With those less-than-melodic accents and a nickname like Beantown, Boston might not come to mind as a romantic city. Check out all the best spots to take your Boston (resident of visitor) bae. Grab a Bostonian bite at nice restaurants with great views of the city or go out on a nice day for a walk to experience some of the oldest parks in the country where the Founding Fathers might have wooed some of their ladies. Top your romantic nights off with views of the Boston skyline at night from 52 stories up.
We promise these Boston date spots will not disappoint.
1. Bond Over Coffee at Thinking Cup
As a college student, caffeine makes up half of your body content, so it probably makes up half your dating life too. Take a trip to downtown Boston and after needing a break from turning your head to the left or the right to see all the historic sites, go to Thinking Cup. Anyone can go to the traditional Starbucks but when traveling—why not check out the New England version? This place features counters of fresh food displayed along with menu chalkboards. Enjoy a variety of hot tea from their menu (maybe you’ve heard of a little thing called the Boston Tea Party) as well as breakfast and lunch sandwiches like the Bacon Egg and Cheese, Smoking Jamaican and Roasted Chicken. The Thinking Cup provides an artsy place for you to sit and vibe with your date.
2. Explore your novel interests at Trident Booksellers and Café
Cozy up with a cutie on an everyday bookstore date—but do it the Boston way at Trident Booksellers and Café. The aesthetically pleasing café provides two floors of exploring. Find your next book with your date: a true show of trust. Then sit down to read it with a nice cup of coffee. No interest in books? You can also find an assortment of foreign magazines and catch up on the gossip from around the world. Go and see what the newlyweds Prince Harry and Meghan Markle up have been up to on their honeymoon.
3. Charles River Esplanade
If their dating profile says, “I enjoy long walks in the park…” Boston will definitely win them over. A park gets tough to deliver with the unpredictable Boston weather but the views make up for everything. Given that one nice day, go to Charles River Esplanade. Take a walk and enjoy the fresh air and a beautiful view of the Boston skyline. You can set up a picnic and nibble on some treats while getting to know each other. Or, go down at night, sit on a blanket and see the breath-taking sunset over the whole city. If neither of those things sound enticing (a total shocker), just take a seat on the dock and enjoy good vibes with your date. Also, we forgot to mention this spot offers a college kid’s favorite price… $0.
4. Skywalk Observatory
Does your date make you feel like you can touch the sky? Show them with a Skywalk visit. The Boston skywalk observatory sits several levels up in the Prudential Center with an overlook of Boston. It provides an ideal spot to watch the sunset or just talk. If heights scare you then this spot may not work best for you… but you can always ask your date to help you overcome your fears (wink, wink).
5. Walk in North End and Bova’s Bakery
Everyone talks about “relationship weight,” those extra few pounds you gain going out for dinner dates and getting comfortable with each other. Try a different route for the good of your bodies and go for a walk in the North End of Boston. Get a little exercise…before going to the best bakery in city: Bova’s Bakery. The best part of this place, 24-hour service. Whether you go at three in the morning or three in the afternoon, enjoy some of the best tiramisu you ever tasted.
6. Laugh Boston
Break the ice on a first date with a good laugh in the city where famous comedians like Jay Leno and Conan O’Brien first discovered their funny bones. Go down to the Seaport and check out Laugh Boston, a comedy club that features the biggest comedians in the city. The club sits inside the Westin and provides laughter for days whether you like dark humor, self-deprecating laughs or dad jokes. Sit down at a table, enjoy a Bavarian pretzel with a couple of drinks and enjoy the show. Awkward silence doesn’t exist on this date, especially when world class comedians get the whole place roaring.
7. Top of the Hub
Visit the Hub with a hunk for a good time. The Top of the Hub sits all the way up on the 52nd floor of the Prudential Center. Like the Skywalk Observatory, you can see a floor-to-ceiling view of historic Boston. Grab some amazing food while taking in some great scenery. Chef Stefan Jarausch cooks up specials daily like cured salmon with avocado and chili oil. Some of the standout favorites include crispy calamari, Maine mussels and Atlantic salmon. Top this date off with sharing a slice of their world-famous carrot cake. “I love romance and a sucker for beautiful views. The cured salmon was the best food I have ever tasted and ending the night with a skyline view of Boston was the perfect way to end my last night there,” Temple University senior Ashely Brader said.
8. Quincy Market
If the food baby from this place doesn’t make you drop, walk outside and shop till you drop. No trip to Boston would feel complete without a trip to Quincy Market. Faneuil Hall Marketplace features amazing food from all over the world and some cute little outdoor shops for you and your date to go check out (maybe get the family a little gift from your trip). Get a little slice of Boston with some of the New England favorites, like clam chowder, lobster rolls, Indian pudding and oysters. Look at some of the small shops like Boston Tote, Best of Boston, Boston Art Gallery and so many more. They all pride themselves on Boston-made items. Shopping, food and a nice walk outside add up to a successful date night for anyone. “I am a huge fan of traveling and I always get souvenirs when I go. I love Boston for all the original crafted things there, there is a wood handcrafted sign shop in Quincy Market that is my favorite,” Temple senior Maeve McCann said.
9. The Chocolate Bar
Do you want to find the key to your S.O.’s locked heart? Look no further. Every Saturday from June to September at the Langham Hotel channel your inner child with your date. Guests travel back to desserts of the past and find some updated versions of their childhood favorites. Everyone loves a little chocolate soft serve on a cone with sprinkles or a fun root beer float. You would go up to the window of the neighborhood ice cream truck and order all of these. Chefs Mark Sapienza and Ryan Pike feature over 100 different combinations that satisfy all your chocolatey cravings. “I’ve been to many places in Philly that claim to have the best desserts or ice cream but nothing I have ever tasted even remotely compares to the variety in flavors at the Chocolate Bar,” Temple senior Hannah Burns said.
10. Boch Center
Think of the old days, women and men all dressed spiffy, going into the city to see a show. You can’t go to a place like Boston and not see a play. You and your date can get dressed in your best outfits (dress to impress, am I right?) and check out Bach Center. Located in the heart of Theatre District, you can see latest musical, dance or comedy performance. Call and reserve two seats in advance for a nice night out with dinner and a show.