5 Cities for Weekend Trips


Everyone has their own criteria for what makes a city great.  My list for the top 5 cities for weekend trips in the US have great food, sights, friendliness (generally), and ambience. While nice weather may influence when I visit, at some point during the year all can be lovely.  If you are in the market for a quick trip (between 2-5 days) start pricing flights and hotels for this summer or fall.

1) New York


New York has it all whether you are a sports fan, art lover, food connoisseur, or a patriot.  The iconic Statue of Liberty, Empire State Building, and Central Park are sights for everyone.

The new Freedom Tower

NYC 009

New York City has the pizza, bagels, and foodie food.  A perfect day of food for me would be a morning bagel, pizza for lunch, and a swanky dinner at a New York hotspot.

John’s Pizza on Bleecker Street:


Finally, take in a show on Broadway or marvel at the crowds in Times Square.

2) Chicago

As a Midwesterner, Chicago was the big city I was closest to and have the most fondness towards.  Catching the Cubs in Wrigleyville or the Bears at Soldier Field are worth the weekend alone.  But don’t forget to chow down on a Chicago hot dog at the ballpark or wait until after the game for some Chicago-style pizza from Giordano’s or Lou Malnati’s.


The Magnificent Mile and neighborhoods provide a nice range of hotel options.  Staying on Michigan Ave (or very close to it) gets you close to the shopping.  Go for a run along Lake Michigan to exercise with other Chicagoans and head for the Field Museum and Planetarium that hang over the lake.


Navy Pier provides some touristy sights and but in the summer find some of the neighborhood streets festivals for some music, drinks, and summertime fun.

3) Charleston


Charleston has the ambiance that is found only in the South- beautiful homes, delicious southern cooking, and friendly folks to make your stay enjoyable.  Personally I could eat out for breakfast, lunch, and dinner at a different restaurant for a week for fun.  The food is so good here!


A run (or walk) along the coast brings you by some gorgeous homes and helps work off last night’s giant, scrumptious dinner.  Have fun looking at all the properties and pick which one is your dream home in case of future lottery winnings.

Porch swings on the pier:


Charleston has parks to chill in, pools to swim in, and patios to drink on.  You should partake in all three.

4) San Diego


Image Source

San Diego is the land of always beautiful weather.  Come here any time of year for a fun time in the sun.  Cosmopolitan restaurants and mom and pop shops provide the array of eating opportunities. It seemed like all breakfast items here come with avocado and that makes me happy!

Here I am being fancy on a rooftop deck around sunset:


Coronado Beach is worth the trip to work on your tan lines.  Petco Park, home of the San Diego Padres has a family friendly park, complete with outdoor sandbox.


Photo by Megan

5) Washington, D.C.

Washington DC is land of the politicos, talking heads, and horrific traffic.  Avoid all that by parking the car and walking all over the United States Capital full of museums and historic monuments.  My personal favorites are the Smithsonian Air and Space, Science and Natural History, the Holocaust, and International Spy Museum.  The United States Archives are on the National Mall as well for good viewing of the Declaration of Independence and the US Constitution.  The Washington Monument is newly reopened to visitors for a great view of the the Mall and its structures.


Food in DC is eclectic much like the nationalities that inhabit it- you can find any type of cuisine.  For the cheap-o’s out there Ben’s Chili Bowl will be a good stop. Fancy restaurants are in abundance for foodies wanting to rub elbows with politicians and celebrities.  Georgetown with its old town charm and Georgetown cupcakes is worth a stroll.


Here are 5 great cities that make great weekend trips. Start your planning and book those hotels

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3 Responses

  1. Hamilton says:

    Charleston, SC seriously does have the best food in the South, and it has one of the best open-air markets that I’ve ever been to.

  2. Wesley says:

    Great tips! New York is such a great city

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