Top Date Ideas Boston From a Matchmaker

Looking for new, special date ideas Boston? With so many charming neighborhoods, waterfront views, and a diverse food scene, Boston is the perfect location for an unforgettable date night. However, with so many options to choose from, deciding on where to take your date can be especially tricky.

As a Matchmaker, I’ve spent over 25 years helping my clients craft lasting connections, and I know just how important the right setting is for creating a lasting spark. I very recently visited Boston for a Hubspot conference, and I had plenty of time to explore the Cradle of Liberty. 

Honestly, I was amazed at Boston’s timeless, yet vibrant vibe. During my visit, I collected my top date ideas in the Boston area to help you plan the perfect romantic date for you and your love. 

Spa Day at Mandarin Oriental

If you’re seeking a day of luxury and pampering, Mandarin Oriental Spa is the best pick on my list! This unforgettable spa experience features a range of treatments, from rejuvenating massages to full-body rituals, all housed in a serene, tranquil setting. They have a package specifically for couples, which includes side-by-side massages for you and your love to relax, unwind, and enjoy.

Spa dates are criminally underrated. Any couple needing some serious R&R in a luxurious, soothing setting should consider booking a massage package with Mandarin Oriental.

Go-Kart Racing at Supercharged

Located just 40 minutes from the Boston metro, Supercharged Entertainment is home to the world’s largest multi-level, indoor go-kart track. Their specially designed go-karts hit top speeds of 40 mph, which makes for a fun, thrilling date! This location also offers a Ninja Wipeout course, arcade games, axe throwing, and bumper cars, so even if racing isn’t your thing, this entertainment center is sure to make a memorable adventure for everyone.

Go-karting is such a fun, low-pressure date for any thrill-seeking couple, but I especially love this idea for partners who are looking to rekindle fond memories of their youth and enjoy a day of adventure.

Explore Beacon Hill

Beacon Hill is arguably Boston’s most scenic, charming neighborhood, known for its rich history, cobblestone streets, and real gas-lit lamps. The nostalgic ambiance is the perfect backdrop for a romantic evening stroll with your partner. With so many local landmarks to explore, like Louisburg Square and Acorn Street, there’s so much to admire on Beacon Hill.

Beacon Hill’s beautiful scenery and historic architecture will spark conversation for any couple! If you and your love could use a nice, leisurely stroll after a big dinner date, this is the perfect place to end your night and get a few steps in. 

Bistro du Midi

This French-inspired restaurant provides a cozy, yet upscale ambiance accompanied by gorgeous decor and a Parisian charm. Serving unique, artful dishes like bouillabaisse and foie gras, this bistro is sure to provide the perfect romantic setting for couples seeking an evening of connection and conversation.

This charming bistro is the perfect spot for any couple planning a celebratory dinner date. Bistro du Midi’s atmosphere and cuisine are a show-stopping, tastefully crafted masterpiece, however, this is one of the more expensive locations on my list, so keep that in mind and plan ahead!

Visit the Isabella Stewart Gardner Museum

This museum is a must-see for patrons of the arts! Set within a breathtaking Venetian-style palace, the Isabella Stewart Gardner Museum houses an unparalleled collection of European, Asian, and American art. The architecture, atmosphere, and indoor courtyard garden make this a romantic idea where you can find plenty of room to spread out from the crowd.

Just about any couple will enjoy this inspiring museum, as its cozy, intimate ambiance makes for great conversation and deep connection. 

Take a Haunted Pub Crawl

It’s no secret that Boston is steeped in history and even some mysticism. Boston’s various haunted pub crawls provide a spooky, yet delightful way to explore this city’s eerie past. There are multiple guided tours available that take couples around Boston’s haunted pubs, where you’ll hear ghost stories, local legends, and chilling facts about Boston’s darker side.

This is a wonderful date idea for more established couples or any couple who takes interest in the mysterious. This unique, unforgettable date is a wonderful bonding experience, but please be sure your date is ready to be scared!

Kayaking on the Charles River

For outdoorsy, adventurous couples, renting a kayak and paddling along the Charles River is a fun, romantic way to spend time in nature. On your journey, you can catch beautiful views of the Boston skyline, the Esplanade, and local wildlife! There are multiple companies that offer kayak rentals along the river if you don’t already own one.

