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By Valerie Moloney

If it was up to me, my passport would be crowded with stamps from around the world. The consolation – and one not lost on me – is that I get to play in travel for a living, hopping from four-star resorts to urban playgrounds the likes of Dubai and Shanghai.

But the latter destinations do not a family vacation make – especially with little ones who actively look for the familiar (read: scribble sheets and crayons, ice cream and fish ‘n chips) or it’s not a peaceful meal for mom and dad.

For its barely-in-the-air flight time from Chicago and historic appeal, Boston wooed us from the get (and, it has to be said, the best bargain flights I’ve ever purchased at 2 roundtrip the week before Labor Day). Here are a few highlights from our trip, including recommendations for Boston hotels:

The Boston Children’s Museum
Rock climbing walls. A bubble-making room. A pair of ruby red slippers with complementary Wizard of Oz exhibit. It was clear who was more wrecked after buzzing around this three-story funporium – the parents – but so worth it judging by the beaming faces and constant cooing.

The North End
It was well-past my girls’ bedtime when we strolled Boston’s Little Italy on the hunt for the creamiest cannoli in the city after a feast of fried oysters, 1.5-lb lobster and flaky scrod at Union Oyster House, America’s oldest restaurant. But it was our summer vacation, and based on the line out the door of Mike’s Pastry, the stop was worth every minute for our airy ricotta, silky vanilla, velvety chocolate and whipped cream yumminess.  On the way home – the luxe InterContinental Boston – we stumbled by Paul Revere’s house, the modest abode from which he departed on the legendary Midnight Ride.

Duck Tours or Trolley Tours
Confession: We had free tickets to a trolley tour – thank you, Christine – so we opted not to board the Duck Tour, the half-truck, half-boat carrying tourists by land and by sea. Instantly recognizable by their bright colors and wig-donning drivers, they’ve sparked my interest for a return visit, if only to hear the loveable quack quack.

The Hatch Shell
We lucked out on this one. We got to live like locals for just a night at The Hatch Shell at the Esplanade, where the Boston Pops perform on July 4. My friend saved us a patch of grass to check out the Boston Landmark Orchestra’s first and FREE performance with the Boston Ballet, an event that would normally cost in the hundreds. As the stars twinkled, my girls twirled in their sundresses, mimicking the big ballerinas on the open-air stage.

The Liberty Hotel
When another friend suggested a quick drop-in to the former Charles Street Jail, my instinct was to say, “For real?” What are a 7-year-old and a 5-year-old going to do in a hipster hotel? And sure, there are plenty of those – along with urban professionals in striped shirts – the biggest surprise was the Yappy Hour on Wednesday nights for hotel guests with pets. Maybe someday the girls will appreciate the jailhouse touches like the holding cells, but for now, the coolest part of the hotel was getting to pet the Maltese Poodle.

Sailing in Rockport
Here was our Kennedy moment: sailing aboard the Wave Dancer around Rockport. Many thanks to Irene for touching down a week prior, leaving us with postcard-perfect weather in the tidy town dotted by ice cream parlors, antique stores and seafood shacks with the biggest honking oysters I’ve ever slurped.

Related resources

• Baltimore hotels
• Boston vacations
• Cape Cod hotels
• New York hotels

Valerie Moloney is a writer for Orbitz who was born in the Philippines, lived in Morocco and married a native Irishman. She now covers hotels around the world and contributes to the Orbitz blog.

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