Travel Guide: Philadelphia

Travel Guide: Philadelphia. Elfreth's Alley | Happily in Pursuit

Grand Cayman's West Bay and Seven Mile Beach from the air

At the end of May, I had been back in Cayman for less than a week before I jet off to Philadelphia for work. Only there for 3 nights and on the clock, I tried to make the most of this opportunity to explore a new American city. I didn’t know much about Philadelphia before I went, so I had no idea what to expect. I quickly learned in those 3 days that Philadelphia is full of history, beautiful architecture and amazing food.

After an awesome three days running around this city, here’s some of my favourite places to check out if you find yourself in Philly for a short trip.

Philadelphia architecture

To Stay

If you’re in Philadelphia on work like I was, you’re likely attending a conference at the Pennsylvania Convention Center, located in the Market East neighbourhood. I opted for an Airbnb, but other options include the upscale Loews Hotel, located in the nation’s first skyscraper, and the Philadelphia Marriott, both situated on historic Market Street. Only 20 mins and a $15USD Uber ride from the airport, even if you’re not here for work, I’d highly recommend staying in this area. Though not very residential, Market East is super close to great shopping, restaurants, and historical landmarks.

Downtown Marriott Philadelphia | Happily in Pursuit

To Eat: Dinner

For dinner, I recommend two options, both located in the Market East area. While I was able to get a table for 2 both times, we were eating early and others behind us were told the wait would be hours, so you should definitely make a reservation.

Tredici Enoteca

Arriving on a rainy Sunday evening, I expected most of the city to be tucked away. Instead, I found myself dodging large groups of smiling folks crowding the street as my colleague and I walked down Sansom between 12th & 13th. The setting sun glinted off the day’s earlier rain through the large open windows of Tredici’s where we found a bright table in the back near the kitchen.

Feeling weary from my 12 hours of traveling, I decided to play it safe and boring (for my standards) and order the spinach gnocchi in a tomato vodka sauce, not knowing it’s a dish they’re critically acclaimed for. Green in colour and seared to give a slightly caramelized crunch, it’s the definition of Italian comfort food. My colleague ordered the scallops, perfectly seared on corn succotash with a hint of basil and curry.

Under different circumstances, this is a place I could have sat for hours with either girlfriends or Ben, starting off with a crisp cocktail at their marble bar, admiring the copper and wood accents, followed by a round of oysters and my go-to, a California Chardonnay (which, I have to admit, I did indulge in a glass of their Three Thieves while there). Small plates and items off the raw bar menu would be shared, before moving on to one of their boards, the branzino with asparagus and cauliflower puree, or maybe the squid ink tonarelli.

I recommend eating dinner here if you’re looking for good service and great food in a beautiful setting.


Located just half a block north of Tredici, this Mediterranean restaurant frequents the top of many a “Philadelphia’s Best Restaurants” list. Luckily the rain held off as we were seated out front on the sidewalk, and I loved the people watching!

At the recommendation of our server, we decided to share a few dishes. First up were the melt-in-mouth caciocavallo stuffed meatballs, because, well, cheese stuffed anything right? I saw a few of these come out to other tables and I knew we had to order it!

Next up was the cheese board, which came laid on a handy printed menu naming each cheese and its flavour profile, with a healthy portion of crackers, jams, and honey. The last dish was an order of seared snap peas with smoked ricotta salata, which added a perfect light and healthy crunch to top off the meal.

Eat here if you’re looking for great share plates and even better people-watching.

Even the Starbucks was stunning!

To Eat: Lunch

High Street

Located in Philadelphia’s Old City, this restaurant and bakery is the perfect spot to duck into while sightseeing. Known for its fresh baked goods, seasonal ingredients, and twists on local sandwich classics, this intimate spot was one I wish I’d had time to visit twice.

The meal started with a sampling of their house-made fresh breads, followed by my order of the smoked duck cubano. This was, in my mind, the perfect sandwich: slightly warm and crunchy bread, smokey duck confit, gooey and rich Swiss cheese, tart pickles and slightly sweet fermented mustard.

