Italy: Siena

Select Experience Tour, Italy: SienaSelect Experience Tour, Italy: Siena

Italy

Siena

overview

The medieval city of Siena is beguiling with its crowded brick skyline, colorful piazzas, historic churches, and passionate locals. In this romantic setting, you’re perfectly poised to enjoy the best of Italy, from Renaissance art treasures to rolling countryside. Based in a 19th-century villa within view of the city walls (and the green rolling hills of Chianti), you set out on a leisurely bike ride down the white-gravel roads of the surrounding fields and picturesque neighboring towns. Experience the highlights of the city center on a guided private tour which leads you through the shell-shaped main square, Piazza del Campo (where the centuries-old annual Palio horse race is still held), to the Duomo, where you find art treasures by Pisano, Donatello, Michelangelo, and Bernini.

 

Activity Level
Activities vary and
are accessible to
most fitness levels;
see full itinerary
Meet
Siena, Italy
Depart
Siena, Italy
Daily Itinerary
Download printable
itinerary
Select Experience 
4 days, 3 nights Trip Includes 

Trip Includes:

  • Three breakfasts and one lunch (day 2)
  • Accommodations in a 19th-century villa
  • Private biking excursion with expert bilingual guide (high-quality bikes and water bottles included)
  • Private lunch and wine tasting at a working farm estate
  • Private walking tour of Siena with expert bilingual guide (4-5 hours)
  • Entrance fees to Siena’s Duomo
  • Basic travel insurance coverage
  • 24-hour emergency service
  • The unbeatable and cumulative experience of the CW staff
Number of Travelers
Total in your party
Price From
per person double occupancy
Single supplement + $0 

*Surcharges may apply for New Year’s, Christmas, or other national holidays

Call 800.234.6900 to book this trip.

REQUEST RESERVATION

gallery

Itinerary and Accommodations

Days
Destination
1
Siena
View on map
2
Siena
View on map
3
Siena
View on map
4
Siena
View on map
Day 1

Siena

Arrival in Siena

Upon your arrival in Siena, step into serenity at an elegant 19th-century villa hotel. Overlooking Siena, this historic family-owned property is set in extensive landscaped gardens with a swimming pool and tennis court. You settle in to views over the rolling hills of the Chianti region of Tuscany.

A small gem, Siena is perhaps best known for the tradition of its centuries-old horse race, the Palio, in which contrade (neighborhoods) compete with medieval pageantry in its Piazza del Campo main square, a UNESCO World Heritage site. It is also a center of masterpieces of medieval art and architecture with its stunning cathedral, frescoes, and paintings. And of course, its location in the heart of Tuscany makes it an important center for the region’s sublime food and wine. Dinner is on your own this evening, perhaps in your hotel’s excellent restaurant or, with recommendations, in one of Siena’s many fine trattorias.

Hotel Villa Scacciapensieri

Siena, Italy

An elegant 19th-century villa, this family-run hotel overlooking Siena and the surrounding Tuscan countryside is set in meticulous gardens and park-like grounds. Spacious and quiet rooms are furnished with classic decor and fabrics. The fine-dining restaurant also serves meals alfresco on a shaded terrace. The main villa has a fireside bar/lounge, library, small private chapel, and a media room. On the grounds are a swimming pool and tennis courts, and complimentary bicycles are available for guests.

Day 2

Siena

Full-day private excursion in the Tuscan countryside: bicycling from Pienza to Lucignano d’Asso and Torrenieri, 17 miles (3 hours), easy; lunch and wine tasting at Azienda Agricola Paradiso

A full day in the Tuscan countryside begins with just under an hour’s drive by private minivan to the picturesque town of Pienza, a “planned” Renaissance town especially known for its excellent cheese. After a brief visit, you depart on your bicycles in the direction of the hilltop wine town of Montalcino. You pass en route lovely Lucignano d’Asso to get to Torrenieri for a short break before riding a stretch of fine gravel, the so-called white roads (strade bianche) that offer incomparable views at every turn—golden hills bordered by lines of cypresses leading to farms and vineyards. (A dedicated driver and vehicle is available should you wish to reduce the mileage!) Your destination for a late lunch is the Azienda Agricola Paradiso, an authentic working-farm estate famous for its production of high-quality olive oil. Here, ample Tuscan specialties are served and accompanied by a tasting of three important Tuscan wines—including of course Brunello di Montalcino. A late-afternoon drive brings you back along scenic roads to your villa for an evening of independent dining.

Hotel Villa Scacciapensieri

Siena, Italy

An elegant 19th-century villa, this family-run hotel overlooking Siena and the surrounding Tuscan countryside is set in meticulous gardens and park-like grounds. Spacious and quiet rooms are furnished with classic decor and fabrics. The fine-dining restaurant also serves meals alfresco on a shaded terrace. The main villa has a fireside bar/lounge, library, small private chapel, and a media room. On the grounds are a swimming pool and tennis courts, and complimentary bicycles are available for guests.

Day 3

Siena

Private guided walking tour of Siena, easy

After breakfast at your hotel, you meet your expert guide for a full-morning walking tour of Siena and its major sights. Enclosed in 14th-century walls, this quintessential medieval city gained influence and wealth through rich merchants and bankers whose stunning palaces make up the center, including the headquarters of the oldest bank in Europe. You begin your tour in this old financial quarter and then cross the famous Piazza del Campo main square, where the Palio horse race is run. This UNESCO World Heritage site was constructed over the old Roman forum and continued as the city’s main marketplace. You then wind through narrow cobbled pedestrian streets to the highest point in the city, the location of the Duomo, Siena’s magnificent cathedral. Completed in 1382, its striking black-and-white exterior is as spectacular as the masterpieces of paintings and sculpture inside by such artists as Nicola and Giovanni Pisano, Donatello, Michelangelo, and Bernini. With your guide’s suggestions for lunch and further explorations, you have the entire afternoon and evening for continued discoveries in Siena.

Hotel Villa Scacciapensieri

Siena, Italy

An elegant 19th-century villa, this family-run hotel overlooking Siena and the surrounding Tuscan countryside is set in meticulous gardens and park-like grounds. Spacious and quiet rooms are furnished with classic decor and fabrics. The fine-dining restaurant also serves meals alfresco on a shaded terrace. The main villa has a fireside bar/lounge, library, small private chapel, and a media room. On the grounds are a swimming pool and tennis courts, and complimentary bicycles are available for guests.

Day 4

Siena

Departure from Siena

Following breakfast at the hotel, you check out and depart at your leisure.

Itinerary Disclaimer

Bear in mind that this is a typical itinerary, and the actual activities, sites, and accommodations may vary due to season, special events, weather, or transportation schedules. We reserve the right to alter the itinerary since tour arrangements are made up to a year in advance, and unforeseen circumstances that mandate change may arise. Itinerary changes are made to improve the tour and your experience. If you are currently booked on a CW adventure, an itinerary has been sent to you for your exact departure date. Please call CW at 800.464.9255 if you have any questions about the exact itinerary or hotels selected for any of our tours.

PDF Download Capture: