Italy: Southern Tuscany & Giglio Island

Depart from home for Italy. The particulars of your arrival overseas are detailed with your flight itinerary.

Upon arrival at the Rome Fiumicino airport, claim your luggage and clear customs. If your luggage is lost, you must fill out a PIR form before leaving the customs area; VBT representatives are not allowed into the customs area. Also, make sure that your VBT luggage tags are attached to your bags so that your representative can identify you.

The Representative will be waiting outside the customs area at Meeting Point #4 in the international arrivals terminal and will be holding a VBT sign. Your local representative helps you transfer by private car (approximately two hours) to your hotel in Orvieto to begin your trip. Your hotel room may not be available until 1:00 p.m. If you arrive early, you may store your luggage with the reception desk.

If you are going to be delayed meeting our transfer representative for more than 15 minutes due to delayed or lost luggage, please let our representative know by calling or sending a text message to +39 335 12 06 921. Please type VBT Guest at the beginning of your text. Our drivers are generally able to wait for up to 45 minutes from the time your flight lands, after which you will be responsible for your own transfer. However, they might be able to reschedule your transfer if they are aware of the delay. You may also contact Allianz Global Assistance to advise of your delay, and they will contact our transfer service.

You have the rest of the day free to explore this wonderful, historic city. Situated in the Paglia River Valley high atop a dramatic volcanic rock, Orvieto boasts centuries of history and architecture, including towers, palaces and noble houses. It began as an important Etruscan center and became prosperous in Roman times thanks to its production of ceramics. After being overrun by several invasions, Orvieto enjoyed the status of a free state in the 11th and 12th centuries. In 1354, it became a city of the Church Estate until 1798. After brief Napoleonic domination, it was finally annexed to the Kingdom of Italy in 1860. During your stay, be sure to visit Orvieto’s impressive Gothic cathedral, with its multi-colored façade of mosaics, stained glass and sculpture. You can also see many Etruscan artifacts at the Archaeological Museum.

In the evening, relax in one of the city’s restaurants and sample the local cuisine.

Hotel: Hotel Duomo

Meet your VBT representative at the hotel in Orvieto at 10:00 a.m. You will transfer by motorcoach (approximately two hours) to Antica Fattoria La Parrina. Note that you will walk approximately a half 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 14 euros), 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 tour begins 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.

Hotel: Antica Fattoria La Parrina
Meals: Breakfast, Dinner

Today’s Ride Choice:
Cumulative Distance Range: 17 km (11 miles)

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.

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 tour 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.

Hotel: Antica Fattoria La Parrina
Meals: Breakfast, Lunch, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 24 – 68 km (15 – 42 miles)

Morning
Parrina to Talamone: 32.5 km (19 miles)

Afternoon
Talamone to Parrina: 24 km (15 miles)

OR
Talamone to Parrina Plus: 35.5 km (22 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.

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.

Hotel: Antica Fattoria La Parrina
Meals: Breakfast, Lunch

Today’s Ride Choices:
Cumulative Distance Range: 29 – 75.5 km (18 – 47 miles)

Morning
Parrina to Orti di Capalbio: 29 km (18 miles)

OR
Parrina to Carige to Orti di Capalbio: 43 km (27 miles)

Afternoon
Orti di Capalbio to Orbetello: 33 km (20 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.

Today, take a pedaling break from your Tuscany bike tour to enjoy the tranquility of the Giglio island. You’ll start this morning with a warm goodbye to your hosts at La Parrina before transferring 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.

Hotel: Fattoria di Magliano
Meals: Breakfast, Dinner

Today’s Ride Choice:
Non-biking Day: Short hike on Giglio Island or relax at beach, guided tour of castle and along the sea on the cliffs.

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 reel 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, where your chef has prepared a delicious soup, local cheeses, fresh vegetables grown locally and gelato!

Hotel: Fattoria di Magliano
Meals: Breakfast, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 20 – 68 km (12 – 42 miles)

Morning
Fattoria to Capalbio: 29 km (18 miles)

Afternoon
Capalbio to La Sgrilla to Shuttle: 20 km (12 miles)
La Sgrilla to Fattoria: 19 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. The longer option includes a final 1.5-mile challenging climb.

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 join the Andreini family at their olive-oil mill. Enjoy a personally hosted tour of the facility and indulge in an interesting olive-oil talk and tasting. After a specially prepared picnic lunch, continue cycling through Magliano. 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 your Tuscany bike tour adventures during a festive farewell dinner at a local farm, featuring organic vegetables from the garden and local wines.

Hotel: Fattoria di Magliano
Meals: Breakfast, Lunch, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 21 – 62 km (13 – 38 miles)

Morning
Fattoria to Oil Mill: 21 or 26 km (13 or 16 miles)

Afternoon
Oil Mill to Fattoria: 11 km (7 miles)
Oil Mill 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 Oil Mill of the Andreini family, our lunch stop. Two options are offered in the morning (13 or 16-mile ride) depending if you want to push your bike into the town of Magliano di Toscana before lunch. After lunch you continue by the walled city of Magliano and the hotel with the short option. Or make a wider and hillier route by Scansano. While it is only 2 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.

