Going It Alone: How to Plan Your Own Wine Tour in Tuscany

Not everyone who comes to Tuscany wants to take an organized wine tour.

There, I said it.

And considering that we've spent many years taking people around Tuscan wine country, you might expect me to try to convince you otherwise.

But actually, you absolutely can visit wineries in Tuscany on your own — and if that's how you prefer to travel, you should.

You just need to know a few things before you set off.

Because wine touring in Tuscany isn't quite like wine touring in some other parts of the world. You generally can't drive along a wine road, spot a tasting-room sign, pull in and work your way through six wineries before dinner.

Most Tuscan wineries are working farms. They're scattered across a surprisingly large landscape. Many are small, family-run estates. Visits usually need to be arranged in advance.

And those beautiful winding roads through the vineyards?

They're beautiful partly because they're winding.

So if you're planning your own day in Tuscan wine country, here's how I'd do it.

First: Choose a Wine Region, Not a List of Wineries

This is probably the most important piece of advice I can give you.

Tuscany is big.

It may not look enormous on a map, and names like Chianti Classico, Montalcino, Montepulciano and San Gimignano can all seem tantalizingly close when you're sitting at home planning your trip.

They're not.

Or at least, not in wine-tour terms.

Trying to visit a winery in Chianti Classico in the morning and then heading down to Montalcino for another tasting in the afternoon might technically be possible, but frankly, it’s a little silly.

But why?

You'll spend a large part of your day in the car, watching Tuscany through the windshield instead of actually experiencing it.

Choose an area and stay there.

If it's Chianti Classico, spend the day in Chianti Classico.

If you've always dreamed of drinking Brunello in Montalcino, make Montalcino your destination.

If Vino Nobile di Montepulciano is calling your name, give Montepulciano the day it deserves.

You'll see more by trying to see less.

And that, incidentally, is a fairly good rule for Tuscany in general.

Tuscan Wineries Aren't Necessarily Tasting Rooms

This sometimes surprises visitors.

In some wine regions around the world, wine tourism revolves around tasting rooms with regular opening hours. You arrive, walk up to the counter, choose a tasting flight and move on to the next winery.

Most of Tuscany works differently.

Many wineries are relatively small agricultural estates where the person welcoming you may also be involved in making the wine, working in the cellar, managing the vineyards or running the family business.

Your appointment matters.

Of course, there are larger estates with dedicated hospitality teams and tasting rooms, and wine tourism in Tuscany has become much more organized over the years.

But you should never assume that you can simply show up.

That handwritten sign saying Vendita Diretta means they sell wine directly from the estate.

It doesn't necessarily mean someone is standing behind a tasting counter waiting for you.

Book Your Winery Visits Ahead

Once you've chosen your region, start contacting wineries.

And preferably don't do this the night before.

Some wineries can accommodate last-minute visitors, particularly outside the busiest periods, but the smaller and more interesting producers may have limited availability.

When you make your reservation, find out exactly what you're booking.

How long is the visit?

Will you see the cellar?

Will someone explain the vineyards and the wines?

How many wines will you taste?

Is food included?

What is the tasting fee?

Do they offer lunch, or should you make a separate restaurant reservation?

There is a big difference between a 45-minute tasting and a two-hour estate visit, and knowing this beforehand makes planning the rest of your day much easier.

And if your plans change, please let the winery know.

At a small estate, someone may genuinely have rearranged their working day to be there for you.

Two Wineries May Be Plenty

I know.

You're coming all the way to Tuscany.

You love wine.

Surely you should visit as many wineries as possible?

Not necessarily.

A proper winery visit can easily last an hour and a half. Sometimes two.

Then there's the drive to the next estate.

And the wrong turn.

And the photo stop.

And lunch.

And that little village you suddenly decide you want to walk around because it looks beautiful.

Before you know it, your carefully constructed itinerary is running 45 minutes late and you're speeding along a Tuscan back road while somebody is trying to call the next winery.

That sounds a little stressful, right?

For most people, two good winery visits in a day are enough.

Three can work if they're relatively close together and the timing makes sense.

Four?

Now you're collecting wineries rather than experiencing them.

Don't Choose Wineries Only Because You've Heard of Them

It's completely understandable to want to visit a famous winery whose bottles you've seen back home.

And some of Tuscany's celebrated estates offer excellent visits.

But don't overlook the little guys.

One of the wonderful things about Tuscan wine is the enormous variation between producers. A highly polished visit at a prestigious estate and an hour spent with a small family producer can both be fascinating, for completely different reasons.

If you're arranging the day yourself, I'd try to create some contrast.

Perhaps visit a larger or more famous estate and then a small organic producer.

Or compare a very traditional winery with someone experimenting with different techniques.

You don't need three versions of the same experience.

And remember that the most famous wine isn't automatically the most memorable winery visit.

Sometimes the bottle you remember years later is the one you tasted around a kitchen table with the person who made it.

Plan Lunch

This deserves its own section.

Please don't assume you'll simply "find somewhere."

You probably will.

Eventually.

But it may be 2:47 in the afternoon by then.

Italian restaurants operate on Italian restaurant hours, particularly once you get away from heavily touristed areas. Kitchens don't necessarily remain open throughout the afternoon because you happened to spend an extra 45 minutes discussing Sangiovese.

