5 nights in Italy.... Florence and ______?!?!

In late October, if you get rain, Cinque Terre will be miserable. How open are you to winging it? Say for example you picked Lucca, you could take a day trip to Cinque Terre, but there are drawbacks to that of course.
I really don't think three places in five days will do any of them justice. I would split it between Florence and one of the train/bus accessible towns like Siena. It's your birthday--you choose!
If you want to do an agriturismo without a car, you'd have to arrange for transfers. As long as you do the car drop at the airport and are aware of ZTLs, the driving is not difficult. Coming from Spain, you would not have jet lag so you could pick up the car right away.

You could split up one of the days that you do not agree on.

You can do Florence and one the tuscan towns Lucca or Siena fro 5 nights combine.

Hi Anna,

This sounds like a fun way to spend your birthday. I like your option of spending a few nights in Florence and a few in the Tuscan countryside. You can add-on the Cinque Terre, but it will make your trip more hectic. The other issue with the Cinque Terre is that towards the end of October, they are winding down the season. I checked and the historical weather for that time is in the low 60s and there is a greater chance of rain. This may not be the Cinque Terre of your friend's dreams.

As for a base in Tuscany, others on the forum can help you with options if you don't have a car. Last June, I went with family and friends and we stayed in a B&B, 20 kms from Siena, but this really requires a car. If you are interested, it is Borgo Argenina. https://www.borgoargenina.it/. It is run by a woman who found this old Tuscan B&B near the town of Monte 20 years ago, and with her young child in tow, completely renovated the property. It is an oasis and the nice thing is that it has two villas (one with two rooms, large kitchen and living room and private outside patio) and the other a single room villa with private patio. The reason I chose this B&B is that it has a cooking class on property. Eleana, the owner, cooks recipes from her family, and they are delicious. Elena can also make arrangements for local wine tasting, truffle hunting. As a fellow foodie, you may appreciate that the local truffle hunter has a restaurant with a pre-fix menu honoring the truffle.

For good food/wine experiences in and near Florence, I can recommend the following.

• Eating Italy: Florence Sunset Tour: https://www.eatingeurope.com/florence/florence-sunset-food-tour/
• Verrazono Winery which has a specular tour and lunch (3 hours), just outside of Grieve in Chianit: https://www.verrazzano.com/en/, they also have an agriturismo. The best way to get there is by car.

Have a great trip,
Sandy

hey anna
look into the town of lucca. (apartmentslucca.com), luccatours.com
come&seeitaly.com has different wine and food tours, a ride to barga and garfagnana from lucca
extravirginalucca.com a cooking class.
cucina-italiana.com chef paolo has half day cooking classes also accomodations
fattoriaaldotto.it a winery close to lucca center
stay within the walled city, rent bikes and ride around, walk thru the piazzas, sit, relax with a glass of vino, people watch.
you can take the train to pisa, if anyone wants to climb tower reserve your ticket online (opapisa.it), walk thru the small town.
train to cinque terre for a day trip. it is late in year and some places may be closed, the weather may be bad then again maybe not, your call.
it's grape harvest and festival time, check into those with tourist kiosk in town center or host/owner of where you are staying. they are so much fun (eat drink and be merry) be careful riding bikes and wine tasting, with 4 of you hire a taxi or driver. seems like travelers all year long, some towns will still be busy and have crowds, i like to stay away from the bigger cities, it's a big country with lots to see, my opinion and 3 cents worth.
hope this gets you started and thinking, have a fabulous 40th and a fun way to enjoy. cheers
aloha

Wow! Thank you all for these WONDERFUL suggestions! I will definitely look into Lucca-- that seems like a great option for compromise and also would provide flexibility if Cinque Terre didn't pan out weather-wise (and we would also have the easy option of splitting up for a day)!. Love seeing your links of places you have stayed and tours! I wish I could visit them ALL! For my 50th, I'll have to schedule a whole month :)

There's several agriturimos near Greve in Chianti in Tuscany. Greve gets regular bus service out of Florence, trip time is about an hour. There are wineries in the area and tasting rooms in Greve itself, which is a cute town. You'd have to arrange for transportation between Greve and the agriturismo, of course, but this plan might suit you. Also an option are wine tours out of Florence. DH and I did an all day tour arranged by the TI in Florence, we visited 2 wineries and Greve, it was really fun.

Foodies and a chef? Then head to Panzano in nearby Chianti region to visit Dario Cecchini’s butcher shop and he also has several restaurants. Go to Chef’s Table on Netflix to meet Dario!

