The short answer

Two of these trips are fixed to a harvest and cannot run at any other time of year: the olive harvest in Soriano every November, and the chestnut festival with the grape harvest in late September. The other three run all season, sited permanently in wine country. On all five the wine is central rather than incidental: small family-run wineries, and time with the people who actually make it.

Two of These Only Exist in Season

You spend the morning in the groves picking olives. Then you carry the full baskets to a stone cold-press mill run by friends of ours, one of the few still working in Italy. The olives are weighed and fed into the wheels, everyone takes a turn at the mill, and you go home with a can of oil you filled yourself.

That is November in Soriano, and it only happens in November. Outside the harvest there is nothing to pick, so the trip does not run.

Guests toasting with wine at sunset on a ridge above the Atlantic coast in Portugal
A glass at sunset on the Portuguese coast. Not every trip here is about the olives.

The second seasonal trip lands in late September and early October, when a medieval chestnut festival in the same town overlaps with the grape harvest across Tuscany and Umbria. When the growers we work with say the vines are ready, we get the call and rearrange the days around it. You pick alongside them, walk a winery mid-fermentation, and we carry a little of the fermenting must back to the next cooking class and turn it into dessert.

The other three trips here are not tied to a harvest, and we will not pretend otherwise. They are our usual trip, permanently sited in wine country.

Barolo and Roero speaks for itself. Tuscany-Umbria runs through Montepulciano, where a fourteenth-century cellar sits under the Ricci Palace and almost no visitor finds it, and through Montalcino, where Brunello comes from small family producers rather than commercial houses. Portugal is centred on Porto, one of the oldest formally defined wine regions anywhere, and a completely different tradition from the Italian trips.

Guests gathered on a flower-lined stone stairway in Pitigliano
Pitigliano in southern Tuscany. Small towns, small producers.

On all five we go to the small, family-run wineries rather than the corporate ones. The tasting is a conversation with the person who made the wine, not a transaction across a counter, and there is time to stay a while.

We try to balance the names you know, Brunello, Vino Nobile, port, against the ones nobody outside the region has heard of, made in quantities too small to leave the country. You go home able to tell a real story about a particular bottle: who made it, why that blend, what the room smelled like. Not a tasting note off the back label.

Wine on Every Week We Run

Two of these are fixed to a harvest and can only run in season. The other three are our usual trip, sited in wine country. Review counts cover every guest, not a wine-drinking subset: we do not collect that.

Harvesting olive it is one of the experience we offer in our Umbrian Vacation. Spend a day harvesting and press olives
Tuscany / Umbria, Italy

Wine, Cooking, & The Olive Oil Harvest - Soriano

Harvest Olives & Make Your Own Olive Oil in Umbria, plus Cooking Classes, Tuscan Wineries, Sightseeing and More.

25 guest reviews

8 days, 7 nights, all 20 meals included

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sagra_sword.jpg
Tuscany / Umbria, Italy

Medieval Chestnut Festival & Wine Harvest Season

Two Weeks Only In October - Experience the Magic of our Medieval Festival & Harvest Season!

16 guest reviews

8 days, 7 nights, all 20 meals included

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All of our food is made with fresh local ingredients, sometimes we even get to pick them ourselves on our Northern Italy
Piedmont, Italy

Wine, Cooking and Castles in Barolo & Roero

A week of cultural immersion and local experiences amidst the backdrop of one of the most pristine wine areas in all of Italy.

33 guest reviews

8 days, 7 nights, all 20 meals included

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prosciutto_soriano.jpg
Tuscany / Umbria, Italy

Wine & Cooking Under the Tuscan & Umbrian Sun

Local Living Cooking Vacation with Wineries, Olive Mill, Cheese Making & Sightseeing in Tuscany, Umbria and Alto Lazio

413 guest reviews

8 days, 7 nights, all 20 meals included

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The Duoro Valley, where grapes are grown that are destined to become Port Wine.
Porto, Portugal

Portugal: Family, Culture, Wine & Cooking

A week of true cultural immersion & local traditions with the wonderful people of Portugal. Discover Port wines in Porto, explore the Douro Valley UNESCO World Heritage Site, breathtaking towns, & cook local dishes.

