I’m ashamed to admit that as a lifelong Connecticut resident I had never heard of the Thimble Islands.  Truth be told, the first time it peaked my interest is when I learned that there was a cool new brewery called The Thimble Islands Brewery.  Oh, I wondered, why would a Connecticut brewery be named after some no name islands?… Well, if idiot me had taken the 34 seconds to Google it, I would have learned that they are probably one of the most beautiful thing our coastline has to offer.  It wasn’t until a friend recommended cruising the Thimble Islands to me that I finally learned about what I was missing.

The Thimble Islands are a group of islands that live in Stony Creek Harbor off the coast of Branford.  There are over 100 of these small beautiful islands that are stable because they are made up of pink granite.  While most of these islands are just wooded, 23 of them have incredible homes on them.  I use the word “incredible” with great emphasis.  To be honest, some of them are eye-popping mansions.  The islands were named after the thimbleberry which is kind of like a blackberry but actually rare to this area- So, I’m not really sure why they picked that name… but okay.

Of course there’s folklore including the idea that Captain Kidd hid his treasure on these islands.


The privately owned islands have great names like Money Island (the largest with 32 houses on it and a library), Horse Island (which is actually owned by Yale and is the only public island that you can visit), Mother-in-Law island (which is a tiny island with a tiny house that has a back story of a mother in law that was left on it by her newlywed child)- and many more.  The Svenningson name is most widely known because they own many of the islands ($36 million dollars worth…  making them the highest tax paying residents of Branford) and because the wife continues to constantly have construction on the islands.

What I found to be the best part of all this is how you can make this an awesome day trip.  There are three boats that regularly tour the islands every day.  You show up to the dock at Stony Creek- Walk to the end- Stand around and there’s three signs up giving a little bit of information on each of the tours.  Three different boats, three different operators, all 45 minute cruises around the islands narrated by the captain, each $12 per adult.  I chose to go on The Thimble Island Cruise Sea Mist.  I chose it because of one reason, it had an upper deck and I wanted to get tan.  (Go ahead, judge me)  It was the right decision.  Seeing the gorgeous islands from atop this boat with about 40 other passengers was awesome.  Long enough to get a real feel of the islands, short enough not to get bored.

One of the coolest part about these tours is that you can charter these boats just for you and all your friends.  Get rid of all the weird strangers and just explore with your buddies! But if that’s not in the cards, sitting next to an obese sweating man isn’t the worst option.

Nevertheless, there’s certainly great eateries nearby, a park for kids, kayak rentals, a small beach, and a bunch more.  It’s the perfect day getaway in Connecticut.  Also, I learned by asking friends from the area that it’s a party.  If you’re looking to hang out on a boat and have a few beers, that’s certainly “the thing” to do in those waters.  I could tell by the amount of partyers while I was out that this was certainly true.

Pack up the car, head to Branford and check out quaint little Stony Creek and The Thimble Islands.  You’ll be glad you did.

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