I think possible, especially if you can push to closer to 18 days. As many have mentioned, it really really depends on the month. If you're trying to stick to 14 days, I'd personally cut Como (gasp, I know). I was there in mid October, which I was hoping would help to avoid the crowds but my god was it incredibly crowded. I truly couldn't imagine the place in August - what a nightmare. If you're trying to hop on the ferries to bop around to different towns during peak season, you may need to plan a 1-2 hour wait in line each way. It's definitely an 'instagram vs reality' spot. For reference, we probably had to wait 45 mins each time, and this was nearing the off season. Thankfully Italy is open container so one of us was able to grab drinks from a local restaurant and bring them back to the line while we waited.
Another Como warning, if you are in fact driving, be advised Como will likely have a good amount of cliffside driving reminiscent of the amalfi coast. We came down from the Dolomites and I was candidly not prepared. We survived unscratched somehow, but that was about 90 minutes of pure adrenaline we didn't plan on. It all depends on your route. If you're actually staying in the town of Como and driving from Milan, you'll be fine.
One more tip, because while possible, you're losing a lot of time in transit with that itinerary. Why don't you try combining Florence and 'tuscany' by finding a nice agriturismo just outside of the city? You should be able to easily hire a driver if you find something within 45 minutes.