This is one of my top date ideas in the Boston area for all nature-loving, outdoorsy couples. This low-pressure, yet fun adventure will take you on a scenic, romantic journey. 

Visit the Boston Athenaeum

The Boston Athenaeum is one of the oldest independent libraries in the U.S. and has so much rich history. The magnificent architecture and stunning reading rooms create the perfect ambiance for a romantic, yet introspective date. The library also has various rotating lectures, where you can learn fascinating theories and connect with your love.

Just about any couple will appreciate the beauty and inspiration of the Boston Athenaeum, however, this idea is highly tailored toward intellectual academics who truly enjoy reading, learning, and insightful conversation. 

Visit Offsuit 

This speakeasy-style cocktail bar is a tucked-away hidden gem in an alley behind Pazza on Porter. The intimate, comfortable setting is the perfect date night idea for couples looking for romance and great drinks.

Offsuit is undoubtedly one of the most unique places on my list. The dim lighting, creative drinks, and alluring, mysterious atmosphere make this a great spot to finish out an evening date with a nightcap. 

Walking Tour of the Public Garden

Boston’s Public Gardens provide a serene, charming escape from the hustle, bustle, and concrete of the city. Any couple who enjoys leisurely strolls among natural features, lush landscapes, and blooming flowers will love this date idea. They also have swan boat rentals available for a more adventurous experience.

I had the opportunity to visit Boston’s Public Gardens on my trip, and it felt like something out of a movie. The laid-back, yet inviting ambiance and beautiful natural scenery create the perfect environment for first dates. 

Deuxave

Nestled in Boston’s Back Bay, Deuxave serves modern French dishes in an upscale, sophisticated setting. With entrees like lobster gnocchi and herb-crusted cod, this is an ideal dinner date for couples looking to explore unique culinary fusions in a romantic, chic atmosphere.

Deuxave is the perfect restaurant for more established couples looking to celebrate an anniversary or special occasion, as this is one of the more exclusive, pricey dates on my list. Be sure to make reservations well in advance!

Visit Spectacle Island

Just a short ferry ride away, Spectacle Island lives up to its name in a breathtaking way. This mini-adventure is home to tons of hiking trails, stunning views of the harbor and city skyline, and unique, pristine sandy beaches.

I love this date idea for all couples, but especially those still in the honeymoon phase of their relationship. This adventurous, yet romantic excursion has so much to offer and provides a scenic getaway not too far from home.  

Wine Tasting at City Winery

Positioned near the heart of Boston, City Winery is a fantastic spot for a date. With great wine, live music, and unique dishes available, this winery is sure to be the perfect location for a night out on the town. City Winery also offers tastings of their locally crafted wines, which is a great option for wine connoisseurs and sommeliers alike! 

If you’re planning an evening of sophistication, relaxation, and unique wines with your love, City Winery is your perfect spot! This is one of my favorite date ideas Boston for couples who appreciate finer things in unpretentious environments. 

Oleana

This Middle-Eastern restaurant in Cambridge is known for its unique shareable plates and a beautiful garden patio, making this a scenic backdrop for a romantic dinner date. With stand-out dishes like quail kebabs and feta cheese saganaki, at Oleana, you’re in for an adventurous culinary experience in an upscale, chic atmosphere!

If you and your partner are self-proclaimed culinary critics who always try to explore new cuisines and embrace new adventures, Oleana should be at the top of your list!

Catch a Movie at Coolidge Corner Theatre

The Coolidge Corner Theatre in Brookline provides an unforgettable film experience for film buffs and movie novices alike. This independent theatre shows a healthy mix of indie, classic, and art house films in a nostalgic, historic setting. The gorgeous art deco design adds to the romantic, intimate feel, making it one of the best places to catch a film in the whole of Boston.

This theatre is a great venue for new couples who are still building their connection. The ambiance and culture of Coolidge Corner Theatre will definitely encourage conversion and create a lasting spark for new couples. 

If you’re a successful single looking for real, lasting love in Boston, MA, LUMA Matchmaking is ready to help. We’re an established Matchmaking firm with over two decades of experience and a proven track record at finding our clients their best possible matches. If you’re ready to invest in your love life, connect with one of our LUMA Matchmakers to discover the LUMA difference and how our dating services can help guide you.