41 guest reviews

8 days, 7 nights, all 20 meals included

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Wine Tasting, Region by Region

When November rolls around, there is a chill in the air and a chance for rain, but every year those that are willing to deal with a little cold weather get a huge reward: The Olive Harvest.

Like clockwork, it always begins on November 1st and runs through the month. The prize for those that are with us during this period is both amazing and truly exclusive.

Thousands of people come to Italy for the Olive Harvest. They come because this is the time for "Olio Nuovo" (New Oil), which is liquid gold, with flavor words simply cannot describe. Most of them come and simply get the new oil.

Fewer come to visit one of Italy's main olive oil mills. And a very select few come to actually participate in the olive harvest, getting the chance to experience the picking of olives that will become the oil they take home.

But OUR guests take it an extra step, and this is a truly exclusive experience. On one morning of our time together, we will make our way to an olive grove in Umbria -- Umbria is known for the best olive oil. We'll spend the morning harvesting olives together. Once we have harvested a certain amount, we will take our baskets to our bus and head to the olive mill.

The mill we go to is owned by close friends of ours and is one of Italy's few remaining "Traditional Cold Press" olive mills.

We will bring our olives inside and weigh them. We'll then dump all of our olives into the mill, where we will watch the huge stone wheels crush them.

Finally, each of us will take a turn actually operating the mill as we layer the crushed olives onto discs that will be brought to the press.

Finally, while OUR olives are being pressed, we will have lunch with the family and do a wine tasting, as this mill is also a winery.

After lunch, one by one, we will each take a one-liter can and fill it with the olive oil we just made, directly from the press.

This experience is something that cannot be properly described. It is truly a life experience you will never forget. All of our guests leave this day with a natural high, unlike anything they have ever experienced.

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In late September and Early October, harvest season is in full swing in Tuscany and Umbria. Many of our friends are wine growers, and when they are ready to harvest their grapes, we get a phone call!

Once we get that call, we make some quick alterations to our schedule and head down to the vineyard.

We spend a morning with our guests at the vineyard harvesting the grapes (we try to harvest more than we eat), filling the baskets, and bringing them up to the winery. Once we have done so for an hour or two, we have the opportunity to get an in-depth visit to a working winery during the winemaking process. This is something our guests never forget!

We'll have lunch together, then we are on our way. We'll always bring a little of the "Must" (fermenting wine) with us, which we will then use in a spur of the moment dessert recipe at our next cooking class, of course!

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We seek out some of the most wonderful wineries in Italy for wine tasting. For us, the vineyards we choose are as much about the wines produced as they are about the winemakers themselves.

We tend to avoid the large corporate wineries (unless you choose to do so on a custom tour), instead, we choose smaller, family-run operations where we have the opportunity to spend time with the owners and winemakers themselves.

We get to know the people because, for us, the people that make the wine are a huge part of the story. After all, you may have a greater appreciation for a certain wine if you have visited the place it is produced, but you will have an infinitely greater appreciation when you can say you have broken bread with the person that is behind the wine.

Our guests will go home having visited the wineries, tasted the wine, and they will have befriended the people behind it. Our guests uncork that bottle with their friends back home and tell stories about Leonardo, and why he chose that particular blend. They tell stories about the lunch they had with Fiorella, and how she made her name in the male-dominated world of Brunello wines in Montalcino, Tuscany.

We further strike a balance between the big names you probably know already, like Brunello, Vino Nobile, and Marsala and the amazing unknown wines that most foreigners have never heard of like Sagrantino, Forcone, and Ruffiano.

