Listing a day by day itinerary may help us all understand more clearly how much time you have in each location.

Sun, 5/5 Arrive Rome in morning; arrive Florence early afternoon
Mon, 5/6 Florence - bike tour to Chianti
Tue, 5/7 Florence - half-day food tour
Wed, 5/8 travel to Montepulciano or San Gimignano or other Tuscany location
Thu, 5/9 Tuscany
Fri, 5/10 travel to Rome
Sat, 5/11 Rome
Sun, 5/12 early flight home

This trip really has you on the move, but it seems like that's what you want. For me, it seems a bit odd that you have the bike tour to Tuscany from Florence, only to go driving in that direction two days later. With so little time there, I might delete Rome altogether and just split the week between Florence and Tuscany to give you more time in the two places in which you seem more interested. Or just arrive in Rome early on 5/11 for one night and a stroll through the old center for a taste of Rome before returning home.

Thank you, elenem, that does make it clearer when you list the itinerary like that. I know the bike tour out of Florence sounds strange when we are heading back to Tuscany. This is a unique tour and its only out of Florence. Are Chianti or the other towns very far from Florence? Curious as to what we could expect in terms of travel time between Florence and those towns in Tuscany. Also, from Tuscany to Rome?

IMHO you need to go at least 20 miles south to see even the homogenized version of Tuscany. The best hill towns are 50 to 75 miles south. I would think again about a bike tour with such a short time.

I agree with bobthenavigator. The bike tour may be "unique," but IMO it's not the best use of your limited time. In looking at the tour itinerary (San Donato, Cortine, Tignano, Tavernelle Val di Pesa), some of the route is on single-lane roads lined by trees and vegetation. This makes for a cooler ride on hot days but doesn't allow for much viewing of the surrounding landscape. I think the route was selected for safety and comfort but isn't in what I would consider the most scenic part of Chianti. You can follow most of the route on Google's Streetview. Just plug in the route and drag the little yellow man to various points.

However, this is your trip, so you should do what you would most enjoy.

But are you sure a shortened afternoon is enough time to see everything you'd like to see in Florence? There is so much more than the Uffizi and the Accademia...

Driving out of Florence can be tricky. If you decide to rent the car in Florence, make sure you identify a route out of the city that avoids the Limited Traffic Zone so that you don't get a surprise ticket in the mail after you get home.

Visiting wineries in Tuscany involves some planning. Most wineries are not set up for drop-in visitors and require appointments. Some towns (Montalcino and Montepulciano, for example) have in-town tasting rooms.

At the other end of your rental, consider dropping the car at Chiusi or Orvieto and taking the train to Rome.

Okay, just what I wanted (more like needed to hear!) I am taking the bike tour off our itinerary. Maybe we can rent bikes in Tuscany. This will give us one full day in Florence in addition to the two half days (arrival day and Taste Florence tour day.) Since that full day is a Monday we will have to strategize as I understand several museums are not open that day.

Thank you, Jean, for looking deeper into the bike tour for that insight. While it might have been fun, it doesn't seem like it would be as scenic as I hoped. Would it be easier to get out of Florence to rent the car? Is it easy to drop it off at a different location (Chiusi or Orvieto).

Bob, we are willing to drive further away to experience a "less homogenized" version of Tuscany. Do you have any favorite hill towns? We would love to stay at a place that would help us feel immersed. For example, we once stayed at a B & B where the owner totally rewrote our travel plans, to our delight. We ended up feeding newborn calves at his family's dairy farm. We ate ice cream from their own cows. He arranged the most exquisite drives and local gems that weren't listed in any travel books we had seen.

Of course--get south of Siena:


BOB’S FAVORITE DIGS IN TUSCANY
A. RURAL LOCATIONS: All have parking and good food options nearby

1. Relais La Saracina www.lasaracina.it 230 to 300E
Fabulous country home near Montepulciano—helpful owners

2. Cretaiole Agriturismo http://www.cretaiole.it/ Good value for families
Isabella also has 2 apts. in Castelmuzio for rent—wonderful—see her site.

