How To Take The Ultimate Vacation In Philadelphia, Pennsylvania

Take A Break is your ultimate guide to the perfect trips to recharge, rediscover yourself and your relationships, and reengage with the world. We’ll cover shopping stops, great bars, restaurants worth your money, photo opportunities, memorable drives and experiences, and other important details you need before you book.

Below, we chat with Caroline Bologna, senior travel and culture reporter at HuffPost, about why you’ll want to put Philadelphia, Pennsylvania, on your bucket list.

What drew you to Philadelphia as a place to visit or explore?

I first visited Philadelphia as a child because my older sister went to college there. Now living in New York as an adult, I’ve had the opportunity to go to Philly for several weekend getaways and always find something new to do. From the amazing food scene to the world-class museums to the endless historic sites, the city has so much to offer. And as a bonus, many of the best attractions are all in walking distance from each other.

What are the best times of year to visit?

I’ve been during all four seasons and truly enjoy the Philadelphia at every temperature. But if I had to choose, I’d probably say late spring and early summer ― in part because of the warm-weather events. Roots Picnic is coming back this year in June after a pandemic hiatus, and there will be a Juneteenth Parade later in the month as well. The Fourth of July is also an exciting time to visit the historic city.

What’s your best tip for getting there? How can you make the travel as stress-free as possible?

Philadelphia International Airport offers nonstop service to more than 100 destinations around the world, so it’s easy to reach by plane from most places. If you live on the East Coast, you can also drive to Philadelphia ― just make sure you know where you’re going to park. If your accommodations don’t include parking, be prepared to pay for a garage or read the street parking signs carefully.

Alternatively, you can take the Amtrak, NJ Transit or SEPTA Regional Rail to 30th Street Station. It’s is conveniently located near downtown Philadelphia and features famous sculptures you can admire while you wait for your return train.

Caroline Bologna/HuffPost

From left to right: George Washington statue in front of Independence Hall, the famous LOVE sculpture and the view from the Four Seasons Hotel Philadelphia.

Where do you recommend staying when you go?

If you’re seeking easy access to tourist attractions, stay in Old City, Center City or Rittenhouse Square. Philadelphia is full of great hotels, but some favorites include Le Meridien, Sofitel and The Logan. The Four Seasons and Ritz-Carlton are truly impressive spaces if you’ve got a budget for luxury.

For those looking for something trendier, consider Lokal Hotel Fishtown ― a boutique offering in one of the city’s hippest neighborhoods. There are also tons of rental options on Airbnb and VRBO throughout Philly.

What are your go-to restaurants or foods to eat while you’re there?

Philadelphia is one of my absolute favorite food cities, so it’s hard to narrow down. I have a major sweet tooth, so I can’t pass up a visit to Federal Donuts to try the latest specials, The Bakeshop on Twentieth for cookies and scones, and K’Far for the best pistachio sticky buns.

For casual lunch options, I recommend hummus from Dizengoff, sandwiches from Middle Child, falafel and tehina shakes from Goldie, or any of the delicious eats at Reading Terminal Market. Don’t pass up the chance to try tomato pie and other local specialties at Italian spots like Pizzeria Beddia, Sarcone’s, Ralph’s, Anthony’s, Iannelli’s and the Italian Market on 9th St.

I’ve never been to Chef Michael Solomonov’s world-famous Zahav, but I’ve had the chance to try Chef Greg Vernick’s restaurants ― Vernick Food & Drink, Vernick Fish and Vernick Coffee Bar (I still dream about the carrot cake pie). Other favorites include The Love, Parc, Hook & Master and Stir Restaurant.

What bars or entertainment spots do you make sure to hit? What’s good to drink there or what else should people know?

I always tell people to grab a drink at JG Skyhigh, the bar and lounge at the top of The Four Seasons. Even if a room there isn’t in your budget, you can still get the luxury experience and breathtaking views for the price of an expensive cocktail.