Thanks for the Netflix tip, Suki. Another Chianti idea is Lamole di Lamole. One of the best restaurants I’ve eaten at and great wine too. It’s a tiny village, so definitely need a car to reach it.

I sincerely hope you are not intimidated about renting a car. With four people you must get a car that can hold you and your luggage, but without a car you cannot explore the gorgeous countryside in the same way. Make sure you have an international data plan for at least two phones and a car charger and you can go anywhere you want -- and if you spot a castle up on a hill, you can pull off and take the road less traveled. My experiences in Italia were made fantastic because I had a car and explored.

Cinque Terre is qutie over rated, especially at that time of the year. It is now overrun with cruise ship tourists and there are other picturesque villages all along the coast that do not have hordes of tourists and offer an authentic experience of a sea village. All of my visitors loved exploring the coast north of Rome up to La Spezia as well as the Italian Riviera. You probably don't have time to squeeze in the coast and the countryside of Tuscany. Stick to the countryside and savor the moments!

OR . . . . skip Florence, spend 2N in Lucca if the CT is a priority and the rest in Bologna. You could day trip to Florence from either. Bologna is the place to be for foodies and you can day trip to lots of towns easily by train - Parma, Modena, Ferrara.

I like Chani's idea! Bologna and Ferrara have some of the best food, very different from Florence.

Oh boy-- thanks to these great suggestions, my possible itinerary seems to be evolving a bit. After looking in to Bologna a bit, I am intrigued to visit-- and, as it turns out, there's a flight in to Bologna that we could take that would fit even better for our overall itinerary. After researching further (and considering your comments), I think I just may nix Cinque Terre as an option-- my friend may be disappointed, but not heartbroken.. and it seems justifiable in light of circumstances :)

Curious to hear your thoughts on this (or something like it).

-- Day 1: Fly into Bologna, early evening. Find Air BNB or other accommodation in Bologna for next 3 nights.
-- Day 2: Sightseeing in Bologna
-- Day 3: Daytrip to Florence by train
-- Day 4: Public transportation to Siena. Sightseeing in Siena. Find lodging in or near Siena for next 3 nights. Maybe evening cooking class?
-- Day 5: Rent car or hire driver to drive along Chiantigiana, visiting Greve, Panzano (I like the Cecchini butcher shop suggestion!), possibly Verrazzano winery (not sure how much we can fit in one day?).
-- Day 6: Day trip to Pienza and Montepulciano. Possibly cheesemaking demonstration at Podere Il Casalea and/or Renting bikes in Pienza? Return car.
-- Day 7: Leisurely breakfast before taking public transportation to Florence for return flight (early PM). (Coincidentally, this is also my 40th birthday, and I quite like the idea of spending it split between morning in Tuscany and evening in Barcelona :)

I'd love any feedback/tweaks on this possible itinerary. I have a hard time envisioning how much time these smaller village stops and driving actually takes. It's so hard to find the balance between seeing as much as you can in a short period of time and not rushing!

As for lodging, I still like the idea of a farmstay near Siena, but mind is numb from the GAZILLIONS out there! Unfortunately, the few that were recommended in this thread were already booked :( If anyone has other recommendations, I'd welcome them!

Once again, many thanks for the helpful information you have already given!

hey anna
see your changes, for your short time in those cities i would look for hotel/B&B. get 2 rooms which has 2 bathrooms. having an AnB, you'll have to wait for keys and maybe no luggage storage if early.
BOLOGNA booking.com: hotel cavour (twin beds)
hotel porta san mamolo (twin beds)
albergo rossi 1936 (twin beds)
Cosmopolitan guest rooms (twin beds)
some have free breakfast and free cancellation. if you know the dates, book it. they are city center for walking, no worry about parking or finding a place for it at extra cost and fines with the ZTL. if you do get a car don't forget to get a IDP (international driving permit) for all drivers from AAA ($25 and 2 passport photos, receive same day), have a DD, italian laws are strict with drinking and driving,
travelingspoon.com, eatwith.com, secretfoodtours.com, bolognagourmet.it
SIENA booking.com Vottoria Design Hotel
Residenza D'Epoca locanda di san martino
Hotel La Perla
cookingclassesnonnaciana.com, cookly.me, ask hotel or tourism kiosk in plaza what's available.
renting a car for a day to drive around, not much time but at least spend the day in the country side, siena-wine-tour.com, scuoladicusunadilella.net, ask if a taxi/private tour to dario the butcher and panzano in chianti.
hope this gives you more info less stress. enjoy and let us know
aloha