Trip planning for 3 weeks in Tuscany in May


New member
My husband and I have a 6 weeks sabbatical and tentatively plan to stay 3 weeks in Tuscany, 1 week in Venice, and 2 weeks in Greece.

For the 3 weeks in Tuscany, we'd like to check out Florence museum, gallery, shopping, church, etc,... for a few days, and then visit other places in Tuscany. We'd like slow vacation, enjoy local culture as much as we can. I guess we need to book 2 bases, 1 close or in Florence, and 1 outside Florence to access other sights.

Please help recommend the base place, transportation, place to stay (not sure which one works best for us among villa, airBnB, or hotel.)

Feel free to throw in suggestion for my stay in Venice and Greece (website, forum like this, etc,...)




Well-known member

Three weeks in Tuscany gives you ample time to explore in a leisurely manner, enjoying the museums, monuments and sites. Dividing your time in two, possibly even three, locations sounds like an excellent idea. You may even want to play with the idea of different types of accommodations during your stay (a hotel in the city, a B&B in Chianti and an apartment closer to Val d’Orcia). Of course there are so many to choose from your head will spin!
Spending time in the city will allow you to visit so many of the wonderful sites without rushing it and risking the famous “Stendhal Syndrome” ;-) My favorite museums, besides the classics like the Uffizi, Accademia, include the Cathedral Complex, Bargello and Bardini.

A B&B would be my first choice, some suggestions are:
Antiche Dimore Fiorentine
Casa dei Tintori
Villa Antea

As a second stop, head out towards Chianti, and spend your time exploring the vineyards, small towns and ancient churches. I particularly suggest that you look outside Chianti Classico, maybe towards western edge of Chianti.

Casolare Libbiano - with its onsite restaurant

Palazzo Malaspina or B&B Giglio inside the walls of a small town with restaurants within walk distance

Taverna di Bibbiano with its view of San Gimignano

Another favorite:

Lastly I would plan a week just south of Siena, where you will encounter some of the most “uncontaminated” countryside. Between the soft rolling hills, fabulous vineyards & wine cellars, olive groves, hot water springs and enchanting medieval towns. I would suggest a weekly stay, where you can sit poolside and relax, cook a meal in you kitchen using the great fresh ingredients that you will find the local markets. Be sure to visit Bagno Vignoni and Arcidosso.

Places to look at could be: - I love that you can walk into town from here not only is this a wine experience, but there is a great little B&B on the property.

Hope this helps you a bit,

Buon Viaggio,

Donna Denise