Travel: City

Become a member of Global Entry, the U.S. government travel program that allows low-risk Americans traveling internationally to navigate security and customs with ease. Sure, you will have to divulge lots of personal information and schedule an interview at one of the Global Entry Enrollment Centers, but a shorter pass through customs when you return to the U.S. makes it worthwhile. Pair this with TSA PreCheck and you may never have to take off your shoes or belt or unpack your computer when traveling domestically.

I love a great hostelry (don't get me started on the joys of a room service hamburger), but if I am going to be in a city for more than a few days I always rent an apartment. Hotels tend to be impersonal and expensive, and I like to make my own coffee, shop the local market and pick up a few bottles of wine.

I turn to sources such as VRBO, One Fine Stay and Airbnb to find amazing pads in wonderful neighborhoods where I can really feel at home.

Develop a relationship with a restaurant or two in cities that you go to often. Visit that eatery whenever you're in town and get to know the maitre d', bartender and wait staff. It's so nice to walk in, be greeted by name and have the staff know your likes and dislikes. Be sure to tip well in appreciation.

Also develop a relationship with a car service, hiring the same driver as often as you can. At hectic arrival areas such as JFK or LAX, there's nothing like someone you know locating you and your baggage without hassle. You've already had a long trip—why not relax and go along for the ride before that big meeting or business dinner?