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A Jet Set Weekend: Boston

Boston is one of the most historical towns in the country and home to the first North American college, Harvard, the original Dunkin’ Donuts, Cheers, The Boston Tea Party, the Red Sox and of course Paul Revere. But what you may not know is that Boston is one of the hippest cities in the US. Let me take you on a tour of my old stomping grounds.

Newbury Street, Boston

The Place to Stay

Boston has some beautiful, culturally historic yet über chic hotels. I’d urge you to stay at one of these to get the real feeling of Colonial and Jeffersonian styling the is Boston.

My Pick: XV Beacon

XV Beacon Lobby

This is (and most likely always will be) my favorite jet set spot in Boston. The hotel’s historic yet obviously modern decor and supreme customer service are the best in the city. XV Beacon’s Back Bay location, only a block from the Boston Commons and a short walk to the famed shopping of Newbury Street definitely keeps me coming back. There may be new hotel blood in the city, but nothing compares to XV!

Another Great Choice: The Liberty Hotel

The talk of the town is the Liberty Hotel. Once an old jail that was built in 1851, The Liberty Hotel has been transformed into one of the new hotel hot-spots. The hotel definitely plays upon its history with the CLINK restaurant and Alibi Lounge. FYI: The first bar of its kind in the country, La Grande Dame bar offers a selection of premier Champagnes by-the-glass from Veuve Clicquot.

The Best Shops

Newbury Street Shops

Newbury Street

Newbury Street began in the 1970’s as a hip street of unique shops, kind of like SoHo. Now, the 8 blocks offer some of the most prestigious shops like Chanel and Ralph Lauren along side trendy inexpensive shops like H & M. However, Newbury Street still has tons of one of a kind boutiques.

My favorites:

Best High End: Louis Boston

Cool Consignment: The Closet

Simple Fashions: Calypso

The Tourist Trap that Can’t Be Missed

Top of the Hub: Enjoy the sunset at the best tourist trap in Boston because on a clear day you can see up to 100 miles away. This bird’s eye view of Boston from the Prudential Center includes Hancock Tower, Boston Commons, Fenway Park and beyond. Skip the Skywalk and dinner and just order a drink and an appetizer in the restaurant and enjoy the view.

Where to Eat

Most Inventive Small Plates: Cuchi Cuchi

The Best of Boston: Oleana

2nd Best Clam Chowda (My Mother’s is #1) :The Union Oyster House

Best Sweets: Mike’s Pastry

Hottest Table: Mistral

Best New England Seafood: B & G Oysters

Things to Do

See the Green Monster at Fenway Park.

Boston Ghosts & Gravestones Tour

Hot Air Balloon Ride

Buffet Brunch Cruise

Private Cooking Party

Boston Harbor Sailing

Where to Sip a Cocktail

Rumor: Plan to dance on the tables on Thursday nights.

33 Lounge: The South End’s home for inventive cocktails like Raspberry Intrigue.

Venu: Guest DJ’s from around the world, great place to dance the night away.

Alibi Lounge: Liberty Hotel’s hot new night spot for a cocktail.

To Find All Rob and Kim’s Secret Hidden Jet Set Spots –

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  • Reply Aaron October 31, 2008 at 9:20 pm

    Friend of ours danced on a table, then fell off and broke both ankles. Would be bad, but this is the second time she has done this. First time was bad, second time was dumb!

    I still love a good table dance!

  • Reply Chris November 1, 2008 at 1:34 am

    WOW – you really got it right about Boston! Even the Union Oyster House! It is rumored that
    Paul Revere used to get so drunk there he would lay down on the sidewalk next to his horse
    and sleep it off. Thanks for adding some old school US culture to your travel blog!

  • Reply Mark Evans November 4, 2008 at 2:26 pm


    Just for fun, I took all the places you mentioned and created “My Jet Set Life’s Boston” within PlanetEye, which is an online travel planning service featuring photographs, maps and content. You can find it here:

    I’d be interested in any feedback you may have.


  • Reply Devin Reams November 4, 2008 at 10:28 pm

    Wow, you posted this the day before we went to Boston for the weekend.

    We found our own great spots but this is excellent. Will keep it in mind next time.

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