Skip to content

Dates in Boston: 30 Ideas for the Best Dates in Beantown

Thinking about going on some dates in Boston? We’ve got a great list of fun ideas to keep you laughing and connecting the whole time.

Share Post:

Whether you’re planning a first date or looking for ways to try new romantic things in your 20-year marriage, we’ve put together a list of some of the best ideas for dates in Boston to give you new ideas. From game nights to sporting events and fun tours, these ideas will help you think outside the box and explore some new things in your city.

Date Night With Adventures From Scratch

Some of the most meaningful dates in Boston can start at home. Pull out the Adventures From Scratch: Date Edition book when you want to get a little closer. Choose between unique activities you can complete at home or outside—just don’t back down after you scratch it off! Deepen your connection with thought-provoking conversation starters, and keep the memory forever in the scrapbooking space. Date night just got a little more interesting.

The 30 Best Date Ideas in Boston, Massachusetts

Set up a picnic in the park.

A picnic is a classic date idea. Grab a collection of snacks, some sandwiches, and something cold to drink and set out in one of the beautiful green spaces in the city of Boston. Bring your own blanket or find a bench or table to use. Spend a few hours chatting and enjoying good weather and conversation. Try the Boston Public Garden right in downtown Boston or pick a quiet spot along the Charles River Esplanade and watch the boats glide by. This is a great budget-friendly date option and can be customized in a hundred different ways just by moving locations or switching up the contents of the picnic basket.

Walk in the steps of the Kennedys.

The Kennedy family was as close as you can get to Massachusetts royalty; their lives were based in Boston and the surrounding area. Spend a day visiting some meaningful places to them and learn more about the president and his extended family. The JFK Presidential Library and Museum is a perfect place to start. See JFK’s childhood home in Brookline and wander the Harvard campus where he went to college. Finish your day of exploration at the Omni Parker with a slice of the famous Boston cream pie, which had a special role in the president’s marriage. Table 40 is said to be the spot he proposed at. 

Enjoy a coffee walk through historic Beacon Hill.

A unique option for a romantic date is a simple walk together through one of Boston’s most beautiful and historic neighborhoods, Beacon Hill. While the streets can sometimes get busy with tourists, the mornings are usually quiet and perfect for a good conversation and fresh air. Grab a coffee at Blank Street Coffee and then spend an hour or so winding through the different blocks, appreciating each home’s history. For more context, you can sign up for a free self-guided walking tour and get some background on specific buildings and homes. This part of Boston has been home to poets, politicians, and celebrities for years, and there is so much to discover on these cobblestone streets. 

Learn something new at the Boston Science Museum.

Museums are the perfect spot for a first date or the thousandth date. You’ll learn something new together and have many interesting conversations while exploring. The Boston Science Museum has exhibits about public health, arctic exploration, engineering, and human biology. Plus, there are new exhibits and temporary exhibits always coming and going, so each trip could be totally unique. There’s even a live animal care center, where experts work with the museum’s animal ambassadors. You can also take in a movie in Imax at the Omni Theater. A couple could easily spend a few hours at the museum together.

Pick up dinner supplies at the SoWa Open Market.

Boston’s South End has a Sunday market called SoWa Open Market. It operates in the warmer months of May through October. It draws a variety of local makers and creators as well as farmers and bakers. It’s the perfect place to walk with a four-legged friend and your date and pick up some tasty ingredients to cook a big Sunday meal together. If you aren’t much of a chef, you can load up on snacks and sample some of the food trucks on-site. There are over 200 tents set up, so there’s something for everyone. Come hungry and leave with fun and unique items.

Get up close with sea creatures with a day at the New England Aquarium.

Boston is a seaside city with a world of creatures living just off the shore. Get up close and personal with these animals at the New England Aquarium. In addition to the local fish and seals, you can also explore other underwater regions of the world. There are Indo-Pacific Coral Reef, Olympic Coast, and Amazon Rainforest exhibits. If you’re brave, visit the touch tank, where you can get really close to sharks and rays. Watch penguins and sea turtles in their habitats. If you want to add to this adventure, you can purchase a combination ticket with a whale-watching tour in the harbor. You’ll cruise out to the Stellwagen Bank National Marine Sanctuary, where they guarantee seeing a whale, or you’ll get a ticket to a future whale-watching trip.

Spend a day reading at the library together.

With Ivy league schools and so much history, Boston is a scholarly town and offers some incredible places to curl up with a book quietly. Consider inviting your significant other to join you for some quiet reading. Pick up the same book and take short breaks to discuss your thoughts on the story and the characters. The Boston Public Library in Copley Square is a great choice. The building is gorgeous, and there are plenty of quiet corners to hang out in for a few hours. Grab a couple of books and spend time just being near each other doing something you enjoy. 

Head to the famous Green Monster at Fenway Park.

