Flight Option Boston to Tuscany area

If you find a good deal to Florence, you’ll be closer to your departure airport and you won’t need to move the last night to spend the night in Rome (or elsewhere) to catch the plane the next morning.

The best connections to FLR are with Lufthansa via Germany (Frankfurt or Munich), with Air France (Via Paris CDG), with KLM (via Amsterdam), with Swiss (Via Zurich). However CDG is a humongous airport which makes any connection difficult.

If you can’t find any reasonable fare to FLR, then I’d go for a non stop from BOS to Rome FCO. Going to Bologna BLQ would still require a layover somewhere in Europe (neither FLR nor BLQ have flights to North America) and although Bologna is one hour closer to Florence than Rome, however the time difference would still not offset the benefit of a non stop flight. And you still would need to spend the last night in Bologna (instead of Rome).

Don’t forget that you will need in any case to spend the last night in the city you depart from because flights to North America depart in the morning.

Try www.kayak.com
From BOS to FLR.
If nothing reasonable is available, then try BOS to FCO.
When comparing airfare prices take into consideration that if you fly to FLR you will save 45€ per person each way in train fare, plus you will avoid an extra hotel night in Rome, and the 48€ taxi from Rome to the FCO airport (the taxi from Florence to the FLR Airport is half as much). So even if flying to FLR costs you more than $300 extra, it might be worth it still.

Roberto's point about considering total cost is a good one that is often overlooked when grabbing a lower airfare. For the Tuscan area we fly from Boston into Pisa PSA for several reasons usually on Lufthansa via Munich as the Bos-Munich flight leaves at 8:30 PM so you get a better (but still bad) night's sleep. The terminals at PSA are more spacious, the car rental area at Pisa is much better than FLR, the train connection is very easy, and there are numerous bus connections. Also FLR tends to have more flight delays due to runway designs. Some of these considerations may have changed recently as FLR is undergoing a major overhaul. For what it's worth 6 nights in Siena is a lot, it's quite a small city.

To find flights use https://matrix.itasoftware.com/#search:research=BOSFLR-FLRBOS

Hopefully this came up with find the lowest fares. When you find one you like go to the airlines site to purchase.

Thank you all very much for your feedback....this was really helpful. Very good point about making the right comparison for value. I am going to look now! Thanks again.

If BOS has a connection with Lufthansa to Munich that is the best airport to connect. There are at least 3 flights daily from Munich to Florence. Frankfurt is bigger but they improved it now as they use upper also lower floor if the same terminal therefore changing planes simply means taking the escalator rather than the long walk required years ago. There are 5 to 6 flights a day to FLR from FRA.
I don’t recommend Pisa in your case because the flight back is in the morning and you would need to sleep in Pisa on the last night. Florence has a new terminal now so it’s not as small as 5 years ago.
FLR new airport project plan received the final approval today in Rome (after years of battles with NIMBYs and courts), so the issues with that airport (mainly short runway) will finally go away in a couple of years.