Rohan,
I think you were at CigarMaster which I had never heard of before. LJ Peretti has an awesome selection of great cigars but I've never actually visited their shop so I don't know if they have any seating. Another place in Boston that many people go to is Churchill's (Tyler's been there for the NERFs) which is right next to Faneuil Hall/Quincy Market.
As far as the 2nd in Hartford, Jim D closes up his shop at 5:00 PM so we'd be outta there then. If you want to, we could meet at a small cigar shop in Vernon, CT which is literally only two minutes from exit 65 off of Route 84. The place is called Have A Cigar I think they're open until 8:00 on Friday nights.
Oh and DO NOT take Route 95 north out of New York City, take the Hutchinson River Parkway which turns into the Merrit Parkway (Route 15) which then turns into the Wilbur Cross Parkway which meets up with Route 91 in Meriden. ESPECIALLY if you're heading out of the city on a Friday afternoon. As you head towards Connecticut, you'll start seeing signs for the Hutchinson River Parkway, it's pretty easy, you barely even need a map. My guess is you'll be coming out of Brooklyn & Queens via the Bronx-Whitestone Bridge and like I said at that point, you'll start seeing signs for "New England" and you'll see two possible routes, the Hutchinson River Pkwy and Route 95 (I think they call that the "New England Thruway" in New York state).
If that's horribly backed up, you can take Route 287 west to Route 684 which brings you to Route 84. It's longer mileage-wise but it's shorter time-wise if there's lots of traffic. You can get to Route 287 from either Route 95 or the Hutchinson River Pkwy.
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