You will go home, having not only had some of Italy's most prestigious wines, but you will bring home new discoveries to share.... new friendships to cherish... Incredible experiences that form lifelong memories.

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Montepulciano is a beautiful medieval and Renaissance hill town in southern Tuscany, but it is most famous as the home of Vino Nobile, one of Italy's most coveted wines. Besides the wonderful wine, Montepulciano is a stunning town, filled with interesting shops and beautiful scenery. It is a must-stop location for anyone visiting the southern Tuscany wine towns along the Orcia Valley Wine Trail, which is the part of Tuscany where most images we have of the region originate.

Vino Nobile

For those seeking wine tasting, Montepulciano will never disappoint. The streets are lined with wine shops (Enoteca), all offering tastings. Many of these shops have wine cellars below that they will happily show you. The most striking and awe-inspiring of these cellars is one that very few visitors ever discover, as it is difficult to find. It sits underneath the Ricci Palace, just off of the Piazza Grande, and is the town's original wine cellar from the 14th century. It is, quite literally, the birthplace of Vino Nobile.

What to See

The 'Piazza Grande' is an incredible sight, especially for those that know Florence. You will find that it looks like a miniature version of Piazza della Sigoria. Here you will find the city hall and the duomo. Followers of the 'Twilight' Saga will recognize this piazza instantly from the movie New Moon.

Just outside of town, you will find the unmistakable 'San Biagio' church, and simply walking around Montepulciano is a sight in and of itself.

Getting There

This is a destination on almost all of our tours. When we visit Montepulciano, we are granted a private tour and tasting of the Vino Nobile cellar noted above (and pictured here), and we stroll the town.

If you are not coming on one of our tours, you will find Montepulciano about 20 minutes off the A1 Autostrada. If coming from south, you will take the Chiusi exit and follow the signs. If coming from the north, take the Montepulciano exit.

Need to Know

For those with trouble walking, keep in mind that you cannot avoid hills and cobblestone streets here.

For our tour guests with trouble walking, if they feel that it will be too much for them, they have the option to be taken to our meeting point. There they can visit the San Biagio Church and relax in a cafe. They will, however, miss the Vino Nobile tasting. Unfortunately, walking uphill cannot be avoided as vehicle traffic is highly restricted here.

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Visit Castiglione and you will certainly wonder why we would have a page dedicated to it. It is tiny and doesn't seem to offer much of anything if you drive through. However, Castiglione is all about wine and oil, and the reason we love it so much is that outside of Central Italy, it is virtually unknown. The reason is that it is on the wrong side of a political boundary. Drive a few thousand feet past Castiglione, and you are not only in Umbria, but you are in "Orvieto Wine Territory".

But being on the "wrong" side of that border means that not only can they not say their wines are Orvieto wine, but they cannot be designated as "Umbrian" wines. The result is that there is no commercial market for them beyond the locals. The quality is fantastic, but the prices are rock bottom.

In addition to wine, Castiglione produces some of the finest olive oil in Italy. The volcanic rock content in their soil contributes to what is considered to be absolute premium olive oil, much better than most Tuscan oils.

We visit Castiglione in Teverina on almost every one of our cooking & culinary vacations based out of Soriano nel Cimino. When we go to Castiglione, we visit a small family-run winery & olive mill. The wines are out of this world, and the olive oil is made with their own antique traditional cold-press method. While there, we have lunch with the family, visit the cellar, and of course taste all of the wine and oil!

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Sorting by who you are travelling with instead? The same trips are covered for couples, friends, solo travelers and families. Who you travel with compares all five.

See Which Week Fits Your Season

The harvest trips sell out on the season, not on demand. See the dates, read what guests wrote afterwards, or ask us which one suits you.

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About this page. These five trips are grouped by season and region, not by a review count: we do not track a wine-drinking guest type and will not invent one, so no trip here carries a popularity badge. Review counts shown are every guest on that trip, read live from our reservation database. Harvest dates move with the crop, so the calendar is the current source.