3. Terre di Nano www.terredinano.com 100 to 155
Both rooms and apartments at rural Agriturismo near Monticchiello

4. Casanova di Pescille http://www.casanovadipescille.com/ 100E
Rural B&B 3 KM from famed San Gimignano—we loved the views of San Gim.

5. Fattoria Tregole www.fattoria-tregole.com 110E to 180E
Has both B&B and apartment accommodations. Near Castellina in Chianti

6. Agriturismo apts. near San Quirico— www.poggiolo.info/ About 110E

7. New historic B&B north of Pienza. http://www.camprena.it/index.htm
Site of filming for THE ENGLISH PATIENT About 90E for double

8. http://www.borgoargenina.it/index.html A special rural B&B in Chianti.
The lovely owner, Elena, will make you feel like family. 170E for double

B. IN-TOWN LOCATIONS: For walking convenience to shops & ristorantes.

1. Palazzo del Capitano www.palazzodelcapitano.com 170 to 210E
Very nice small hotel in center of San Quirico—perfect location to explore.

2. Vecchia Oliviera www.vecchiaoliviera.com/ 150 to 200E
Nice 4 star hotel at the gate into lovely Montalcino---has pool.

3. Palazzina Cesari www.montalcinoitaly.com 80 to 110E
Lovely small B&B in heart of Montalcino—great value—2 night stay minimum.

4. Locanda di San Francesco www.locandasanfrancesco.it 180 to 200E
New boutique B&B in a lovely location in Montepulciano—great reviews !

5. Politian apartments http://www.politian.com/ Good value apts. with
minimum stay of 3 nights in Montepulciano---helpful host---85E

6. Palazzo Ravizza www.palazzoravizza.it 170 to 250E
Very nice & popular hotel in Siena with parking.

jayhawk,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

I get the impression you're more interested in rural Tuscany and not so much in Florence. So why not stay in rural Tuscany and daytrip into Florence? If you stayed in Siena, you could take a bus into Florence. Farther south traveling to Florence is not so quick.

The archetypical Tuscan countryside is farther south, in the Val d'Orcia. I like the towns of Pienza and San Quirico d'Orcia as bases; they're easy to drive in and out of. You do need a car for this area. But don't plan to drive immediately. If you arrive after a long, overnight flight, you'll be jet-lagged and sleepy for the first day or so.

And I assume you already have your plane tickets. Otherwise consider flying into Pisa. It's an easy train ride to Florence.

Thank you, everyone, for your input. Bob, I love all your suggestions. Just the kind of place we are looking for. Saw a couple that aren't available so that helps a bit. Ha ha!

Mimar, we really do want Florence AND Tuscany. Actually, we want Florence, Tuscany, Venice, the Amalfi, Rome, Milan etc. I thought I was being good to cut it down to just two areas! Lol!

I feel kind of behind as I am booking lodging. Many places I was interested in we're already booked. I was able to secure this B & B. http://www.booking.com/hotel/it/trentatre.html?aid=304142&label=postbooking_confemail&et=UmFuZG9tSVYkc2RlIyh9YW9flJFRaW9dpAfTMiWYMt+vhQwv7qG2hdDAFZB8K1DTwB3h1hjODaTSg6J3BbT7WIh4gmlw8M7qugn5G7dzG/3jB7Xtd2rhfWuaT7GG7SCzHMBckN+z8buOtaQdkPTl8EEUFGhrR3buPTs3xyNzqfM=
I understand it is out of the city center a bit. Is that a big deal? I hope not because the reviews look really good.

With the really short amount of time you have in each location, it is really important to stay in the city center. There are lots of options but it's best to stay as close to the center as possible to avoid spending a lot of time getting to the main sights.

I can't believe you can't work Venice in. The most beautiful and romantic city.
Florence can be crowded but really a nice place with history, museums and ambiance.
Rome is big, busy and crowded.
You can see my trip reports at - http://www.rimerson.com/

I for one applaud the OP for NOT trying to work Venice in. This is only a 7-day trip!

