Tuscany and Umbria, Italy

I love this magical world of rolling hills, vineyards and serene sunsets in central Italy.  I backpacked in Florence right after college, visited Tuscany in 2006, stayed in Umbria in 2009 and rented a villa with my amazing family near Sienna in 2013.  I would highly recommend staying in a little B&B or villa.

Top 5 Days

1. Gubbio – This is an austere, medieval town hanging on the side of a mountain that makes for a perfect town hike on a Sunday afternoon.  The town doesn’t have a lot of tourists – the only folks that are going out of their way to see this authentic town are there for the ceramics or to see the Piazza Grand overlooking town.  It is nicknamed the City of Silence and you will feel like you stepped back in time.
2. Hiking the Hills – Definitely try to stay someplace where you can hike the local hills from right outside your door.  You can visit little hilltop towns or just meet the locals on the way.
3. Hit the vineyards – This can be easier to do in Tuscany than in Umbria because they are around every corner.  Your villa hosts or the locals will make great reservations.  If the area isn’t too hilly, you can do it on a bike. We loved Castello D'Aalbola newar Radda in Tuscany. Sign up for the tour and do lots of tastings.
4. Take a Cooking Class – What better way to learn about the local food?  We took a class at Villa Bordoni that included making fresh pasta.  Somehow I can never seem to replicate the food in the States.
5. Drive the Countryside -  We loved driving in a tiny Fiat Panda through the countryside.  I can’t say enough about the Panda.  Despite its meek appearance we were able to take the car through some off-road terrain that would have given a Range Rover some trouble. It seems like every little town is more perfect than the next.  

Top 5 High Style, Low Maintenance Hotels

1. Chic Retreats - The best place to find a cute little private place to stay up in the hills is on chicretreats.com.  This London gal definitely finds great little gems that are high style and most are low maintenance.  You pay $15 to join and get 10% off any of the places you book, so it is well worth if even if you stay one night.
2. Villa Bordoni-  These English restaurant owners spent years searching for the ideal property in Italy to open a luxurious but unpretentious country house hotel and found it in Florentine Chianti.  When they found it, Villa Bordoni was in a dire condition and slowly decaying into the poetically beautiful landscape which surrounds it.  But they opened this 10 room boutique hotel and you can see the love they put into it.  The food and tiny bar are precious.
3. Palazzo Terranova – High upon the hills of Umbria you will find a Palladian-inspired palazzo with dream views of the valleys below.  Pallazo Terranova  is up a windy dirt road and sits on 30 acres of idyllic countryside perfect for hiking among farmhouses and stone homes.  There are only 8 rooms and we stayed in the La Boheme room with big windows overlooking the valley.   For those travelers that are fishing enthusiast, there is even a small pond which is located about a 10 minute walk from the villa with loads of bass.  The place is quite flush and a bit fancy – we would have been just as happy staying at a smaller, less expensive place in Umbria so only stay if you are feeling extravagant.  Unfortunately, vineyards were at over and hour away.
4. Villa del Cielo with Caminetto - we stayed in this wonderful 7 bedroom villa right outside of Sienna.  It had a pook and was a converted chapel.  Quirky but cool.  It was a bit chilly as we had unseasonably cool weather in May but a summer stay should be fine.
5. Mr. and Mrs. Smiths - Check out their website or books for ideas.  Lots of Italy options.

Top Foodie Finds

1. Taverna del Lupo- This 5 star food find in Gubbio was one of the most simple, delicious lunches in all of Italy.  We got this recommendation from Mario Bartelli’s website, who recommends regional local cuisine all throughout Italy.  We had the most wonderful rustic vegetable bean soup with olive oil and crostini and ham, porcini and pea lasagna that was more like a crisp pastry.
2. Truffles – This is the land of truffle mushroom country and makes for fantastic risottos and fresh pastas.
3. Salamis and Hams – Even the truck stops have beautiful cases of prosciutto ham and salamis to choose from.
4. Osteria – this is a perfect place to stop for a thin-crust pizza in Citti de Castello.
5. Villa Bondoni – The food in this small kitchen was suburb and the chef takes great pride in every dish.

Top Tips

1. Don’t be too picky about location – There are so many darling hilltop towns and villas in the remote areas, that you should just pick a villa you like maybe near a town you are interested in the right price range and go for it.  I could be happy with so many locations. We loved Sienna, Radda and Montepuciano.
2. Car rental is easy – Rent the most basic, small car and you’ll have a blast zipping through the incredibly clean and well-marked motorways and small dirt roads.  We got the navigation tool from Hertz and it made it even easier.
3. Know a few key Italian phrases – Unlike the big cities, many of the locals don’t speak a lick of English, so make sure to know a few phrases and bring your phrasebook for binds. Ciao!, Buon Giorno, Per Favore, and Grazie go a long way.
4. Skip July and August –This can be really hot and August can be odd, as all of Italy is on holiday and head for the beach.  May, June, September and October are ideal.
5. Italian Trains – The train system here is clean, efficient and an easy way to travel.  You can easily hop to all the major cities.  Just search online first for time tables. 

Top Misses

1. Skip an overnight in Florence – If my time was limited in Italy, I would go for more time in the smaller towns.  There is fantastic art here but Firenze is quite touristy – without the intensity of a cool bustling city like Rome.  Maybe pick a villa to stay at within an hour’s drive and just go for the day.
2. Check the Euro – The value to the dollar has been all over the map the last few years.  If it is outrageous, opt for really cheap apartments and save your money for a delicious pasta.
3. Don’t move too quickly – It is tempting to want to hit a new place every night since there is so much to see in Italy.  But stay at each location at least 2 or 3 nights so you aren’t spending all your time traveling and to get a bit of information on a place.
4. Heels – Your Manolos may be from Italy but they don’t fit the cobblestone streets.
5. Look for hidden costs – With the small local-owned villas, be clear to settle on a price beforehand (like your extra 10% for Chic Retreats) and make sure it comes off your bill.  And dinners, waters and drinks can rack up at these places.  It seems like you are staying at a friend’s place, but these are still hotel prices.