Some wineries offer food.

Some offer full lunches.

Some give you a few bites with the wines.

Some serve nothing at all.

If food isn't part of your winery visit, book a restaurant.

You want to balance your intake of wine, water and food throughout the day, so you can still give your full attention to that second winery visit after lunch.

Now We Need to Talk About Driving

There is one fairly obvious problem with organizing your own wine tour.

Wine tasting involves wine.

And somebody has to drive.

This is something you really need to decide before the day begins, rather than after your second tasting.

Tuscan country roads can be narrow, winding and unfamiliar. Add alcohol to that equation and things become considerably less romantic.

Have a designated driver, arrange a private driver for the day, or make another sensible transportation plan.

And here's another useful thing to know:

You are allowed to spit.

Really.

Nobody at a winery will be offended.

Winemakers do it. Sommeliers do it. Wine professionals do it.

If you're driving and still want to taste the wines, use the spittoon.

That's what it's there for.

Tip for those who like to drive in style. You can rent a classic car for the day with our friends - they can deliver the car or you pick it up in Poggibonsi! Rent a Classic Car

Don't Underestimate Tuscan Roads

Google Maps (definitely the way to go) may tell you that two wineries are 23 minutes apart.

Treat this information with a certain amount of Tuscan skepticism.

You may encounter narrow roads, gravel roads, tractors, cyclists, roadworks, confusing entrances and gates that don't appear to lead anywhere.

The winery address may correspond to the estate rather than the exact entrance you're supposed to use.

And mobile reception isn't guaranteed everywhere.

Give yourself a buffer between appointments.

If Google says 25 minutes, don't schedule your next tasting 25 minutes later.

And download your maps before you leave if you're heading somewhere particularly rural.

Getting slightly lost in Tuscany can be charming.

Getting slightly lost when you're already late for an appointment is considerably less so.

Leave Space for Tuscany to Happen

This might be my favorite piece of advice.

Don't over-plan the day.

One of the joys of traveling independently is that you don't have to be anywhere every minute.

Perhaps you'll stumble across a beautiful village.

Perhaps you'll want an espresso.

Perhaps your winery host is fascinating and you end up talking for another half hour.

Perhaps you'll simply see a view and want to stop the car.

A schedule that looks beautifully efficient on paper can make for a surprisingly exhausting day in reality.

Tuscany rewards people who slow down!

Buy Wine - But Have a Plan for Getting It Home

Of course, at some point you'll taste something wonderful and decide you need twelve bottles of it.

Before getting carried away, ask the winery about shipping.

Many Tuscan estates are accustomed to shipping wine internationally, but where they can ship, how much it costs and how the process works will vary.

If you're planning to put bottles in your luggage, check your airline allowances and the customs rules for the country you're returning to.

Don't automatically assume that buying at the winery means you're getting a dramatically cheaper bottle than you would back home.

But buying directly from the producer is wonderful because you know exactly where the bottle came from. Opening it six months later can transport you straight back to that afternoon in Tuscany. It's one of the best ways of reliving your Tuscan holiday, and by buying directly, you've supported a Tuscan farmer too.

A Little Wine Homework Goes a Long Way

You don't need to become a sommelier before you come.

But knowing a little about the region you're visiting will make the day considerably more interesting.

If you're going to Chianti Classico, learn why the Black Rooster matters and what Sangiovese tastes like there (read more here).

If you're heading to Montalcino, know the basic difference between Brunello and Rosso di Montalcino (read more here).

If you're visiting Montepulciano, remember that Vino Nobile di Montepulciano is a wine, while Montepulciano d'Abruzzo is something entirely different (read more here).

That one alone may save you an awkward conversation.

You don't need to memorize regulations and percentages.

Just arrive curious. And ask questions.

Most wine producers love talking to someone who is genuinely interested.

And Finally: Don't Try to Recreate an Organized Wine Tour

This may sound strange coming from someone who organizes wine tours for a living.

But if you've decided to explore Tuscany independently, take advantage of the fact that you're independent.

Don't try to squeeze our eight-hour itinerary into your rental car.

Do fewer things.

Stay longer.

Have lunch.

Stop in a village.

Buy some cheese.

Sit somewhere beautiful.

There are, of course, advantages to going with someone who knows the territory.

A good wine tour isn't simply transportation from Winery A to Winery B.

It's knowing which producers make sense together. It's knowing which back road is worth taking and which "shortcut" absolutely isn't. It's understanding what you're seeing in the vineyards as you drive past them. It's asking questions you didn't know you had. It's translating not just the language, but sometimes the culture around wine.

And, perhaps most importantly, it's allowing everyone in the car to drink the wine.

We've been doing exactly that at Grape Tours for many years, and naturally we think it's a pretty wonderful way to experience Tuscan wine country.

But it's not the only way.

If you're going it alone, my advice is simple:

Choose one wine region. Make a couple of good appointments. Don't rush. Book lunch. Drive responsibly. Ask questions. Leave room for the unexpected.

And please don't measure the success of your day by how many wineries you managed to visit.

Two wineries, one long lunch, a wrong turn and a case of wine coming home with you?

That sounds like a pretty successful day in Tuscany to me.