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Custom Tuscany Luxury

Pedal La Bella Toscana: Siena area

Surrender your senses to the “allegria” of Tuscany from the saddle of your bicycle. Awash in the rich sights and smells of the endless vineyards, the quiet, rolling roads of the Tuscan countryside offer gorgeous terrain that's a joy to pedal for cycling experts and novices alike. Discover the breathtaking scenery around Val d’orcia while climbing up to Monte Amiata. Explore beautiful hill towns including Siena, a medieval town with red-brick lanes square which every year hosts a famous Strade Bianche race. We will also drive more to the North to conquer the local’s favorite Monte Serra. When you are not riding, take in the view of the rolling Tuscan hills from your Villa and relax with a glass of wine. "La dolce vita" is nowhere more evident than it is here—you're sure to fall under its spell on this cycling vacation of a lifetime.
From:
$2999 Per Person
Duration:
9 Days & 8 Nights
Rider Type: ?
4 - Avid
Hotel Style: ?
Luxury
Reviews:
From $2999 per person View All Details
Trip Wows
Bike through the town of Siena and enjoy lunch on Piazza del Campo
Ride along quiet roads lined with cypress trees and golden hills overrun by vineyards and olive groves.
Test your legs on region's famous climb Monte Amiata and Monte Serra
Bike to San Gimignano where you’ll be met with vibrant colors and sights.
Watch the Experience
Another spectacular adventure! After an incredible trip to Napa with Trek Travel, we were excited to explore yet another amazing area with you. Tuscany was absolutely awesome, and we are already debating where we should go with Trek Travel next. Thanks for all that you do – we can’t imagine anyone doing it better.
-Melissa

Dates & Prices

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There are currently no dates available to book for this trip or it is by request only. Please contact a Trip Consultant for more information on available dates.
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Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. All you need to do is pick any open trip date, get your group together and we will do the rest. Private trip pricing is as follows:
  • 10+ Guests Price as advertised*
  • 8-9 Guests +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
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*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Your Trek Travel guides will meet you at the Florence Airport on the first day of the trip. You’ll then shuttle 90 minutes to your luxury Villa Ferraia. Your guides will brief you about plans for the upcoming week and assure that your bikes are set up for the first Tuscany ride tomorrow.

Hotel:

Villa Ferraia

Buongiorno! After a typical Italian breakfast, your guides will meet you at the hotel to take you for the first ride in Tuscany. We will leave slowly from the Villa on a gravel road toward the village of Tocchi where we join an asphalt road. Passing Monticiano we will take a left turn and see one of the typical views of the ruins of San Galgano. Around 9 miles into the ride, we will start a climb of the day up to Montieri. It’s about 4 miles long with an average of 4% and maximum 9% grade. After a well-deserved descent, we will bike through forested hills and olive groves. We will stop at a local bar for lunch. The afternoon ride presents a few uphills before we reach Monticiano again and turn back to your luxury Villa.

Today's Ride:

Monticiano Loop
Approximately 62 miles with 4,800 feet of climbing

Hotel:

Villa Ferraia

Included Meals:

Lunch

Today you can look forward to one of the most typical rides in the region with some of the most stunning views in Tuscany. There is no significant climb of the day but rather continuous rolling hills through Val d’Arbia and Crete Senesi area, which is usually described as “lunar” with its soft sloping gray colored hills, almost entirely deprived of color. We will go through the little town of Asciano, surrounded by 13th-century walls. After a few more hills Siena will appear on the horizon. Siena is one of the most beautiful medieval towns in Italy, famous for its Dome and Piazza del Campo that is the place for the finish of Strade Bianche race. We will have lunch at our friend’s bar – Paolo and Fabrizio have their restaurant right in front of the red brick Siena tower. After lunch at this special place, we will head back to the hotel.

