40th birthday girls' trip! Bologna, Florence, Siena

I would just spend your arrival and next day in Bologna then move on to Florence and new lodging. The back and forth train trips eat up a lot of time. Bologna is wonderful, but Florence deserves more time. Where is your lodging in Bologna? I can make recommendations for nearby places we enjoyed. I spent my 65th birthday in Bologna last year. Where do you fly out of Italy?

Congratulations on hitting the big 4 - 0. I assume you meant "Florence by train" on Day 3.

Yes, the back and forth to Florence sounds inefficient. I would either spend day 3 in Bologna or make the move to Florence. You don't say if you plan to hit the museums in Florence, but you'll need a couple of days, even with a guide, for the major ones. With your limited time in Tuscany, I would either do a Chianti wine tour OR do a tour south of Siena that would include a winery or two and sightseeing in Pienza and Montepulciano, but I wouldn't try to do both.

Lastly, are you leaving from Siena to make your flight in Florence on the same day? With a 1:45 departure, you're going to be leaving Siena quite early. That would make me nervous, as I always stay in the departure city the night before.

hey hey Anna
Happy 40th!! How fun, you’ll have a fabulous time, go with the flow. Stop at cafe have some vino people watch.
One important issue with renting a car, you will need an IDP (international driving permit), coincides with your drivers license. Pick up at AAA/CAA wherever you live. $25 and 2 passport photos, receive same day, all drivers need one. Enjoy
Aloha
PS: come&seeitaly.com for wine tours
siena-wine-tours.com
eatwith.com
eatingeurope.com

Is it too late to rearrange things to go straight to Siena after Bologna and then spend your last night in Florence before flying out? Bologna to Siena by train or else train and then a bus is 2 hours and a bit. Either way you change in Florence, but you're not roaming around Florence or backtracking. Do your tours from Siena instead of Florence? Look at ToursbyLocals. Minimize driving yourself --- not that it's at all scary or difficult but it's just another thing to organize and it takes time to rent and return a car. Do all of your Florence sightseeing (although it pains me to say this since I love Florence) on the day of the night you are staying there.

Happy 40th Birthday. What a fun way to celebrate! I would suggest not driving especially if none of your friends are going to be much help with planning/driving. Plus there's so many train/bus options and amazing tours so that you can relax, drink wine and have no stress. I booked a tours by Roberto a couple years ago and we visited some gorgeous off the beaten path villages and had a great lunch. A lot of his tours leave from Siena.

Have fun! I'll also be in Florence around October 22-24th.

I second the suggestion to try to rearrange your trip. You could spend your first 3 nights in Bologna, head to Florence early on day 4 to meet your wine tour trip to Siena and return to Florence early on day 6, but that eliminates one of your days in Siena. It might be better to spend your first 2 nights in Bologna, head directly to Siena for 2 nights and take your wine tour trip on the way back to Florence on day 5. If you choose 3 nights in Bologna and need an extra activity, day trips to Ravenna, Modena/Parma or Ferrara are easy. A visit to the FICO (Eataly) food park just outside of Bologna would be another option.

If you're unable to rearrange your itinerary, then stay in Florence on night 3 and on day 7 take the 9:18am train from Siena to Firenze Rifredi station, from which it's only a short taxi ride to the airport terminal. The next train gets you there too late.

Why do not you check in Florence in the evening of Day 3. It would save you a night in Bologna and you will have another night in Florence and going back from Florence to Bologna. You would also have one more night in Florence. Two days in Bologna is far enough.

Why do you take a taxi from Florence to Siena. Train or bus connections are very easy and much cheaper from Florence.

I'll echo Nancy, if at all possible do this.

Bologna 2 nights.

Bologna-Siena. Train bus combo will drop you in the center of town. Siena 2 nights.
Try this tour from Siena, and avoid the car.

https://www.getyourguide.com/siena-l435/small-group-pienza-and-montepulciano-full-day-tour-t47141/?referrer_view_id=34d30f011fbe52730d62fc9d0d4f2468&referrer_view_position=7

Siena-Florence by bus.
Florence 2 nights. Check to see if you can rearranged your tour date into Tuscany.

All:

Once again, many thanks for all your suggestions and input. Based on your comments, I have tweaked my itinerary slightly... I cut our Bologna stay down to two nights and moved the Florence sightseeing portion to the end of the trip, so we can stay there on our final night (no back and forth trains) and have an easier and more predictable route to the airport for our flight out. I also think that with the two tours, we'll be able to hit most of the sites I wanted to see without having to rent a car.

Thanks again!

Anna

Day 1: Fly into Bologna in PM, check into Air BNB in the city.
Day 2: Casual sightseeing, eating and drinking in Bologna
Day 3: Check out of Bologna Air, BNB, Travel to Florence by train, meet private guide in Florence for a full day Chianti wine tour, get dropped off at accommodations in Siena.
Day 4: Sightseeing in Siena.
Day 5: Small group tour to Pienza and Montepulciano.
Day 6: Travel back to Florence by public transit; spend day sightseeing.
Day 7: Morning sightseeing in Florence, then head to Florence airport for flight back.

Sounds much better Anna.

Edit: make sure your driver will accommodate your luggage between Florence and Siena.