SusanP - five days will add a lot of expense (lodging, renting a car, food). Also, I don't know that I can get all this planned in two months. Just the initial search for apartment/villa suggestions has given me a ton of information - and a headache (literally...I just took two Tylenol). Also, not sure that I can get by in small villages with no Italian.

Also, do I want to do my "dream" trip through Tuscany in November? Would it be better to see it in early spring when plants are starting to bloom? (By the way, DH hates crowds, so we have found that traveling off season is good for us.)

Easy decision. Nov 10 to 17 or Nov 10-22?
Your first choice gives you 5 full days in Italy and if you go to Venice you will lose the better part of 1 day going and coming. Your second choice gives you 10 full days to enjoy Italy. No brainer for me.
I, however did ok in inorganic.
So, to change Ira"s itinerary abit, I would still train to Venice on your arrival. You will be tired your first day in Europe so you might as well keep traveling. Taxi from Florence airport to train station is a short jaunt. Eurostar train takes about 3 1/2 hours. Three nights in Venice. Rent car to drive to Tuscany unless it is much cheaper to rent the car in Florence to return to Florence in which case I would train back to Florence and rent there. Base yourself somewhere in Tuscany and do day trips by car. Turn car in at Florence and spend the last three nights there.
If you do not want to drive around Tuscany you could base yourself in Florence and do day trips by bus or train to places like Siena, Lucca, Pisa, San Gi......
You can easily plan this trip in 2 months as you are going off season and should have no problems getting hotels, car rentals etc. Learning alittle Italian will help your trip but it is not necessary.
Have a great time !

mjs - great insight! One question - if I rent an apartment or villa for a week, do I have to arrive/depart on a Saturday? If so, that ruins plans to go straight to Venice since we'll be arriving in Italy on a Friday morning. What I was thinking was arrive in Florence Friday (our flight doesn't land until 2 pm so we won't see much that day) then either explore Florence Saturday or grab our car and meander down to wherever we've chosen to stay. Then base ourselves in Tuscany Saturday to Saturday, heading back to Florence (again, we could take our time and stop along the way) to sightsee until we leave Tuesday morning.

Hi jr,

May I suggest that you are overworking this problem.

There will be plenty of hotels available, no need to limit ourself to a Sat-Sat villa rental.

You won't have to know much Italian to get along. Buy a phrase book. Have pen and paper handy for drawing pictures.

Take the full two weeks.

Enjoy your visit.

((I))

I would still do the longer trip to Italy even if cost were an issue. It is not inexpensive to fly to/from Europe these days and even though you are using points, it is still a cost. If you amortize the cost of flying to/from Europe over 10 days vs 5 days your per day cost of the trip is lower with the longer trip.
To save money I would consider not using a car and just base yourself in Florence for a week after your jaunt up to Venice for 3 to 4 days.
I have only rented an apartment once in Florence and I am afraid it is out of your budget range so I cannot give you a personal specific apartment reccomendation. However, I am sure many people on this board may have specific recommendations.
I also think that because November is off season you probably would not be confined to weekend to weekend 1 week rentals for apartments. Windows on Tuscany is an apartment company run by the Ferragamo family that I have looked at and I do not believe they have a weekend to weekend policy. In the off season you may also be able to rent apartments for slightly less than a week in some cases.

ira - thank you for being blunt. I am over thinking this! The thought of a place to stay in the country just sounded so good, I totally forgot that I have many other options.

mjs - just talked to DH and told him that we could extend our stay and his response was (could you have guessed this?) "Sure." To which he added (thinking just like you) "If we're going all the way over there, we might as well stay as long as possible." You see, I fret about details and costs, he doesn't. We make a good team!

"To which he added (thinking just like you) "If we're going all the way over there, we might as well stay as long as possible."

So, now that you're staying for a year. . .


If you do a search her under Italy for Il Poggiolo, I think you'll find a number of reports including mine. I found those apartments here, and since going several other Fodorites have stayed as well -- all have loved it.
Regarding smoking, I couldn't say. We didn't smoke, and I didn't smell smoke, but I'm not sure if they forbid it or not. No we didn't cook, but there is a nice kitchen if you wanted to, and you can eat at the pretty tiled table in the kitchen, on the porch, or out in the garden. There are at least a dozen good restaurants within the village in walking distance. These apartments sit about half way up the hill (Montepulciano is essentially two major streets running up a hill to the main square at the top).

Funny you ask about air conditioning. I don't think so, but you know it was very hot while we were there and the apartment was certainly cool enough. I don't remember. But I have no idea why you're asking if you're going in November. By the way there is a fireplace in the living room as well as the open one on the porch/terrace of #3.

Though I think others may have already convinced you, let me just add that I have been to Italy in November a few times, and it has its bonuses. Fewer crowds, yes, but also chestnuts, porcini, truffles, and olio nuovo - newly pressed olive oil are but a few of the gastronomic delights.

Congrats on the trip! May I suggest you look at La Saracina for the Tuscan portion as opposed to renting an apartment. If apartments have a Saturday to Saturday only rental, and you don't have a Saturday to Saturday to rent, I'd check out this lovely place which (if memory serves me) StuDudley on this forum recommended to us. We stayed there this past May and couldn't have been happier (returning this May). The owner, Simonetta, has an apartment with bedroom, living room (with fireplace), kitchen, that can be rented by the night with the most spectacular view. It has an ideal location between Pienza and Montepulciano (you can see from the grounds) and takes less than ten minutes to drive to each. For your trip, I'd divide the time between Florence and southern Tuscany, as previously suggested. Hope this offers another alternative...

Patrick - I would love to stay for a year! Alas, I now have until the 22nd - just called Delta and managed to change our flights. Yeah! As to Il Poggiolo, I did visit their website and it looks very nice. Always good when people on this board approve. I need to figure out where we want to go, then get my bearings (not sure how far apart destinations are - everything looks so far away on a map), then just pick a place.

dorkforcemom - good recommendation! I'll definitely check it out!

Hi jr,

>...not sure how far apart destinations are - everything looks so far away on a map)...

Go to www.mappy.com and www.viamichelin.com for driving times and directions.

Go to www.trenitalia.com for train schedles and prices.

Check www.novarentacar.com and www.autoeurope.com for car rental.

((I))

ira - how did you answer my next question before I even asked it? This morning I was thinking "I wonder if there's a website that tells the travel time between towns." Thanks!

---We've done Tuscany several times. Undoubtedly our best was last year renting a week in Montepulciano and going out daily to other towns of South Tuscany -- the best part of the region to me.---

Partick - just curious as to what towns specifically you like in the Montepulciano area. I'm trying to make an itinerary and would love your input, as well as suggestions from others. Thanks!

3 nights in Florence was plenty for me (and I am a city person). I'd say 2 nights in Florence & the rest driving round some of the rest of Tuscany.