We are very excited to participate in our first RS tour - Best of Tuscany beginning May 1. We are well-traveled, but have never joined a group tour. We consider dining to be an important part of our vacations and would like to know if we should make dinner reservations now for those evenings where dinner is not a group event; or should we wait until the tour begins and ask the local guides for recommendations? Would it then be difficult to get reservations on short notice? Appreciate any suggestions!
Rick's advice this year is, if you really want to eat somewhere, you really need a reservation. Europe is full up.
It really depends on the area, the restaurant and the time of year but generally yes, it's a good idea. You might want to check out the RS Florence & Tuscany Guidebook, or the new RS Italy for Food Lovers for some recommendations and this forum here as well.
A few things to remember - generally Italians eat later so you might have a better chance at a restaurant if you book an earlier time. Also, pizzerias usually do not take reservations so worst case, you could enjoy an Italian-made pizza. :)
Some of your overnights will be in smaller locations, so I would go ahead and make reservations as soon as they share your exact towns. Dinner in the smaller places usually begins around 8pm, although the tables are busy beforehand in some piazzas for the apertivo social time.