How to Spend a Romantic Three-Day Weekend in Greater Philadelphia

Start your morning in picturesque Old City. Colorful and cozy Cafe Ole serves coffee and Mediterranean cuisine, including a delicious variety of shakshuka. Or visit Riverwards Produce Market to build your own picnic to enjoy as you stroll the cobblestone streets. The independent grocery store carries locally sourced produce, meats, breads, cheeses, vegan products and grab-and-go meals in a refurbished early-1900s building. Grab a made-to-order raw juice concoction at the juice bar for an extra pick-me-up.

After breakfast, head east toward the Delaware River to Independence Blue Cross RiverRink. The seasonal waterfront attraction hosts an outdoor roller skating rink in spring and summer (Summerfest) and an ice skating rink in winter (Winterfest). Lace up your skates and hit the boards or ice for some laps overlooking the river and the Benjamin Franklin Bridge. Then grab a couple of spots by the fire pits or two Adirondack chairs (depending on the season) and cozy up to enjoy some of Philly’s famous Chickie’s & Pete’s Crabfries or Black Iron BBQ for lunch.

Walk back through Old City and stop at The Franklin Fountain, an old-timey ice cream parlor and soda fountain where the bow-tied staff serves up milkshakes meant to be sipped nose-to-nose from two straws. Wind your way through the neighborhood’s historic gardens — The Rose Garden, Signers Garden and 18th Century Garden — dotted between Chestnut and Walnut Streets from 3rd to 6th Streets. At 6th Street and Walnut Streets, enter the Curtis Center for a visit to one of Philly’s hidden masterpieces, The Dream Garden, a massive Maxfield Parrish mosaic comprised of more than 100,000 pieces of Tiffany glass in 260 different colors. Take a few minutes to appreciate the beauty of art … and one another. (Cue your favorite love song here.)

Talula’s Garden’s lush, rustic setting makes for a seriously romantic dinner spot. The cuisine at this Washington Square West spot is homey with an elegant twist, just like the roasted chicken with truffle gravy and brown butter gnocchi. Many diners choose to start with “The Master Class,” a.k.a. a plate of artisan cheeses, candied nuts, honey, house-made jam and a mini-lesson plan. End the evening with one of the rotating dessert selections and a glass from the well-rounded wine list or a nightcap like the locally sourced maple Manhattan made with Talula’s exclusive single-barrel Aged Dad’s Hat Rye.

Head to the Callowhill Street location of one of Philadelphia’s most beloved brunch spots, Sabrina’s Cafe, a Philly institution with more than five outposts around town. The thick-cut challah French toast stuffed with cannoli cream is a must-try. Just two blocks away is the Barnes Foundation, home to one of the largest collections of French impressionist and post-impressionist paintings in the world. Très romantique! The Renoirs, Cezannes and Matisses hang among African sculptures, American paintings and Native American textiles in arrangements originally designed by Dr. Albert Barnes himself.

Don’t leave the Barnes without exploring the four-and-a-half acres of landscaped grounds and grabbing lunch at the Garden Restaurant, where the art inspires the beautifully plated dishes, decor and table settings. Diners are treated to views of the museum’s private walled garden, and al fresco seating is available when weather permits. Cross 21st Street to another celebration of French arts excellence, the Rodin Museum. Dedicated to Auguste Rodin, this small-but-mighty museum houses over 120 (that’s more than anywhere outside of Paris) of the artist’s sculptures both inside and out, including The Gates of Hell and a bronze caste of The Thinker.

Experience sunset from the 60th floor at JG SkyHigh. The sleek and glamorous lounge is perched atop the Four Seasons Hotel Philadelphia at Comcast Center, offering stunning views and delicious cocktails. Cheers to another day of romance with a lychee raspberry martini and watch the city’s lights come to life.

For a true splurge, head down the waterfall-encased staircase to Jean-Georges Philadelphia, a AAA Five Diamond restaurant. Internationally renowned chef ​​Jean-Georges Vongerichten offers a six-course tasting menu designed to create an unforgettable experience amidst the floor-to-ceiling windows and 360-degree views of the city.

For a more affordable option, head to Fairmount’s A Mano for dinner. Meaning “by hand” in Italian, A Mano celebrates handcrafted seasonal cuisine. It’s also one of the city’s many bring-your-own bottle (BYOB) spots, so make sure to bring an extra special one.

Looking to end the night with the ultimate romantic indulgence? Impress your special someone with a visit to the Four Seasons’ Night Spa, where late-night massages come with private access to the 57th-floor spa and heated infinity-edge pool. Pop open a complimentary bottle of champagne and soak up the soaring city views.

Start the day with a French-Lebanese-inspired brunch at Café La Maude. Stepping into this jewel box of a cafe feels like visiting a vintage Parisian cafe. The menu embraces flavors of Lebanon with dishes like foul moudamas, house-made hummus topped with marinated fava beans, scrambled eggs, chopped tomatoes, parsley and za’atar pita.

After your morning feast, set off for the idyllic Chester County, with a first stop less than an hour away at Longwood Gardens. Walk arm in arm through the more than 1,000 acres of botanical beauty. No matter the season, there’s always plenty of nature indoors and out to inspire visitors at the Italian Water Garden, Flower Garden Walk and Peirce’s Woods, a year-round woodland garden.

Trattoria La Tavola is situated in the heart of charming Kennett Square. The Italian BYOB takes advantage of its location within the “Mushroom Capital of the World” and features dishes like risotto with Kennett Square mushrooms and shrimp and the Kennett Square truffle mushroom pizza.

After an intimate lunch, continue exploring Chester County. The Brandywine Valley Wine Trail conveniently connects the five wineries and one cidery that dot the county, with the closest two (Harvest Ridge Winery and Galer Estate Vineyard and Winery) each just seven minutes away.

Or pay a visit to the Brandywine Museum of Art, a renovated 1864 gristmill surrounded by wildflower gardens and the winding river, only 13 minutes away from Trattoria La Tavola. Much of the art inside is inspired by the nature just outside.

Plan for dinner at The Gables at Chadds Ford, set inside a renovated barn and featuring soaring ceilings and expansive windows that lend to its elegant charm. While it dates back to pre-Revolutionary War times, the restaurant serves up a modern menu, complete with dishes made with locally sourced ingredients. Spend the remainder of the evening relaxing at the 18th-century stone Brandywine River Hotel, furnished with four poster colonial-style bed frames, jacuzzi tubs and fireplaces. Or check in to the Inn at Whitewing, a 1700s farmhouse that houses 10 rooms. Don’t miss breakfast in the morning, served in a fully restored 1796 hay barn.