My husband and I spent a few days in the Tuscany Florence area last October and I have to say of either place I would spend more time in Tuscany than in Florence. If you are going to the Ufizzi or the Accademia GET RESERVATIONS! (the concierge at your hotel can do it for you) It will cut your wait time in half, do the same with the Vatican (this must be done online). Also, paying the extra money for the high speed train from Florence to Rome is well worth it! We stayed at a very nice and reasonably priced hotel( which included breakfast) right across the street from the train station in Florence. It was very convenient when it was time to leave, no need for a taxi, we just grabbed our luggage and headed across the street. It was called Hotel Ambasciatori.
You have probably made your hotel reservations by now but I just have to add the Villa Vignamaggio in Chianti Tuscany was a heavenly place to stay. Like many it is a working vineyard and the former home of THE "Mona Lisa". The staff was very friendly and accommodating. We would stay there again in a heartbeat. The movie "Much Ado About Nothing " was filmed on this property, there is also a delicious restaurant with a gorgeous view at the Villa. I think the best advice for any trip is do your research then make your trip your own! The most magical moments on a trip happen when least expected and many times in the unplanned.

Yep, I agree that Venice should be left for next time.

I just booked this Agriturismo as recommended by bob. Thanks, bob!! The reviews seem like just what we looking for.

http://www.terredinano.com/index.asp?lang=eng

Just have to get our digs in Rome arranged!

I noted your 25th Anniversary posting with much pleaseure - we visited Venice, Florence and Rome last year to celebrate our 25th AND DH's 50th. We had a wonderful time, of course!

I think that B&B is a bit away from where you'd want to be, and in a direction of Florence that's less interesting. Consider Casa dei Tintori - we'd didn't stay here on our anniversary trip, because they were booked, but stayed there previously. It's near Santa Croce, the rooms are delightful, clean and beautiful, in a historic building. The owners are helpful and welcoming, and serve a very nice breakfast.

Terrific---you will love it.

Be sure to eat at least once at Osteria La Porta---book in advance.

Lex, I'm having trouble with that b and b's website. It won't accept my email address when I try to make an inquiry. How about this one? http://www.florence-view.eu/bed-and-breakfast-firenze/index.aspx

Will do bob! Thanks

Bob, I hope I can pick your brain again. I just heard back from Elena at Borgo Argenina. She has a room available but for three nights minimum. We had only planned two in Tuscany. Her letter was lovely. She mentioned how much she would like to help us enjoy the area. Should I cancel Terre di Nano, book Borgo and cut Rome down to one night? I know this sounds sacrilegious, but our time is so limited. This trip is kind of last minute, but this is the only time frame that works for us.

So it comes down to this, is staying at Borgo Argenina worth changing our plans?

Thanks in advance!

Wow---that is a toughie since I am fond of Elena and her place is the real thing. However, if you have seen my postings on Tuscany over the years I always opt for location first. Borgo Argenina is in the south part of Chianti and is not my favorite location in Tuscany. The Pienza/Montepulcinao region will give you more highlights and better eating options. I would choose Terre di Nano because of location.

Okay, I know I've put this off for too long. I am finally booking our lodging in Rome for our last two nights (May 10-12) These are available on our dates. We will need to get to the airport on Sunday the 12th for our 9 a.m. flight out. Any opinions?

http://www.thehomeinrome.it/

http://www.tripadvisor.com/Hotel_Review-g187791-d3989397-Reviews-Hearth_Hotel-Rome_Lazio.html

http://www.tripadvisor.com/Hotel_Review-g187791-d2322789-Reviews-Domus_Rachele_B_B-Rome_Lazio.html

http://www.tripadvisor.com/Hotel_Review-g187791-d571039-Reviews-Angetode_B_B-Rome_Lazio.html

http://www.booking.com/hotel/it/bed-and-breakfast-el-dorado.en-us.html?sid=97ee1369c0fbbb1d78d98db207ed018f;dcid=1;checkin=2013-05-10;checkout=2013-05-12;pr=140,200;pr_cur_code=USD;srfid=b6aa073463f7a8ae0687f029b33c6af34f1448e1X16

