HI Jrale, You have mentioned a subject dear to my heart. My late wife and I used to sail to Avalon and drop anchor for a week every year. We always left Cabrillo Beach early in the morning and motored part way til the wind picked up. Don't leave late afternoon because the wind can come through the slot and blow like hell. There is no ideal month to go. Avalon is usually 10 degrees warmer in the Winter and 10 degrees cooler in the Summer. We went over once in February. Had the whole place to ourselves. It's about 22-23 miles to Avalon. 5+ hours. Set your compass on Zero and depending on wind and drift it will put you at Long Point about 4 miles west of Avalon and then drop down east. If you want to rent a can in the harbor don't go without an advance reservation through the harbor master. If you anchor out and you don't have a dinghy the shore boat is expensive. Also everything is more costly in Avalon due to being shipped over, bring what you can. Contact Avalon Chamber of Commerce and they will send you a "boatload" of info. Lots of history. Don't miss the Casino, Botanical Gardens, etc. You can walk anywhere, rent a bike or golfcart. Nice Golf course by the way. First tee used to be home plate for the Cubs during spring training. Wrigley brought the whole team and families over. Let me know if I can offer any more help. Fair Winds and Full Sails...