Looking for some advice and opinions on our Tuscany itinerary. We are mother and daughter (30’s & 50’s). This our second trip to Italy, we were in Rome & Florence in 2008. We will be there in early November, and will have 9 full days.

Day 0 – Land in Florence 6pm
Stay in either an airport hotel or Agriturismo very near Florence
Day 1 – Agritourismo Chianti area
Explore Chianti, wine tasting
Day 2 – Siena
Explore area, potentially using Hills & Roads
Day 3 – Siena
Explore Siena – Market day
Day 4 - Val d'Orcia (Pienza or Montalcino)
Explore area
Day 5 - Val d'Orcia (Pienza or Montalcino)
Explore area
Day 6 – San Gimignano
Explore Area
Day 7 - San Gimignano
Explore town
Day 8 – Lucca
Explore area – stop in Pisa
Day 9 – Lucca
Explore Town
Day 10 – Depart Florence 10 am

I know we have a lot of moving around. It’s not ideal, but our thinking is we’d rather not be driving at night. So we can spend the day driving and exploring, and then come back to our town for the night and have dinner, drink some wine and wander.

Questions/Advice Needed

• For our first night we will be landing relatively late (6 pm). Our first thought is to stay at an airport hotel, drop off our stuff, then take the bus into Florence for dinner. Then the next day pick up the car at the airport. But I really don’t like the thought of being in 2 hotels the first two nights. So I found a couple of Agritourismo hotels near Florence, so we can spend the first two nights there. http://www.poggiopiano.it/index.php?lang=eng&pag=home or http://www.montereggi.it/montereggi%...iturism.en.htm . My mom though is not onboard w the idea picking up the car when we arrive and drive in the dark and jet lagged. I was thinking we are flying business class (award tickets) with only one connection, so hopefully we won’t be complete zombies. Anyone have any opinions on this one way or the other?

• My mom is young and active but has moderately severe arthritis in her ankles. So walking up and down hills day after day is going to take a toll. Does anyone have any tips to save some wear and tear on mom’s ankles? Are there any towns to visit that are relatively small and flat? Any to avoid, lots of walking w/o a huge payoff?

I’m sure I will have a million more questions as time ticks by, but I’d love any feedback.

TIA!

hi Tiai,

i'm with you mum here. I would pick a nice hotel in Florence and spend the first night there [you're arriving relatively early and should be there by 7pm] then in the morning pick up your car, and have a nice gentle drive to Chianti, where I suggest you stay 2 nights. then Siena for 3 nights, followed by Val D'Orca, then back to florence.

I suggest doing San Gim as a day trip from siena, and leaving out Lucca altogether - IMHO you've just got too many places to stay in a trip of this length. your best bet for preventing your mum having trouble with her ankles is to cut down the amount of moving about. when you stay longer in a place, you get to know it and where the places are that you like, and you don't waste time wandering around looking for your favourite bar, cafe, restaurant, etc.

have a great time!

I agree with your mom and annhig about arriving and driving in the dark. And I would not stay at an airport hotel - stay in Florence.

Pienza is very small and flat. There's limited parking arrive early. If you can't find any parking there's a supermarket not far away (5 minutes on foot) where you can park your car and then walk to the town.

In Siena, get a letter from your hotel so you can drive to the hotel and pickup and drop off your mom so she doesn't have to hike uphill from the parking area. Keep this letter for a very long time after you return (at least a year) in case you get a ticket for driving into the historic center.

Thank you for your replies!

I was really hoping they wouldn't agree with mom though!

As far as actually staying in Florence our first night, mom is adamantly opposed. She said she doesn't want to deal w Florentine traffic w luggage after flying. So it's either an airport hotel, or convincing her I'll be fine driving that night.

I know we have too many locations, but I can't bear to be leave any of them out. I'll have to think on it ....

Thank you for the advice about getting a letter from our Siena hotel, will do!

You wouldn't drive into Florence after your flight. Just take a taxi to a hotel in the city center. Go back to the airport the next day and pick up your car.

What you must do is not eliminate locations, but rather eliminate hotel changes. You can visit some of these places as a day trip from one or two of the remaining places.

I realize we wouldn't be driving in Florence. What I meant by traffic was as being a pedestrian. For reasons I don't fully understand myself, my mom found crossing the street in Rome and Florence incredibly stressful (NYC as well, but to a lesser degree).

