The Best Date Ideas In The City Of Boston

Cheesy Fries

Boston is known for its rich history and vibrant culture.

It’s home to some of the best museums, parks, and restaurants in the country.

Which is why it comes to us at no surprise that there are some fantastic options for date night here, as well.

Boston, the largest city in New England, offers a plethora of romantic date spots for couples. From beautiful historic buildings, to museums and parks, and many wonderful restaurants, there is something for everyone in this great city.

Whether you’re looking to impress someone new or simply spend quality time with a long term partner, Boston has plenty of date spots that are sure to make an impression.

Here are some fun date ideas for a day in the Boston area, local neighborhoods to visit, and all of the restaurants in the areas surrounding them.

Boston Common


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Boston Common is a great place to start your date. It’s the oldest public park in the country, and the most beautiful park I’ve ever been to. You can take a stroll hand in hand while enjoying the scenic views.

During the summer months, there are often live music events and free concerts hosted at Boston Common. These events are perfect for a romantic evening out. You can bring a picnic lunch, enjoy the live music, and watch the sunset over the city.

And in the winter months, what better way to spend a day than by ice skating on the iconic Frog Pond?

This is the perfect spot for a date, because there’s so much versatility here.

You walk around for an hour, or sit and relax and spend your whole day here.

It’s also quite the cost effective date; this can be totally free if you really wanted it to be.

Or, you could use this other great date idea, and go for a ride on one of the iconic swan boats that give Boston its world renown fame.

So, grab your date, and head on over to this wonderful place for a good time.

If you’re still looking for a bite to eat after the fact, here are all of my favorite restaurants in the areas surrounding Boston Common:

  1. Parker’s Restaurant
  2. Earl of Sandwich
  3. Shaking Crab
  4. El Jefe’s Taqueria
  5. Artisan Bistro
  6. No. 9 Park
  7. JM Curley
  8. Contessa
  9. Buttermilk and Bourbon
  10. Saltie Girl
  11. Nash Bar
  12. Rock Bottom Brewery
  13. Citrus and Salt

lasagna 4 pack

The Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum is another great date spot. It’s a unique museum with a beautiful courtyard garden, which is perfect for a romantic stroll or a quiet conversation.

The museum itself is filled with priceless works of art from all over the world. You can spend hours wandering the halls, admiring the stunning artwork.

This museum was also the site of a major art heist, so for all of you true crime fanatics out there, there is some really rich history regarding this fun fact.

Afterwards, take a look at all of the great food in the area.

Here are some of the best restaurants near the museum:

  1. Lilly’s Gourmet Pasta
  2. Squealing Pig
  3. Chilacates Mission Hill
  4. Mission Bar & Grill
  5. Laughing Monk Cafe
  6. La Esperanza

Fenway Neighborhood


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Fenway Park

If you or your date are sports fans, Fenway Park is a must-visit. It’s the home of the Boston Red Sox, and one of the oldest ballparks in the country.

You can catch a game together, go to a concert, or take a tour of the ballpark. Either way, it’s a great way to spend an afternoon or evening.

Sometimes, Fenway Park even has outdoor movie nights with some popular classics.

There’s always something going on here.

Even if you’re not a huge sports fan, it’s always fun to enjoy the Fenway Park atmosphere.

Jillian’s Lucky Strike

If you’re visiting Boston during the winter months, odds are Fenway Park won’t necessarily be open for business.

But don’t worry, there are still tons of options.

I visit this area quite often, and one of our favorites to go to is Jillian’s Lucky Strike.

It’s a massive arcade and bowling alley that’s exclusively for adults 21+.

That’s right, all of your favorites without the annoyance of a few bratty kids that didn’t win enough tickets to collect the prize they wanted.

Their arcade level is filled to the brim with all of your classic favorite arcade games and fun immersive experiences that are perfect to experience with that special someone.

Tired of playing games? No problem! Their top floor serves as a massive bowling alley bar, where you can bowl the night away in a chic, upscale alley.

