agenda for flying back to Boston

Should we drive back to Florence, drop off our car and fly home that same day or stay over night in Florence for a more leisurely trip back?

Depends on what time the flight would be, and where it goes.

There are no flights from Florence to North America, only to other European cities, therefore to fly to Boston you will need to connect at some European gateway, like Paris, Frankfurt, Munich, etc. since flights to North America from those gateway cities depart in the mid to late morning, that means that your flight out of Florence to make that connection will be the first flight out of Florence, generally departing between 6:30am and 7:30am. You need to be at the FLR airport at least 1 hour or so before that European flight (Florence airport is small and security procedures are quick). You also need to drop off your car at the airport but the airport rental center opens at 8am so I presume you’ll need to drop off the car keys somewhere at the rental center and hope the shuttle is operating that early.
For all of the above reasons, whenever I depart from Florence, I sleep in Florence at a hotel the night before, even though my country home is only one hour away, and return the rental car also the day before my flight. A taxi can take you to the airport in less than 20 minutes from any hotel in Florence (the airport is close to the city center). You should do the same, unless you like to experience intense stress and anxiety.

We need your flight time to advise you.

Roberto--thanks for your detailed reply. After I posted, it dawned on me that I could drop the car off at the airport which would save a lot of time and expense. I've looked at flights and I think there are a few late am flights, so that may be a great easy solution. We're spending 2 weeks in Italy, so I'd prefer to go to straight to the airport. The drive is around 90 min.

Thanks to everyone for posting!

Since you haven't booked your tickets, you should also look at flying to/from Pisa airport. There are more car rental choices and somewhat easier car pickup/drop off. Driving in and out, and access to trains is easier than Florence. It's closer to Lucca and Volterra, and there's an easy bus to Florence as well. Our favorite Italy route from Boston is to Pisa via Munich as it's an easy transfer.

Mike,
I'm assuming you are suggesting we stay in Pisa?? Our last trip 20 yrs ago we were in Florence, but only stayed 2 days. Would like to spend more time there. We've booked an apartment for the week in Florence. We do plan on taking a train to Lucca perhaps, to Pisa too. Do you think we should visit Pisa? So much to do and sadly, not enough time!
Thanks!

I don’t recommend to fly out of Pisa in your case since you are staying in Castellina, which is closer to Florence. Pisa airport has more flights than Florence but they are largely European low cost airlines, since Pisa is a RyanAir hub. If you are looking for a traditional airline with connection at a European hub (like Air France, Lufthansa, Swiss, etc.) Florence has more options than Pisa.

You said there are flights later in the day. I know that. There are 4 to 6 flights a day to major destinations like Paris or Frankfurt, spread throughout the day. The problem is that if you intend to fly to Boston on the same day you depart from Florence, you may have to depart from Florence in the morning to make the connection on time to Boston from the European hub you choose to fly from. For example the latest flight from FRA to BOS departs at 10:50am. Paris has a later flight to BOS Departing at 1:35pm, but you still need to be in Paris by 11:30am at the latest and it’s a 2 hour flight from Florence to Paris. Munich and Zurich have afternoon flights to Boston (with Lufthansa and Swiss respectively), so those may be the only options if you want to leave later in the morning from Florence.

Robert is correct. You will need to stay over near your departure point as Castellina is a drive too far for the available flight times. The part of my Pisa comment relevant to your original question is that you don't need to fly out of Florence just because you arrive there or rented the car there.

Using skyscanner.com, found 4 one stop options that depart FLR in the afternoon ( 1210PM , 130PM, 250PM, and 320PM) and arrive BOS between 6PM and 830PM. ( Random date in May) Depending on the airline, connection is MUC, CDG or ZRH.

Taking one of the later afternoon flights would be my choice and eliminate having to make an additional hotel change to be in Florence the night before to catch an early flight.

Hi Joe,
Thanks for your help! That's what I was thinking! We are headed home on June 24. I only saw one flight on Delta that was around 12:00. I'm assuming all the flights that I'm seeing are just a plane change, not an airport change correct? We traveled a few times abroad, but it's been awhile. A bit nervous about booking the flight. Don't want to make a mistake! How long should I figure it will take for car drop in Florence, taking the shuttle and checking into our flight. We don't like stress and it's much more complicated than flying within the US. It says driving distance/time from Castelina DI Chianti is an hour but I've heard it can be confusing to find the car rental drop off. Is there ever much traffic?
Thanks again to everyone for their generous offer of help! I so appreciate it!!!
Sheila

P.S. Any thoughts or comments about best airline to fly on and car rental company?

These are your options on Jun 24, 2023 from FLR to BOS with one stop only (I excluded the early morning departures):

TAP Airlines: dep. 11:45AM arr. 8:20pm (via LISBON)
Delta or KLM (codeshare): dep 11:20 arr. 4:55pm (via AMSTERDAM) - (FLR-AMS operated by KLM)
AirFrance or Delta (codeshare): dep 9:50 arr 3:00pm (via PARIS CDG)
AirFrance or Delta (codeshare): dep 12:10 arr 8:30pm (via PARIS CDG)
Swiss: dep 10:35a arr 3:20pm (via ZURICH)
Swiss: dep 1.55pm arr 8:05pm (via ZURICH)
Swiss: dep 2:50pm arr 8:05pm (via ZURICH)
Lufthansa: dep 10:30a arr 3:25pm (via FRANKFURT) - (FLR-FRA operated by AirDolomiti)
Lufthansa: dep 1:30p arr 6:00pm (via MUNICH) - (FLR-MUC operated by AirDolomiti)
Lufthansa: dep 2:40p arr 8:25pm (via FRANKFURT) - (FLR-FRA operated by AirDolomiti)

I rent cars through this broker: www.autoeurope.com

You need to check in about 75 min prior to departure. Allow about 30 min for the car return procedures and the 5 min shuttle ride.

The drive from Castellina to the airport is only about 50 min without traffic. However there is traffic getting into Florence between 7:00am and 9:00am, therefore give yourself an extra 20 min plus another 20 min to get lost and find your way to the rental car center on Via Palagio degli Spini. It's not hard at all if you choose to go to the Firenze Nord exit and come down to the airport from there. So my suggestion is to leave Castellina 3+ hours prior the flight departure.

EDIT: Since you fly on June 24, that is a Holiday in Florence (St. John's the Baptist, Florence's patron saint day), therefore there should be no substantial traffic. The holiday is only in the municipality of Florence, not surrounding cities. But it's a Saturday (which is not really a holiday in Italy), therefore traffic shouldn't be too bad.

Hi Roberto,

You are so very kind! I can't thank you enough for your time!
Great info! I did some research and Delta Airlines has great reviews. There's an 11:30 flight which would still be a tad rushed. I think we would want to add additional time to your timeline, since we're not experienced travelers like you. There's a 3:30 flight which would be ideal, but it's $300 more. Flight is over $3,000 for the 2 of us, so we're leaning toward the earlier flight.
Just curious, our trip is in June. How far in advance do you book your flights?
Thanks again!!!
Sheila

Why not drop the car in Florence, take the fast train to Rome (1.5 hours), book a room for one night & catch Delta 113 back to Boston direct? It worked out great for us this past June when we returned for the RS Heart of Italy 9 day tour!