Top 5 preppy summer vacation destinations

As The Man and I figure out where to go on vacation this summer (I only get one week of vacay days, so unfair), here are our top contenders. He went to boarding school as a kid in New Hampshire, so that’s always his top choice.

1.) Nantucket Island

Specifically, Cliffside Beach resort. Nothing says “preppy people on vacation” like frilly blue and green beach umbrellas on a shoreline. This place sure ain’t cheap, but it’s right on the water and simply gorgeous. On this little island there’s no shortage of blue skies, cute little shops to enjoy scones and tea, and big bright blooming lilac bushes.

2) Martha’s Vineyard

This is my favorite place to rent a bike and just explore. It never gets unbearably hot on Martha’s Vineyard and the ferry ride over from Cape Code is not only fun but also an almost laughable preppy fashion show (believe me you will never see more popped collars and Bermuda shorts than on that ferry). I love staying at the Hanover House because it’s easy to pretend that it’s your own gorgeous island abode. There’s even a Dairy Queen on the island, which is convenient if you have an addiction bordering on obsession with cherry-dipped cones as I do.

3.) Hampton Beach, New Hampshire

There’s an old-fashioned boardwalk in this town, and it’s my understanding that this really is a summer spot, the locals vacate only to return in September when the beach-going tourists leave. That being the case, it’s fun and affordable to rent a house here, and there’s history everywhere. Hampton Beach also has casinos nowadays, but I am happy to bypass gambling and head over to Sanborn’s Sweet Shop for real old-fashioned salt water taffy. A short drive away, one will find the Kittery Outlet Mall. Izod store? Yes, please!

4.) Bethany Beach, Delaward

If cute little townhouses with flowers in window box are your thing, this is a very cute town for you to consider! Bethany Beach always has a whole summer of family events planned, including a huge blowout with fireworks on the 4th of July, complete with a blueberry pie eating contest.

5.) Cape May, NJ

Forget everything you’ve learned about the Jersey Shore from MTV. You may find fake tans in Cape May, but you are much more likely to stumble across old-fashioned bath & body apothecaries and antique shops in this cute little town than you are to meet greased up, drunken goons. There are frequent art fairs throughout the summer, and the Cape May Popcorn Factory really ought to be on your list of must-see local attractions.



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