Active Gourmet Holidays
Active Gourmet Holidays

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Tuscany, Italy - 6 nights
Available May/June and September/October  


Enjoy a fantastic wine and walking tour in Montalcino and San Gimignano. There will be morning hikes and afternoon wine tastings offering an active tour for foodies and wine aficionados. Plus, there’s pecorino cheese in Pienza, art in Siena, and Gregorian chants in Montalcino.



SAMPLE ITINERARY (can start on Sunday or Monday)







From Florence, shuttle to Montalcino for a welcome lunch at a winery-run restaurant. A loop hike covers the north side of Montalcino hill, passing by vineyards and stone farmhouses. At the hike's end, we'll stop for an introduction to Brunello, among Italy’s best wines, at a boutique winery. Our wine dinner in town features Tuscany’s woodland-based cuisine, such as wild boar (cinghiale), beef shanks braised in wine, and plenty of homemade pasta.







Pienza is famous for its Renaissance architecture and its pecorino cheese. We’ll visit this “ideal city” and sample three types of pecorino. Then we embark on a beautiful walk over rolling hills lined with cypress trees to the town of Montepulciano. Here we’ll learn about Vino Nobile di Montepulciano. Beloved by nobles, this wine was a favorite of Thomas Jefferson and Voltaire. We'll visit a Vino Nobile estate, such as Icario, a terrific up-and-coming winery, or Poliziano, one of the leaders in Vino Nobile’s renaissance in the 1980s. Dinner features elegant nouvelle renditions of classic Tuscan cuisine.







Walk back in time to the medieval Abbey of Sant’ Antimo, where monks still live. This hike is a popular trail that goes through lush forests and along hill crests to the Romanesque abbey. We’ll arrive in time to hear the monks chant.




After lunch, we’ll taste Brunellos from the south side of the DOCG zone, either at Ciacci Piccolomini di Aragona, an historic estate with highly rated wines, or one of the emerging stars in Brunello.




Free time to explore the wine shops of Montalcino or visit the crenellated fortress of Montalcino.  









Explore the twisted Gothic streets of Siena. After a cappuccino at Nanini, Siena's most famous coffee bar, we visit the city’s most famous sites: the Piazza del Campo, where the palio horserace is run; the Palazzo Pubblico, which houses masterpieces of Italian Gothic art; and the Duomo, home to artworks by Michelangelo. Then there’s free time for lunch, shopping, or a visit the Enoteca Nazionale, Italy's national wine museum/wine bar. We then drive to San Gimignano, a hilltop city that bristles with medieval towers, and settle into our accommodations at a country inn.


Before dinner, an informal tasting offers an introduction to San Gimignano’s historic white wine, Vernaccia di San Gimignano.






Today's hike encircles San Gimignano, going down cypress lanes, past stone farmhouses, and through vineyards. Our afternoon wine tasting at Panizzi spotlights the various styles of Vernaccia di San Gimignano, a wine made since the 1100s. Visit San Gimignano to see its towers and exquisitely beautiful frescos in the main church.


Dinner is in town, where we'll learn the proper way to dip biscotti in vin santo, a golden dessert wine first created by medieval monks.







The Etruscans planted Tuscany’s first vines. We’ll revisit this ancient civilization on our hike to Volterra, an Etruscan stronghold. There will be free time for lunch and a visit to the Etruscan museum, where this sophisticated culture comes alive. For our afternoon wine tasting, we head back to San Gimignano and visit Cesani, a small family estate that produces a superb Super Tuscan, as well as two excellent versions of Vernaccia.


Our farewell dinner is in San Gimignano.







Buon viaggio! A shuttle to Florence and assistance with your travel plans.



*Itinerary changes very slightly each year so as to improve the tour





A minimum of 2 participants is required to run this tour and the tour in limited to a maximum of 14 participants.


(The number of participants refers to how many persons are required to run the tour, not to how many persons you must have in your party. Please inquire.)






Meet: Florence Train Station
Depart: Florence Train Station


*It is necessary to arrive in Italy the day before the tour begins, in order to meet the morning shuttle.


*These details are provided as additional information. Please check below to see if transfers are included in this tour.







2020 Fees Per Person


Double Room/US$3995 (for groups of 2)
Single Room Supplement/US$400


*Please inquire about price for groups of 4 or more


*Standard accommodations are two people per room


*Pricing may vary depending on market fluctuation




After availability is confirmed, a 30% non-refundable deposit per person and the completed and submitted registration form will secure your reservation. Final payment is due in full 75 days before your arrival date. 


2020 Dates

Private departure for 2+ pax in May/June and September/October - please inquire



*Six (6) nights accommodations (double room) in two 3-star hotels, with breakfast buffet
•Five (5) gourmet dinners (three courses with wine)
•One (1) welcome lunch
•All wine tastings mentioned
•Admission to Siena’s Palazzo Pubblico, San Gimignano’s Collegiata church
•Shuttle at beginning/end of tour, as desribed


Transportation: We provide one van pick-up on day of arrival/departure at designated train station or airport (call for times). All ground transport during stay.


Not Included:

*Travel to meeting point
*One (1) dinner on your own and most lunches
*After dinner drinks or special wine tastings that are not provided as part of what is provided to the group
*Personal expenses  

For further inquiries or to register, click here.


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Please contact us for cancellation policy information. Travel insurance is highly recommended.





Patricia J., New York City, New York

"I've lived and traveled in a lot of countries, but I honestly can't remember a more beautiful experience - the countryside, the food, the wines, the people. Everything was about as perfect as could be."


Hob B., Seattle, Washington

"We thought ourselves very lucky to be in a group of knowledgeable wine people and benefited at lot from their experience. We loved Tuscany and thought the tour was an excellent introduction to the region." 


Kelly D., Chicago, Illinois

"It was a great tour and a terrific way to get a feel of the region." 


Sally O., Fairborn, Ohio 

"I appreciate all the research that went into finding beautiful walks, great restaurants, and interesting wine tastings and tours. Thanks for a great week."


Valerie M., Midland Park, New Jersey

"I've never had better support on a bike tour. I learned a lot about wine, but also about architecture, art, food, and Italian culture. Keep up the good work!"


Nancy D., Portland, Oregon

"I feel like I've become a "mini-expert" on the wines of Piedmont. Instead of being baffled by the variety of Italian wines available, now I can say, here's something from Alba, and this little Dolcetto will go well with my dinner." 


Mary B., Atlanta, Georgia

"I really did not know what to expect. I'd never been to Italy, knew very little about Italian wines, and never had been on an organized tour. I kept saying tomorrow just can't top this, and then it did. This truly was an awesome experience."


Bonnie H., Denver, Colorado 

"The trip was awesome, just what I was looking for. ...wonderful guides who picked great hikes that were off the beaten path and very scenic and interesting. It was a good combination of hiking, sightseeing and culinary experience. They arranged for some wonderful wine tastings and dinners. (Amazing how you can hike 10 miles a day and still manage to gain weight). I also enjoyed the hotels they had arranged, very comfortable and beautiful. Thanks again!"


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This exciting region is depicted below. You can also access Google MapsTM by clicking HERE. 



*In some cases mapping may give clients a general sense of location due to changes in venue. Please inquire about specific location.

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“This was the experience of a lifetime.  It was more than a culinary excursion, it was an unforgettable life experience from learning new cuisine to finding serenity in olive country.  I was introduced to a wonderful world of Spanish cuisine and the down-to-earth lifestyle that defines Andalusia.  I cannot wait to go back!” - Opal H., Northport, Alabama

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