I'm very fortunate that my mom lets me do all the travel planning, and is generally very easy going. But when she puts her foot down on something, like she is about staying in Florence, I have to respect that.

How about this plan instead:

Day 0 – Land in Florence 6pm
Airport Hotel, dinner in Florence

Day 1 – Agritourismo Chianti area
Explore Chianti, wine tasting

Day 2 – Agritourismo Chianti area
Explore area, potentially using Hills & Roads

Day 3 – Siena
Explore Siena – Market day

Day 4 - Siena
Daytrip Val d'Orcia

Day 5 - Siena
Daytrip Val d'Orcia

Day 6 – San Gimignano
Explore Area

Day 7 - San Gimignano
Explore town

Day 8 – San Gimignano
Explore area – Daytrip Pisa

Day 9 – San Gimignano
Daytrip Lucca

Day 10 – Depart Florence 10 am

To me what you're saying about your first night is more stressful than what the others are suggesting for you. Go to a decent hotel in Florence via taxi and then walk somewhere nearby for dinner. Checking into an airport hotel and then getting the bus to go into Florence for dinner and then going back to the hotel just doesn't make sense for someone who wants to avoid traffic. Make this a simple evening to rest and relax to get a fresh start the next day.

Take to heart what the others are saying about making day trips and trying to avoid checking in and out of hotels. For example, San Gimignano is less than 20 miles from Siena. Why would you move to SG for 3-4 days instead of just making it a day trip from your base in Siena? We spent a day in SG and it's wonderful but I don't see any real purpose of staying there for several days.

Frankly annhig's suggested itinerary is spot on to me.

I understand what you're saying about staying in Florence the first night. But disregarding one of the few things my mom has insisted upon for this trip will not make it "a simple evening to rest and relax". I know if I pushed my mom she would agree to stay in Florence. But I know she will be stressed about it, and not be able to relax on the flight. It would really start the trip out on the wrong foot. I'm not saying this is logical, but it is what it is!

I see what you're meaning about San Gim not being a good move from Siena. I should have spent some time w Google maps before posting my revised itinerary. I like annhig's itinerary, but I really want to include Pisa & Lucca. I think Lucca is a bit far from Siena as a day trip, for me personally, especially considering it will be short winter daylight hours.

Attempt # 3:

Day 0 – Land in Florence 6pm
Airport Hotel, dinner in Florence

Day 1 – Agritourismo Chianti area
Explore Chianti, wine tasting

Day 2 – Agritourismo Chianti area
Explore area, potentially using Hills & Roads

Day 3 – Siena
Explore Siena – Market day

Day 4 - Siena
Daytrip Val d'Orcia

Day 5 - Siena
Daytrip Val d'Orcia

Day 6 – Lucca
Visit San Gim on the way

Day 7 - Lucca
Explore town

Day 8 – Lucca
Explore area – Daytrip Pisa

Day 9 – Lucca
Explore area

Day 10 – Depart Florence 10 am

Am I getting closer? (Well except for the Florence part!)

Yes! The only change I'd make would be to return to Florence morning of Day 9. Enjoy the day there and you'll be close to the airport the next morning.

There will be lots of walking on this trip. I also have arthritis in my feet. I generally just wear a comfortable pair of flats (not with leather soles) preferably with some cushioning in the sole. I take a celebrex or some other anti-inflammatory pill with me for the days when my feet may get achy. Generally makes getting around ok.

Attempt #3 is better. Lucca will be a good town to be based in at is is completely flat, easier on mom. It's also big enough to be interesting for the time you'll be there. Eat at Buca di Sant'Antonio. Get the veal. It melts in your mouth.

I guess I am pretty dense but what in the world is the difference between taking a taxi to a hotel in Florence for the night vs. staying in an airport hotel and taking a taxi into Florence for dinner? Seems to me you will be in Florence in any case.

For your departure, you should return to Florence (or airport hotel) the night before. The airport is scarcely 15 minutes from downtown.

Yay! Thanks for all the help tweaking this!

I had actually been thinking about where to spend the last night. I still think mom will veto staying in Florence (I know, I know, I know). I really don't want to spend another night in an airport hotel. I was thinking since our flight isn't super early, and Lucca is only an hour away, it wouldn't be so bad? I just really hate the thought of losing our last half day in Italy moving to an airport hotel.

mamcalice - It really comes down to luggage. Our last trip to Italy had the taxi dropping us blocks away or walking from the train station w our luggage. My mom has many virtues, but being a light packer isn't one of them. Also my mom came down w a stomach bug days before our last Italy trip, and had just begun to recover upon our arrival. So she was weak and clammy and shaky, and not so fondly recalls me saying, "just one more block". So add that to the crossing the street phobia, and there you have it. It may not be logical to us, but it is what it is.

