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Welcome to My Fall Leaves Road Trip on the East Coast: Travel Guide

Going from Vienna and Madeira to Philadelphia was quite a culture shock — but I’m back in the United States (for the first time since February!) to do a fall road trip with my partner Kyle!

Here are all of the stops on our East Coast road trip where we’ll be eating lots of freshly picked apples and watching the leaves change!

• Philadelphia, Pennsylvania (1 day)

• Berkshires (quick stop)

• Burlington, Vermont (1 day)

• Portland, Maine (2 days)

• Salem (quick stop)

• Providence, Rhode Island (3 days)

Let’s fall into our first destination, shall we :)

Working Remotely in Philadelphia, Pennsylvania: Travel Guide

I’ll be honest: Philly feels like a city trying to recover from a zombie apocalypse but still needs some work. The urban grit and dirtiness of the city diminish the old-world charm that pops up in the random corners of this city — like the full-scale organ and insane art that’s hidden inside of a random Macy’s.

But the real star of Philly is its vibrant food scene: from the cheesesteak that bears the city’s namesake to the bustling Reading Terminal Market, I was surprised by how great the restaurants and food experiences were here.

This city, known for its pivotal role in American history, offers a unique blend of old-world charm and contemporary urban living, but it comes with its share of challenges for digital nomads. Kyle and I explored the city's rich history and even ventured out for a spooky night tour, but often found ourselves navigating through the city that left something to be desired.

Where to Stay in Philadelphia for Digital Nomads and Remote Workers

We stayed in this great apartment* near Rittenhouse Square Park on Walnut Street. It was right down the street from an Equinox and a Bluestone Lane (clear indicators of a wealthy neighborhood.) The proximity to Rittenhouse Square meant we had easy access to some of the better food options and green spaces. Our place had huge ceilings, intricate crown molding, and was pretty quiet even though we were located on a bustling one-way street.

I definitely recommend staying here as it’s a spacious, nice apartment — but just be aware there is no in-unit washer/dryer, and parking can get really expensive in the city, which isn’t ideal for longer-term stays.

My Biggest Philadelphia Travel Tip: download the SpotHero app for deals on parking spots. Parking can be a nightmare in Philly, and this app was a lifesaver in finding affordable spots near our apartment. Also, once you park, try to rely on walking or public transport — it's easier than constantly moving your car.

Also, another tip from one of the locals we met: avoid the subways. Apparently, there have been an uptick in robberies and other not-so-great stuff since COVID.

What to Do in Philadelphia for Digital Nomads and Remote Workers

While we spent most of our time working and exploring the local food scene (which, I can't emphasize enough, was the real star of our visit), we also did these 3 great tours that I recommend:

• Bad Ass Women's History Walking Tour.* This eye-opening tour, offered by Beyond the Bell Tours, starts at George Washington's old farm and covers often-overlooked aspects of Philly's history, including the first monuments constructed to slaves. It's a great way to understand the city's complex past.

• Center City Philadelphia Food Tour with Reading Market.* This tour was a highlight of our trip. Our guide Margaret was wonderful. We got to sample local specialties and learn about Philly's food culture. The Amish stalls in Reading Market were particularly interesting, offering fresh, handmade goods straight from their farms. (You hit Goldie and Cleavers on this tour as a heads-up!) My favorite bite on this food tour was the vegetarian Philly Cheesesteak, which was made with mushrooms. Overall, this is one of my favorite food tours I’ve been on this year.

• Dark Philly Adult Night Tour.* Listen, I expected this tour to be a ghost tour. It was not. However, there are some ghost stories on this tour — which presents an adults-only history-focused look into the darker side of Philadelphia’s past. Our guide was very engaging and had some good stories, and I learned quite a bit more about Philly on this tour. Just be aware that this isn’t your standard spooky tales tour — it’s more of an elevated historical walking tour that covers the more gritty stories of this city.

What to Eat in Philadelphia for Digital Nomads and Remote Workers

If there's one thing that truly shines in Philadelphia, it's the food scene. Here are some standout spots that made our stay memorable:

• For Brunch: Honeysuckle Provisions. A bit outside the city center, this brunch place is worth the trip. It's a great spot to hit on your way out of town.

• For Breakfast: K'Far. This Israeli-inspired spot from Chef Mike Solomonov is a breakfast dream. Don't miss their pastries, toast, and their amazing take on bagels.

