Wines and Hill Towns of Tuscany

Week 1: September 20-September 27, 2025 (Available to Adams group only)
Week 2: September 27-October 4, 2025 (Fully Available to book)

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.

This tour program, with small changes and upgrades has been scheduled in 2017, 2022, 2023, and 2024 with outstanding success. This 12-bedroom Villa in Torrita di Siena exceeds every expectation.

You have two weeks from which to choose, and each week is limited to just 16 guests. Week 1 is combinable with a 7-night Croatia Yacht Cruise. which runs from September 13th to 20th. Week 2 is combinable with Croatia as well, with a Yacht cruise that operates from Split October 4th to 13th. Croatia details will be posted to this site very soon.

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
A truffle hunt and lunch
Limited to 16 guests

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.

The Villa

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)

Suites
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 07/10/24)

Week 1 September 20 to September 27, 2025

Week 2 September 27 to October 4, 2025

Villa Tour pricing for 7 nights

Villa Carrera $4350 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, 2025.

Pricing is based on payment by Visa or MasterCard. If you choose to pay by check, your discount is $140 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.

Itinerary

Day 1: saturday: Arrive Florence airport

Florence Airport/Peretola (FLR) is relatively small and easy to navigate. The scheduled pick-up time for guests at Florence Airport is at 1:30 PM, placing you at the villa a little after 3:00 PM. Meeting Place is the small seating area just outside the arrivals hall door. Our guide will meet you there and coordinate with our driver. We’ll use Whatsapp to facilitate the meeting at the airport.

Upon arrival at Tenuta Villa Rocchi, you’ll be greeted by the owners Cristina and Giuseppe. The villa is perched near the top of the village with panoramic views of the surrounding countryside. There are 13 bedrooms, an outdoor pool, stocked bar with liquors and wine, and a guest laundry.

After you’ve had time to settle in, we’ll meet in the breakfast room for a tasting of the estate’s wines and olive oil. Dinner is scheduled for 7:30 this evening at the villa. Overnight Torrita di Siena (D)

Torrita di Siena is a pretty sleepy place, not on the major touristic track. You’ll find an ATM, coffer shop, bistro. Farther into the commercial side of town is a grocery, clothing store, and other shops. Montepulciano is 17km away.

Day 2: Sunday: Siena

We start the day in Siena where we’ll meet a local guide in the city center for a walking tour of the city and a visit to a local Pasticceria for a sampling of the pastries and cakes Siena is known for. You’ll have some free time for shopping or more food sampling after our tour. Lunch is on your own, but you might just want to enjoy a gelato since we’ve got a food and wine pairing at our afternoon wine producer.

We’ll set a time to meet up to rejoin the coach for a short drive to Azienda Agricola Montechiaro, just outside the city of Siena. We’ll enjoy a tasting of 6 wines and some local bites.

Suggestions for your afternoon include a visit to the Duomo, see the Frescoes and climb the tower at Palazzo Pubblico, or shop for locally made leather goods at Casa Della Pelle.

Dinner tonight is 7:00 PM at Piccolo Ristorante, a local restaurant just outside the walls of the villa. We’ll meet to walk there about 6:50 PM. Overnight Torrita di Siena (BSD)

Day 3: Monday: Montalcino

We’ve got a late morning tour and tasting at the winery Canalicchio di Sopra located just outside the town of Montalcino. This is a special vertical tasting of 6 of their wines, including Rosso and Brunello.

After tasting, we’ll spend a little time in the town of Montalcino for a quick lunch on your own. Next, we’ll travel to the town of Pienza for a visit to Taverna del Pecorino for a sampling of fresh and aged cheeses, salumi, prosciutto, and balsamico, followed by free time in the historic center.

From Pienza we’re scheduled for a short tour of the farm by the owner at Podere il Casale followed by our 5:30 pizza making class and subsequent pizza eating session. We’ll return to the villa later in the evening about 8:30 PM. Overnight Torrita di Siena (BSD)

Day 4: Tuesday: san gimignano

This morning we visit Podere la Marronaia, a family owned biodynamic estate set in the hills north of San Gimignano, for a morning truffle hunt in the estate forest with a certified Cavatore, or truffle hunter. The hunt ends and a light truffle lunch begins featuring wines from the estate. Following this lunch, we’ll have a bit of free time in San Gimignano for shopping, photos, and exploring. San Gimignano is home to Dondoli Gelato, arguably the best in Tuscany.

In the late afternoon, we visit La Rocca, the fortress at the top of the town, and home to The Vernaccia Wine Experience. We’ll enjoy a tasting of this unique white wine local to the area.

We’ll depart from San Gimignano about 5:30 for return to Torrita di Siena. Dinner is scheduled at a fantastic restaurant just a few miles from the villa called Fondo Ristorante at 7:30 PM. Overnight Torrita di Siena (BLD)

Day 5: Wednesday: Chianti

Our day in Chianti with a departure at 9:00 AM for the 11^th century abbey and gardens at Badia a Coltibuono for a tour and wine tasting. We then travel on to Radda to the Casa Chianti Classico for a lunch and tasting there.

We’ll return the villa about 5:00 this afternoon with time for a drink by the pool. Dinner tonight is at the villa at 7:30 PM. Overnight Torrita di Siena (BLD)

Day 6: Thursday: Montepulciano

We depart the villa after breakfast for our shortest day of touring in that we’re only 17 km from the town of Montepulciano. Our first visit in the morning is at Avignonesi at 11:30 AM for a tour of their Vin Santo production, tasting of wine and buffet lunch.

We’ll travel from there to spend time in the town of Montepulciano before our second appointment of the day at a small family-run winery called Tenuta Valdipiatta. We’ve got time to tour and taste here before continuing for dinner at 7:30 PM at Il Covo, a small restaurant on the outskirts of Montepulciano. Overnight Torrita di Siena (BLD)

Day 7: Friday: Orvieto

We’re departing Tuscany for the day to visit to Umbria and the ancient hill town of Orvieto. You’ll enjoy a walking tour of the town with a local guide and time for lunch and/or shopping on your own. We’ll visit a local winery nearby before heading back to the villa for our farewell dinner together. We should arrive back at the villa by 5:00 PM. Overnight Torrita di Siena (BSD)

Day 8: Saturday: Arrivederci!

Your transportation is provided from the villa to Florence Airport this morning. You’re encouraged to book late morning departures home. Arrangements are available for guests departing on early flights as well. (B)

The Towns

The Vino

The Experiences

Truffle hunt and lunch

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 1:30 PM. Come early for an extended stay in Florence to acclimate to the time or consider the pre-tour option of a seven night cruise in Croatia.

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 (7/10/24) fares are priced at $1100 from Seattle. I usually check fares from Vancouver as well, but see that they are roughly the same as Seattle fares at about $1100 round trip.

I expect that you should find Seattle fares closer to $1100 round trip. The longer you wait, the more you’ll likely pay. I waited until about 30 days out last year and still had a fare under $1400. My suggestion is to set up a fare alert on Google Flights or 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.