A Boston original, Legal Sea Foods is a place to experience real New England cuisine. It’s the type of place you can go to in jeans or a little black dress. It can be a little pricy but its well worth it. The Kendall Square location is great because it’s right off the Red Line but there are also locations in Cambridge, Watertown and at the Burlington Mall.
9. Concert and Appetizers at The Middle East, Central Square
Also right off the Red Line is one of the coolest clubs you will ever step foot in. Live bands perform here regularly and it features basic Middle Eastern cuisine such as hummus and pita plates or falafels. Each room has individual admission to the performance so be sure to buy tickets in advance. The venue hosts small indie bands, sketch and stand-up comedy groups as well as national bands such as Bowling for Soup who will perform there on March 12.
8. Lizzy’s Ice Cream, Moody Street
This is the perfect place for that first date that you’re not sure is actually a date or a casual Friday night delight with your long-time lover. It has more than 30 flavors of ice cream with 15 toppings and even has an “adult” menu that lists alcohol infused ice cream such as rum raisin and baileys. With its cozy couches where people sit and play board games, Lizzy’s is the perfect place to sit and have a great conversation while eating delicious desserts.
7. A walk down the Historic Freedom Trail
Enjoy some of the history a Boston education has to offer and dedicate a day to walking with your date down the 2.5 miles of brick paved streets. The trail has markers, which allow you to be your own tour guide while you see 16 places of national importance such as the U.S.S. Constitution and Paul Revere’s house.
6. Visit the Seals at The New England Aquarium
Easy to get to because of its location between all the T lines, spend a day enjoying the wonders of the sea at the Aquarium. Be sure to visit the exhibits on penguins, because there just so cute, and the jellyfish installation because who doesn’t want to take advantage of that awesome blue mood lighting coming from the tank.
5. A quiet rainy day at the MFA (Museum of Fine Arts)
Spend a day inside learning your date’s likes and dislikes as you discuss the beautiful art and relics housed in the MFA: from 20th century photography to ancient Egyptian pottery to the masters all know like Rembrandt and Van Gogh.
If you go on a Sunday morning, you can even enjoy brunch from 11 to 3 at the beautiful but reasonably priced restaurant in the museum, which has live local entertainment.
4. Tuscan Grill, Moody Street
For a spontaneously planned yet classically romantic dinner be sure to visit Tuscan Grill. They take reservations but you don’t need one; you can usually call an hour or two before to put your name on the list or just walk in and wait at the bar, where you can start on appetizers or have a drink if you’re older than 21, until a table opens up. The friendly staff and small size in addition to the candle light ambiance makes the spectacular Italian food even better.
3. Solea, Moody Street
Voted Diner’s Choice Restaurant by Opentable.com in 2009, this tapas bar is a favorite even outside the Waltham city limits. People come in from Boston just for this restaurant and it’s always busy, so make a reservation or be prepared to wait a while. It’s great for double dates because of its tapas menu, which allows you to order several small entrees (tapas) and share with others at your table. It has an extensive wine list, specifically from Spain and Portugal, where tapas style dining was created. It also has several vegetarian dishes.
2. Red Sox Game, Fenway Park Whether you’re a sports fan or not this is a must do while in Boston. Tickets can be really inexpensive in the early season and it’s just an experience. Red Sox fans are notoriously devoted and they make a strong competition for what’s more entertaining: the baseball game or the people watching it. Fenway also has a few great restaurants in it or you could just go for the hot dogs, pretzels, beer and soda during the 7th inning stretch.
1. Boston Commons
Whether it’s warm and time for a Saturday afternoon picnic or it’s freezing outside and you can bundle up and ice skate, Boston Commons makes for the comfortable, sneakers-and-jeans-date, as well as the romantic date you’ll never forget. Often compared to Rockefeller Center, Frog Pond is the spot to grab a hot chocolate and people-watch or fall on your butt on the ice.
If the pond has melted—no fear—put on some shorts, grab a blanket and sit on the grass to read a good book, people-watch or try your hand at navigating a swan-boat. If it gets too hot, don’t be afraid to chase each other around in the spray pool and get an ice-cream cone.
