A Week of Wine in Tuscany

Transportation details Tuscany

Venice Transportation details

  • Week 1: September 18-25, 2022
  • Week 2: September 25-October 2, 2022
  • Week 3: October 2-9, 2022

The Villa | Pricing | Itinerary | FAQ | Reserve

Small group touring of wineries and hilltop towns and villages throughout the region. Stay in your own private villa with old and new friends. We’ll enjoy wine, olive oil, black and white truffles, local cuisine, architecture, history, and the natural beauty of the region.

An identical tour was offered in the fall of 2019 with outstanding success. This 12-bedroom Villa in Torrita di Siena exceeded every expectation.

You have three weeks from which to choose, and each week is limited to just 16 guests. Week 1 and 3 are combinable with a seven-night, all-inclusive cruise on the Po River and Venetian Lagoon.  This cruise departs begins in Venice on September 25th, ending in Venice the morning of October 2nd.  Transportation is provided from the villa to the ship and vice verse.

Here’s what the tour will include:

  • Seven nights in a Private Villa in Southern Tuscany
  • Your choice of 12 en suite bedrooms
  • Breakfast buffet each morning
  • Dinner each night: 3 at the Villa, 4 in local restaurants
  • Vino with dinner
  • Four lunches during tour visits
  • Services of a local guide
  • Seven full days of touring in Tuscany
  • Round trip coach transportation-Florence Airport
  • Air-conditioned motor coach transportation
  • Walking tours of Montepulciano, Siena, San Gimignano, and Montalcino
  • Evening Classical Concert
  • A truffle hunt and lunch
  • Limited to 16 guests
  • Optional balloon excursion

Choose from one of two weeks at the Villa. On any one of our tour days, you’re free to take the day off to hang out at the pool, stroll the countryside, or visit one the shops or restaurants in the village. Consider extending your time in Italy with seven nights cruising in the Venice Lagoon and Po River. Combining the Villa Tour with the Venice cruise provides an overall discount of 5% for both tours.

If a week in Tuscany would simply whet your appetite, you may want to consider this tour option before or after the villa week.

Additional tours available for Villa Week 1 (September 18-25):

Additional tours available for Villa Week 2 (October 2-9):

The Villa

Villa Carrera Villa Carrera is a short 200-yard, level walk from the medieval village of Torrita di Siena with the larger hill town of Montepulciano just 12 minutes away by car. It’s a beautiful, historic building with a great deal of public space, 12 well-appointed bedrooms, and an attractive pool area. Meticulously restored, Villa Carrera is designed for sophisticated travelers seeking a high degree of comfort and refinement.

Guests enjoy the freedom of walking to the nearby café to start the day with a frothy cappuccino or taking an evening stroll to two restaurants or a pizzeria. Along the same street is a small grocer who doubles as one of the area’s most notable butchers. On Friday mornings, opening the gate reveals the outdoor market that comes to the village.

Inside the gates, guests are welcomed by copses of cypresses and an idyllic country view over gently rolling Tuscan hills draped in acres of olive groves belonging to this country estate. An outdoor living area sits just above the swimming pool to take in this delightful panorama.

The entire villa is air-conditioned, smoke-free and adorned with frescoed ceilings and large, sun-filled windows. An elevator allows access to all three floors. Each of the 12 well-appointed bedrooms is adorned with treasured family heirlooms, a wall safe and a marble-clad, en-suite bathroom with built-in hairdryer. All bedrooms may be configured as queens or with two singles beds.

Awaken each morning to a breakfast buffet that is served outdoors under the arched, fully shaded loggia or in the main dining room. Torrita di Siena overlooks one of Italy’s most visually striking landscapes. The Val di Chiana valley is dotted with colorful hill towns yielding highly rated Vino Nobile di Montepulciano red wine and the velvety Pecorino cheeses of Pienza.

Bedroom options

Some rooms are slightly larger than others. Some may offer a more desirable view. Larger rooms with views come with a (weekly) surcharge. Smaller rooms with less interesting views show a (weekly) credit.   Here’s a thumbnail description of each room. The description lists first floor and second floor. Keep in mind that the main floor is where the public areas are. First floor is one level up. Second floor is two levels up.

Superior Suite
Firenze(1): First floor master-corner room with French Balcony (+$600)

Junior Suite
Pienza(2): First floor bedroom-rear of villa facing pool (+$450)
Lucca(7): Second floor-rear of villa overlooking pool (+$450)
Siena(6): Second floor-master corner suite overlooking village (+$500)

Pisa(5): First floor bedroom with French balcony (+$300)
Montalcino(11): Second floor bedroom with expansive view of the pool (+$300)

Deluxe Rooms
Cortona(8): Second floor bedroom-front of villa facing the village
San Gimignano(3): First floor bedroom-rear of villa facing the pool
Montepulciano(9): Second Floor bedroom-front of villa overlooking village

Classic Rooms
Chiusi(4): First floor bedroom, side of villa-shading trees (-$200)
Volterra(10): Second floor-bedroom with shading trees outside window (-$200)
Monteriggioni(12): Second floor-smaller bedroom with country views (-$200)

Photos of Tenuta Villa Rocchi guest rooms and public areas may be found at this link.

Available rooms for each week:  (updated 11/12/2021)

Week 1          September 18 to September 25

Sold out for week one

Week 2         September 25 to October 2

Sold out for week two

Week 3         October 2 to October 9

Space available for 4 guests.  Cortona, Montepulciano, or Lucca (2 doubles available)

Villa Tour pricing for 7 nights

Villa Carrera$3690 per person, based on double occupancy. Single supplement is $300, but limited to 3 single rooms. Deposit of $1500 per person is required to confirm your villa accommodations. Balance of payment is due March 1, 2022.

