I'm no cruising veteran but as long as you pack light (hopefully easy at that time of year) you shouldn't have any problems. The tent thing is a great idea. I think you'll have a fine time.
Keep us apprised as your plans solidify and maybe we'll see you on the water. You're two kids ahead of us but it would be nice to see how it's working out for you!
s/v Laelia - 1978 Pearson 365 ketch
s/v Essorant - 1972 Catalina 27