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A bit further out from our neighborhood, Chianti and vicinity:

il Granaio, Rapolano Terme.  Just down the Siena-Bettole highway heading east.  A beautiful little ancient village, very close to the San Giovanni Terme (mineral pools and wonderful day spa).  Closed Tuesday
http://osteriailgranaio.it
The famous 'Butcher of Panzano' Dario Cecchini, in Panzano.  About a 30 minute drive heading north towards Greve in Chianti.  GREAT place for Sunday lunch; reservations a must.
http://www.dariocecchini.com/en/
Osteria Castello Brolio, about 10 minutes north of property.  1000 year old castello still in the Baron Ricasoli family.  Great wines and lovely restaurant set just below the castello.  You can tour the gardens around the Castello before or after lunch.
http://www.baronericasoli.com/restaurant
La Taverna, Vagliagli, about a 15 minute drive.  More traditional Tuscan food; lovely outdoor terrace dining when it's warm.
http://www.tripadvisor.com/Restaurant_Review-g668215-d1171691-Reviews-La_Taverna_di_Vagliagli-Vagliagli_Castelnuovo_Berardenga_Tuscany.html
Le Contrade, Gaiole.  About 10 minutes north of the property.  Fabulous inventive chef, Andrea.  
http://www.lecontrade.com/ristorante.html
Papevero, Barbischio (just beyond Gaiole up on a lovely hill).  Great place for lunch on their terrace because of the views.  Good Tuscan fare with a little twist.
http://www.osteriailpapavero.it

Wineries in and around Tuscany ... just a little sampling of each area.

Chianti Wineries:
Felsina, just south of you towards Castelnuovo Berardenga.  Wonderful wines, including several unusual wines for the Chianti area.  
http://www.felsinawine.com/#
Rocca di Montegrossi, just beyond Brolio outside of the little town of Monti.  The owner, Marco, is delightful.  Probably one of the best Rosato wines in the area, and award-winning Vin Santo.
http://www.roccadimontegrossi.it/estate.htm
i Selvatici, near Montevarchi.  Giuseppe, the son, is charming and will share a lot of history of the area with you.  
http://www.iselvatici.it/english.asp
Castello Brolio, tasting room is right on the highway about 10 minutes north of the property.  Website above.
Volpaia, just beyond Radda in Chianti up on a hill.  Beautiful setting; probably the best winery tour in the area.  Call ahead to book, for sure.
http://www.castellodivolpaia.com/en/tasting/
Castello d'Ama, just beyond Gaiole.  Probably the most difficult winery to book for a tasting but well worth it.
http://www.castellodiama.com/en/winery-visits/

Montalcino Wineries:
Altesino, a favorite Brunello producer
http://www.altesino.it/ita/premi_2.php?id=6
Fattoria Resta, very small, exclusive producer; owner Annalisa will enthrall you with her stories.
http://www.fattoriaresta.it
Casanuovo Neri, just up the road from Altesino and Resta ... really fine Brunello producer
http://www.casanovadineri.it/en/tenuta-nuova-brunello-di-montalcino.html
Biordi Santi, the oldest and most respected Brunello producer.  South of Montalcino.  Reservations are difficult to get.
http://www.biondisanti.it/Eng/home_en.php

Montepulciano Wineries:
Avignonesi.  In the countryside not too far from Cortona.  Beautiful setting; lovely cantina where you can have lunch before or after your tasting
http://www.avignonesi.it
Gattavecchi, tasting room is right in the heart of the old town of Montepulciano.
http://www.gattavecchi.it/en/
Poliziano.  Again in the countryside of Montepulciano.  
http://www.carlettipoliziano.com/eng/azienda.html

Florence:

Ceramics: Sbigoli Terrecotte, near the center of Florence.  It is at the corner of Borgo Pinti and San Egidio.  The family who run it are very honest, and can source just about anything you would like.  
Before or after your visit, you can walk across the alley (Borgo Pinti) to the restaurant La Giostra, run by Soldano.  Great for lunch (Monday-Friday) or dinner.  
A few favorite Restaurants:  Sostanza (very old Florentine trattoria, shared tables, no credit cards), Giovanni's (lovely dining room with excellent Tuscan fare), i Latini (raucous atmosphere; shared tables; excellent roasted meats), Osteria Belle Donne, via Belle Donna.
Other great (and quieter) Museums with great Collections and Special Shows through the year ... the Bargello and Palazzo Strozzi.  Of course the Accademia for statue of David (make a booking for a reservation; best to go mid-to-late afternoon)
People-watching in the afternoons ... the terrace outside The Savoy Hotel for a prosecco; the terrace at Riviore in Piazza Signoria
Before or after dinner cocktails with a view ... SeSto at the top of the Excelsior Hotel in Borgo Oggnisanti