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.  Mark 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 rapidly approaching 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

Best cities for a long weekend. The long weekend travel guide. The best travel guide for long weekends find it at https://meetat-thebarre.com


Chicago Travel Guide

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

New York

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 than around 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.



Boston Trip

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

New Orleans Royal Street

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

Indie Market St. Pete

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.

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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.  I hope you check them out!  Please pin and share away xoxoxo

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44 responses to “5 Best Cities for a Long Weekend Trip in the Summer”

  1. I am all about the long weekends! And New Orleans, I really have to visit!

  2. Love taking weekend trips in the summer! I really need to get up to Boston this year! And NOLA of course. I love that we live where everyone comes to vacation. There are so many gorgeous places to visit in FL! <3, Pamela Sequins & Sea Breezes

  3. New Orleans is definitely our favorite city! Our next place is NYC next year. I just can’t decide what time of year I want to go there!! :) Great list of places!

  4. Of course I agree that Boston is the best city for a long weekend trip! xo, biana –BlovedBoston

  5. Such great city picks! I am really wanting to go to Boston, hopefully I will get there soon. Ok, that lobster is insanely big! Great travel guide!

    Whitney & Blaire
    Peaches In A Pod

  6. Love that you included our beautiful Bay Area! So many neat places with a short drive!

  7. Nadine says:

    New York and Chicago are on my list of cities that I must visit!!! I have been to New Orleans and while I am not brave enough to visit it in the dead of summer, a early fall trip there would be perfect!!! You really can eat your way through that city. For our beach weekend get-away we head down to Gulf Shores, Alabama for the weekend. It’s a four and a half hour drive from our house and Chris’s family has a condo down there on a private beach. It is always a great trip! We are planning to go over the 4th, as always :)

  8. Jaelan says:

    I’ve never been to any of these. Eeek. I know. It sounds like our life is about to be turned upside down… The east is calling us so we will have to visit these places!

  9. Caroline says:

    Obviously I agree with you about Chicago and NY! :-) September is also a very nice month to visit here. Chicago is a pretty fantastic though! Except for the winter here… :-/ New York is the city that I grew up going to so it has a special place in my heart. We are going to Boston in August and I’m excited since I haven’t been there in like seven years. Thank you so much for sharing and I hope that you have a lovely day!! :-)

  10. I am doing a weekend trip to Boston and NYC this month and we’re headed to Denver in July! I can’t wait. Popping over to see your recaps now…

  11. Nichole says:

    Love this list! We were just talking about summer vacay. We went to NYC in August one year, and believe it or not, the weather was PERFECT, so you just never know. I went to Boston in 2009 with friends in June, and it was still ‘chilly’, and I had to buy a sweatshirt, so this Florida girl was happy!

  12. Lindsay says:

    Do you have plans to visit Chicago any time soon? I’m only 20 minutes from the city, but Justin and I are going to spend a weekend downtown in a few weeks : ) Staycationnnnn.

  13. OK, obviously I am a BIT biased but isn’t Chicago great! Next time you are here, we will have to try to meet up! We still go to Chicago all the time (we are only 1.25 hours away, we both grew up there, and only moved 18 months ago!) I love Boston too! I never have spent much time in the city though, but I do love Newbury street shopping! And New Orleans is on my bucket list! We always used to go to Miami for sailing as a kid every winter so I love the weather but yes, not easy on the wallet! We have to look into St. Petersburg because our winters are TOO LONG! High today = 46 :( You have the absolute best travel guides, so I sent my brother (disposable income and no kids) your website to take his girlfriend on! He loved your SF post too (he lives out there!)

    xo- Annie

  14. Amanda says:

    I’m dying to go to all of these cities! I was born in NY and have been many times, but am itching to go back — and also itching to go to all of the other cities! I think every anniversary trip we should knock one of these cities out!

  15. Zelle says:

    So fun! I love a long weekend in NYC – I’m wanting to head back there this summer! And NOLA is definitely on my go-to list!

    Southern Style

  16. A weekend in NYC is never wrong, and would love to go to NOLA! Xx


  17. Karly says:

    This was a great post! Gotta love Chicago, my hometown. :) Boston is on our list of cities to visit, I’m glad to hear that we easily could do it in a long weekend (I’ll be revisiting that post of yours). And, you’re so lucky that some of the best little beaches and towns are so close to you!

  18. Jaclyn says:

    Love that Chicago is on here, it’s my hometown and so special to me. A long weekend in NOLA this summer sounds super appealing, I may have to look into that!

  19. I think you could have skipped Chicago… But I’ve just never had a good time there. Also, it’s like a larger Minneapolis and since I’m from Minneapolis, I’ll just go there ;) I’d omit that and insert Miami and then I’d 100% agree with this list – especially Boston and NOLA! I could spend far more time in NYC and still not see/do everything, but I get overwhelmed with all the people in far too small of a space, so a long weekend there is really all I can take, lol!

  20. christina says:

    yes, come back to boston anytime!! :)

  21. Lindsay says:

    This list is so fun! I love weekend getaways! My favorite that we have taken so far is to Savannah, GA..it is perfection. New Orleans is definitely on our list to get to next!
    Linds @ Not A Mom

  22. Love this list! I have never been to Boston , Chicago or Tampa, I need to change that! OOh my rec for Denver is always Snooze for breakfast/brunch. It is so good! Good recs for New Orleans. When I tell people I am from here they gasp…like people don’t actually live here! It ain’t all Bourbon Street!