Lucky for you, in addition to the many sausage stands (S/O to the Sausage Connection, my personal favorite) there are tons of spots to visit for food and drinks around the ballpark. Though I could never list all of my favorite spots, here are some of the places that come to mind:

  1. Loretta’s Last Call
  2. Cask n’ Flagon
  3. Lansdowne Pub
  4. Yard House
  5. Time Out Market
  6. Max and Leo’s
  7. Thornton’s Fenway Grill
  8. Cheeky Monkey Brewing
  9. Boston Burger Company

Castle Island

Since I was a kid, this has been one of my all time Boston favorites.

Castle Island is one of the best places to take in the views of the Boston Harbor, and has plenty to do.

This has been the site of a fortification since 1634, and is still standing ever since.

It’s not often that you come across something with that much historical significance here in America, but if you do, it comes at no surprise that it’s in Boston.

Here, you can find local events and sailing lessons happening on the regular.

You can take your bikes and ride around the oceanfront, or take a blanket and sit out for a nice picnic.

Aside from all of the great historical aspects, Castle Island is home to the famous Sullivan’s Restaurant, for some of the best seafood, hamburgers, hotdogs, chicken, and milkshakes the City of Boston has to offer.

You can take your food to their grassy lawn and watch the boats go by and planes take off, or sit along the beach and watch the ocean and many surrounding islands nearby.

I won’t go into too much detail about the other restaurants in the area, because my top pick for Castle Island is Sullivan’s—it’s a must do.

South End


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The South End is a trendy neighborhood that’s perfect for a night out. There are plenty of restaurants, bars, and shops to explore.

What I love about the South End is all of the great things you can do in the area.

Visit during the day, and you can check out the ever so popular SoWa vintage market. If you hit it just right, they might be holding their artisan craft fair on whichever day you choose to visit. Here, you can explore locally made products from all of Boston’s talented creators.

You can go on a walk around the neighborhood and explore the beautiful brownstone buildings and parks.

There’s truly so much to do here during the day, but I highly recommend visiting in the evening as well.

You can start the night with dinner at one of the many restaurants in the area, then head to a bar for drinks and live music. If you’re looking for a more laid-back evening, there are also plenty of coffee shops and bakeries to enjoy.

Here are all of my favorite spots to visit in the South End for delicious food and cocktails:

  1. The Beehive
  2. Barcelona Wine Bar
  3. Greystone
  4. Yellowdoor Taqueria
  5. Anchovies
  6. Five Horses Tavern
  7. Coppa Enoteca
  8. Toro
  9. Frenchie Wine Bistro
  10. Le Comptoir
  11. Banyan Bar

The Charles River

The Charles is another great spot for a date.

One of Boston’s most popular date locations, the Charles River is super accessible from many locations, including Cambridge, Brighton-Allston, Watertown, Back Bay, and Beacon Hill.

You can take a bike ride along the river, go kayaking together, or enjoy the views and rowers from a beautiful riverside bench.

There are also plenty of parks and green spaces along the river where you can have a picnic or simply relax and enjoy the view.

This is a wonderful place for a date, both romantic and platonic, because the views just can’t be beat. Especially from the areas that overlook Cambridge, it is just a beautiful view year round.

Since the Charles River is so large, it’s hard to pinpoint an exact location for restaurant recommendations. But here are my favorite places in each area that we haven’t covered yet:

  1. Little Donkey – Cambridge
  2. Felipe’s Taqueria – Cambridge
  3. Area Four – Cambridge
  4. Boston Burger Company – Cambridge
  5. Stockyard – Brighton
  6. Buttermilk and Bourbon – Watertown
  7. City Works – Watertown

Beacon Hill

Just north of the Boston Common we mentioned earlier is Beacon Hill.

Beacon Hill is another beautiful historic neighborhood that’s ideal for a date. It’s known for its narrow streets, brick sidewalks, and gas lamps, giving Boston that iconic feel that it’s known for all around the world.

Ever hear of the Esplanade? It’s located in Beacon Hill! That’s right, you can take a stroll through this famous park right when you visit.

