Experience Philly – The Most Romantic Things to Do in Philadelphia in 2025

Fall in love with Philadelphia (all over again)

For visitors falling for the city for the first time, future Philadelphians wondering if this could be home, and locals who just need a reminder of why they never want to leave — this page is written for you.

Whether you’re planning your first trip to Philadelphia, scouting neighborhoods before a big move, or you’ve lived here forever and simply want to see the city through fresh, heart-eyed glasses… let me show you the softer, slower, more magical side of Philly.

Below are my hand-picked, absolute favorite Philadelphia tours and experiences — the ones that make people whisper “I didn’t know Philly could feel this romantic.” Think secret speakeasy evenings, sunset cruises on the Delaware, candlelit food walks through Italian Market, private Old City ghost tours, and cozy cheesesteak & craft beer adventures that feel like dates with the city itself.

All instantly bookable through my trusted partner, Viator.

A gentle (and required) note: 
Darling Philly is a proud Viator affiliate partner. If you click one of the experiences below and end up booking, I may earn a small commission at no extra cost to you. Every booking helps me keep writing love letters to this city — thank you from the bottom of my heart. ♡

↴ Scroll down for the experiences (or jump straight to your vibe):

• Food & Drink Tours in Philadelphia → #food  
• Romantic & Sunset Experiences → #romantic  
• History & Walking Tours → #history  
• Hidden Gems & Off-The-Beaten-Path → #hidden  
• Best Day Trips from Philadelphia → #daytrips  
Why these are the best things to do in Philadelphia right now. I personally test or deeply research every single experience I recommend. These aren’t the big-bus, megaphone tours — they’re the small-group, local-led moments that make you fall a little deeper for Philadelphia. Perfect for couples, solo travelers, relocating scouts, or locals playing tourist for the day.

Ready to make some Philadelphia memories that feel like movie scenes? Pick your adventure and let the city steal your heart.