Boston, known for its rich history, beautiful architecture and world-class cultural experiences, is also a perfect destination for couples looking for a romantic getaway. From candlelit dinners in charming North End restaurants to picnics in the lush Boston Commons, there are endless options for creating special memories with your significant other. This article aims to provide inspiration for planning a romantic trip to Boston by highlighting 15 of the most romantic things to do in the city.

From classic experiences like dining at the top of the Hub to unique adventures like exploring an escape room, this guide has something for every couple. Whether you’re planning a surprise proposal or a milestone anniversary celebration, the romantic options in Boston are endless.

Dining and Food Experience

All the below options will provide you with an unforgettable dining experience and make your trip to Boston more romantic.

Enjoy a fancy dinner in Boston’s North End.

The North End, also known as “Little Italy,” is the perfect place for a romantic dinner. This historic neighborhood is home to some of the city’s best Italian restaurants, with many featuring cozy and intimate settings. Take a stroll through the streets and enjoy the sights and smells of the neighborhood before sitting down to a delicious dinner of pasta, seafood, and of course, wine. Some popular options include Trattoria Toscana, Mamma Maria, and Terra.

If you’re looking for something more casual but still want to enjoy a fantastic meal in this charming part of town, check out Pizzeria Regina or Santarpio’s Pizza. Both offer delicious wood-fired pizzas made with fresh ingredients in an unpretentious atmosphere that’s perfect for dates or even just hanging out with friends on a Friday night.

Visit the Boston Commons for a picnic.

Boston Commons is a beautiful and historic public park located in the heart of the city. It’s the perfect spot for a romantic picnic, with plenty of grassy areas, gardens, and monuments to explore. Pack a basket of sandwiches, fruit, and a bottle of wine and find a quiet spot to enjoy each other’s company. If you’re feeling adventurous, take a ride on the Swan Boats or visit the nearby Boston Public Garden.

If you’re more interested in enjoying each other’s company than exploring nature, there are still plenty of ways to enjoy yourselves at Boston Commons! Take advantage of free WiFi while you sit on the grass and people-watch. Or grab some friends and organize your own impromptu game of Frisbee or soccer—you’ll have plenty of space!

Dine at the Top of the Hub

The Top of the Hub, located on the 52nd floor of the Prudential Tower, offers a truly romantic dining experience. The restaurant boasts panoramic views of the city, making it the perfect spot to enjoy a special occasion. The menu features classic American cuisine, with a focus on seafood, and an extensive wine list. The atmosphere is sophisticated and elegant, making it a perfect spot for a proposal or anniversary dinner.

Located in downtown Boston’s Back Bay neighborhood, The Top of the Hub is easily accessible by foot or public transportation. If you are coming from out-of-town, there are several hotels nearby that offer complimentary shuttle service to and from this restaurant. If you are looking for more options when choosing where to stay in Boston, we suggest checking out our guide on where to stay in Boston.

Eat at Max Brenner

If you’re looking to do something romantic in Boston, look no further than Max Brenner. This restaurant offers an intimate, chocolate-themed dining experience that’s perfect for couples.

Max Brenner offers a wide range of choices on their menu, including the chocolate fondue, waffles, and chocolate drinks. If you’re looking for something unique, try the chocolate sushi—it’s delicious!

You can also get a taste of their amazing desserts at their sister location in Newbury Street. They have an extensive selection of cakes and ice cream flavors to choose from; it will be hard to decide which ones you want!

Cultural and Historical Experiences

All the below options will provide you with an unforgettable cultural and historical experiences and make your trip to Boston more romantic.

For the couple that loves books: Visit the Boston Public Library.

The Boston Public Library is a stunning architectural masterpiece and a must-see for any literary-minded couple. Take a stroll through the library’s grand halls and admire the beautiful murals, sculptures, and frescoes.

The library also has a number of special exhibitions, lectures, and events throughout the year. Be sure to check out the rare books collection and take a moment to read a favorite book or poem together in one of the library’s quiet reading rooms.

Explore One of the Art Museums/Galleries

Boston is home to a number of world-class art museums and galleries. The Museum of Fine Arts, Isabella Stewart Gardner Museum, and the Institute of Contemporary Art are all great options for a romantic outing.

