Vacation Home Specialist
February 03, 2014


For an Italian, there are few things more exciting and pertinent than the olive oil harvest – what this means is they will have olive oil, for the next year – oil to use on bread, in pastas, for baking, for storing vegetables for the winter. They use it for everything! Besides the grape, the olive is THE most important crop in Italy, specifically, Tuscany and Umbria.  During the last weeks of October (depending on the summer and fall weather) families, neighbors, friends, acquaintances of all ages come together to harvest the olives from someone’s grove. This is a fast job and it takes many hands – the olives need to be shaken from their trees and need to be transported to the frantoio (olive mill) as soon as possible to be pressed and bottled as soon as possible.

I have been to Italy many times and most specifically, Tuscany. It is my most favorite place on the planet so I am always happy to return each year. This past October’s trip was my colleague, Elizabeth’s first time in Europe so it was a different kind of trip for me and I welcomed the opportunity to see Italy through the eyes of someone who has never been there before. Poor Elizabeth as her introduction was not a restful one at all – In 6 days, we covered A LOT of ground – almost 50 villas and 2000 km on those windy country roads of Tuscany and Umbria.

Most Americans will plan a vacation to Italy for the summer. This makes complete sense for families with school-aged children and the summer is a wonderful time to visit – however, it is more crowded with tourists from all over the world and prices for everything are their height. Of course, there is nothing like lazing by your pool during the summer, listening to the cicadas and truly relaxing – a vacation full of dolce far niente (the sweetness of doing nothing). However, another time to visit Italy, specifically Tuscany and Umbria, would be at the end of October/early November – while we were there this year, the weather was unseasonably warm and a t-shirt would have sufficed during the days and a light sweater at night.

it2At this time of the year, the gorgeous rolling hills of Tuscany and Umbria are abuzz with apes (small 3 wheeled trucks) and tractors hauling crates full of freshly picked grapes to be moved to the co-op to be sorted, pressed and aged; nets are being gathered from the ground by all ages (children, parents, grandparents, friends, neighbors – everyone drops what they are doing for this – it TRULY “takes a village” for the harvest), collecting the olives for quick transport to the frantoio for pressing into the viscous, green, peppery oil (treated like gold) which will be cherished and used for the next year; hunters (business men from the city who have country villas or the contadini) gather on weekends sporting their bright orange vests and their special cinghiale hunting vehicles for their weekend pastime of hunting for wild boar; cars parked on the side of the road in the country have people returning from the wood with wonderful hand woven baskets resting on the crook of their arms – bursting with wild mushrooms, just harvested from the forest floor; Men, accompanied by very well trained dogs, enter the woods in search of the almighty truffle – THIS is the season to experience Italy. This is when Italy comes alive and Tuscans/Umbrians specifically are passionate about this time of year.

Here are some of my suggestions of villas in Umbria and Tuscany which are PERFECT for experiencing the harvest:


Villa Ada Located in Umbria, close to the border with Tuscany – offering day trips to Perugia, Orvieto, Arezzo, Cortona and even Florence and Siena – great for a large group of friends or an extended family vacation. There is a country restaurant within walking distance from the villa and tennis courts for the guests’ use.

FiorebiancoA gorgeous villa for a family with close proximity to Todi and Orvieto – private gym on the property and has a great price!  A gourmet farm store is a short drive away to supply you with all of the bounty of the season.

Casale Cerfoglio: I fell in love with this gorgeous property – the views are outstanding – Todi and Orvieto in the distance. Great villa for all ages.

Casa LazzariLocated in Umbria close to the Tuscan border – very comfortable and stylish family villa – amazing views and very private.



La Pozza di Volpaia: Located in the heart of Chianti – situated in a tiny wine making village with two restaurants and a farm store – a true foodie’s delight! Easy day trips from here to explore Tuscany and even a short drive to Florence or Siena for dinner!

La Giara: Live like a Florentine noble in this foodie’s heaven – set among the olives and grapes –this property is perfect for someone who LOVES to cook –  a full kitchen garden, chicken coop and stocked pantry with honey from the property, jams, root vegetables from the garden etc. This is one of my new favorites – a truly sophisticated villa outside of Florence.

La Bianca: A great, small property for a family of four – very close to Siena and surrounded by olives. There is a farm across the street with Chianina cows which might be fun for kids to visit.

Allegra: Great villa for four couples just outside of Siena – there is a small village nearby which can be reached by car or on foot through the vineyard surrounding the property.

ToscanaAnd for the eco-conscious, Villa Toscana is just outside of Casole d’Elsa. This wonderful villa has been carefully renovated and restored lovingly by the Florentine owners who spend time with the guests upon arrival.


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