Pittsburgh is one of those surprising cities that may not come to mind first as a destination for a romantic getaway, but in truth is worthy of strong consideration for such ventures. The city features a wealth of attractions that appeal to couples, and has a great many romantic dining venues and hotels which would be ideal for rekindling a romance and enjoying everything the city has to offer.

According to Forbes and the Places Rated Almanac, Pittsburgh is rated the #1 Most Livable City in the U.S., and even if you aren’t thinking of relocating to the city, a weekend visit will be enough to show you how it has earned that designation. Here are some ideas for your visit to Pittsburgh to help make it a memorable and romantic time for you and your loved one.

Pittsburgh Restaurants

The Capital Grille

The Capital Grille of Pittsburgh is one of the most popular of the downtown Pittsburgh restaurants, situated ideally on Fifth Avenue in the heart of the Golden Triangle district, and specializes in dry-aged steaks and world-class wines. With more than 5,000 selected bottles on hand at all times, the perfect accompaniment to your fine dining experience is assured.

Bella Vista Ristorante

As its name might infer, Bella Vista Ristorante Italiano is a venue offering authentic Italian-American cuisine, served up by members of a family owned and operated enterprise. If Italian food is what you crave, this is the place for it, and the full wine list contains the perfect complement to your chosen entree.


Isabela on Grandview is worth a visit just for the magnificent view it affords of the Pittsburgh skyline, which you can enjoy while sipping a glass of fine wine and awaiting your world-class menu selection. Located atop Mount Washington, the beautiful city panorama opens up beneath the gazes of you and your companion.

LeMont Restaurant

The LeMont Restaurant is another Mount Washington venue providing a wonderful perspective of the entire city below, and it has exquisite dining to match that view. LeMont is an award-winning restaurant which is well-known for providing just the right romantic touches for a totally satisfying romantic evening out.

The Oyster House

The Oyster House has been in continuous operation for nearly 150 years in the eclectic Market Square, and is downtown Pittsburgh’s oldest bar and restaurant. Its status as a historic landmark doesn’t obscure the fact that it still offers the finest cuisine in the area, in a newly refurbished setting, and has played host to hundreds of celebrities as well as all the locals and visitors to the city. This is the one restaurant in downtown Pittsburgh that any visitor simply must see and experience!

Pittsburgh must-see attractions

The Gateway Clipper

The Gateway Clipper Riverboat operates on the Monongahela River, and is one of the best ways to see Pittsburgh. Cruises can be arranged which are sightseeing ventures only, or an accompanying dinner package – perhaps the Captain’s Dinner Dance – can be included to add wonderful memories to the experience. This is a unique way to see the city, while enjoying the romance of traveling on an old world riverboat.

Duquesne Incline

The Duquesne Incline offers a great way to see Pittsburgh and the confluence of its three rivers from high above it all. You can ride to the top of the Observation Deck in a trolley car that is almost 140 years old, and from the top of the incline, you can see one of the ten most beautiful views in the entire country, according to USA Today Weekend Magazine.


The Fine Arts are well represented in Pittsburgh at the Carnegie Museum of Arts with its world-class collection of paintings and exhibits that incorporate a broad spectrum from the Old Masters to contemporary works. The Andy Warhol Museum includes more avant-garde exhibits, sure to engage the mind and the eye of all appreciative visitors.

Cultural District

The downtown Cultural District of Pittsburgh hosts more than 2,000 performances annually of all manner of Performing Arts, and among these, there is sure to be something that appeals to everyone coming to the city. Theater, music, drama, and dance are all represented magnificently here, in theaters all over the city. The Pittsburgh Civic Light Opera (CLO) also stages Broadway shows each year, which are well-attended by both residents and visitors to the city. The Pittsburgh Irish and Classical Theater (PICT) consistently produces well-staged and popular theater programs that are a delight to young and old.

Market Square

The recently renovated center of activity in downtown Pittsburgh is teeming with activity, even on business weekdays when office workers fill the square at lunchtime to take advantage of the many eateries in the area. You’ll find the historic Oyster House here, a fixture in the square since 1871, alongside pizza shops, coffee shops, cafes, and even a bakery. Having evolved from its original 1784 design into a European-style meeting place in the heart of the city, the Market Square today also provides dining, shopping, and summer-long entertainment.

Of course, no night in Pittsburgh would be complete without capping it off in a luxury downtown Pittsburgh hotel. Make the most of your date night by booking your suites with the DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown. Located merely minutes away from all the hustle and bustle of downtown Pittsburgh’s Cultural District, the DoubleTree Pittsburgh Downtown is the perfect ending to your date night in downtown Pittsburgh. Take advantage of their special offers and book your downtown Pittsburgh accommodations today!