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I've come to the conclusion that I prefer sailing to a destination more than just going for a day sail.

Don't get me wrong. Much of the sailing I do is just day sailing on the Chesapeake. And when I say "destination" I don't meant long cruises to exotic destinations (at least not yet). I'm talking about destinations of 25-35 nm per day and mostly lastly 2 - 4 days, sometimes more.

And I do like day sailing. Any kind of sailing. It's just that I find destination sailing more interesting. Partly I suppose that I like dropping the hook after being on the water and I really like waking up to the sunrise in a pretty cove with a steaming cup of tea. But somehow the sailing too is different. Maybe it's the navigation. But that's not all that much in the Chesapeake.

When I'm just out for the day, I find I often have to look for entertainment. Which is usually picking out a sailboat in the distance and trying to overtake and pass her. (And when passing the other boat, making sure I appear to be completely oblivious to their presence.)

Anyone else feel the same? Anything you do to liven up the day sail?
 

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I wholeheartedly agree that I prefer sailing to a destination. It doesn't even have to be 10 miles and it's always the getting there that is the most fun for Nikki and I. One day last week, we left Chatham Bay, and sailed around to Clifton to clear out. Then up the anchor again and a half hour sail to Petite Martinique for fuel. Then off to Tyrrel Bay in Carriacou. All told maybe 4.5 hours of sailing, but 4 places, 3 islands, in 2 countries, all in one day. What fun.
 

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We almost never leave and return to the slip on the same day, which I suppose is what constitutes a day sail. Essentially, we consider a day sail to be one where we stay in the Bay and anchor overnight. May not even leave the boat.

A destination would be out to one of the islands or up/down the coast. With enough time, I prefer a destination as well. However, the nearest offshore spot for us is 3+ hours in ideal sailing conditions or motoring. 5 hrs is common. In order to get there in reasonable time, you need to be on your game, stay properly trimmed, chart an efficient course, etc. If we have to go out and back on the same weekend, it depends on our mood. Sometimes I just need to get offshore (ish) and go somewhere. Others, ghosting along in the Bay to a quiet cove, crack open a few beers and BBQ is just what the doc ordered.

But sleeping at anchor or mooring is almost always required.
 
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