Enjoy wandering through the galleries, admiring the art, and discussing your favorite pieces. Many museums also offer lectures, tours, and special exhibitions, which can be a fun and educational way to spend the day together.

Attend a Show at the Boston Symphony Orchestra

The Boston Symphony Orchestra offers a wide range of classical music performances, from symphonies to chamber music, and is one of the most renowned orchestras in the world.

Attending a concert together can be a beautiful and memorable experience. The Symphony Hall, where the Orchestra performs, is a stunning architectural masterpiece and is an experience in itself.

Marvel at the New England Aquarium

For a unique and romantic experience, visit the New England Aquarium. The aquarium is home to a wide variety of marine life, including sharks, penguins, and sea turtles.

Take a stroll through the ocean tunnel, where you can watch sea creatures swim overhead, or visit the IMAX theater for a thrilling film about the ocean. Couples can also take a sunset cruise or a whale-watching tour together to see some of the ocean’s most majestic creatures.

Visit the Skywalk Observatory

For a breathtaking view of the city, visit the Skywalk Observatory, located on the 50th floor of the Prudential Center. The observatory offers 360-degree views of the city and its surroundings, including the Charles River, Boston Common, and Fenway Park. Take in the views while holding hands and enjoy a romantic moment together.

Active and Outdoor Experiences

All the below options will provide you with an active and outdoor experiences and make your trip to Boston more romantic.

Go Bowling

Going bowling can be a fun and casual way to spend an evening together. King’s Bowling in Boston is a popular option and offers a trendy and upscale atmosphere. The alley features 20 lanes, a full-service restaurant, and a lounge. It’s a great option for couples looking for a unique and active way to spend the evening.

Watch a Game From One of Boston’s Local Teams

Boston is home to several professional sports teams, including the Red Sox, Bruins, Celtics and Patriots, and catching a game together can be a fun and exciting way to spend an evening. Whether you’re sitting in the stands or watching from a sports bar, cheering on your team together can create a sense of camaraderie and bonding.

Walk Along the Charles River Esplanade

The Charles River Esplanade is a beautiful 3-mile-long park along the Charles River. It’s the perfect spot for a romantic stroll or bike ride, with scenic views of the river, the Boston skyline, and the historic Hatch Shell, where you can catch a concert or movie during the summer. Take a walk hand-in-hand, enjoy the sights and sounds of nature, and watch the boats go by.

Ice Skate at the Boston Common Frog Pond

Boston Common Frog Pond is the perfect spot for a romantic winter activity. The pond is converted into an ice-skating rink during the winter months, and it’s a great way to spend a cold winter evening. Skate hand-in-hand, enjoy the holiday lights, and warm up with a cup of hot cocoa afterwards.

Unique and Fun Experiences

Both of the below options will provide you with a unique and fun experience and make your trip to Boston more romantic.

Do an Escape Room

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An escape room is a fun and unique way to spend an evening together. You and your partner will be locked in a themed room and have to solve puzzles and clues to escape within a set time limit. Escape rooms in Boston offer a wide variety of themes and difficulty levels, from haunted houses to spy missions. It’s a great way to test your problem-solving skills and work together as a team.

Have a Pint at the Samuel Adams Brewery

The Sam Adams Brewery offers tours and tastings of their famous beers, and it’s a great way to spend a unique and fun evening together. Take a tour of the brewery and learn about the brewing process, and enjoy a tasting of some of their signature beers. After the tour, you can sit down and enjoy a pint together in the brewery’s taproom. It’s a great way to experience a piece of Boston’s history and culture, and also a great way to bond over your shared love of beer.

Final Thoughts On Romantic Things To Do In Boston

Boston offers endless opportunities for couples looking for a romantic getaway. From fine dining in the North End, to exploring the city’s cultural and historical landmarks, there is something for every couple.

To make your trip even more romantic and memorable, consider booking a room with a city view at a luxurious hotel, or taking a sunset cruise on a boat. Additionally, you can consider planning a surprise activity or event, such as a proposal or a special dinner reservation. Boston is a city full of romantic possibilities, and with a little planning, you can create a trip that you and your significant other will never forget.