Other menu items I was coveting as they passed my table included ribollita (an Italian stew), the mushroom melt, and the chef’s salad filled with local and seasonal ingredients.

To Explore

Philadelphia is one of America’s largest cities and steeped in history, serving as the backdrop of the American Revolution. While American politics might not be the greatest topic of conversation these days, there’s no denying that some monumental events, that continue to shape the world today, occurred in this city 241 years ago.

Below are some of the places I managed to explore in just a couple of hours (with a refuelling trip to High Street in the middle), so these are all highly doable if you’re short on time.

The Liberty Bell

Liberty Bell, Philadelphia | Happily in Pursuit

Probably Philadelphia’s most well-known landmark, the Liberty Bell is an absolute must-do. Engraved around the circumference is “Proclaim Liberty throughout all the land unto all the inhabitants thereof,” and while historians agree the bell could not have been rung exactly on July 4, 1776, it has nevertheless carved itself a place in American constitutional history as a symbol of freedom and democracy.¬†

Independence Hall

Independence Hall | Short Trip to Philadelphia Guide | Happily in Pursuit

Where the founding fathers, including John Hancock, Thomas Jefferson, Samuel Adams, and Benjamin Franklin debated and signed the Declaration of Independence on July 4, 1776.

United States Post Office

Located in the Old City area, this building is an example of the classic Georgian-style architecture prevalent throughout the area. This post office was named after Ben Franklin, the founder of the postal service (I’m just full of fun facts!).

Chinatown and Reading Terminal Market

Located at 10th and Arch, the Chinatown Friendship Gate is a beautiful work of art. While I didn’t have time to check them out, Philly’s Chinatown is known to have many delicious and authentic restaurants.

Just one block west is Reading Terminal Market. I immediately felt at home, as though I’d walked into Toronto’s bustling St Lawrence Market. According to the market’s website, “in 1890 the Philadelphia and Reading Railroad Company purchased this block for its new terminal. The merchants’ refusal to relocate for the new building resulted in an agreement to erect a new market tucked beneath the train shed and tracks.” Head here to see what’s in season in Philly!

United States Mint

The Philadelphia location is one of only two US Mint facilities of the six across America that offers tours, and the city was also the location of the original US Mint. Even if you don’t go for a tour (I didn’t), the building itself is a serious fortress and interesting to check out.

Constitution Center

With Ben Franklin at the Constitution Center | Happily in Pursuit

My final night in Philly was occupied by a work event hosted at the Constitution Center. The building is beautiful with a rooftop overlooking Independence Mall, and this is definitely the place to go if you want to be instilled with that “USA! USA!” type patriotism, not to mention you get to pose with this life-size statue of Ben Franklin… guess I have a thing for Bens ūüėČ

Elfreth’s Alley¬†

Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit

Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit Elfreth's Alley, Philadelphia | A Short Travel Guide to Philadelphia | Happily in Pursuit

Elfreth’s Alley was my¬†favourite¬†stop in Philly. It’s called “the nation’s oldest residential street” dating to 1702, with all the homes currently here built between the 1720s to 1830s. I loved everything about this street. The colourful shutters and matching doors. The leaded windows and cobblestone streets. The worn-in crooked stoops. The alley cat that gave me a tour. The overflowing flower boxes.¬†Everything.¬†If you can only visit one landmark in Philadelphia, make it this one.

For Fun

Harp & Crown

This classically beautiful restaurant is more than it appears. Once you enter the leaded glass doors, admire the expansive ceilings and cozy decor, but head to the door on your left and walk and walk and walk some more, and you’re transported into what I akin to a prohibition-era speakeasy alongside…wait for it…two full bowling lanes!!

I can’t remember the last time I went bowling and it was SO FUN! Whoever’s idea it was to head to 1525 Samsom after our work dinner at the Constitution Center, I salute you. Head here for some SFW fun!


I hope you found this guide helpful! I’d love to know if you’ve ever been to Philly and what your favourite spots were.

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