The humans of Philadelphia are a lot of wonderful things – and being fiercely loyal and passionate are at the top of the list. You can bet that a proposal in this city will make for magical one.

Philly boys in love don’t mess around, so once you’ve decided to not propose at Eagles stadium, here’s the inside scoop on how to plan the most magical Philadelphia proposal and engagement celebration!

Throw her off with a bar crawl…

Do this at your own risk, of course 😉

Kerry and Jaclyn both grew up in the Philadelphia suburbs – meeting in high school, reconnecting after college, and now building their life together in Fishtown. 

They had discussed getting engaged and agreed on “after the Eagles 2018-2019 season” for the timing. . . so come spring 2019, Jaclyn was on the lookout for proposal clues and had to be thrown off track in order to pull off this once-in-a-lifetime surprise.

Kerry set the proposal date for Friday, May 26th and booked the most enchanting sunset and twilight spots in Philly to propose and then throw a surprise party for her immediately after to celebrate with their family and friends.

Very little gets by Jaclyn, so on that day, he kept it cool and suggested doing a local, casual bar crawl to their favorite places since it had been a long week. She agreed without a second thought (or proposal suspicion), and they hopped on bikes and headed out.

Romantic proposal at Admiral’s Tavern

It’s hard to imagine anything more celestial in Philly than a proposal from your sweetheart while floating on the Delaware River at Admiral’s Tavern! 

Admiral’s Tavern, the most historic ship in Philadelphia, has been one of Jaclyn and Kerry’s favorite spots since they moved to Philadelphia, frequenting their floating beer garden on the weekends since 2017.

The staff there couldn’t have been any sweeter in helping arrange this surprise with a stunning Ben Franklin Bridge backdrop.

Jaclyn and Kerry arrived at 5pm to an empty ship, blue skies, and the sun beaming down on them. 

Jaclyn, not knowing what was about to happen, got distracted and started walking away to explore the historical ship before Kerry pulled her aside and got down on one knee.

The look on her face at that moment says it all!

The newly engaged couple then stayed at Admiral’s Tavern for another hour to soak in the moment, sip some wine, and enjoy the views together.

Surprise sunset celebration at Morgan’s Pier

Expecting just to see her and Kerry’s parents at Morgan’s Pier, Jaclyn’s face was priceless as she walked in and saw 75+ of their family and friends cheering for them.

Morgan’s Pier iconic city views with Ben Franklin Bridge in the immediate background make this spot a must-experience in Philly, and a no brainer for planning a magical AF surprise engagement party.

The Morgan’s Pier management and staff were all very helpful in arranging the surprise party and making it as extraordinary as possible.

Morgan’s Pier is a cool spot with great vibes whether you arrive at 4pm or 11pm, making it a consistently solid location in Philly for a celebration – whether you’re proposing, or just because it’s Friday.

We all celebrated from sunset through twilight, never getting enough of the electric Philly energy and city views.

Make your own magical Philly memories

Our family could not more highly recommend checking out and experiencing both Admiral’s Tavern and Morgan’s Pier for yourself when you are in Philadelphia – whether you’re planning a magical proposal or a lively happy hour after work!

We collaborated with two local Philadelphia photographers to capture all the sweet, super surprised candid moments you’re seeing here. Mike Chism and Dom DiFilippo both did an amazing job photographing all of the magical moments of the proposal and the surprise engagement party afterwards.