• For Lunch: Goldie. Another Solomonov gem, this falafel joint serves up some of the best hummus I've had. Their tahini shakes are supposedly incredible — save room for one!

• For Bubble Tea: Chi Cha San Chen in Chinatown. If you read my Singapore blog then you already know about this heavenly drink place. It’s a must-visit drink everywhere you go if it is there. We like the various “creamy” drinks they have. The rotate them out based on seasonality.

• For Snacks and Drinks: Reading Terminal Market. This is one of the few touristy spots that's actually worth your time. Don't miss the Amish stalls here. Their whoopie pies are a freshly made delight that can brighten up a tough workday.

• For a Korean Snack: Mari Mari. They have these amazing concoctions called inari — that are tofu skin wrapped around rice with a topping. They have garlic mushroom which was delectable. It’s so unique — you have to check it out. I hear all the other flavors are just as good!

• For Vegetarian Philly Cheesesteak: Cleavers. For a vegetarian take on the classic Philly cheesesteak, head here. It's also a great option for plant-based eaters looking to try local specialties.

• For Dinner: Zahav. We didn’t go, but we were recommended it by a friend. It’s the dinner restaurant from Chef Mike Solomonov. If this is even half as good as Goldie and K’Far you’re in for a treat.

Overall Thoughts on Philadelphia as a Digital Nomad

Philadelphia presents a mixed bag for digital nomads. While the food scene is truly exceptional and there are pockets of charm, the overall experience can be challenging. The city's compact layout means you can easily explore on foot, but you might not always want to, given the state of some neighborhoods.

The rich history provides interesting exploration opportunities from iconic sites like the Liberty Bell to hidden gems uncovered on specialized tours. However, the urban grit and visible social issues can be draining over time, especially if you're used to working from more polished cities.

Finding good work spots can be hit or miss. While there are some nice cafes, particularly around Rittenhouse Square, they're not as abundant or welcoming to remote workers as in some other digital nomad hotspots.

My Ratings of Philadelphia as a Digital Nomad

Affordability: ⭐️⭐️ 2/5 stars. While not the cheapest city, Philly offers decent value compared to nearby NYC or DC.

Food Quality: ⭐️⭐️⭐️⭐️ 4/5 stars. The culinary scene is the true highlight of Philadelphia.

Vegetarian Options: ⭐️⭐️⭐️ 3/5 stars. Good options are available, especially at newer, trendier spots.

Adventures/Day Trips: ⭐️ 1/5 stars. Day trips? Near Philly? Not that I’m aware of. America is also just so sprawling, and there weren’t any day trips that jumped out to me near Philly.

Cafes/Co-Working Space Availability: ⭐️ 1/5 stars. While there were some corporate coffee chains like Bluestone Lane where I saw people with laptops working in, this is not a haven for co-working compared to other cities.

Digital Nomad-Friendly City: ⭐️ 1/5 stars. Philly can feel like a warzone. The streets are grimy, many areas feel unsafe to walk around, and there isn’t an abundance of third spaces and coffeeshops/co-working spaces that would really draw a digital nomad crowd. It felt pretty corporate in most spaces, rather than artsy or innovative.

Value of Accommodations for Remote Workers: ⭐️⭐️ 2/5 stars. Decent options are available, but you might have to compromise on location or quality.

General Weather: ⭐️⭐️ 2/5 stars. Philadelphia's weather can be unpredictable and sometimes harsh, which can impact your ability to enjoy the city. As it turns out, it’s not always sunny in Philidelphia.

Air Quality: ⭐️⭐️ 2/5 stars. The air quality is typical for a major U.S. city. Meaning? Pretty bad for your health.

Water Quality: ⭐️⭐️⭐️ 2/5 stars. People say the tap water safe, but we tested the tap it and it was hard water. Better to go bottled.

Overall Rating: ⭐️⭐️ 2/5 stars. While Philadelphia has its charms — particularly its food scene — the challenges of working remotely here outweigh the benefits for many digital nomads. Philadelphia is a city that requires some grit and patience from its visitors. If you're a food lover and history buff who doesn't mind navigating some urban challenges, you might enjoy a short stay here. However, for long-term digital nomad living, there are likely better options that offer a more comfortable and inspiring remote work experience.

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