I suggest you book the boat in advance during the busy season. We reserved the same day (the rental location is right by where you'll have breakfast), but we were there in the off season. Also, pack snacks and water for your hike, there will be drinks at the top available for purchase, but we stopped a few times to take a break and recharge.
Since this activity is majority outside, I wouldn't recommend it during the winter months.
Heading to Lake Como with kids? This family-friendly day is going to give you a full view of what Lake Como has to offer. Boat riding, castles, hiking, pizza, and more! Begin your day with breakfast on the beach at Bar il Molo and enjoy fresh fruit, crepes and lattes. Then head to Castello di Vezio and climb to the top of the tower of this historic castle. You’ll see all of Lake Como and beyond. After your hike, pick up some pizza at Albergo Del Sole Varenna and go for a boat ride on the lake. Who doesn’t like a boating picnic?! Cruise around while taking in views of the Swiss Alps, sneak a peek at George Clooney’s home and pull over for an afternoon espresso and tiramisu. It will be a jam-packed Italian adventure that you and your nuggets won’t forget.