Plan the Ultimate City Weekend

Ultimate city weekend

The suburbs are great, limited noise and traffic are only a couple of the advantages that come with green lawns and two-car garages, but sometimes I need an escape. With my trip to NYC coming up, I am reminded why I love cities. Whether it’s New York, Boston, or Chicago, any metropolis gets my pulse quickening. Towering skylines and bustling sidewalks make me think of the many ideas and opportunities that are stirring inside a scant number of square miles. I now know that I want to get away to the city lights more often. So get ready, here’s my guide to planning the ultimate weekend to the city of your choice!

Transportation: How are you going to get there? Are you going to drive, fly, go by train? Think about how long getting there is going to take and how you’ll travel upon arrival. Consider the cost of parking, mass transit, or taxi rides. Pack your comfy shoes, grab a map, and walking can effectively get you where you need to go without bumper to bumper traffic. Along the way you’ll even get a local’s view of the city!

Accommodations: Ideally, you have friends with plenty of space that live near where you want to be. If not, websites like Trip Advisor and Hotwire are helpful in finding cheap lodging for the short hours you’re not out exploring.

Activities: This is both the easiest and hardest part of trip planning. There is an endless number of possibilities and you have to pick and choose what to squeeze into your few days. I like to make a list of everything I want to see and do. A typed itinerary can keep you from feeling overwhelmed. Consider museums, shopping, shows, landmarks, and tours.

Cuisine: Yes, allow yourself one big, fancy dinner, but don’t go too crazy. Food is more expensive in cities (just like everything else!) so be sure to check out menus online if you are unsure of a restaurant’s price point. You want to enjoy your vacation, not think of the rent payment you just spent on a meal for two. And don’t forget, cocktails aren’t cheap either! Think of starting night the night off with water and finishing the night with a delicious cocktail or two. Try not to wake up with a bar tab hangover (I bought how many drinks?!). I like using Urban Spoon, it’s helpful in locating eats by city, neighborhood, and food type.

In the end, a well researched trip makes for the best trip. Now bon voyage!


weekend trip
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  • Reply October 20, 2012


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