It’s located at the end of the Charles River, so if you wanted to start a stroll, Beacon Hill is the perfect place to begin.

You can take a walk through the neighborhood and admire the historic homes. There are also plenty of restaurants and cafes to stop at along the way.

Here are some of my favorites:

  1. Toscano
  2. The Paramount
  3. 75 Chestnut Beacon Hill
  4. Bin 26 Enoteca
  5. Beacon Hill Hotel
  6. Peregrine
  7. Cheers

Back Bay – Newbury Street

Back Bay is one of the most picturesque neighborhoods in Boston. It’s home to the famous brownstone buildings and tree-lined streets that the city is known for.

You can take a stroll down Newbury Street, which is lined with high-end shops and restaurants. Or, you can simply wander the side streets and admire the architecture.

Newbury Street is one of the most popular shopping destinations in the city. It’s lined with high-end boutiques, galleries, and restaurants.

It’s truly Boston’s shopping district.

If you’re looking for anything, odds are Newbury Street is where you’re going to find it.

If you don’t need to purchase anything, you can take a stroll down the street and window shop, or stop in at one of the many cafes for a drink or a bite to eat.

For some of the best restaurants in the area, refer to the Boston Common restaurant section above, this is all in that area!

Seaport – Institute of Contemporary Art (ICA)


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Located in the Seaport District, the Institute of Contemporary Art is a must-visit attraction for art lovers.

The building itself is a work of art, with its glass walls and stunning views of Boston Harbor. 

Explore the galleries and exhibitions with your partner, attend a performance or lecture, or enjoy a cocktail at the Water Cafe.

Aside from the ICA, there are also plenty of other things to do in Boston’s Seaport.

Enjoy a night out at Kings, with bowling and arcade fun, or try your luck in Flight Club, a darts focused bar.

Puttshack is brand new, located right down the street in Fort Point, and is the perfect place to get your competitive edge on.

For dinner, check out all of these great places:

  1. Trillium Brewery
  2. Committee
  3. Bartaco
  4. City Tap
  5. Harpoon Brewery
  6. Ocean Prime
  7. Lolita Cocina & Tequila Bar
  8. Smoke Shop BBQ
  9. Pastoral
  10. Mooo
  11. Pink Taco

Symphony Hall


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If you’re looking for live music with a historical vibe, the Symphony Hall is the place for you.

Home to the Boston Symphony Orchestra, this venue offers a range of performances from classical to contemporary

Dress up for a romantic night out and enjoy the world-class acoustics in the company of your loved one.

Even if live music isn’t so much of your thing, you are sure to be amazed by all of the architectural components of this fabulous building. With all of the historical architecture, this is one of the most romantic places in the city.

Of course, no night out is complete without a bite to eat.

Here are my favorite restaurants in the area:

  1. Symphony Sushi
  2. MIDA
  3. Ichiban Yakitori Sushi House
  4. Dumpling Palace

New England Aquarium

One of my personal favorite spots to visit in the city of Boston is the New England Aquarium.

This family-friendly attraction features a variety of marine life, including sharks, penguins, and sea turtles. 

Take a stroll through the Giant Ocean Tank hand-in-hand with your partner, or attend a special event, such as the Friday Night Jazz series.

From interactive exhibits, to shows, to live visualizations, a day spent at the New England Aquarium is a successful day, in and of itself.

After your visit, be sure to check out the local restaurants:

  1. Pasta Beach
  2. James Hook
  3. Granary Tavern
  4. Vintage Restaurant and Lounge
  5. Warehouse Bar and Grill
  6. Rowes Wharf Sea Grille
  7. The Palm
  8. Lily’s Pizza
  9. Milk Street Kitchen
  10. Casa Razdora

Food Truck Visits


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For a more casual date, head to one of Boston’s many food trucks and food truck festivals.

These events showcase a variety of cuisines, from Mexican to Korean to Italian.

Grab a bite to eat and enjoy the lively atmosphere with your significant other.