10:00 AM isn't too bad and with a one hour drive from Lucca I think it would be manageable to stay there vs an airport hotel.

Alternatively you can look into changing your ticket to depart from Pisa. We've flown in/out of here a few times and it is a breeze. The airport is small and the car rental place right there. It's also only 30 minutes or so from Lucca.

mamcalice - It really comes down to luggage. Our last trip to Italy had the taxi dropping us blocks away or walking from the train station w our luggage>>


??? - was this because you were staying somewhere with very poor access [this happened to us in Rome where the taxi couldn't get down the street]. if you pick a hotel on a main street [like via cavour for example] and has a good restaurant, i can't see the problem. Italy is going to be hard on your mother [and you!] if she can't cross the road!

however, as Florence airport is north of florence - why not drive from there to Lucca, and spend the first might there; it's not much further from there to "chiantishire" and you will have ticked Lucca off your list.

your real problem IMHO is that you still have too many places!

A few of thoughts/ideas-

I think you should base in 3 locations-

1. An agriturismo in Chianti. Visit San Gimiagno and Siena from this base.

2. Pienza or a nearby agriturismo in the Val d'Orcia. Pienza is a flat town and beautiful. There are plenty of lovely towns and sights to visit nearby.

3. Lucca.

Siena is hilly, and may be challenging for driving into/out of. I think the three bases I mention will make life much more stress free and relaxing.

Something you and your Mom may not realize- the hotels near the Florence airport are in a busy area and not attached to the airport. You will probably need to take a taxi or a bus just to reach one. If it were me, I would much rather take a taxi directly to a hotel (they will drop you at the door- no need for dragging luggage through the streets) in central Florence for that first night. Eat at restaurant near the hotel. Have the hotel arrange for the taxi back to the airport in the morning.

Agree with zoecat that Pienza is a good base because it is small, flat, and and easy to get around. There are (or were) several restaurants in town to walk to for dinner, and November should be relatively less crowded with tourists. Our hotel had parking available.

I'm attempting to switch my flights so I'm in and out of Pisa.

Stay tuned!

Great advice here; I agree with most everything. While it sounds like your Mother is immovable, the hotel in Florence the first night makes huge sense. I stayed at the Hotel Rosso on the Piazza di Santa Maria Novella; it's only a 15 minute ride from the airport and an easy 10 minute (at most) walk to the car rental shops on Borgo Ognissanti (where the rates will, in general, be cheaper than at an airport).

Making day trips to Siena and San Gimignano from the Chianti Agriturismo (if you're staying around Castellina in Chianti) is really easy and convenient.

Regardless of whether you go further south in the Val D'Orcia (like Pienza) or go northwest to Lucca, I'd second the recommendation to return to Florence the day before your flight. It will take all the stress away from getting to the airport your day of departure.

Sounds like a wonderful trip. Good luck. —C

I am unable to change my flights into or out of PSA at this time, there is no award availability currently. So I'm going forward with planning to arrive and depart from FLR. But I have my alerts set up in case award availability opens up.

annhigg- Yes, in Rome our street was narrow and wasn't accessible by car. For Florence we took the train, and walked to the hotel a few blocks away. My poor mom, I've made her sound like a crazy person who can't cross a street! We all have our quirks and Italian street crossing anxiety is one of hers. She can and will do it, but it causes her more anxiety than it does most others. She admits that she is a weirdo about it! This trip to Tuscany is her dream trip, and she wants it be be all about hill towns, scenery, etc.. She doesn't want this to be a city trip, which is part of her opposition to staying in Florence. As I said, it may not make sense to us on here, but compromise is part of traveling with someone.

I like the idea of driving to Lucca, you're right that it's not much further, especially in drive time than any of the agritourismos on the outskirts of Florence. Especially since FLR is on the NW side of Florence. How difficult would you say that drive would be in the dark, for someone who had never driven in Italy before?

I was looking up sunset times for when I'll be in Italy, and the sun will be setting about 5 pm. Despite everyone's advice on here, it makes me wonder if basing ourselves in fewer locations and doing daytrips is the best idea. Won't we be missing magical, less tourist filled evenings San Gim or Pienza, etc.?