Go For a Wine Flight at 23rd & Vine in South Side

We're suckers for a good wine bar, and it didn't take long after 23rd & Vine opened in Pittsburgh's South Side for us to make it in for a couple of flights of wine.

While this one is heavily tilted to a few regional producers in Italy and California, we have to admit we loved the variety in the wine list here and can see returning many, many times in the future.

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A 5-Mile Walking Tour of Pittsburgh to See 17 Unique Highlights

Note: The Clemente Bridge is currently closed for rehabilitation. Those who take this walk will need to cross on the Warhol Bridge one block to the east. Likewise, from August to approximately December 2022 (TBD) the Monongahela Incline will be closed, so we recommend avoiding the Incline segments on this route until the Incline re-opens. This is listed as our optional detour just before the Duquesne Incline section of this article.

When we visit cities around the world as travelers, one of the first things we do is figure out a grand walking tour in order to get a feel for the city. We generally take anywhere from a half-day or full-day to do these self-guided city tours and really love checking things out on foot.

Until now, we had never put together one of these guides for Pittsburgh as our 90 neighborhoods often make it difficult to get around and see them all. Still, the neighborhoods in and around the central business district in downtown Pittsburgh have quite a lot to see and many of these spots are on the radar of those visiting Pittsburgh for the first time as well as long-time residents.

So in this one, we wanted to share what we consider to be the ultimate walking tour of downtown Pittsburgh! This walking tour covers five miles in the North Side, downtown Pittsburgh, Mount Washington, and Station Square and has 17 unique highlights worth checking out. 

So put your walking shoes on and get to exploring this beautiful city!

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Bonfire Review – A Wood-Fired Oven in the First Floor Restaurant

Bonfire is a two-story restaurant concept in South Side by Chef Chris Bonfili, former chef of the now-closed Avenue B restaurant. While the South Side neighborhood may not have historically been on anyone's radar as a dining destination, restaurants like Bonfire are helping to slowly change that.

At Bonfire, you can dine in the more formal upstairs space with dishes like mussels, blistered shishito peppers, arctic char, and strip steak. Or, you can relax in the more casual space downstairs with options like flatbreads, mac and cheese, and sandwiches. Either way, the menus are a far cry from the bar food typical of this neighborhood.

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An Attraction, Drinking, and Eating Guide to South Side

Pittsburgh's South Side is often known as its bar crawl neighborhood, and you do not need to spend much time exploring this one to understand why that is- the bars are everywhere.

While this one is incredibly popular for college kids looking for a cheap drink and anyone in need of a night out with libations, there is actually quite a bit going on in the neighborhood beyond your typical bar. For us, while we visit this one for a periodic adult beverage ourselves, we often visit for other reasons, and wanted to highlight some of our favorite attractions, restaurants, and of course, bars in this neighborhood guide!

It is worth noting that the following is not a collection of every business in South Side. This article only features businesses that we personally visit when we explore the neighborhood. As such, it should only be taken as a starting point and is certainly not a list of every establishment. If you see an interesting business while exploring the South Side, do yourself a favor and go inside!

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The Library Review – A South Side Gem for Cheap Eats and Drinks

Sometimes when we try and find a new bar to hit in South Side, we go numb at the sheer number of choices. In many cases when visiting this neighborhood we often pick a reason for going out (deals, cocktails, draft list, etc.) and then limit our options down from there in order to make a choice.

On a recent night out we wanted to keep our tab low while having good beer and settled on The Library. Known for a cheap craft beer list and happy hour food specials, an affordable outing was exactly what we got!

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Cocktails from the Crypt Review – Halloween Themed Libations

In 2022, Cocktails from the Crypt will be located at 705 Liberty Avenue downtown and is opening on October 6th. The below review is from a visit of ours in a prior year when the bar was located in South Side.

Pittsburgh's Halloween season is in full force with a number of hauntingly fun attractions to enjoy. Naturally, some pop-up bars have jumped onto the scene to celebrate this spooky season with themed libations!

One of these themed bars is Cocktails from the Crypt, a South Side pop-up managed by Spencer Warren of The Warren (a popular cocktail bar in downtown Pittsburgh).

I checked this one out shortly after it opened for its limited run and share a bit more on what the bar and cocktails are like below! 

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The Traveler’s Rest Hotel Review – Rooms for Many Group Sizes

Note: We stayed at The Traveler's Rest Hotel when it formerly operated as a hostel. Now the hotel has overhauled its offering to offer private rooms for various group sizes with shared facilities and is much more in line with a traditional boutique hotel. As such, we have updated the language of this article accordingly.

As avid travelers, we've done our fair share of overnight stays in hostels and boutique hotels- from $3 hole-in-the-walls in central China to high-end lodge-esque accommodations dedicated to hikers in Patagonia. Whenever we need to travel economically, we look toward shared dorms and private rooms in order to meet our travel goals.

One thing that always bothered me about the Pittsburgh hotel scene is that our budget and boutique hotel offering is much more limited compared to chain offerings.

Traveler's Rest is one boutique hotel that opened up in South Side near Station Square and it certainly fills a need!

I was invited to the hotel for an overnight stay and wanted to share a bit more about this hidden gem in the South Side.

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Cambod-Ican Kitchen Review – Go for the Cambodian Staples

If you find yourself in South Side and are looking for dinner, or a late night snack, or a late late night snack, a visit to Cambod-Ican Kitchen may be for you. This particular spot serves staples from Cambodia from 6pm until 3 or 4 am!

So if you are in the mood for a different kind of Asian fare, you may want to try this one out!

During my first visit I opted for a Cambodian classic which hit the spot!

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