I visit Italy at least four or five times a year, but I can never seem to align my schedule with the Palio – the famous horse race around the Piazza del Campo, which is held twice each summer in Siena – July 2nd, and August 16th.  Apparently, the actual race takes only a couple of minutes, and each year, a few of the bareback riders are thrown before making it to the finish line.  I would love to see the race someday, and I can imagine how much fun it would be to stay nearby in the days the lead up to the Palio, in the middle of all of the pageantry and anticipation. On this visit to Siena, however, I stayed at the Grand Continental, which is quite near the Piazza del Campo.  For clients who want to be in the thick of the race, I have access to an apartment that overlooks the track!

When clients find out that I am in Italy, they often ask me to “find them a villa,” and indeed few things are more romantic than an Italian villa perched on a hill in the countryside.  In fact, by the time I returned home, I had two or three Tuscan villas in mind for my own family.  When I visit a villa for clients though, I temporarily keep my romantic nature in check and focus instead on details that they are likely to take for granted.  With each home I visit, I have a few specific clients in mind, and I try to anticipate their day-to-day wants.  One thing I have learned is that the vagaries of private homes are a never-ending source of surprise.  For example, an elegantly appointed home with nine bedrooms and its own vineyard may not have air conditioning, or it may have a shower and no bathtub, or sometimes the reverse.  A lot of people are surprised to learn that king-sized beds are really an American phenomenon, and outside of the States, even very upscale hotels won’t always have them.  In general with a villa, WiFi can be a little hit or miss as well, so if you plan on working while you travel, you might be better off in a hotel. When helping someone decide between a villa and a hotel, I learn from the client what is most important to him and what are the creature comforts that he needs to enjoy his stay.  Whether the choice is hotel or villa, it is my job to then troubleshoot every aspect of the stay, making it as seamless and fabulous as possible.  No matter what clients decide, I can match them with unbelievable properties and accommodations, and as this trip will attest  -- I am always on the lookout for new places.

In between the private villa and the five-star resort, there are myriad small hotels that provide the best of both worlds for their guests.  They are quiet, hosting only a few guests at a time, charming and authentic, and they provide some of the services that you do not necessarily get with a private villa – for example, many have first-rate kitchens.  One such stop is Villa Bordoni in Chianti.  The 16th century villa has undergone a loving and painstaking restoration.  It sits on a hillside with spectacular views of Chianti below.  The food here is amazing, and if you just can’t get enough of it, you can sign up for cooking lessons with the chefs.  I didn’t have a chance to try the cooking classes on this visit, and because of the early April weather, I didn’t have a chance to linger in the beautiful walled garden either – so I have at least two reasons to schedule a return trip during warmer weather.  Despite the drizzle, the experience was utterly charming.  Shown in the photo is the magnificent view from Villa Bordoni.