Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza

Tuscany Getaway

4 night self guided bike tour in Italy

We put together this short bike tour for those who do not feel like taking a vacation entirely on a saddle, besides each day there will be a choice for short easier bike rides and more challenging ones.

Whether crowned by timeless villages, covered by vineyards and olive groves or strewn with wildflowers, the hills of Tuscany have one thing in common: they’re perfect for exploring on two wheels. Pedal to lofty hill towns, spin through broad valleys and follow sinuous country roads past cypress-lined lanes and quiet woodland.

Off your bike, discover unforgettable Renaissance art and architecture, visit winery and cellars: you will be in the heart of Brunello wine land, savor meals created from the finest local ingredients and relax in charming Tuscan retreats.

Highlights

• Pienza
• Montepulicano and Monticchiello
• Bagno Vignoni, a thermal spa town
• Catiglione d'Orcia
• Siena
• Etruscan Museum
• Renaissance-era architecture
• Vineyard landscapes

Learn More

Learn more about our self-guided tours or see more bike tours in Italy.

Daily program

Day 1: Welcome! Benvenuti in Toscana
Pienza the "perfect town" is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll about its cobblestone streets. Meet and Greet, we'll fit your bikes and introduce you to each day ride. First loop to San Quirico (14 miles/22 km) to test the bicycle and the equipment!

Day 2: Vino Nobile di Montepulciano (34 or 21 miles/55 or 35 km)
Loop bike tour to Montepulciano and Monticchiello. Start your day with a pleasant downhill, you’ll follow a route checkered with vineyards and cypresses. Highlight of the day is Montepulciano, which is famous for the production of Vino Nobile. Back to Pienza through Monticchiello, another hilltop village.

Day 3: Montalcino and Brunello wine (29 or 21 miles/46 or 34 km)
Today bike trip to Bagno Vignoni, a thermal spa town right before reaching the beautiful Castiglione d'Orcia. Enjoy a long downhill to the monastery of Sant'Antimo. On your way to the Etruscan village and wine town of Montalcino, where you will stay you’ll pedal through magnificent vineyards.

Montalcino is a fortified town which was used as a shelter by Siena nobles during the 16th Century, but today it is even more famous thanks to the production of one of Italian’s premier fine red wines, Brunello di Montalcino.

Day 4: Siena and Palio race (36 or 32 miles/58 or 50 km)
Ride from Montalcino to Siena. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and perhaps have lunch at the restaurant. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands.

Easier: Start with 10 km descent and pass through Buonconvento. Heading northbound to Siena, you’ll be treated to more gorgeous cycling along secondary roads. In the village ofMurlo, you can visit the fascinating Etruscan Museum. Continue to Ville di Corsano always on a breathtaking scenery and end up in Siena arch gate Porta San Marco.

You'll have time to take a leisurely stroll around this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo. Piazza del Campo is famous because here it is held twice a year the disputed DzPaliodz horse race, which opposes the 17 Dzcontradedz of this fascinating city.

Day 5: End of tour
End of bike tour after breakfast.

Surface and terrain

Tuscany is a hilly region, but each day you will have a choice for more challenging or shorter, easier bike rides.

Hotels

These are sample hotels and may vary by availability.

The accommodations are 3-star hotels.

Hotel Il Chiostro di Pienza, Pienza
www.anghelhotels.it

or luxury upgrade:

La Bandita Townhouse, Pienza
www.la-bandita.com

Hotel Giglio, Montalcino
www.gigliohotel.com

or

Si Montalcino, Montalcino
www.hotelsinmontalcino.com

La Villa STR, Siena
www.lavilladistr.it

or luxury upgrade:

Villa del Sole, Siena
www.villadelsolesiena.com

Luxury hotel upgrade pricing upon request.

Please note any visitor's taxes are not included in the tour price. These taxes range from €1-5 per person daily, payable to each hotel.

Interested in visiting other areas before or after your tour? Visit our hotels page to learn more about lodging options.

How to get there

Tour start and end
Nearest airport: Rome Fiumicino or Florence Peretola airports

From Fiumicino airport, take the Leonardo Express train (about 30 minutes) to Termini train station.

From Florence Peretola, take a bus or taxi to Florence station.

To get in Chiusi by train (www.fsitaliane.it) and once in Chiusi, take a bus or taxi to Pienza.

Bus: from Chiusi to Montepulciano, there is a bus every 30 minutes. The bus ride is 40-50 minutes, and the fare is approximately €4 per person. From the bus terminal in Montepulciano, take the bus to Pienza, about a 15 minute ride (this connection is not available on Sundays).

Taxi: from the small train station, the cost is €60-65 per person.

At the tour end, you can easily take a bus or train from Siena to Rome or Florence.

Tips on getting to and from your tour

Dates

Prices

Included services

• 4 nights accommodation in excellent 3-star hotels
• 4 breakfasts
• Route notes, maps, elevation gain and city maps
• Sightseeing, restaurant and shopping suggestions
• Luggage transfers
• Pick-up of bikes and gear in Siena
• Complimentary water bottle

Please note any visitor's taxes are not included in the tour price. These taxes range from €1-5 per person daily, payable to each hotel.

Bike rentals

Bikes available for rent (in advance at the time of booking) on this tour are:

• Hybrid touring bike, 27 or 30 speed, equipped with:
  • Aluminum frame
  • Carbon forks
  • Shimano Deore components 27/30 speed
  • Gel saddle
  • Upright handle bar
  • 28 road wheels
• Road bike, 20 speed, equipped with:
  • Carbon fiber or Scandium frame
  • Carbon forks
  • Shimano Ultegra compact gear 20 speed
  • Drop handle bar
  • 28 race wheels
• Electrically assisted bike with 250w Sunstar motor*

*More about electrically-assisted bikes >

Equipment included with bike rental:

• Handlebar bag or map holder
• Water bottle
• Repair kit (mini pump, inner tube, tire levers)
• Computer mileage counter
• Lock (one lock with key per 2 bikes)

Pedals:
The bikes will have toe clips or flat pedals. You can also bring your own pedals and shoes, along with the necessary equipment for installing the pedals.

Seats:
If you plan to bring your own seat, please don't bring the seat post. The tour company can assist you with installing.

Helmets:
Helmets are required on this tour. Helmets are included in the tour package; however, we recommend you bring your own helmet for safety and hygiene reasons.

Tour Company