The hills, food, wine, castles…they all attack your senses from every angle.  Sit in an outdoor restaurant, with glass of wine in hand, eating fresh pasta with wild boar ragu and understand how life should be lived!

I, Chuck, and two foodie friends, Dona and Nick, over many glasses of wine in the summer planned a holiday for Fall 2014.  Our criteria were great food, vineyards, and unique countryside hotels.  So the short list was Provence and Tuscany.   Tuscany won as we were in Provence the year prior.  And so the planning began.

This trip culminated in my first attempt at a Blog.  Dona and Nick thought I did such a good job on our itinerary that they talked me into setting up a site to share it with others.   And I loved writing about our travels…who would have known.

I believe in general, that when you travel you need to stay in one spot for at least 2-3 days to get a feel for the place.  I hate one night stands.  So I booked two nights in Lucca, four in a Castle south of Siena, and the last two nights in Florence (had been there twice prior but always ready to revisit).

Did my research and booked the hotels, restaurants, vineyard visits and our day trips.  And this is where I made my one mistake of the trip, the hotel in Lucca, Relais La Cappella.  The location was stunning, high on a hill overlooking the valley, and the B&B itself as was a beautiful old building.  But the owner was not hospitable.   Our flight over was the trip from hell, delays on the NY leg to Paris, and the Paris leg to Florence, culminating in a nine hour delay.  We arrived exhausted and hungry at 9:00 PM the next evening, and were told we missed dinner time (had made reservations, and called twice to let the owner know we were delayed), and basically we would have to go to bed hungry (as there were no other restaurants anywhere in the vicinity)!  So we begged to get some bread, ham, cheese, and wine, which he grudgingly set up for us.  And his demeanor never changed.  But the next B&B, Castello delle Serre, more than made up for it.

Family owned and run (it took Salvatore, the dad, 20 years to renovate) the father and son hosts were charming, helpful, and made you feel immediately at home.  Sal is a great cook and we took a cooking lesson one evening, and found out halfway through the course that we were cooking for all the guests!  We were applauded at the end of the meal, so I guess we pulled it off.

We used Castello delle Serre, located in Serre di Rapolano, as our base to visit the vineyards in Montalcino and Montepulciano as well as the hilltop towns of Siena, San Gimignano, Volterra, and Monteriggioni.  Monteriggioni is a bit touristy, but a cute medieval town with a lovely restaurant for lunch, Restorante da Remo (order the pasta with truffles and you can smell it the moment you arrive).

Montepulciano brings together the best of everything in Tuscany,  a lovely hilltop town and great vineyards.  It sits on top of a built-upon narrow ridge with tasting rooms where you can sample their delicious Vino Nobile after your climb up.  Siena is much larger, with a grand cathedral (1200’s), and the Piazza del Campo (main town square that is home to the Palio – the most infamous horse race in the world). We had a wonderful lunch in a family run, casual café in Siena (La Torre di Monte Oliveto) and the father/chef gave us his recipe for Wild Boar Stew.  Nick and I have since made it to the delight of many of our friends. It is available for anyone who would like it, just ask.

Wine and Food

We visited some wonderful vineyards for wine tastings and lunch, and an amazing wine room, Enoteco de Piazza, in the town of Montalcino.   One of my favorite wines is Brunello and this wine boutique carries them all. It is possible to taste wines from over 100 different wineries and I think we may have tasted everyone (probably one of the reasons I sent back 4 cases!).

Enoteca di Piazza Wine Room, Via Matteotti 43, 53024 Montalcino, Italy,   0577 848104

So many vineyards to choose from and so little time, try Mastro Gianni, Poggio Antico, Tenuta Fanti, and Ciacci Piccolomini. We especially loved Tenuta Fanti, family owned and run (dad was actually picking through the grapes by hand when we arrived). They prepared a light lunch with our tasting in a lovely farmhouse setting. It was the perfect afternoon. Don’t miss the Abbey of Sant Antimo on your way to or from the vineyard, where you can listen to the Gregorian chants of the monks who live there. The time varies so check before you leave for your day trip.

While in the countryside, we ate close to our hotel as we were lacking a designated driver (we all love our wine way too much). But we did eat at three memorable restaurants, Ristorante Giglio in Lucca, Ishieto Farmhouse and Davide Cannella (the most amazing, hidden gem, of the trip) near Serre di Rapolano.  Davide Cannella, in Rapoiano Terme, needs a special mention. This chef can really cook! His food is not only some of the best I have ever eaten, but beautiful to look at. The restaurant is in an old 1800’s wine cellar, hidden away in a small village that is difficult to find, but worth all your efforts. I cannot stress enough that you MUST eat here. My mouth is watering just thinking his cooking.


The highlight of this trip to Florence was the walking food tour we did with “Taste Florence”. This lovely young Tuscan woman, Toni, took us to the markets, small bakeries, the best gelato in Florence, chocolate makers, and a wine and olive oil tasting, were we got to taste numerous luscious treats.

Lunchtime is great for wine and pizza. For great pizza, with good people watching, visit Trattoria Borgo Antico in the Piazza Santo Spirito. Sit outside, get a carafe of wine, and watch the people strolling by while you feast.


Everyone has to try the Florentine steak, bistecca alla florentina, from the special white cows, Chianina. The steak is quite large and meant to be shared by the whole table (with a price tag to match). It’s eaten very rare, so don’t even try to ask for it medium as most chefs will “just say no”. We had ours at Osteria da Giovanni and weren’t disappointed.

Did all the regular touristy rounds, i.e.: Uffizi Galleria, The Accademia (David), The Basillica di Santa Maria del Fiore, Foret di Belvedere, and wished we had another week to stroll leisurely.   Ahhh, next time.

Misc. Tips

Car Rental – got a great deal from Europe Co. and it was quite a bit cheaper than the big guys. We don’t get their insurance as we paid with AMEX. The car came with GPS that got us everywhere. We got the car at the Florence Airport and dropped it off in Florence proper, one block from our hotel, for no additional charge.

Shipping Wine Home – is very, very expensive, so unless it is a special bottle you can’t get at home, don’t do it. I learned my lesson in sending home all that wine (seemed like a good idea after a few glasses!).


Olive Oil – Only buy reputable extra-virgin and make sure the bottle does not allow much light inside.  Look for details on the bottle, i.e.:  date harvested, name of farm, and expiration date.  Some reputable labels of high quality:

  • Chiarentana – considered among the best olive oils in Tuscany (
  • Il Palagio – organic farm in Chianti (
  • Manni – Thomas Keller’s pick used at Per Se (
  • Altomena – outside of Florence ( & at
  • I Greppi di Silli – between Siena and Florence, the farm produces 7 different varietals (
  • Fattoria Ramerino – organic farm south of Florence, Bagno a Ripoli (
  • Balduccio – made near Pistola and considered one of the best in the area (
  • Intini – organic and conventional oils in Puglia, near Alberobello (
  • Stasi Aziende Agricole – farm in Puglia (
  • Galantino – Puglia farm making olive oil since 1926 (
  • Le Tre Colonne – small family run farm in the north of Puglia (
  • Panarale – Puglia family making olive oil for four generations (





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