I am lucky enough to travel for work. Fun travel, though. I'm not flying out every week, being rootless and living out of hotels. But, I do average about one trip a month to a nice domestic destination. Unfortunately, my next trip isn't coming for another 4 weeks.
So for this month, or week, my ideal destination is New York City.
I have visited NYC before, with a group of guys in a mom van, too poor to go shopping, and not enough time to do anything besides Central Park and a Yankee Game. 
It has been my lifelong desire to go to New York, and not only enjoy a good tourist experience, but go crazy shopping.  So just throwing some ideas around, here would be my ideal NYC itinerary: 
-The Statue of Liberty 
-The Guggenheim, the Metropolitan Museum and the MoMA  
-Running/Boat Rowing in Central Park  
-Rockefeller Center Ice Skating 
-A substantial, multi-day, multi-sectional food crawl (including food trucks) 
-A Yankee and Mets Game in each of their new stadiums  
-NY Rangers Hockey Game at MSG 
-Audience Tickets for Late Night with Jimmy Fallon (particularly for Slow Jam the News) 
-Book of Mormon on Broadway 
-Shopping at Bergdorf's 
-Serendipity 
-Afternoon Tea 
-Cocktails at Top of the Rock -A New York Bagel and Lox brunch -Big Gay Ice Cream Shop -Used book shopping at Argosy and The Strand 
-Metropolitan Opera House and Museum 
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