  23. Nikki says:

    Great list of places, after reading your description of each of the cities I found myself nodding my head. I completely agree that Chicago and New York are the best in the summer, I’ve never been to Boston, but it’s definitely on my list of places to visit so I will keep the summertime in mind. I love New Orleans, but hate Bourbon St, the first night we got to NOLA we veered there and just decided to stay away the rest of the time, agreed that there are SO many other things to do besides that.

  24. Jenn says:

    I am a weekend warrior myself and agree with this list! I enjoyed my times at all these cities, some more than once, and always finding more fun things to do. My bf is headed to Boston for work this month and I’m bummed that I’m not able to tag along. I’d also add Nashville and DC to this list, particularly in the spring or summer months. So much to do at each, walk around, monuments, bars, brunch, museums, music. I went to Seattle last year for 4 days and LOVED it way more than I thought I would. Definitely would return when I have more time to explore outdoorsy things (we only stayed in the city), but Seattle is a bit longer to get to from the east coast.

  25. Jenn says:

    Chicago was by far the best long weekend trip ever last summer! Loved everything about that city!

  26. Totally agree with you about visiting NOLA for a long weekend! I feel like 3 or 4 days is about the extent of all that food and drinking that I could take! I’ve been to Boston once, and would love to go back! It’s so pretty, not to mention the amount of history that’s there! You can never go wrong with NYC for a long weekend either! Such great choices!

  27. Meg Taylor says:

    Boston is my favorite in the summertime! If you took out the word “summer” I would totally say Charleston, but you very well know the HEAT and humidity here :) We have a trip planned to Denver next week, so if you have any suggestions, I’d love to hear them!

    Meg, Borrowed Heaven

  28. emelia says:

    YES to all this. We went to Chicago for the first time in the summer, boy was it hot…but it was so fun. So many great outdoor activities. Yes, again traveled to NYC in the summer, but it was great to walk around and not worry about snow! We are thinking of taking my stepson there this summer as a surprise, he has such a huge interest in seeing the 9/11 Memorial and checking out everything there. I haven’t been to Boston in years (since I was a child), but again…went in the summer. You’re so on point with all of this, haha! We have a few friends in the Tampa area so we’ve visited a few different times out of the year and I would love to New Orleans as we have friends who are living there now from being stationed in the Coast Guard. What a great roundup of information, love it Amanda!

  29. I agree with all of these, especially Chicago, of course! :)

  30. NOLA is one of my very favorite cities for a long weekend (and you’re right about NYC, it definitely empties out on weekends once the weather is nice). I’m leaning towards doing a long weekend in Nashville this summer!

  31. I haven’t been to Boston yet but I agree with all of these and maybe throw in San Francisco in there. St Pete beach area is my favorite Florida beach town.

  32. Lindsay says:

    Boston is my fave!! Especially in the Summer! You have to let me next time you’re up here and have free time!!

  33. Sarah says:

    I really want to visit Chicago and Boston! They seem like such fun cities with plenty to do. I have been to New York City a bunch of times and I definitely like it, but just for a weekend haha, I could never live there. Of course I love the Tampa/St Pete area too, born and raised over here!

  34. Heather mylittlehea says:

    I was hoping Tampa/st. Pete was included! I just went to Redington beach this past weekend and while I still like Clearwater it was nice!

  35. Rachel says:

    Totally agree with all of these! Love that you threw in a little local love to Tampa too :)

  36. Sara says:

    Idk girl! Boston in the fall has my whole heart!! ;). NYC in September too!! I do love Boston, MYC and Chicago though!!

  37. I hate that we never go together when I lived in Chicago and you were visiting!! I’m still only 2 hours away so maybe we need to coordinate in the future ;) Totally agree with every city on this list, although I’d have to add Charleston because I love it so much!

  38. Tiffany says:

    I should do one of these for the west coast, ha! I could spend a week in NYC and want to stay longer. It’s my favorite city in the US. Boston is so great as well. Good list!

  39. Danielle says:

    Long weekend trips are the only budget friendly option for me at the moment! My favorite was when I visited Atlanta in the summer last year. Beautiful parks, outdoor art exhibits, free outdoor concerts, and loads of fun shopping. The only downside was the CRAZY drivers and highways but luckily my aunt is a native down there and led the way. Hotlanta was a blast!

  40. kristen says:

    this is so awesome! i wish we could go on more long weekend trips.. it’s a bit hard because even though i can take a friday/monday off here and there, KC can’t really, and the days he are off are the days every one else in the country is off, including my bosses.. so we stick to longer trips in the summer, sigh. we really absolutely need to go back to chicago though, it is so close to us that we could easily drive down friday night and spend saturday and sunday.

  41. Carly says:

    Great list! I love visiting all of those places. Chicago is up high on my list when we get home- I haven’t been in years!

  42. new orleans is my FAVE city in the US, so I’m glad to see it on there. I love to see it in the fall, and great people watching too!

  43. Great suggestions! Boston & NOLA are at the top of my list! xo, Champagne&Suburbs

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