Help me plan my cruise North!

We are planning on venturing out of the Chesapeake (for the first time) with the intent to head north, hopefully to Marthas Vineyard, then stop a few places in between on the way back.

We don't have a long time, 16/17 days total leaving July 4th and returning to Rock Creek/Patapsco River by July 19th or 20th.

I am finishing up a few last projects and should be ready to cast off in time.

Any thoughts and suggestions on places to stay(like should I make reservations asap), must see, things to know, etc...

I need/want to get an EPIRB, should I rent a liferaft? The furthest from shore we'll be looks about 50 miles or so during our straight shot from Cape May to the Vineyard...otherwise the rest will be inside LIS or along the Jersey coast on the way back.

Thanks...I look forward to hearing what you experienced folks have to say.