#5: Horatio Harris (Munroe) Park

Although small in stature, this park is bursting at the seams with character. The winding paths and enormous puddingstone outcroppings create a unique background for photos or (if there’s a sudden February heat wave) an outdoor lunch. One side of the park is also fronted by an ornate residential complex, with Swiss-influenced design features. Together the park and building create the illusion of being on a romantic holiday abroad, but without the hassle of converting your money or packing a suitcase. After a brief stroll around the park, walk a few blocks down the street and warm up at the Museum of the NCAAA, Roxbury's art museum.

Franklin Park, the crown jewel in Olmstead’s Emerald Necklace, is not the kind of jewel some people would expect to see on Valentine’s Day. However, this jewel is just as good at creating memories together: hiking through the woods, strolling around the park, observing the animals at the zoo, or enjoying lunch at the golf clubhouse. Some locations in the park are even reminiscent of rural areas, which should help you and your special someone forget that you’re in the middle of the city and make it easier for you to concentrate on your time together.

Dudley Square’s Haley House Bakery Café is one of those places that couples of all stripes can enjoy. Health nuts can canoodle over vegetarian options and macrobiotic beers. Artists can profess their love while enjoying the rotating art exhibitions. The area’s many community activists, lawyers, and politicians may even be inspired to find new common ground in the café’s welcoming atmosphere. But, if there’s one thing we’re confident of, it’s that everyone will fall in love with the café’s delicious meals and baked goods.

Wally’s Café has been a Roxbury institution for generations. Founded in 1947, Wally’s is the only remaining jazz club in existence from Boston’s jazz era. But, Wally’s also has the perfect qualities for romance: it’s cozy, warm, and pulsing with passion. While you may not always be able to hear your sweetheart during the live music sets, the close quarters will make it easy for you to hold hands under the table and move your seats together for a little snuggling.

The site of a former military fort and an industrial water tower wouldn’t be the first place most people would think of kindling romance. But Highland Park may just be the one place in all of Boston to defy those expectations. Once the location of a fort used during the Siege of Boston, the Victorian-era water tower built to replace the fort was decorated to resemble a castle tower. Unfortunately visitors can no longer enter the tower, however, the quiet oasis of Highland Park itself evokes a fairy tale atmosphere that even Rapunzel would find hard to leave.