My Favorite Date Ideas in Boston as a Local

Looking to spark a connection with loved ones in Boston? I’m a local and love planning dates around the city. Whether they be solo dates, dates with my daughter, dates with my besties, or planning a first date. 

Boston offers endless ways to connect, and this guide covers the best date ideas in the city. They include biking through the vibrant streets of the South End, rooftop cocktails with skyline views, and more of Boston’s best attractions. 

Let Boston’s history, culture, and cozy vibes set the stage for unforgettable moments with loved ones.

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21 Best Boston Date Ideas

The View Boston

Captivate your date with panoramic views of the Boston cityscape. 

📍 Google Maps | View Boston Website | 💖 Best for: First-Time Visitors

Take your date to new heights at the View Boston, located in the Prudential Center. If it’s your first time in Boston, I suggest you climb to the 52nd floor in the Prudential Center to experience a different perspective of the city. 

The View Boston provides 360-degree panoramic views of the city. From historic sites to modern skyscrapers, you are bound to have a memorable and educational experience. 

There are two floors to explore with your date. These floors feature interactive exhibits, a restaurant, a bar, and an open-air deck observatory.

Visit the View on a weekday and reserve the lunch experience. This package includes one menu item and one non-alcoholic beverage per person, minus the crowds! Otherwise, you can purchase your admission tickets here.

Boston Red Sox Game

Take your favorite sports fanatic to watch a Boston Red Sox Game. 

📍 Google Maps | Red Sox Tickets | 💖 Best for: Sports Fanatics 

Watching a Red Sox Game at Fenway Park makes for an iconic date. Fenway is a small ballpark, but it gives off a larger-than-life energy.

Grab a Fenway Frank hot dog with your date and sing “Sweet Caroline” with other Red Sox fans in the stadium. Keep your night going and hop around the restaurants and bars that surround the historic landmark. Head to my personal favorite, Hojoko. It’s a Japanese tavern located in the Verb Hotel. 

Concerts in the Courtyard, Boston Public Library

This iconic Venetian-style courtyard is filled with music during this free concert series.

📍 Google Maps | Boston Public Library Website | 💖 Best for: Music Lovers 

Concerts in the Courtyard at the Boston Public Library are a cultural experience. The central library in Copley Square isn’t just a library, it’s an architectural treasure in the heart of the city.

Here’s why this date idea is a must. These concerts are hosted inside the library’s Italian-style courtyard. The courtyard vibes are peaceful and picturesque with the perfect ambiance.

The concerts run from June through August within this iconic landmark. Each concert runs for about an hour. Registration is not required. However, I recommend you and your date arrive early as seating is first-come, first-served.

Boston Public Garden

Elevate your picnic to a luxury experience at this botanical gem in the city. 

📍 Google Maps | Boston Public Garden Website | 💖 Best for: Casual Dates 

The Public Garden is a Boston gem and offers a picturesque setting for a casual picnic date. This park is located in the Back Bay neighborhood and was made for relaxing with loved ones. 

I always enjoy taking scenic strolls under the weeping willows and setting up a picnic on the green lawn. The green spaces, flower beds, and small lagoon elevate any picnic into a luxury experience.  

The Public Garden is a botanical treat for any occasion. No alcohol is permitted in the park, though. And please carry out what you brought in and dispose of your trash.

Frog Pond

Hold hands while ice skating at Frog Pond for a memorable winter date.

📍 Google Maps | Boston Common Frog Pond Website | 💖 Best for: Winter Dates 

Ice skating in the winter is a great excuse to hold hands during a date. Frog Pond reopens as a skating rink every winter at Boston Common. Enjoy ice skating, skating lessons, performances, and other activities for holiday fun. 

Visiting the skating rink at Frog Pond is one of the most popular things to do in Boston in the winter. You can people watch, laugh at each other’s falls, and share mutual awkwardness on the ice. Be sure to grab some hot chocolate to warm up afterwards!

Salsa Dancing Along the Charles Esplanade

Spice up your summer evening with salsa dancing along the Charles River.

📍 Google Maps | Boston Outdoor Bachata and Salsa Instagram | 💖 Best for: Summer Dates

Watch the sunset over Cambridge as you dance salsa along the Charles River Esplanade. This river divides Boston from Cambridge and offers a variety of things to do during the summer. 

I had a memorable second date at this outdoor dance party hosted by Boston Outdoor Bachata and Salsa. This free event takes place on Mondays from 6 – 9 pm on the Charles River Docks behind Hatch Hall. 

This is not a dance class, so you are free to dance with your date or group of friends all evening long. One side of the dock plays salsa through a speaker, while the other side plays bachata. 

Hatch Memorial Shell

Enjoy wholesome performances at this riverside amphitheater.

📍 Google Maps | Hatch Shell Website | 💖 Best for: Casual Dates

Pack your blankets and head to the DCR Hatch Memorial Shell for wholesome entertainment. This riverside amphitheater is a popular date spot. 

Enjoy performances as the sun sets over the Charles River Esplanade. The Hatch Memorial Shell hosts concerts, movies, performances, and other family-friendly events under the stars. 

