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Pittsburgh Weekend Itinerary

Pittsburgh has never been a top destination to visit on my bucket list, but when my friend invited me to come visit her family with her for the holidays since I couldn't visit mine (due to COVID), I of course said yes! For the first time ever though, I decided to go into this trip WITHOUT a fully planned out itinerary... gasp! I had a few things in mind of things I wanted to do and content I wanted to shoot, but nothing set in stone. I also dropped a question box on my IG Stories and made a TikTok asking for recommendations and got a lot of great suggestions!

Keep reading to see what we ended up doing during our trip! Enjoy!





Travel day!

Fly in and land mid-afternoon

Shower, chill for an hour, get ready for dinner

Dinner at The Urban Tap (Great drinks & food and welcoming / "locals" environment)

Going out to the bars in the neighborhood that dinner was at called "Southside"

Bar to go to: Carson City Saloon - something to note is that no one goes out until 11:00pm!

Bar/club to avoid: Foxtail - it looks really cool online so we went and it was very unsafe / locals said there is a lot of violence here and to avoid it all costs! Such a bummer because it was really cute inside.


Sleep in / Grab Starbucks

Bundle up for a day exploring downtown!

Head over to The Yard for brunch (open till 4pm on Saturdays/Sundays!)

Walk across the street to the Christmas Market in Market Square - a winter market where local vendors sell their goods! There is also live performances and delicious food & beverages!

Grab a hot beverage and walk down to the ice skating rink and giant Christmas tree

Dinner at Primanti Bros.

Head back to hotel to relax for a bit and then get ready for the night!

Uber to Tequila Cowboy for bar foods (the soft pretzels are to die for!) and dancing! Best bar we went to during the trip! They have 3 rooms: country, karaoke, and 90s. Great music & people! But waiting in line was SO cold so make sure to bring a jacket!


Sleep in and pack! Leave luggage at front desk

Grab brunch at The Urban Tap - it was so good we had to go twice! MUST order the "Breakfast Breads" and get a few mimosas... so delicious!

That wrapped up our weekend in Pittsburgh itself! From there, my friend's dad picked us up and drove us 2 hours north of the city to their hometown where we enjoyed the snow, watched Christmas movies, and relaxed for a few days! We flew out later that week. It was really cool to explore a new city and also get out of my comfort zone by just playing things by ear instead of planning every second of every day! ;)

My biggest tips for a trip like this: layer up when you go out (I mean it!) and live in the moment! Also, you can never go wrong with ordering hot soft pretzels lol.

Enjoy your time in Pittsburgh and feel free to send me a DM on Instagram HERE if you have any questions or recommendations!




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My name is Kimberly Cobb and  I'm a Lifestyle Blogger + Podcast Host living in San Diego, California! I'm also a fashion lover, Pomeranian mom, + travel girlie! I use this blog to share my favorite places, people, and products for thousands of women all over the world!

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