I did this exact sail a few years back (Sandy Point Park to Annapolis to Sandy Point Park).
My sail took me to the main city dock in Annapolis. There are a couple of restaurants that we may be able to pull up to and get tables next to our Islands!
I did do a brief detour and got caught up in a Naval Academy sailing regatta...
The wind did die and I used my outboard in a couple of places.
The YouTube video below shows most of the trip including the boat ramps, city docs, Naval Academy and some light wind sailing. This was in July (high season). Fair number of boats on the water. I did use my motor a couple of times when the wind died. Late April should have fewer boats.
Per the questions:
- Distance from Sandy Point to the Annapolis city docks is about 8 miles
- Time to sail to Annapolis is very wind dependent - but estimate ~ 2-3 hours
- Recommended meeting time is 9 AM with boats ready to head out by 9:30 or so (flexible, but wind will dictate)
- Recommended safety gear - what ever you need for cool water (upper 50s to low 60s is my best estimate).
- One or more lines to tie you boat up is recommended
- Motor is optional (I always take my outboard for safety reasons).
For those not familiar with the area, I hope this helps give you an idea of the sail.
https://youtu.be/FnZbbrZlS0Y