Don’t forget to bring picnic baskets and snacks. Or, roam freely around Back Bay or Beacon Hill for something to eat after the show.

After Hours at the Museum of Fine Arts, Boston

Experience this renowned art museum after hours. 

📍 Google Maps | MFA Late Nites | 💖 Best for: Late Night Dates 

The Museum of Fine Arts, Boston is one of my favorite museums to visit in the city. This renowned museum is located in the popular Back Bay Fens neighborhood. 

Head to the Museum of Fine Arts for an after-hours experience. The MFA Late Nites and MFA First Fridays offer gallery exploration, music, dancing, and art-making activities.

The MFA Late Nites events only happen a few times a year, so purchase your tickets in advance. MFA First Fridays take place on the first Friday of select months. Tickets are required to attend. However, prices vary depending on whether you are a member or not. 

Coolidge Corner Theatre

Elevate your movie night at this historic independent cinema.

📍 Google Maps | Coolidge Corner Theatre | 💖 Best for: Movie Lovers 

Movie lovers in Boston adore the Coolidge Corner Theater in the Brookline neighborhood. This landmark venue is a nonprofit, independent cinema that shows art-house classics and new releases. 

Take in the golden-age architecture of the cinema with your date. The theater offers a historic feel and comfortable seating. Their lineup of movies includes indies, classics, features, international, documentaries, and sing-alongs. 

Their menu features local foods and beverages along with traditional popcorn and candy. The local food vendors include Q’s Nutz and Taza Chocolate. 

Samuel Adams Brewery

Come for the history and stay for the beer at this iconic Boston brewery.

📍 Google Maps | Sam Adams Boston Brewery | 💖 Best for: Beer Lovers 

The Samuel Adams Boston Brewery is for those who have a passion for well-crafted beer. Take your date on a tour of this historic brewery that blends tradition and innovation.

Travel to the Jamaica Plain neighborhood to learn about the company’s origins through an educational and enjoyable tour. You can expect to see the barrel and aging areas, learn the brewing process, and taste exceptional beers.

The samples are generous, and some brews aren’t available anywhere else in the world. The Sam Adams Brewery promises a memorable and flavorful date. 

Kayak on the Charles River

Work together as a team and kayak along this urban river for a relaxing activity. 

📍 Google Maps | Community Boating Boston | 💖 Best for: Active Couples

The Charles River is iconic for recreational activities. The urban river is 80 miles long and offers plenty of watersports to enjoy.

Take your date kayaking on the Charles. The river is a beautiful setting for a relaxing activity in the heart of the city. 

Community Boating Boston is located along the river and offers rental equipment for a memorable kayaking experience. It’s a great opportunity to work together as a team and see how you do.

L.A. Burdick Chocolates

Indulge your sweet tooth at this charming, tiny chocolate house. 

📍 Google Maps | L.A. Burdick Chocolates | 💖 Best for: Chocolate Lovers 

L.A. Burdick Chocolates is a charming chocolatier in Back Bay. This cafe is the spot for chocolate lovers. It offers high-end chocolates, pastries, coffee, and rich hot chocolates.

This chocolate house is very popular among locals. It’s a cozy spot with a relaxed and inviting atmosphere. The tiny store has a vintage-inspired interior with limited seating. It makes for the perfect intimate date to unwind and indulge. 

This chocolate haven has something for every taste. Options include truffles, hand-crafted bonbons, chocolate-dipped fruit, and my personal favorite – their signature hot chocolate. It’s rich, thick, and sweet. 

Stargazing at the Boston University Observatory

Grab your tickets quickly to see the stars and cityscape from a Boston rooftop. 

📍 Google Maps | Open Night at the Observatory | 💖 Best for: Budget-Friendly Dates

Take your date to see the night sky at the Observatory at Boston University. Tickets are free and can sell out quickly as guests are eager to peek into massive telescopes. Tickets need to be reserved in advance.

This experience is for astronomy lovers. Climb up the stairwell to the observatory on the fifth floor of a building on Commonwealth Avenue. Three telescopes are waiting outside on the roof. 

Each telescope points to something in the sky. There are guides by each telescope to inform you about what you are seeing. 

I got to experience this event on a date and had a magical evening out on the roof. I saw a cluster of stars, among other things, and incredible views of the city.

The Liberty Hotel

Take your date on a tour of a unique luxury hotel that was formerly used as a jail.

📍 Google Maps | The Liberty, A Luxury Collection Hotel | 💖 Best for: Special Occasions 

I suggest you book a stay at The Liberty Hotel if you’re looking to celebrate a special occasion with a loved one. This luxury hotel is unique in the sense that it was once the Charles Street Jail.

This boutique hotel is the perfect example of Boston’s magic in transforming something old into something modern. Pictures are hung throughout the hotel to depict the history of the prison.

Contact the front desk or concierge to book your reservation for a tour. Every Wednesday, the concierge team takes you back in history on a guided 30-minute tour. At the end, you are offered a complimentary glass of champagne. 

