5 Best Cities for a Long Weekend Trip in the Summer

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I consider myself the connoisseur of long weekend traveling, which allows me to make some bold statements as to which are the best cities for a long weekend trip. My husband and I are always planning our next weekend away jaunt.  It saves those precious PTO days and allows you to travel within a budget.  Since the Summer months are upon us and people are looking for travel inspiration, I thought I would share with you some of my favorite cities to spend a long weekend in and why.  I should also note, that we currently reside in FL.  We live near a major hub that has a lot of direct flights, which allows for these quick weekend trips. In no particular order, here are my five best cities for a long weekend travel especially for the Summer months.


Five Best Cities for a Long Weekend Travel Within the US

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We would pretty much go to Chicago every single 4th of July weekend.  The shopping, the food, the easy transportation, the amount of activities the city has to offer, it is no wonder why this has made the top five.  Our first trip we managed to stumble on tickets to see the Counting Crows play at the Pier.  It has still been the best concert I’ve ever seen by them.  Adam Duritz playing for three hours straight, being so close I could touch him, plus free food and drinks? Chicago, there is always something fab going on there in the Summer.  Plus, Chicago only has a few months of gorgeous weather so you know the Summer is all about fully enjoying those outdoor festivities.  Take an architectural tour along the river, catch a baseball game, eat all the pizza, shop till your heart is content. Chicago is one of my absolute favs. Interested in hearing more? Check out my full Chicago Travel guide here (this is one of my most pinned original throwback posts.....my photography has come a long way!).


New York

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We just booked a long weekend in July for New York City.  Yes it will be hot but I don’t care.  I love the city.  While all the locals are out in the Hamptons, you can have the city to yourself.  The hotels are more affordable in the Summer as opposed to the Winter holidays, hello to all the outdoor dining, and rooftop bars ― yes, please.  New York is one of my absolute favorite cities and there is no surprise as to why it makes the top five. Here are more New York recaps here and here.  If you are looking for hotel recommendations while in the city, make sure to check out the Knickerbocker Hotel.  We just stayed there the last time we were in the city and it has been our favorite hotel to date.  I have a full review that you can see for yourself here.



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When I tell people I’m from Boston the next thing out of their mouth is usually about how much they love the city.  I immediately follow up that question with one of my own, when did you travel there?  What do you think their answer is every single time?  “Summertime”. There is no greater city in my personal opinion than Boston in the Summer. Bostonians deal with snow, cold temps and lack of sunshine for pretty much 10 months out of the year I swear.  I mean it was still snowing in April!!  When those warm temps finally arrive, Boston knows how to take full advantage of it. Catch a game at Fenway, shop on Newbury street, dine outside on the rooftop overlooking the harbor, go to a local brewery, and eat all the lobster.  If you have an extra day head to the Cape.  Boston is the best city for a long weekend in the Summer. Check my Boston recap here.  I want to go back just thinking about how much fun we had up there.


New Orleans

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Yes it will be hot but I guarantee you can find a cold drink to wash it down and some Creole food to make up for it.  Being in FL with a direct flight into NOLA on Southwest, we pretty much go to NOLA at least once a year.  We are not huge party people but we know how to eat.  Head to Magazine street for shopping, ride a street car and look at all the mansions, catch a live show on Frenchman street, rent a car and go out to the Abita Brewery.  There are so many things to do in NOLA that don’t involve Bourbon street.  New Orleans is the most perfect city for a long weekend. Check my NOLA travel guide here.


Tampa/St. Pete/ Clearwater Area

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I always have to remind myself that I live where people vacation.  I can hop in my car and in 45 minutes, I’m at the most beautiful beaches in the country.  I’m very partial to Siesta Key beach in Sarasota but Clearwater and St. Petersburg also are home to beautiful beaches as well. I was just talking to Mark the other day about getting a hotel room at the beach and having a mini staycation to relax and have a little fun. If you want more than beaches, you can always catch a sporting event, go on a brewery tour, dine at some of the best restaurants, Nationally recognized museums and tons of shopping.  Have you checked my local travel guide here?  I can see why so many people visit every single year.  Plus, I’m always down for meeting up for an adult bev or having you in my barre class.  So that is total incentive right? Miami is always a great long weekend as well but is definitely a little harder on the wallet.


There are my top five best cities for a long weekend to travel to in the United States. Did your favorite city make my list?  So far we have two trips for the Summer planned, one to NYC and one to Denver.  I’m always open for hearing more options! Where are your favorite cities to travel to for a long weekend?  I hope I gave you some travel inspo for this Summer.  Make sure to check my travel tab here for all my travel guides and recommendations!  I always try to travel within a budget while still enjoying all the cities have to offer.  Please pin and share away xoxoxo

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