Today's Ride:

Siena loop over Asciano
Approximately 63 miles with 6,100 feet of climbing

Short Option:

Asciano to Siena with shuttle
Approximately 42 miles with 4,000 feet of climbing

Hotel:

Villa Ferraia

Included Meals:

Lunch

This morning we will get on a shuttle heading to the north part of Tuscany. We will stop for one more espresso before getting on your bike, and now it’s time to climb Monte Serra, a very popular climb for local cyclists and several pro riders. It dominates the horizon between Pisa and Lucca. There are three different roads to reach the top, and today you get to experience all of them. We will start from Calci and get through a series of tough ramps with 10% grade. After reaching a TV antenna that is the summit at 2,950 feet, we descend on the side to Lucca. Stretch your legs on a flat part before reaching a picturesque village of Buti and start to climb probably the most known side. Before the top, we turn toward Calci again and enjoy a smooth descent on a wide new asphalt road. It’s time for well-deserved pasta and a glass of beer before we get on a shuttle to drive back to the Villa.

Today's Ride:

Monte Serra Loop
Approximately 37 miles with 5,400 feet of climbing

Hotel:

Villa Ferraia

Included Meals:

Lunch

Today is a perfect day to go for a leisurely ride and rest your legs before another challenging day later in the week. Your guides will take you for a spin around Val di Merse. We will start biking toward a tiny village of Iesa. We descend down to the valley and start a 4-mile climb to Casciano. From Casciano, we descend back to the valley and get back up to Castello di Tocchi. If you prefer to bike more today the guides can take you for a longer loop. From Casciano continue to the medieval hamlet of Murlo and Buonconvento, followed by a 4-mile climb to Montalcino, famous for its renowned red wine Brunello di Montalcino. We will finish the ride in the historical center of San Quirico before we get on an hour shuttle back to the hotel.

Today's Ride:

Relaxing ride to Casciano
Approximately 24 miles with 3,100 feet of climbing

Short Option:

Castello di Casole to San Gimignano w/shuttle to hotel
Approximately 20 miles with 2,100 feet of climbing

Avid Option:

Casciano to Buonconvento to San Quirico Loop
Approximately 53 miles with 5,400 feet of climbing

Hotel:

Villa Ferraia

Included Meals:

Lunch

This morning we will start with a short transfer again in order to get closer to an awaited climb of Monte Amiata, the highest peak in the south of Tuscany. We will warm up on a flat route taking us to the beginning of the climb in Castel del Piano. From this side, the climb is nearly 9 miles long with an average 6.8% grade. The steepest slopes are on the bottom, and it gets easier as you get higher. On the top feast your eyes on the indescribably beautiful view. We will descend toward San Salvatore Abbey and loop back to Castle del Piano. It’s time to get a well-deserved aperitivo before hopping on the shuttle to enjoy a relaxing evening in the Villa.

Today's Ride:

Monte Amiata to Castel del Piano
Approximately 50 miles with 7,400 feet of climbing

Hotel:

Villa Ferraia

Included Meals:

Lunch

Today you’ll head north again to the wide Elsa Valley, across vine-covered slopes and up to the medieval town of San Gimignano - the city of the hundred towers or also called the medieval Manhattan. Take your time for a walk in the historic center where you will find artisan shops, wine cellars, and food producers. After you enjoy vibrant colors and sights of the town, you will continue uphill towards Castel San Gimignano where you should turn right on to the main road and bike for around 2 miles before getting to the junction for Casole d’Elsa. We will stop for a quick and light lunch before getting back on the road to Monticiano and Tocchi. This evening is yours to enjoy before tomorrow’s last day in beautiful Tuscany.

Today's Ride:

San Gimignano Loop
Approximately 83 miles with 6,900 feet of climbing

Short Option:

San Gimignano with shuttle from lunch
Approximately 60 miles with 4,800 feet of climbing

Hotel:

Villa Ferraia

Included Meals:

Lunch

Today’s ride could be called a medieval journey as we bike countless medieval villages. After we pass one of them - Sassofortino, we will enjoy a long descent to Montemassi surrounded by unspoiled nature. Make sure to stop and enjoy a view of the Montemassi castle before the following climb to Meleta, which is around 4 miles long and the biggest one of the day. But don’t be mistaken you still have enough hills to enjoy before we get back to Monticiano and your luxury home. Raise your glass to a week of cycling in beautiful Tuscany.