Eataly Boston

Discover rich Italian foods with hands-on cooking classes.

📍 Google Maps | Classes & Events Eataly Boston | 💖 Best for: Foodies 

Eataly is a top destination for foodies in the Prudential Center. It offers a refined Italian experience. Shop produce, prepared foods, homemade cheeses, cured meats, gelato, and wine. 

Eataly is not just your average Italian market. I love that it is also home to authentic Italian restaurants and a cooking school. 

Take your date on an immersive experience and book a hands-on cooking class. Learn how to make pasta with fresh and delicious ingredients. After your culinary class, shop for the ingredients in the market and attempt to make your dish back at home.

Boston Ballet

Celebrate any special occasion at the elegant Boston Ballet. 

📍 Google Maps | Boston Ballet Performances | 💖 Best for: Birthdays & Special Occasions

Celebrate a birthday or special occasion grandly and beautifully at the Boston Ballet. Impressive performances and a live orchestra offer a sophisticated atmosphere for any special occasion.

The Boston Ballet is one of the most important dance institutions in the country, and it’s housed in the Citizens Opera House. World-class dancers bring a diverse program to life with classic and contemporary performances.

What’s the best show for a romantic date night? Try Swan Lake or Romeo et Juliette. After the show, grab dinner at one of the many nearby restaurants.

Boch Center-Wang Theatre

A sophisticated date night calls for a visit to the ornate Wang Theatre.

📍 Google Maps | Boch Center Shows & Tickets | 💖 Best for: Anniversaries 

Boston is known for its vibrant culture and theater scene. So consider visiting the Wang Theatre when planning a sophisticated date night. 

This beautiful venue has a diverse program to fit any date vibe. Enjoy award-winning musicals, live jazz performances, or a night of comedy regardless of your preference. 

The theater has a beautiful and ornate interior. It offers a true regal experience with Baroque details and chandeliers. You will have a great view no matter where you are seated. The acoustics are also incredible. 

Boston Symphony Orchestra

This prominent orchestra delivers a charming date night experience. 

📍 Google Maps | BSO Concerts & Events | 💖 Best for: Anniversaries 

The Boston Symphony Orchestra is a prominent American Orchestra that delivers awe-inspiring performances. This cultural outing offers a special experience for a charming date night.

Visit the Symphony Hall to watch the Boston Symphony Orchestra in a magnificent setting. The historic venue has beautiful sculptures that line the walls of the halls with exceptional acoustics. 

👉 Pro Tip: Do not sit in the front row, as you will not be able to see the whole stage. 

Hop on a Blue Bike

Hop on a bike and experience Boston together in a unique way. 

Blue Bikes Boston | 💖 Best for: Active Couples 

Hopping on a Blue Bike is a fun and flexible way to explore the city. Being on a bike gives you easy access to different charming neighborhoods in Boston. 

Start your date at the Museum of Science and bike along the Dr. Paul Dudley White Bike Path for beautiful views. Or perhaps go discover the South End on bike. Ride along the vibrant streets and stop at yummy restaurants, such as Kava. 

Blue Bikes operates in the Metro Boston area with 480 stations and thousands of bike options to rent out. You can easily find an available bike on the Blue Bikes app, kiosk, or website station map. 

You can rent a bike for a single ride or opt for a day pass. The single ride allows you up to 30 minutes on a classic bike. The day pass offers unlimited 2-hour rides within a 24-hour period. 

F1 Arcade

Grab a group of friends and turn up the competition in F1 simulators. 

📍 Google Maps | F1 Arcade Boston | 💖 Best for: Group Dates 

Plan your next group outing at the F1 Arcade in the Seaport district. This is an epic arcade bar with 69 F1 race simulators. 

This place is perfect for big groups and double dates. You’ll be divided into teams to elevate the competition racing in simulators. You’re bound to have fun racing. You can feel every single movement in your seat as if you were racing an actual car on the track!

F1 Arcade offers a fun and posh vibe. There is something for everyone here. Including classic arcade games, modern arcade games, F1 simulators, and F1 watch parties.

Reservations are required in advance as simulators book up fast.

Beehive’s Live Jazz Brunch

Enjoy Sunday brunch with live jazz music for a relaxing vibe. 

📍 Google Maps | Live Jazz Music at Beehive | 💖 Best for: Music Lovers 

Beehive’s is one of my favorite places to eat in Boston. It’s located in the stylish South End neighborhood and makes for a great place to meet up with your significant other or friends. 

Their Sunday Brunch offers the best vibe and an inviting atmosphere with live jazz music. Nothing beats the combination of food, cocktails, and live music. 

This delightful restaurant is rather large, with two floors of seating. Make a reservation in advance and see if you can book a table near the stage. 

Beehive’s focal point is its food and entertainment. It’s known for its coffee cake, but I always go for the shakshuka. Check out the Beehive calendar for live jazz music performances. 

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Boston is full of unique ways to make memories together. Get out there and enjoy casual outings and romantic escapes. If you’re looking to venture outside the city for a longer getaway, check out my guide on the best day trips from Boston.