A Thanksgiving Destination Wedding

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Another blog post from Mr. Deals…

Wow, Thanksgiving seems like it was forever ago. Now we are almost at Christmas/New Years. Where does the time go? I think I have finally recovered from the whirlwind travel adventure I embarked on for the Thanksgiving holiday and few days after. This year the Thanksgiving “break” was much different than most, with a best friend of mine getting married the day after Turkey Day and a bunch of out-of-towners wanting to be tourists in my home city.

It started out like any other Thanksgiving. A trip up to the Boston area to see the in-laws and parents. Actually, now it’s not really us going to see them, it’s about them getting to see Baby Deals. They’ve now lost interest in seeing us (I guess we aren’t cute enough anymore). After making the rounds, I had to part ways from the families to embark on a little road trip with some buddies from college.

Friday after Thanksgiving at 8am, I met 2 of my friends at Boston’s Logan Airport, not to fly anywhere, but to rent a car with the goal of being in Montauk, Long Island NY by 4:30pm for a wedding. This destination wedding was on an island, a cold island, and not one you’d typically think of for a destination wedding in the winter. Now for those of you not familiar with New York’s coastline, Montauk is nicknamed “The End” because that’s exactly where it is, at the end of Long Island. Roughly a 3 hour drive from NYC and even further from Boston, we had a hefty trip in front of us.

You have a few options to get to Montauk from points north. The first is to obviously drive all the way out there by driving just to the edge of Manhattan and then driving all the way out to Montauk. I would never recommend this option. It’s just so damn far. The other option is to take the Cross Sound Ferry from New London, CT. It’s going to take you roughly the same amount of time, but with a nice 1.5hr ferry ride to break things up. This is the option we took, but here’s the downfall. Once you get off the ferry in Orient Point (the northern tip of LI), you need to drive around a big hook that can take anywhere from an hour to 2 hours just to get to Montauk (southern tip of LI).

So after leaving at 8am, hopping a ferry, we made it to the wedding with about 45 or so minutes to spare. I will say, the Montauk Yacht Club is a great venue for a 120 or less crowd. And Montauk in the offseason is a place that everyone should try to visit if ever venturing to the outer areas of Long Island. During the Summer Montauk is becoming a ritzy weekend hotspot for the wealthy NYC crowd and understandably so. I would go as far to say there’s some of the nicest beaches I’ve ever seen as you go out in that direction. Now if we could only get that Caribbean blue water!


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  1. Mr. Deals!! We’re so thrilled that you joined John and I for our big day! BUT I think that what you forgot to mention to your readers was that the Montauk Yacht Club rooms are normally $599 during the summer with a 2 night minimum. During Thanksgiving they are between $99 – 129 a night. THAT’S a deal, right?

    MYC always books up over Thanksgiving, as people like to come out for a long weekend with the highlight being the annual Saturday-after-Thanksgiving lighting of the light house that is literally located at the eastern most point of NY State!

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