My wife and I will be going to Italy for 3 weeks in October. Using all the websites and guidebooks, I have pretty well worked out what we want to do. 5 nights Rome, 4 nights Florence and 4 nights in Chiante and 4 nights in Montepulciano.
I am ready to start booking hotels, trains and a car. I am concerned about booking through Italian websites as I have no recourse if there are issues. Also, after checking and comparing rates between Hotel and car rental websites, it looks like it might be cheaper to book everything through a travel agent that specializes in Italy. As we are based in Toronto, with a large Italian expat communities and a number of Italian Travel agencies, I was wondering if anyone had an opinion or advice on the benefits of self booking or booking through a local travel agency?

I'm not the best person to be giving advice, but I just booked by trip to Italy. I found that contacting the hotel directly usually got me the best price.

I email the hotels directly. Car rental I do via the company web site, and mostly I wait until I'm Italy to buy train tickets. I don't know what you mean about no recourse. If you charge to a credit card, you can always contest the charge.

Mike...

I just returned from three weeks in Italy today... I'm a little weary, so will keep it short...

Car rentals... I booked through AutoEurope prior to leaving for Italy... best rate I could find... I picked up and dropped of the car in Florence. A Volkswagon Polo... 10 days rental cost me Cdn$482.00 (approx. Euro 300.00) All insurance included. No complaints...you don't need or want a car for Rome or Florence..

I did 5 nights Rome.. 4 nights Florence, then rented the car.. one night Lucca.. one night Sienna... one week vacation rental in Montepulciano (Le Manzinaie)...it was great, I highly reccommend it. from there you could take day trips into chianti if you wished. After that we railed from Florence to Venice for two night and then rail back to Rome for one night and then fly home.

If I were you, I would reduce Rome to 4 nights.. do 4 nights in Florence...rent a car and find a vacation rental for a week in either Chianti or Montepulciano area, then perhaps one or two nights roaming around Tuscany or Umbria.

If you want to e-mail me for any suggestions, feel free, as my itinerary was almost identical to what you are suggesting...

Train tickets... buy them when you are in Italy, perhaps one or two days before you travel..

Regards

Mike

Mike,
I travel to Italy from Toronto. I book the air with my travel agent...business class seats on Skyservice through Alba Tours. But in the future I'll probably go with Air Canada...as they are starting to fly to Rome (non-stop).
I use the click thrus on this message board to book the car with Auto Europe...works out great and is very reliable. ( one year I booked rental with Canadian tour company and had a bit of a problem but they did compensate me quite well.)
And I have also used the click thru on this message board to book apartments and hotels...Venere. These have worked out very well for me also, they did not charge my credit card...just put it on hold. I paid cash at the end of my stay.
There are many recommended apartments, vacation rentals, and some hotels on this site you can read about. Good Luck.

Thanks to all for the advice. I will start booking on-line - except trains, which I will book in Rome).

Hi Mike,

Next month will be my 4th trip over to Italy. I've used initaly.com for most of the arrangements and been very happy with them. Their prices are slightly cheaper than direct with the hotels and they do a great job in screening out nice places. Their site also connects you with AutoEurope for rentals at a slight discount as well. Good luck!

Also, if you reserve a car with AutoEurope, check their Web site every so often for deals. If you find a better rate, they will give you that rate on your reserved car.

If you book directly through the hotel Web sites, always look for special deals or Internet specials...sometimes they are very good.