Planning a Romantic Weekend Getaway in Pittsburgh
There’s something undeniably romantic about Pittsburgh. Between the historic architecture, riverside views, and vibrant cultural scene, it’s the perfect backdrop for a weekend filled with love (and if you're extra bold, maybe a little hand-holding). Whether you’re celebrating an anniversary, planning a surprise getaway, or just need a good excuse to escape your Netflix queue, Downtown Pittsburgh delivers.
Here’s your guide to a swoon-worthy weekend - with The Priory Hotel as your home base for charm and comfort.
Day 1: Check-In and Set the Mood
Start your weekend at The Priory Hotel (yes, we're biased) - a boutique little gem nestled in the Northside. Our historic hotel combines cozy elegance with modern amenities, making it the ideal spot for a romantic escape. If you want to live your best life, book our Romance Package which includes a dozen roses and a charcuterie board on check in. Yes, this is how weekends should always begin.
Once you’ve settled in and raised a glass to your excellent decision-making, it’s time to head out.
Afternoon: Take in the Views
No romantic weekend in Pittsburgh is complete without a trip to Mount Washington. Hop on the historic Monongahela Incline, which will whisk you to the top for breathtaking views of the city skyline. Stroll along Grandview Avenue, stopping at one of the scenic overlooks. Pro tip: this is the spot to sneak in a selfie (or two) - no shame in documenting your romance with Pittsburgh’s famous three rivers in the background.
Evening: Dine and Delight
Dinner options Downtown are obviously plentiful, but for a romantic vibe, consider Vallozzi’s for upscale Italian or The Capital Grille for steak and seafood. Both restaurants offer an intimate atmosphere perfect for whispering sweet nothings—or just debating which dessert to split (hint: get two).
After dinner, step into Pittsburgh’s cultural scene. Catch a live jazz performance at Con Alma, a swanky venue with great music and a killer cocktail menu. If you’re feeling more classical, have an late dinner after an evening at Heinz Hall for a night with the Pittsburgh Symphony Orchestra. Nothing says romance like a sweeping symphony performance.
Day 2: Lazy Mornings and Artsy Afternoons
Start your day with breakfast in bed. Once you’re fueled, take a leisurely stroll over to the Andy Warhol Museum, just minutes from the hotel. It’s quirky, thought-provoking, and a great way to keep the conversation flowing (even if it’s just debating whether that Campbell’s soup can is truly art).
Afternoon: A Riverside Stroll
Get ready for dinner with a stroll along the Three Rivers Heritage Trail, which winds along the water and offers stunning views of the city.
Evening: A North Shore Adventure
For a fun and lively evening, take the shuttle over to the North Shore. Start with dinner at Hyde Park Prime Steakhouse, where you can indulge in perfectly cooked steaks, fresh seafood, and a refined atmosphere that sets the tone for a memorable night.
Afterward, keep the good times rolling at one (or two) of the North Shore’s popular bars. Stop by Southern Tier Brewing Co. for craft beers and a relaxed vibe or Bar Louie for creative cocktails and a bustling atmosphere. If you’re feeling adventurous, hop between a few spots—there’s no shortage of energy in this part of town.
Why Stay at The Priory?
Mainly because we said so. And isn't our word good enough? But if you need a better reason it's the historic charm, quiet courtyard, and proximity to Downtown’s best attractions, The Priory Hotel is more than just a place to stay - it’s part of the experience. Whether you’re sipping champagne in your room or reminiscing about the weekend’s highlights over breakfast, this boutique hotel has everything you need to make your romantic getaway unforgettable.