansedonia, passing elegant villas and gardens and enjoying splendid views of the sea and the old watchtower that once defended this coast. Enjoy a picnic lunch along the way at a typical Maremma family-run country farm that grows its own organic vegetables. This afternoon, you’ll cycle through a thick pine forest, and then roll alongside a sandy beach; if you wish, you can pause here for a refreshing swim. This is one of the most beautiful routes of the week.

Later, you’ll continue to the old town of Orbetello, traversing a cycling path built on the lagoon. Explore the lush byway around the lagoon, then rejoin your trip leaders and follow them to a great gelato spot. A short shuttle ride will take you back to your hotel.

Tonight, you’ll shuttle to Orbetello for a stroll and maybe some shopping before enjoying dinner on your own; you can opt to remain at your hotel if you prefer.

Today’s Ride Choices

Morning Parrina to Orti di Capalbio — 32 km (20 miles) OR Parrina to Carige to Orti di Capalbio — 43 km (27 miles)

Afternoon Orti di Capalbio to Orbetello — 28 km (17 miles) | Orbetello WWF — 5 km (3 miles)

What to Expect:

Our morning route is easy, surrounded by vineyards and sunflower or wheat fields on paved roads with little car traffic.  A longer easy to moderate loop takes you on a panoramic route on the hills near Capalbio. In the afternoon, the ride is almost all flat, with the exception of a short steep climb to Ansedonia. It is followed by a 5-mile stretch in a nature reserve near the sea and beach where the terrain here is packed unpaved. After, a flat, well-paved bike path follows a shallow lagoon, leading to our final destination in Orbetello. You can take our support vehicle to avoid the climb to Ansedonia.

Cumulative Distance Range: 32 — 76 km (20 — 47 miles)

Included Meals: Breakfast, Lunch

Today, take a pedaling break from your Tuscany bike tours to enjoy the tranquility of the Giglio island. You’ll start this morning with a warm goodbye to your hosts at La Parrina before traveling to the bustling harbor and quaint village of Porto Santo Stefano. From this port town, board a ferry to Giglio Island, arriving in the village of Giglio Porto. With a local guide, you’ll shuttle to the walled hilltop town of Giglio Castello, where you’ll explore the imposing Rocca Pisana fortress. Giglio Castello is the oldest inhabited center on the island and still retains much of its medieval atmosphere.

After, continue westward to Campese Beach for an informal lunch in one of the restaurants. You have free time to swim or relax on the beach. If you prefer, opt for a hike along the Faraglione cliffs: Learn about the 700 different species of wildflowers and plants that grow in this remote corner of Tuscany. On your way back to Giglio Porto, stop for a gelato before ferrying back to the mainland.

This evening at Fattoria di Magliano, our small local country resort and your home for the next three nights, you’ll have time to relax by the pool and enjoy the sunset from the landscaped gardens. Dinner is at the hotel.

What to Expect:

Short hike on Giglio Island or relax at beach, guided tour of castle and along the sea on the cliffs.

Included Meals: Breakfast, Dinner

After breakfast, cycle to the medieval town of Capalbio. Dating to the 11th century, historic Capalbio is surrounded by massive walls. Stroll along these ancient ramparts above the city and take in the panoramic views of the surrounding countryside. Then enter the historic center through one of two gates—the Sienese or the Porticina—and visit the city’s Romanesque Castle of Saint Nicholas, with its dramatic bell tower. The tower features two rows of mullioned windows dating to the 12th century. Explore the town’s winding cobblestone streets, medieval churches, and shops. Finish your day with a rewarding ride all the way back to the hotel. If you prefer, you may hop our shuttle.

Back at the hotel this afternoon, relax or swim in the pool before sipping local wines—produced right on the farm—during an included wine tasting. Fattoria di Magliano is one of the region’s most renowned producers of the Tuscan wines that have changed the Italian wine industry. Dinner is at our agriturismo tonight.

Today’s Ride Choices

Morning Fattoria to Capalbio — 29 km (18 miles)

Afternoon Capalbio to La Sgrilla to Shuttle — 20 km (12 miles)

What to Expect:

After an exhilarating downhill from our hotel on a paved road with little car traffic, you cycle along a slightly rolling road before a gradual uphill to Capalbio. Loop back on a different route, mostly downhill on a very scenic road. You may take the support vehicle back to the hotel from La Sgrilla or continue on a rolling road with little traffic. Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 20 — 49 km (12 — 30 miles)

Included Meals: Breakfast, Dinner

After a leisurely breakfast, set off on quiet country roads, passing fields of poppies and sunflowers and vineyards gently sloping down to the sea. Tour the wine roads south of Scansano, famous for red Morellino wine. Then stop at the Magliano olive oil shop and former mill to indulge in an interesting olive-oil discussion and tasting. Continue cycling through Magliano and enjoy an included lunch on the medieval piazza. In the Middle Ages, this walled city was the winter home of the Aldobrandeschi court. Some of its 14th-century city walls are still intact.

From Magliano, those who wish to sample the hills of Tuscany on two wheels can join an optional, gentle-but-steady climb to the lovely villages of Pereta and Scansano.

Tonight, enjoy an aperitivo as the sun sets behind the Tuscan horizon one final time during your trip. Prepare to share stories of your Tuscany bike tours during a festive farewell dinner at a local osteria, featuring delicious specialties and local wines.

Today’s Ride Choices

Morning Fattoria to Magliano — 27 km (17 miles)

Afternoon Magliano to Fattoria — 5 km (3 miles) | Magliano to Scansano and Fattoria — 36 km (22 miles)

What to Expect:

The entirety of today’s route follows rolling terrain as we cycle toward the walled city of Magliano—our lunch stop. In the afternoon you can opt for a short ride to your hotel or choose a wider and hillier route by Scansano. While it is only a few miles back to the hotel, the shorter route includes a very challenging climb, but a five-minute shuttle will allow you to bypass it. The longer loop to Scansano features a long but moderate climb and rewards riders with breathtaking Tuscan vistas

Cumulative Distance Range: 27 — 63 km (17 — 39 miles)

Included Meals: Breakfast, Lunch, Dinner

After an included breakfast, complimentary transportation is provided back to the Orbetello-Monte Argentario train station by private motorcoach, arriving at approximately 9:30 a.m. If you prefer, you are welcome to board our coach to Rome and continue with your own travel plans from our Rome hotel.

Included Meals: Breakfast