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post #1 of 9 Old 08-26-2016 Thread Starter
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Ideas for first trip

Hi! New here and newer to sailing! We are looking to take our first trip with children. Thinking Mystic? Greenport? Any suggestions? Leaving from Westbrook, CT. Thank you!
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post #2 of 9 Old 08-26-2016
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Re: Ideas for first trip

From Westbrook it's an easy hop to Shelter Island/Greenport. You do need to time the current at Plum Gut. Either the town marina (with its carousel) or Townsend Manor (with pool) are good places to stay with kids.

Mystic is also a good stop, especially if you can get space right in the Seaport. Kids will love that.

Another good choice is Stonington/Watch Hill. Get a mooring at Dodson's in Stonington and/or go through the channel to Watch Hill and anchor behind the beach. Easy walk to town for lunch, ice cream, or a ride on the 1880s Flying Horses (if they're young enough).

If you are adventurous, there's always Block Island. Maybe save that for next year.
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post #3 of 9 Old 01-28-2017
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Re: Ideas for first trip

Though this is an old thread, but would like to say that Westbrook is a lovely place. Hope you enjoyed your trip and had a great experience. The last time I went for a trip, was quite a nice experience, but had a lot of tanning and sun burns. So when going out with family it is must to see that along with other important things you also take care of your skin. Sun hats, sunscreens, sunglasses are must. You get a good collection of UV protected sunglasses at many online stores. You can have a peek here to get some idea.
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post #4 of 9 Old 06-29-2017
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Re: Ideas for first trip

We LOVED Block Island, though did not have kids at the time. It's definitely worth a visit with or without kids!
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Re: Ideas for first trip

I suggest... West Harbor, Fishers Island and then Stonnington... Mystic and return.

Watch your tides... they can be a ***** if you fight them.

BI is a lovely reach from Watch Hill and it's a fun place.... but beware of the holding in the Salt Pond... it's not good...
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post #6 of 9 Old 12-02-2017
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Re: Ideas for first trip

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Originally Posted by JimsCAL View Post
From Westbrook it's an easy hop to Shelter Island/Greenport. You do need to time the current at Plum Gut. Either the town marina (with its carousel) or Townsend Manor (with pool) are good places to stay with kids.

Mystic is also a good stop, especially if you can get space right in the Seaport. Kids will love that.

Another good choice is Stonington/Watch Hill. Get a mooring at Dodson's in Stonington and/or go through the channel to Watch Hill and anchor behind the beach. Easy walk to town for lunch, ice cream, or a ride on the 1880s Flying Horses (if they're young enough).

If you are adventurous, there's always Block Island. Maybe save that for next year.
it sounds a great option!... glad I READ THIS POST.

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post #7 of 9 Old 12-03-2017
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Re: Ideas for first trip

I no longer go to Block Island in July or August. It's insanely crowded. No comfortable room in the anchorage and if you don't drag, the dope next to you probably will. Moorings are first come first serve and you're not likely to get one on turn over, unless you are prowling the mooring field at 8am. The marina will frequently raft up boats in mid-summer. Pass.

The best times for Block are mid-May (once the dinghy docks are reinstalled) through the weekend the kids get out of school around the third weekend in June. Then again, in September, after Labor Day.
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Re: Ideas for first trip

Block is fine if you show up mid week. Tuesday or Wednesday is best. Anchor near the tug on the left coming in. Avoid the dinghy docks and run dinghy in on the left then walk across to get to the beach. Great fish taco stand right there. Important to put no strain on anchor when you first drop it. Eventually it will sink through the muddy soup and find holding. Donít back down on it for 15-20 minutes. Same technique as you use in the Chessie

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Re: Ideas for first trip

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Block is fine if you show up mid week. Tuesday or Wednesday is best. Anchor near the tug on the left coming in. Avoid the dinghy docks and run dinghy in on the left then walk across to get to the beach. Great fish taco stand right there. Important to put no strain on anchor when you first drop it. Eventually it will sink through the muddy soup and find holding. Donít back down on it for 15-20 minutes. Same technique as you use in the Chessie
Love the anchoring technique. I've been able to get a set in the spring fairly easily. By Sept, we seem to grab a discounted mooring ball (half price after Labor Day). My theory has always been that the bottom gets plowed up all summer.

Yes, we've beached the dinghy many times at Block. I was just giving highest and best times to go. Our beach spot is to the right of the Oar. This is probably because, if the Oar isn't open, we're not going. It's not uncommon for the town to get a late start putting the docks in. It's a nostalgic spot for us. I've been going since the 70s (I was a kid on parents boat). Family had an Oar there from back then, till just two years ago, but they took it down, when working behind it. My Father inquired this past summer about it and the Manager got very snotty with him. The guy is a jerk, you can tell. Back in the day the Oar was nothing like it is today. Just the inside part, two beers on tap, no glass in the windows and NO Sushi Bar! Have to admit, I'm a fan of the lobster grilled cheese and the Lobster Club now.


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