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Wine Geek on the Road – Tuscany


As has been noted in all of our previous Wine Geek on the Road posts, it seems that most of the world’s great wine regions happen to be beautiful. Think Napa Valley, Santa Barbara, Stellenbosch, Central Otago, Piedmont…and Tuscany. Add to this (and/or because of this), wine tourism in these has helped create a ‘support system’ of hotels & restaurants of all levels, tilting towards luxury in the last several years. Tuscany is one of the regions that has elevated their wine tourism game dramatically over the last couple of decades, and we the wine world is much the better for it.

On that long list of stunning wine regions, Tuscany is probably near the top—both in beauty and in visits from Americans. Napa is #1 of course due to ease of access. Geek had the great pleasure of visiting Tuscany and all of its far-flung sub-zones

last January and will happily share some details and suggestions for our customers to use…once we can travel to Europe again.

Though Geek’s trip was fantastic, January would not be considered to be the best time to visit Tuscany by most. First, much to many people’s surprise, it snows there, so no use of the wonderful swimming pools that most of the nice hotels & inns have. More importantly, add the snow to the very hilly terrain and: we had to use tire chains for the entire trip—hardly ‘Under the Tuscan Sun’. The other downside is that at least one third, if not one half of the restaurants and hotels (and some wineries) are closed during this off-season month. Of course, there are still plenty of places to stay and eat, but we had to skip a couple of favorite stops since they were chiuso. The good news however is that there are no crowds: you can actually walk thru Siena without the usual swarm of tourists. Also, the hotel rates are downright cheap and when visiting wineries, it seems they have all day to chat with you.

For the uninitiated, Tuscany is pretty big—a bit smaller than the state of Oregon. This isn’t driving from Calistoga to Carneros in an hour or so and covering ‘all’ of Napa Valley; just visiting the ‘Holy Trinity’ of top Tuscan zones—Bolgheri, Brunello di Montalcino and Chianti Classico — would take a full day. Add to this the numerous other pockets of zones worth visiting such as the Maremma, Montepulciano, Carmignano and Chianti Rufina, and we are talking several days at least. Most visitors to the area will stay in Florence where there are countless museums, restaurants, hotels and shopping (of course) and day-tripping to the various zones. But it is a good 45 minutes to an hour to the closest hive of activity, i.e. Chianti Classico. In Geek’s opinion, if going on a wine trip more than a vacation, stay in the Classico zone—or at least in Siena—you’ll be much better poised to shoot to Montalcino or the Tuscan Coast where Bolgheri and the Maremma are located. And Siena has excellent shopping should one need to scratch that itch. Bottom line, we strongly recommend a visit to Tuscany if you love wine, food and culture.


Depending on time allowed, one can fly into Florence (via a European connection) or into Rome and make the 2ish hour or so drive up from there. You will need a car: we are always amused when friends ask us if they need a car while visiting region X or region Y. If staying in Rome or Milan or Florence, not only do you not need a car, you don’t want a car. But to visit the wine regions/wineries, a car is usually required. This said, one could stay in Florence and hire a car & driver for day trips to wineries, but last we checked, that would run around $700-$800 a day. We typically recommend and repeat that renting and driving a car around Italy is pretty much the same as doing it here. No worries.


There are literally hundreds and hundreds of great hotels in the region, both in the cities (Florence and Siena) and sprinkled throughout the countryside. There is something for all tastes and budgets, but a few we’ve enjoyed:

Florence—The Continentale and The Brunelleschi. Both very lovely and perfectly located to enjoy the city.

Siena—Grand Hotel Continental. A classic, beautiful, old-school hotel.

Classico Zone—Il Borgo di Vescine and Borgo Scopeto Relais. Both gorgeous, romantic country inns.


The number of great restaurants in the area is epic. Yes there is some ordinary/touristy food—mostly in Florence, Siena and San Gimignano, but in those cities there are GREAT alternative, and for a real slice of Tuscany, the restaurants and Inns in the countryside can be outstanding. Just a few recommendations:

Florence—IO Osteria Personale, Cibreo, Osteria dell’Enotecca, Cantinetta Antinori. And for the greatest lunch of your lifetime: La Loggia Restaurant at Villa San Michele hotel in Fiesole in the hills above Florence. A great wine list and the best view in Florence.

Siena—Osteria Le Logge, Tre Cristi Enoteca, Salefino. All great, authentic restaurants with cool wine programs

Countryside—La Locanda di Pietracupa, Da Delfina, Il Falconiere.  So, so many great places out here, but these are three GREAT ones. The recommendation is to pick a place near where you are staying: the country roads after dark–and after some Chianti—can be treacherous.


As with the great restaurants, there are gobs of cool places to visit, large and small. Where any potential visitors might want to visit is based on their personal preferences, so it would be unnecessary to list a bunch of places here, however one place that’s a must is the incredible, half-billion dollar Antinori project—Antinori nel Chianti Classico in Val de Pesa. A stunning facility with a great restaurant to boot.

More important to consider is where in Tuscany you want to go, or better put where you have time to go…because there is much that is worth seeing. As referenced above, the three ‘main’ sub-zones that are sorta musts are: Chianti Classico (the classic wine region that reflects the whole Under the Tuscan Sun vibe), Montalcino (in southern Tuscany, the home of Brunello di Montalcino, the ceremonial king of Tuscan reds), and Bolgheri (on the Mediterranean coast, an area where Cabernet is king, boasting wines such as Sassicaia, Ca’ Marcanda, Guado al Tasso to name a few). One can easily squeeze in visits to these three area in three full days.

Go see the world!

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