Awesome, sounds like something "I would do"!
I reread your plan and it is what you didn't say that was worrisome.
The following are a list of items that if true would be in your favor.
1. You are an experienced sailor.
2. You know this boats rig well.
3. You know how this boat handles well.
4. You know this boat is rigged for single handling or you have experienced crew.
5. You know both harbors and the route well.
6. You have good experience in using the ground tackle on this boat and know it is in good shape.
7. You have a few extra days to make the trip.
8. You are certain that everything else about the boat is sound like the standing rigging, hull and steering
You see we don't know much about you. The more of the above positives the higher the chance you will have a good trip. You may have grown up on these waters know them well have sailed every summer on ketches similar to the one you bought and the boat has been professionally surveyed, including a rigging survey and you have two weeks and a life long sailor for a mate. You might just make it.
If you answer no to more than half of the above questions you will most likely be on the phone to 911 which can get costly and besides the embarrassment, which you will get over, may cause you to abandon sailing which would be the real loss.
In short we just don't know enough to know enough about you to give sound advice.
What you might find interesting is if you asked your question in a different way.
How many experienced sailors would attempt to make the trip by sail only based on what you tell us about the boat. That I would like to hear myself.