Italy

October should be OK. Still nice weather but not too hot. Crowds should be smaller, too. Fly to Venice, back from Florence. The best hotels are also most expensive. Google the hotels and check the Trip Advisor. Have one day (at least) for each Siena and Florence.

Thanks for response IIja.

Gina,

1. I usually find May/June or Sept./Oct. are the best times. There can still be crowds during those times, but not as many as in July and August. Travelling too early or too late can also be a bit of a gamble, as weather may not be as favourable.
2. The answer to that may depend on where you're flying from. As you didn't indicate that, it's difficult for those on the forum to offer more specific suggestions.
3. The "best" hotels for one person may not be the same for another. You need to provide more information on your price range and the comfort level you want. There are lots of hotel suggestions in the RS Italy guidebook, so you might find it helpful to buy a copy and pack it along on the trip. There's lots of other good information in the books too.
4. I suppose Siena could be covered in a day, although at least two nights there would be better. Spending only one day in Florence wouldn't allow you to see much. At least three nights there would be better.

How are you planning to travel between cities during your time in italy?

Hi Gina, you have chosen wisely for a short trip. Are you flying in from US/Canada, elsewhere in Europe, or somewhere else? I myself think the best months are April, May and October. June, July, August and even September are the hottest and most crowded with travelers. The winter months, Nov thru March can be good, but you can also run into more bad weather. As for flying, the ideal would be to fly into Venice and out of Florence, or vice versa, so you don't spend time or money backtracking for your departure flight, but the area you have identified is pretty compact, so flying in and out of either Venice or Florence would probably be OK too, or even in and out of Milano if that is a lot cheaper. Just realize that if you schedule a morning departure flight, you will likely need to spend your last night in the same city as that airport. Florence and Siena certainly cannot be adequately visited in the same day. For most people, Florence merits at least two days given its beauty and many wonderful sites and museums, and Siena is an hour away and also merits at least a full day. Many people stay in Florence and make Siena a day trip, while others spend one or two nights or more in Siena. If you have seven nights, one idea would be to fly into Venice for three nights and then go to Florence for four nights, and day trip to Siena, although that might make it difficult to build in horseback riding. With more nights, you might do three nights in Venice, three nights in Florence and two nights in Siena, or something like that. You could also do one or more day trips to visit other Tuscan towns, wineries, etc. either on your own or by tour. I don't know if you are traveling alone or with family or friends, but another option would be to spend some nights at an "agriturismo" in Tuscany, which is a farm which also offers lodging, usually B & B style. Some are very lovely, with pools, restaurants, and maybe horses. Most people rent cars when they stay at agriturismos, but not always. Other people here on the forum may have different ideas for you, and would certainly know more than I do about agriturismos and horseback riding in that area. For hotel recommendations, we would need to have some idea of what type of lodging you are looking for, how many people are traveling, and your budget. In those cities, you can go from very budget-priced to very elegant and expensive. You could also benefit from a good Italy guidebook if you don't already have one. The Rick Steves 2016 Italy book will give you lot of detailed information about sites, transportation, various types of hotels, etc. Happy trip planning!

1. Italy is generally very hot from the latter part of June to the earlier part of September. However nobody can predict the weather exactly so far in advance. Some years you have cooler than average summers, as in 2014, in other years you have heat in early June or late September. May or October are very rarely too hot, but occasionally have more rain than average. The cities you are visiting will be crowded throughout April to October. The slightly slowest period in those cities during that timeframe, according to government statistics, is actually end of July and particularly August. Probably because Europeans prefer seaside or mountain localities to cities during the hottest months.

2. VCE in, FLR out. However more flight options (and sometimes significantly lower prices) can be usually obtained by flying to Milan (MXP or LIN). When you make your decision, however, factor in the cost and the time of traveling from/to Milan. The train ticket costs money, and time has value as well.

3. Can't help you here. There are thousands to choose from and everybody has their own preferences. Do a search on TripAdvisor.

4. Florence needs a couple of days (3 nights, or at least 2). Siena can be a day trip from Florence (75 min by bus, 90 min by train, less than 1 hour by car, each way). Given your short stay, I don't think it would be efficient to change hotels from Florence to Siena. You cannot go horseback riding in Siena itself. But there are places where you can do so, outside of Siena, in the countryside, throughout Tuscany actually. I have no experience of specific places, but you can do a search online.

For hotels, I use www.booking.com or www.venere.com Choose first by location (so you don't get stuck too far away from sights and have to taxi in) Double check rating on Tripadvisor.com

Either airport works...fly into one, out of the other, or as others have said, check how expensive other airports might be, Milan, etc. But also consider the transportation time. That said, flying into and then out of the cities you plan to visit would be most effective use of your time (who wants to land, then have to take a train to another city? - better to take a taxi to your hotel and get started on your visit)

Florence is worth 1-2 days by itself. If you want to visit some museums, you'll need that extra time. Siena can be done in a day trip..and it's worth it. Take the bus, not the train....the bus will drop you off just outside the old city center, if you take a train, you'll have the added expense of a taxi to and from city center.

As far as horseback riding, here's a suggestion : http://www.viator.com/tours/Florence/Horse-Riding-in-Chianti-Day-Trip-from-Florence/d519-5049CHIANTI

Just don't go in the summer -- now May-Sept.

Is it your first time there? The Rick Steves Italy 2016 book provides excellent coverage of those three locations. It will be the smartest money you spend on your vacation.

You may find Milan offers more flight options.
Perhaps try and open jaw with Venice.
Venice(3) >> Florence(3) >> Siena(2) >> Milan(2)
Late September or early October would be my choice.

I just read a Fodor's article suggesting that the best time to Visit Venice is January-February (except for the 2.5 weeks of Carnevale) if you want low season rates and very few tourists. I don't think Siena would be very nice in the rain, but Florence has so many indoor sights that it works too. The soft winter light and misty mornings and evenings make Venice really magical.