Hello smilin05, and welcome to the forum!
You'll go through Milan going to and from Lake Como so it would make sense to put it at the end so you'll be heading there to fly home. From there I guess it's up to you as to whether you want to Beach > City > Lake or City first and then relaxation.
As mentioned if you're going for beaches there are better choices than CT for beach activities. There are many cities on the coast north of CT with beach access. Maybe look into Levanto which would give you coastal access to beaches as well as train and ferry access to CT towns.
Como itself is a big city so most people here look at Varenna for small town lake access with a train station.
There are a number of business hotels within walking distance of the central train station in Milan which will work for late and early access. It's not the most exciting area of Milan but it's convenient and its a big metro stop so you can visit other parts of the city if you want to. Also know that the biggest airport MXP is an hour outside the city so be sure to add that into your time allocations for "Milan" versus Milan airport.
Have a great trip!
=Tod