Today's Ride:

Montemassi Loop
Approximately 57 miles with 5,400 feet of climbing

Hotel:

Villa Ferraia

Included Meals:

Lunch

Sadly it's time to say good-bye. You will say farewell to your guides at the Villa Ferraia. You’ll depart by private shuttle to Florence which takes approximately 90-minutes.

Hotel:

Villa Ferraia

Hotels

hotel image

Villa Ferraia

Tocchi, Italy

Charming and Luxurious Villa in Tuscany among the hills around Siena.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.

bike

Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019 we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More

WHAT'S INCLUDED

  • Three experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with the guides and our support van
  • 7 lunches
  • Option to ride a Trek Domane SL 7 disc road bike
  • Up to two daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Bontrager cycling jersey and socks to keep
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, flat pack, front and rear Bontrager Flare R lights, a Bontrager saddle and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals)
  • Bontrager WaveCel helmets
  • All gratuities for drivers, local experts and hospitality staff
  • All luggage transfers and transportation during your trip
  • A personalized photobook of your trip
  • Entrance fees for all activities, private tours and events

GEAR

  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting
  • Trek Travel Bontrager cycling jersey and socks to keep
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights and a flat pack
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Upgrade your bike to include carbon wheels (+$200)
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.

WHAT'S NOT INCLUDED

Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.
  • Accommodations during the trip
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Daily breakfast and dinner
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • Gratuities for your guides

More Information

Rider Level: 3 - Active?

AVERAGE DAILY MILEAGE:
54 miles
TOTAL MILES:
378 miles
AVERAGE DAILY ELEVATION:
5,600 feet
TOTAL ELEVATION:
39,000 feet
TERRAIN: HILLY
The terrain is consistently rolling, with quiet, narrow, and winding roads. Many towns sit atop hills and, although the ascents are not exceptionally steep, they are often upwards of 3 miles long.
NON-RIDING ACTIVITIES:

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our Today’s Ride options.

Travel Details

How to Get There

FLY INTO:
Amerigo Vespucci Airport (FLR)
MEETING TIME:
TBD
MEETING LOCATION:
Amerigo Vespucci Airport, Florence, Italy

Say Farewell

FLY OUT OF:
Amerigo Vespucci Airport (FLR)
DEPARTING TIME:
TBD
DEPARTING LOCATION:
Villa Ferraia

Arriving

Your Trek Travel guides will meet you at the Florence Airport on the first day of the trip. You’ll then shuttle 90-minutes to your luxury Villa Ferraia. Your guides will inform you about plans for the upcoming week and assure that your bikes are set up for the first Tuscany ride tomorrow.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip starts with their names and contact details. If you cannot reach them, please call our first hotel, Villa Ferraia (+39 0577 757102) and leave a message with your expected arrival time and contact details. You may take a taxi to the first night’s hotel for $225. The trip takes an hour and a half from the Florence Airport.

You will say farewell to your guides at the Villa Ferraia. You’ll depart by private shuttle to Florence which takes approximately 90-minutes.

View our pre hotel recommendations

Planning For Your Trip

Packing and Weather

Spring in Tuscany is usually clear and sunny, with warm daytime temperatures (70F-85F) and evening temperatures 10-15 degrees cooler. You will need a jacket for the evenings. Rain is always a possibility so be prepared with wet-weather gear in order to best enjoy your vacation. Packing List

Before and After Your Trip

before

Before: Florence, Italy

Florence is the majestic heart of Renaissance art and intellect. Several days can be spent wandering the streets in the shadow of Brunelleschi’s Duomo and strolling beside the Arno. Along with the Duomo and Ponte Vecchio, the Uffizi gallery, a pillar of the Renaissance and Medici eras, merits a visit. Michelangeo’s David in the Galleria dell’Arte is not to be missed. Keep in mind while exploring Florence that opening hours vary and are quite often inconsistent. Different museums are open on different days and lines can be very long. It’s worthwhile to pay a few extra euros and pre-book your tickets—this will enable you to bypass long lines of visitors at the entrances. We recommend the following accommodations for your pre-trip hotel.

Customer Reviews

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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