I would get on the other side of the Tiber from the Vatican closer to Piazza Navona or the Pantheon. You seem to be cost sensitive and that may be a problem. Heer are some options:

Bob’s favorite ROME hotels---2012

All are located in the centro historical area of Rome and are within :30 walking of most of the major tourism sights. Prices assume a double room.

SMALL B&Bs:
• www.nicolasinn.com Near Colosseum with helpful hosts—160E

• www.daphne-rome.com Tasteful B&B in two locations—150 to 200

• www.baldassinibeb.it/eng/index.html Great location---good press

FULL SERVICE 3 STAR HOTELS: Prices vary from 150 to 220E & by season

• www.albergocesari.it Perfect location—my wife’s favorite—200E

• www.hotelsancarloroma.com Near Spanish Steps---about 160E

• www.smeraldoroma.com Good location and fair prices

• www.hotelportoghesiroma.com North of Piazza Navona—has quad

• http://www.residenzacellini.it/ Centro hotel with good reviews


BUDGET 2 STAR OPTIONS: Prices from 90 to 140E for double in season

• www.hotel-giardino-roma.com Good location---nice people

• www.residenzasanpantaleo.com Good value near Piazza Navona

OTHER GOOD OPTIONS TO CONSIDER: Prices from 150 to 350E---by season

• www.hotelmozart.com Nice place---good family/apt. options

• www.hotelmodigliani.com Good reviews and helpful owners

Thank you so much, Bob. I have contacted the B & B's you recommended. I have to wait for them to get back to me to see if they have any vacancies.

Your 3rd B & b recommendation has two properties but only one is available. Is this a good location?
http://trastevere.freshcreator.com/eng/where

Thank you!!

Lots of folks like Trastevere, but I see it as an extra :15 walk to the places I want to see. If you like to walk then may be a good option---I am not a good walker.

Bob, I was able to book Hotel San Carlo!

Thank you so much for your advice.

Good choice---have fun !

Okay, now to nuts and bolts. Does anyone have dining recs for Florence and the Monticchiello area? We are less interested in fine dining and would prefer places that are more homey and less touristy. Also, I've read about some of the outrageously priced leather shops and alternately, some places that sell shoddy knock offs. Are there suggestions of places to find good buys or unique items like pottery? We'll have a car for our time after Florence on our way to Monticchiello.

Osteria La Porta in Monticchiello---have them call and reserve for lunch on the terrace.

http://www.fodors.com/community/europe/need-some-restaurant-help-in-florence-right-now-168699-2.cfm

http://www.fodors.com/community/europe/good-reasonable-restaurants-in-florence.cfm

Just a quick note out before I do a proper TR. we are in Italy as I type this. We have finished our glorious Florence leg and are now at our agriturismo, Terre di Nanno. I just wanted to give props to bob thenavigator. Dude, you seriously rock. My hubby was a bit wary about all the choices I made based on the suggestions of someone we've never met. This agriturismo is probably the most wonderful place we've EVER stayed in! The views make me want to cry. It is at the crest of a huge hill and there are views of Pienze, Multipulciano and Monticchielli. Our room is elegant and rustic at the same time. My husband and I were both reminded of the original Parent Trap movie with Brian Keith and Hayley Mills. If you remember Brian Keith had a pretty spectacular ranch. This is that ranch, but better! Oh, and we ate at La Porta our first afternoon. Gorgeous on the terrace. we ordered only the specials and everything was delicious! The sleepy, winding streets of Monticchiello were perfect after the hustle and bustle of Florence. Kind of reminded me of Mont St. Michel but without the loads of tourists. Will finish a TR later. Again, many thanks to bob!! When this man suggests, BELIEVE him!!