Maybe it's the therapeutic outdoor morning showers, or the privilege of getting the sunrise before anybody else on the east coast, or the simple fact that it is devoid of a tether to whatever "real world" you left behind at Hyannis. Nantucket is magical in the summer. Worry seems to roll off your shoulders, like beads of sweat erratically migrating down your cocktail.

The island, aside from its locals, is home to an inherently preppy summer colony. It is beloved in part for the geographical fact that it's a pain in the ass to get to. The harder the trek, the preppier the locale. And Nantucket is perhaps the preppiest (edging out Martha's Vineyard and its trailer parks). If you're not flying into ACK, you have to cross the moat to the WASP kingdom via an hour long ferry.

Despite the inconveniences, The Grey lady more than quadruples in size come June. Frankly, it gets crazy around the Fourth. But that's not to say you can't get alone. This secluded beach I photographed Alise Shoemaker* on a couple years ago is on the South Shore somewhere between Nobadeer and Tom Nevers. It's a great spot if you can find it. Odds are good that you'll have it all to yourself for a picnic, skinny dipping, or whatever else bakes your (crab) cake. As for how to get there exactly, well, it wouldn’t be preppy if I made it that easy.

*click on the image above to download a wallpaper version

Frank Clegg is closer to an artist than a master-craftsmen (though I assure you he is both). Each time I pack for a long weekend I'm reminded of this. His Signature Duffle, a triumvirate of beauty, craftsmanship, and utilitarian design, only gets better with age. It's cloaked in simplicity—a design meticulously reduced to only what is necessary to get you there and back again. Case in point, there is no interior liner. A frivolity to Clegg. After all, there is nothing to hide since he only employs the finest vegetable dyed leather he can get his hands on. Swiss RiRi zippers, brass hardware, and double thick leather bottom round out the exceptional construction.

After a few trips with my Signature Duffle in hand, I offhandedly mention to Clegg that I would love to see it in a smaller size. I think selfishly I just want to carry my bag not just on weekend getaways but every day. Not long after our conversation, Clegg makes short work of what is now his Small Signature Duffle. The new overnight bag, featured here in chocolate*, is ideal for overnight trips or just daily jaunts to the gym.

At $765, the Small Signature Duffle is a far cry from an impulse buy. But you don't really want that in a heirloom piece. You want something that you can aspire to. You want something that is going to sting a little. And Clegg offers that at an incredible value. See, Frank Clegg sells his bags directly to his customers. If he didn't, Bergdorf Goodman would be peddling them for upwards of $1300. And that is probably why Clegg doesn't allow that, the hard working American that he is. He understands the value of craftsmanship and that of a dollar...especially when it stings.

*courtesy of Frank Clegg Leatherworks

Nothing tops "being there" when Vampire Weekend took to the Roseland for their sold out hometown show in New York recently. A live filming of the show directed by Steve Buscemi comes in a close second though.

It’s finally reeking of summer in New York. That’s right, I’m talking about the subways. But there is a silver lining—lobster rolls. Of preppy summer fare, there are few greater and none more satisfying. The best are teeming with fresh lobster and served up in cardboard trays and wax paper. Rebecca and I rolled up to the food truck laager in the Flatiron District last night to usher in the season of leisureliness properly.

Connecticut style (right) and Maine style (left) lobster rolls ($16)

Red Hook Lobster Pound specializes in fresh catch lobster. Susan Povich and Ralph Gorham, who founded the seat-of-your-pants operation in 2008, drive up the coast of Maine several times a week to round up their crustaceans. They serve up rolls in Maine (chilled lobster, celery, house mayo, light spices) and Connecticut style (warm lobster drunk on butter). In a moment of indecision I order both. Nine minutes later, no regrets. It is easily one of the best lobster rolls in New York (and I’ve had Lunch before).

Nantucket doesn't let you sleep in. At least not in Siasconset. The Sun rises at a quarter past five over the eastern bluff the sleepy village teeters on (one house has already tumbled down the eroding cliff with a handful more sure to follow). Let there be no mistake, I'm of the ilk that enjoys Nantucket by way of work, not exclusively by way of play. But such are most of my travels. I'm hardly interested in jetting off anywhere unless it involves a business write-off.

I pop into Murray's Toggery Shop, the birthplace of Nantucket Reds, to pass some time before my buddy Jon Terbell and I begin building out his summer pop-up shop, One Orange. It's what one would expect from a small town sportswear clothier. But after I wander into the back room (where there is everything you could ever imagine in Nantucket Red) I notice a small stash of Boast piqué polos hanging in the corner. While certainly a fan of the brand, their fit left a little to be desired since I last pulled on the "Japanese Maple Leaf" a couple years ago. Rumor had it Boast revisited their polo's fit* recently and I secretly hoped it to be true. The arm holes are higher, the body sits closer to the torso while the tennis tail hits at just the right part of your backside. I happily left with one in Carolina Blue. Back in play, as they say.

Never heard of Boast? Enjoy this animated abridged history of the irreverent squash inspired sportswear company to get up to speed.

*It would seem as if Boast embraced vanity sizing as where I was once a medium, I now wear their small (I'm 5'11", 175lbs)