Pricing is based on payment by Visa or MasterCard. If you choose to pay by check, your discount is $125 per person.

Because payments are non-refundable, it’s strongly suggested that you consider travel insurance for this investment.

What if I need to cancel my flight, tour or cruise?

Both of the companies listed below have a policy rate calculator online.  Enter the cost of your tour and personal data to receive a no-obligation cost estimate.

Two recommended companies are:

Generali Travel Insurance
Travelex Insurance

Cancellation insurance will range in price based on the cost of your travel and the age of the applicant.  Get a quote at the websites above before making a purchase.  If you have a pre-existing condition to cover, you usually must purchase your policy within 2 weeks of the initial deposit.

There are three villa weeks in 2022 from which to choose:

  • Week 1: September 18-25
  • Week 2: September 25-October 2
  • Week 3: October 2-9


Day 1: Sunday: Arrive Florence airport

Meet your driver and travel 90 minutes to your Tuscan Villa. The afternoon is free to wander the village. We have a late afternoon wine tasting arranged prior to the welcome dinner at the villa in the early evening (D)

Day 2: Monday: Siena

We’ll start the day with wine beginning with a visit to La Lastra for a tour of the cellars and a tasting of Chianti as well as some lesser known varietals from the area. … The Tuscan Wine School will provide a foodie tour of the historic center of Siena. Free time in the afternoon to wander the town or shop. Dine in Siena this evening. (BLD)

Day 3: Tuesday: Montalcino

Two amazing towns today, starting with the home of Brunello. First Montalcino with high-end shops, wineries, and restaurants. We’ll start our morning with a cellar tour and tasting at Canalicchio di Sopra, followed by a walk through the town. We’ll break for lunch in Montalcino, then travel to the medieval town of Pienza for a walking tour. We’ll visit a local producer to sample Pecorino cheese and olive oil, enjoy a bit of free time for photos, shopping, or additional wine tasting.

Our final stop of the afternoon is at Podere il Casale for a pizza making class and, you guessed it, more wine. Return to the villa in the early evening. Since we’ve enjoyed late afternoon pizza and wine, dinner is not provided. If you’re still feeling peckish, I suggest wandering down to one of the restaurants in the village. (BD)

MontepulcianoDay 4: Wednesday: Montepulciano

We’ll start with a morning walking tour of the village of Montepulciano. Our next stop is a light lunch and wine tasting at Avionesi Winery. We’ll have our second tasting of the day at Palazzo Vecchio. We turn for home with a final stop not far from the villa at Poliziano Winery. We’ll dine al fresco at a restaurant in Montepulciano this evening. (BLD)

Day 5: Thursday: Chianti

Driving north from the villa, we enter Chianti Classico Country. We’ll stop at Felsina for a tour of the cellar and taste some of their vino. A stop for lunch in Radda and time to visit Casa Chianti Classico for an education into the varietals of the region. A final visit another respected producer, Castello di Ama, for a tasting before returning to the villa in the evening for dinner. (BLD)

Day 6: Friday: San Gimignano

This morning we visit Tenuta Torciano in the hills north of Poggibonsi for a light lunch, and wine tasting, followed by short introduction to Truffle Hunting. We’ll visit the towered hill town on San Gimignano this afternoon. We’ll walk through the town, ending at the Vernaccia Wine Museum for a tasting of this unique white varietal. We then travel to Volterra for a visit to a wine cellar in town followed by an evening dinner in the village. (BLD)

Day 7: Saturday: Option Day

Today is option day. You may choose to spend more time in Montepulciano or Montalcino on your own. Transportation will be provided. You might choose to take a hot air balloon ride over the Tuscan Countryside. See below for options. Our farewell dinner is in the villa this evening. (BD)

Day 8: Sunday: Arrivederci!

Transportation is provided from the villa to accommodate early flights home. Guests departing early will be provided with a boxed breakfast. Later morning transportation is provided for guests with later flights from Florence. Guests traveling to board the ship in Venice will depart mid-morning from the villa. (B)

The Towns

The Vino

The Experiences

Frequently-Asked Questions (FAQ)

Typical weather in the region:

Conditions are very similar to the Seattle area, though Montepulciano gets about 1⁄2 inch less rain for the month of October and is about 5° warmer. Daytime highs will be close to 70°. Nighttime lows can get down to freezing. In 2019, our October dates were slightly later, but didn’t keep many guests from using the pool.

Flight suggestions:

Florence (FLR) is the best option for commercial flights. Seattle departures are available for reasonable itineraries with one stop. For guests arriving in Florence in the morning (suggested), your transportation will depart from the airport to the villa about 1 PM.

Air France and Delta offer arrivals at 11 AM. Lufthansa arrivals are at 2 PM. If you arrive on the later LH flight, your coach will depart close to 3 PM, with an anticipated arrival at the villa by 5. Today (3/10/21) fares are priced at $1500 from Seattle. Fares from Vancouver are under $1100.

I expect that you should find Seattle fares closer to $1100 round trip. My suggestion is to set up a fare alert on Kayak.com. It’s a great feature and there is no charge to set up an account.

Many of the return departures from FLR to the USA depart quite early. We’ll provide a shuttle to get you back on time. Remember that you’ll want to depart the USA (or Canada) the day before the villa week begins. You lose a day flying to Europe.

Make Your Reservation!

If you have any questions about this tour, please contact Brad Cilley at brad@nwtravel.com or by phone at 425 375 2676.

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Photo in header by Martin Falbisoner, licensed under the Creative Commons Attribution-Share Alike 3.0 Unported license.