Well, alrighty then! In the spirit of sharing and learning, here's how the passage went:
6 days total. Two of the days were relatively short. Others were somewhere between with one day being quite long.
Day 1 - Alexandria to Belmont Bay Marina in Woodbridge VA (short day)
Day 2 - Belmont Bay to Colonial Beach Yacht Center, Colonial Beach VA (long day)
Day 3 - Colonial Beach to Point Lookout, MD (medium day)
Day 4 - Point Lookout MD to Solomon's MD (long day as I was heading into the wind and waves once passing from the Potomac River into the Chesapeake Bay)
Day 5 - Solomon's MD to Tilghman Island MD (medium day)
Day 6 - Tilghman Island to Annapolis (short day).
Things I experienced:
1. Every day is different so be prepared.
2. When weather shifts, be prepared. On Day 2 down to Colonial Beach, the wind shifted as I got into a section of the Potomac that was miles wide with no real anchor points or marinas to sail into so I just motor sailed my way to Colonial Beach, with the wind aft and my mainsail fully up (no genoa out). Was flying at about 7-8 knots but man was it challenging and tiring. There were no other sailors on the water that day and only one motorboat seen in the last half of the journey. Check it out on google maps and you'll see it's quite the haul.
3. You'll sleep like a baby.
4. Bring plenty of warm clothes, blankets and hats/gloves. Even though the weather was warm during the day, it got chilly at night and I was a little light in this category so slept in a down vest, hat and pants.
5. Have fun (this is obvious but even when things got a little rough or scary, I was enjoying the adventure of it all.
6. Going from the potomac at point lookout into the bay turned out to be much rougher than expected. Again, there were little to no other sailors on the water with the exception of a crab boat. I was battling 5-8' swells into the wind heading up the bay to Solomon's and when I pulled over to chat with the crabbers they just looked at me and kept working. Nothing to see here folks. This gave me confidence that I could continue and make it safely to calmer waters.
7. Know what your boat can and can not do. I learned afterward that my boat could do up to 15' swells so had I known this I would have been more confident fighting the 5-8' swells I was seeing.
8. Cover up. UV rays are tough out there. Long sleeves, hats, sun screen on anything not covered.
9. Make lunch the morning of the trip. Single handed sailing, without a autopilot, doesn't give you a lot of freedom from the tiller while under sail so have all food and bev ready before launch.
10. Plan your route but also plan your exit.
11. Study the carts well the night before and know what to look out for.
12. Take a lot of photos. It's really beautiful out there and you'll likely not be returning any time soon. Besides, sharing this with others is a good way to whet their sailing appetite.
13. Always, always, always check in with the fine folks on Sailboat Owners Forum before making a big passage. I really can't thank you all enough for the advice given and thoughtful responses to my questions. It really made all the difference.
14. Pay it forward. Folks are kind and helpful when you're in need so be sure to always be ready to do the same.
Fair winds and seas. - Glenn