Hello,
I've searched extensively for various tug charters for several years. I have never seen anything on the East Coast. Here in the Midwest there are 1-2 outfits that charter and they have a Nordic and CHB 35. From what I could find, you'll have to head west! In the PNW there are two good options: Anacortes and San Juan Sailing. Both have Rangers in different sizes and configurations and I have had good experiences with them. I absolutely agree with chartering first since it gives you a chance to try different size boats and options like a command bridge. By spending a week or so on a boat you'll get plenty of time to see what works best for you and an opportunity to visualize how you'll be using it (e.g. overnight on the ball, staying at marinas, cooking all your meals on board, etc.). The PNW offers fantastic places to see during the charter and you can experience a lot of fun boating activities. Good luck!