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Weekend Trips From Chicago

Old 03-22-2020, 11:47 AM
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Default Weekend Trips From Chicago

I recently purchased an Oíday 322 sailboat and Iím looking to plan a few weekend trips this summer. Does anyone have any good destinations within a day sail of Chicago? I was thinking maybe Milwaukee, WI or South Haven, MI but Iím looking to hear from people who have made day trips from Chicago. Iíll be moored in Monroe Harbor downtown and Iím not highly experienced so I would prefer to avoid being under way at night. I would like a few options and then maybe if the weather is right one weekend I can try out a few longer destination sails. Thanks everyone I appreciate the advice!
Old 03-22-2020, 08:16 PM
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It depends on what you want from your destination. Are you looking just for a place to moor for the night before you head back, or are you looking for things to do, nightlife, museums, etc., at the places you stop?
Old 03-22-2020, 08:30 PM
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Originally Posted by ssobol2533@aol.com View Post
It depends on what you want from your destination. Are you looking just for a place to moor for the night before you head back, or are you looking for things to do, nightlife, museums, etc., at the places you stop?
Definitely looking for things to do; dinner, nightlife, beaches, anything really that would make a good summer weekend trip!
Old 03-23-2020, 05:33 PM
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On a good day with a decent wind ,a few tracks and light chop you might go about 5-7 mph . So in reality I would not want to plan a trip that was more than 30 or so miles as the crow flies from your home port. You also have to sailback which may entail less than favorable wind direction along with 3-5 ft waves.If it was me and I was relatively new to sailing I would start out at 20 miles. If it got to rough to come back your close enough to get a car ride back and be able to wait out the weather if need be for a week.Pay attention to your NOAA weather reports on your radio ,they are more accurate than your TV weather people.Not exactly a beginner sailboat , so rough water is not a big issue, but if your crew are rookies as well , you might not see/sail with them again if your out in 4-6 footers.

Last edited by mr 88; 03-23-2020 at 05:39 PM.
Old 03-23-2020, 05:50 PM
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Originally Posted by ssobol2533@aol.com View Post
It depends on what you want from your destination. Are you looking just for a place to moor for the night before you head back, or are you looking for things to do, nightlife, museums, etc., at the places you stop?
I would prefer to have something to do like nightlife or a town nearby so that my friends who are less into the sailing can enjoy the trip a little more. However Iím also open to just having a safe/comfortable place to moor if there arenít a lot of options within a dayís sail.

Originally Posted by mr 88 View Post
On a good day with a decent wind ,a few tracks and light chop you might go about 5-7 mph . So in reality I would not want to plan a trip that was more than 30 or so miles as the crow flies from your home port. You also have to sailback which may entail less than favorable wind direction along with 3-5 ft waves.If it was me and I was relatively new to sailing I would start out at 20 miles. If it got to rough to come back your close enough to get a car ride back and be able to wait out the weather if need be for a week.Pay attention to your NOAA weather reports on your radio ,they are more accurate than your TV weather people.Not exactly a beginner sailboat , so rough water is not a big issue, but if your crew are rookies as well , you might not see/sail with them again if your out in 4-6 footers.
Really good advice thank you! The wind direction trying to return within a day or 2 is one of my concerns. Iím not sure how steady the wind direction is in the southern part of Lake Michigan. Iíll definitely keep listening to the NOAA reports though and maybe after a few months Iíll have a better idea for how conditions change within a few hours/days.

So I guess to better phrase my question...Anyone know of decent marinaís within 20-30 miles of downtown Chicago? Preferably with something to do for a few hours at night and then return within the next day or 2.
Old 03-24-2020, 09:20 PM
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The other thing to consider is the prevailing winds. You might be able to get somewhere relatively quickly, the the return might be a long slog. Or vice versa.

Reasonable distance places east of Chicago are Michigan City and New Buffalo. Probably more to do in Mich City, but New Buffalo is a longer sail. Depends on whether the destination or the trip is your priority.

In full disclosure, I have not been to either place so I can't say what they are like, although I have considered stopping at both.
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Old 03-26-2020, 10:13 AM
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Originally Posted by Themerryman View Post
Definitely looking for things to do; dinner, nightlife, beaches, anything really that would make a good summer weekend trip!
A great way of relaxation especially together with loved ones.
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