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Thinking of taking my boat for a longer over the horizon trip from San Diego Bay where I do most of my sailing.

I've been sailing for years, but haven't yet taken a solo trip any further than Mission Bay from SD Bay.

I'm thinking of either going to Catalina or San Clemente for my first longer distance trip. They're both about the same distance, but in slightly different directions.

1. Catalina: Much nicer destination. Can go ashore and grab a brew. But might have prevailing winds on the nose more than heading west to SCI. Also, having not done it, I'm a bit nervous about threading my way to a mooring ball in a crowded field while I'm solo and possibly exhausted from the passage.

2. San Clemente: Not as nice a destination, can't go ashore. But can fish and explore with the dinghy. Might have better sailing winds going to and back. Dropping the hook in a much less crowded area seems easier than Avalon.

Thoughts? Anyone gone to both and can share insights?

-Charts
 

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Catalina is the better option.

Avalon Bay will be very crowded during the summer, extra crowded on weekends and forget about Labor Day. There are moorings in Descanso Bay just north of Avalon which may be a little easier to locate and or pick up but they can be pretty exposed.

West end coves: Isthmus, Cherry and 4th of July are less crowed than Avalon. In my experience Isthmus harbor master is much friendly and more helpful than Avalon harbor master. In Isthmus cove they will lead you to your mooring and even help you pick it up if they have time.

San Clemente is probably a no go. Island is owned by the Navy and used for special warfare training. Day anchorage may be possible in certain areas but overnight anchorage probably not going to be allowed.
 

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San Clemente is probably a no go. Island is owned by the Navy and used for special warfare training. Day anchorage may be possible in certain areas but overnight anchorage probably not going to be allowed.
Although SCI is owned my the military, is is OK to anchor there as long as you avoid areas with active military operations. See: HERE
You're supposed to call Island Security before heading out (you can find the number on the Net).

However, for your first "long distance" trip, I would recommend Catalina. There are no services available on Clemente, and you can't land (if you wanted to do so). Catalina Harbor, on the SW side of the "Isthmus" of Catalina Island, is probably the most relaxed harbor with any services on the island; as well as the most protected. On the other hand, Avalon is the closest to your home port. If you want more seclusion, you can try Little Harbor (about an hour south of Catalina Harbor). There are no services, including moorings. It's also pretty small (as the name implies), so if you try going there be prepared to use Catalina Harbor as an alternate if Little Harbor is full.
 
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My first "big trip" from SD was to Ensenada for a bottom job. That kinda thing is complicated with all the check in stuff so I would also recommend Catalina. However when I go up there I usually hop up the coast in short legs and then take the long run down from catalina in one hop. Its a little easier that way imho.
SD/MB to Dana Point would be a nice long jump. Also, Dana Point is pretty cool place to stop in for a night or two. Motor straight west in the early am to set yourself up for a tight reach north from 1100 until you get there.
From DP its pretty much straight west to Avalon, a little over 40 miles I think.
From Catalina to SD is about 70 miles. When I did it I left 2 Harbors at 0600 and got the SD buoy a round 2300. It was a long day but a fun one.

I have never made it out to San Clemente. I would love to but that lack of facilties is kind of a bummer. However If I do ever get out there I will defineitly have a pole or two. Its supposed to be quite fishy.
 

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Not to hijack the thread but does anyone recommend a good bareboat charter co out of oxnard or ventura? Im looking at an october date and know nothing about the area. Ive never sailed the Pacific and heard the channel islands and catalina would be nice to see.
 

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I concur, you definitely want to head to Catalina. I would spend one night in Avalon then head up to Two Harbors. If you want more adventure, head up over the top and circumnavigate the island - come down the Western side before heading back to SD.
 
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