After breakfast, transfer 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.

If you have chosen the independent Post-trip Extension to Rome, you’ll remain at this hotel for the next three nights. Upon your arrival, a VBT Rome representative will be there to answer your questions. Optional walking tours of Rome, including an interesting tour of the Vatican City, will be offered. Check your VBT City Information for all the options.

Hotel: Hotel River Palace
Meals: Breakfast

After breakfast* this morning, you will transfer to the Rome airport (approximately 40 to 60 minutes, depending on traffic) for your departing flight**. Please ensure 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 recommends that you check your transfer time in your “Transfer Reminder.” 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

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 your arrival at Orbetello-Monte Argentario train station is scheduled later than 2:15 p.m. or if you are delayed, you must take a taxi at your own expense (approximately 30 euros) to Antica Fattoria La Parrina (approximately 10 minutes). Contact the hotel if you need help getting a taxi.

If you prefer, you can meet your group at the hotel in Orvieto (Hotel Duomo, Vicolo Maurizio 7, Orvieto, phone +39 0763 341887) at 10:00 am. You will transfer by motorcoach (approximately two hours) to Antica Fattoria La Parrina. If you arrive at our Orvieto hotel later than 10:00 a.m. or if you are delayed, you must take a taxi at your own expense to Antica Fattoria La Parrina (approximately 250 euros/two hours). Please contact Antica Fattoria La Parrina to advise of any travel delays or changes, and the staff will pass your message on to your VBT trip leaders.

Hotel: Antica Fattoria La Parrina
Meals: Dinner

Today’s Ride Choice:
Cumulative Distance Range: 17 km (11 miles)

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.

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 tour 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.

Hotel: Antica Fattoria La Parrina
Meals: Breakfast, Lunch, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 24 – 68 km (15 – 42 miles)

Morning
Parrina to Talamone: 32.5 km (19 miles)

Afternoon
Talamone to Parrina: 24 km (15 miles)

OR
Talamone to Parrina Plus: 35.5 km (22 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.

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.

Hotel: Antica Fattoria La Parrina
Meals: Breakfast, Lunch

Today’s Ride Choices:
Cumulative Distance Range: 29 – 75.5 km (18 – 47 miles)

Morning
Parrina to Orti di Capalbio: 29 km (18 miles)

OR
Parrina to Carige to Orti di Capalbio: 43 km (27 miles)

Afternoon
Orti di Capalbio to Orbetello: 33 km (20 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.

Today, take a pedaling break from your Tuscany bike tour to enjoy the tranquility of the Giglio island. You’ll start this morning with a warm goodbye to your hosts at La Parrina before transferring 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.

Hotel: Fattoria di Magliano
Meals: Breakfast, Dinner

Today’s Ride Choice:
Non-biking Day: Short hike on Giglio Island or relax at beach, guided tour of castle and along the sea on the cliffs.

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 reel 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, where your chef has prepared a delicious soup, local cheeses, fresh vegetables grown locally and gelato!

Hotel: Fattoria di Magliano
Meals: Breakfast, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 20 – 68 km (12 – 42 miles)

Morning
Fattoria to Capalbio: 29 km (18 miles)

Afternoon
Capalbio to La Sgrilla to Shuttle: 20 km (12 miles)
La Sgrilla to Fattoria: 19 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. The longer option includes a final 1.5-mile challenging climb.

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 join the Andreini family at their olive-oil mill. Enjoy a personally hosted tour of the facility and indulge in an interesting olive-oil talk and tasting. After a specially prepared picnic lunch, continue cycling through Magliano. 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 your Tuscany bike tour adventures during a festive farewell dinner at a local farm, featuring organic vegetables from the garden and local wines.

Hotel: Fattoria di Magliano
Meals: Breakfast, Lunch, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 21 – 62 km (13 – 38 miles)

Morning
Fattoria to Oil Mill: 21 or 26 km (13 or 16 miles)

Afternoon
Oil Mill to Fattoria: 11 km (7 miles)
Oil Mill 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 Oil Mill of the Andreini family, our lunch stop. Two options are offered in the morning (13 or 16-mile ride) depending if you want to push your bike into the town of Magliano di Toscana before lunch. After lunch you continue by the walled city of Magliano and the hotel with the short option. Or make a wider and hillier route by Scansano. While it is only 2 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.

After breakfast, transfer 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.

Important: Flight departures from the Rome airport prior to 3:30 p.m. are not recommended. If you depart earlier, you must make transfer arrangements from the last hotel at your own expense. Taxi cost to the Rome airport is approximately 300 euros (travel time approximately 3½ hours). Taxi cost to the Orbetello-Monte Argentario train station is approximately 40 euros (travel time approximately 30 minutes).

Meals: Breakfast