One of the most common places to find a food truck is by visiting one of Boston’s many artisan craft fairs. Here, Food Trucks will be stationed all by the surrounding streets for you to peruse.

Another way to explore local food trucks is by visiting the area’s breweries.

Oftentimes, breweries will contract out different food trucks for the day, and some will even have multiple. This is the perfect opportunity to explore local street food and area tastes.

There are also a few food truck festivals that occur every year. Be sure to check out the dates in advance to see if you’ll be able to make them. Though some only occur once a year, trust me, they’re worth it.

Two of my personal favorite festivals are the SoWa Boston Food Truck & Craft Beer Festival and the Boston Food Truck Festival on the Greenway. Give them a shot, you won’t regret a thing!

Mount Auburn Cemetery

I know what you’re thinking, “I’m not bringing a date to a cemetery.”

Hear me out.

The scenic and historic Mount Auburn Cemetery features beautiful landscapes, architecture, and monuments, as well as the final resting place of many famous figures.

Located between Cambridge and Watertown, this was the country’s first rural cemetery, and is now an official national historic landmark. Take a picnic and enjoy the peaceful surroundings with your partner.

Refer to the Charles River restaurant list for some of the best spots to dine at after the fact!

An Ice Cream Date

Who doesn’t love ice cream?

Boston has no shortage of delicious ice cream shops, all over the city and the surrounding areas.

This is a cheap, fun date that just about everyone with a soul will love.

The best part about ice cream is that it’s good rain or shine, 24/7.

Here are my personal favorite spots:

  1. Boston Ice Cream Factory
  2. New City Microcreamery
  3. J.P. Licks
  4. Chill on Park
  5. Christina’s Homemade Ice Cream
  6. Cookie Monstah
  7. Crescent Ridge (Boston Public Market)
  8. Delini Gelato
  9. Forge
  10. FoMU
  11. Gracie’s Ice Cream
  12. Honeycomb Creamery
  13. The Ice Creamsmith
  14. Lizzy’s
  15. Picco
  16. Ron’s Gourmet Ice Cream and Bowling
  17. The Scoop N Scootery
  18. Taiyaki NYC
  19. Tipping Cow
  20. Far Out
  21. Toscanini’s

Jamaica Plain

Escape the hustle and bustle of the direct city and explore Jamaica Plain, one of the best neighborhoods in Boston’s outskirts.

This neighborhood offers a variety of charming shops, cafes, and restaurants, as well as the Arnold Arboretum, a 281-acre park with beautiful gardens and walking trails.

Take a leisurely stroll through this picturesque area with your loved one, enjoy a picnic, or spend hours enjoying the beautiful landscapes and city views.

Or, take a run or bike ride along the gorgeous Jamaica Pond, a beautiful area right inside the neighborhood. 

Some of the best restaurants in the area are as follows:

  1. Delfino
  2. La Taqueria
  3. Tonino
  4. The Real Deal
  5. Costello’s Tavern
  6. Tres Gatos
  7. JPizle Kitchen
  8. Pikalo
  9. Top Mix Bar & Kitchen
  10. Alex Chimi’s

Museum of Fine Arts

For an educational and enriching date, and one of my favorite museums I’ve ever visited, visit the Museum of Fine Arts.

This world-renowned museum features a vast collection of art from around the globe, including works by Vincent van Gogh, Claude Monet, and John Singer Sargent.

Attend a gallery talk or lecture, or simply wander through the exhibits with your partner.

Here, you can find art, immersive historical exhibits, shows, events, you name it.

It is a crown jewel of Boston, and one you certainly shouldn’t miss out on.

After you visit, refer to the list of restaurants under the Symphony Hall section of this article to plan out the rest of your day.

In Conclusion

Boston is a city full of beautiful buildings, cultural attractions, and natural wonders that make it an ideal location for a romantic date.

Whether you’re exploring museums and parks, attending concerts and performances, or enjoying food trucks and ice cream, there’s something for every couple in Boston, and a bunch of unique date ideas that are sure to impress.

So why not plan your next date in this vibrant city and create unforgettable memories with your loved one?


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