I have done the ALIR 2014-2018 and I will be doing it again this year.
I think it's a fun race. It's long enough so that you will experience every type of weather: no wind, too much wind, cold, hot, wet, dry, etc., but you never HAVE to be out of sight of land. Two years ago the start was moved to NY Harbor. That was a great idea and start is really great. It is a challenge to get a good start, get clean air, and avoid the ferries, commercial traffic, and other distractions. Then it's under the Verrazano bridge and into the Atlantic ocean.
Anyway, what else would you like to know? I race on a well set up C&C 35 mark 3. it usually takes us about 36 hours to do the race. We have a good sail inventory and we usually end of flying each sail at some point in the race. We try to have a crew of 6 experienced people. Would you be sailing spinnaker or non spin class? Personally, i would not do it on a non spin boat - it would just take too long. Feel free to ask any questions.
Some Chessie and other thoughts:
-I've been sailing on the Long Island sound since 2003. I plan on retiring in 4-5 years. I would like to move somewhere on the east coast - with a longer sailing season (the season here is really mid May to mid October), lower cost of living, and and active racing and cruising scene.
-I looked at Oriental (too sleepy) and New Bern NC (not good sailing)
-I looked briefly at Gloucester Point VA - also too sleepy, and a little bit at Hampton VA. I think Hampton has promise. Any comments on Hampton VA from a retirement / sailboat racing and cruising perspective?
I'm looking at possibly doing the Around Long Island Regatta this year for the first time. Does anyone have any experience with it? The dates for 2019 have not been posted yet, but it is usually toward the end of July. Part of that decision is if I'll be doing it on my boat, which involves a cruise up and back from Philly or on my brothers boat which is already up in NY but may not be available.