Assembly Rooftop Lounge at The Logan is also a scenic spot to have a drink or two, and the Ranstead Room and Hop Sing Laundromat are nice cocktail bars with speakeasy vibes. For more casual fare, check out Ray’s Happy Birthday Bar, McGillin’s Old Ale House and Bob & Barbara’s Lounge.

From left to right: pastries from K'Far, a cookie from The Bakeshop on Twentieth, and Vernick's carrot cake pie.

Caroline Bologna/HuffPost

From left to right: pastries from K’Far, a cookie from The Bakeshop on Twentieth, and Vernick’s carrot cake pie.

What are your favorite shops and what do you look for when you’re there?

When I was younger, I always wanted to go outside Philadelphia to the massive King of Prussia Mall. Now that I’m older, however, I have a greater appreciation for the local shops around Rittenhouse Row and Chestnut Hill.

During my last visit, I picked up local artisanal chocolates from Éclat Chocolate and explored the Fishtown bookstore-meets-gallery-meets-restaurant-and-lounge LMNO. Other great local bookshops include Harriet’s Bookshop, Hakim’s Bookstore & Gift Shop, Book Corner, Uncle Bobbie’s Coffee & Books, and Shakespeare & Co.

What’s your single favorite spot to go for photos and why?

Philadelphia’s Magic Gardens is a unique spot and definitely makes for some incredible photos. It’s an impressive folk art environment covered with mosaics that features an indoor gallery, labyrinth and more.

What tourist attraction should people skip and what should they do instead?

If you only have time for one art museum, I’d skip the Philadelphia Art Museum and go to the nearby Barnes Foundation instead. There’s no other museum quite like it ― from the unique structure of the building to the layout of the displays to the interesting history behind the collection. (Still, while you’re in the area, take a minute to check out the iconic “Rocky” steps and statue outside the Philadelphia Art Museum.)

Where do you feel the most relaxed, calm or happy?

I feel most at ease strolling around Rittenhouse Square. The neighborhood is so scenic and charming and perfect for people-watching.

What scenic spots do you recommend checking out?

Boathouse Row is an underrated scenic spot along the Schuylkill River. You can rent a kayak for peak viewing opportunities. I also recommend Talula’s Garden for a meal in a lush outdoor setting.

From left to right: JG Skyhigh, the Barnes Foundation, and Eastern State Penitentiary.

Caroline Bologna/HuffPost

From left to right: JG Skyhigh, the Barnes Foundation, and Eastern State Penitentiary.

What’s one thing you make sure to pack if you’re going and why?

Philadelphia is very much a walking city, so make sure to pack comfortable shoes to carry you through the day. And leave the heels at home if you’re staying in Old City, where you’ll find a number of cobblestone streets.

What are some specific planning tips to know before you go so you’re not stressed?

Don’t try to cram too much into one day. If you’re a U.S. history buff, remember it will take time to get through Independence Hall, the National Constitution Center, Liberty Bell Center, Betsy Ross House, African American Museum in Philadelphia, Benjamin Franklin Museum and other major sites.

To avoid lines, consider getting the Philadelphia Pass and try to go to the popular attractions at off-peak times. Check out temporary exhibits as well, like POOL: A Social History of Segregation at Fairmount Water Works.

If early U.S. history isn’t your thing, there are plenty of other other museums as well, including the Mutter Museum, The Franklin Institute, Eastern State Penitentiary, The Colored Girls Museum and the Rodin Museum.

What surprised you about Philadelphia when you went the first time?

I grew up in the South, so when I first went to Philadelphia as a child, I was in awe of all the cobblestone streets, historic buildings and iconic monuments. It really is remarkable to think about how many pivotal moments in U.S. history took place in the City of Brotherly Love.

Anything else visitors should know?

A lot of popular restaurants are BYOB, so make sure to check the alcohol policy before you dine and pick up a bottle of wine to enjoy with your meal at places like Bistro La Baia, Perla, Pumpkin and Charley Dove.