Bostonians love the Red Sox, so you can’t go wrong with a date at Fenway Park. If you aren’t lucky enough to win the raffle each year for tickets on the Green Monster, you can show up a few hours before the game and take a tour of the stadium, where you can take in the views from some of the most coveted seats in all of the MLB. Once the game starts, enjoy some ballpark franks and overpriced beers and cheer on the home team. Sing along to Sweet Caroline and Dirty Water and share this iconic New England experience with each other.

See some live music at a jazz club.

Plan a night out on the town to see some live jazz music at one of the best clubs in the city. Grab a nice dinner beforehand and then slide into a booth and enjoy jazz performers’ smooth tones and incredible talent. Scullers Jazz Club is underneath a highway overpass, but once you’re inside, you’ll feel like you’ve been transported to New Orleans. The lineup features well-known musicians and students from local music schools, so you never know what you’re going to get. Wally’s Cafe is another popular spot for live jazz. It was New England’s first African-American-owned club and has been operating since 1947. The hole-in-the-wall spot has seen some pretty big names on the stage, so it’s going to keep you on your toes, too.

Cruise the Boston Harbor on the Boston Odyssey Brunch Cruise. 

Climb aboard a luxury yacht for a romantic cruise around the Boston Harbor. For two hours, you can feast on a buffet brunch while enjoying beautiful views of the city skyline, the naval yard, and some of the harbor islands. Food is included in your ticket, so you can fill up on both breakfast and lunch favorites. There are multiple decks to hang out on with a live DJ and dancing, so move around a bit and explore. Sip on champagne and toast to a day on the water with your date.

Sample craft beers all over town.

If you live in Boston, you’ve probably been to the Samuel Adams brewery. It’s a classic place to enjoy some local flavors and have some fun. Once that’s checked off your list, there are plenty of smaller craft breweries in the city to explore. Plan an afternoon and visit a few. You can sample beers by sharing a flight at each stop. Rate the beers and pick your favorites. Bring a deck of cards to play a game while you’re sipping or just chat and hang out. Check out Distraction Brewing, which is great on a summer day. Trillium Brewing has a seasonal pop-up near Fenway or a year-round spot just outside of the city. Night Shift Brewing has a great location and also roasts coffee beans, so you can try beer and coffee.

Lace up your skates on the Boston Common Frog Pond.

Located in the center of Boston Common, the Frog Pond is a popular meeting spot. It’s fun in all four seasons, but the ice rink in winter is the perfect spot for a date night. The rink is open seven days a week for most of the day. You can rent skates or bring your own and spend an hour or so gliding around on the ice. Whether you’ve skated your whole life or you’ve never stepped foot on the rink, this pond is small enough that it isn’t intimidating and can be lots of fun. Take a hot chocolate break when you need to warm up. You’ll feel like you’ve been dropped into a holiday romantic comedy with this date night idea.

Act like a tourist and ride the Ducks.

Take a ride on Boston’s most popular guided tour. Who cares if you’re a local? The tour takes you on a vehicle that travels both on land and by water. You’ll learn some fun trivia about the city, hear cheesy jokes from your tour guide, and enjoy a fun and interesting experience together. You’ll pass by the State House, Quincy Market, Cheers bar, Trinity Church, and much more. It covers about an hour on land and another 20 minutes by water. Once you’ve finished your tour, you can grab a drink and swap the favorite fun facts you learned. 

Rent an igloo at the Envoy Hotel.

Looking for a fun way to be outside in the cold weather without freezing? Rent an igloo on the rooftop of the Envoy Hotel in the Seaport district. You’ll have beautiful views of the Boston skyline and stay warm in the heated enclosures. Ever thought about planning a group date? Now you can! The igloos hold up to 10 people. There’s a good variety of snacks and specialty cocktails you can order, too. It’s the perfect blend of indoor/outdoor fun that allows you to experience winter in Boston without freezing.

Take the ferry for a day trip to Provincetown.

Want to get away from the city for a day? Take the fast ferry to Provincetown. The ride is about 90 minutes and cruises through the Boston Harbor and out to the tip of Cape Cod. Provincetown is a small, coastal resort town with a beautiful little Main Street. There are great dining options and cool art galleries and shops lining the small downtown area. Enjoy some fresh seafood or take a trolley tour around the town. You can also visit the Cape Cod National Seashore and listen to the waves crash and hang out in the sand if the weather is good. Extend your trip for a weekend if you want or jump back on the ferry and return in the evening. It’s a fun way to escape for a while and enjoy a change of scenery.

Find your favorite pastries in the North End.

The North End is the oldest residential neighborhood in the city, with homes dating back to the 1630s. It’s known for its Italian-American residents who’ve opened some of the best Italian restaurants on this side of the Atlantic Ocean. It’s definitely a place to visit when you’re hungry. One fun way to explore the neighborhood is by doing your own tour of the incredible bakeries. There’ve been many arguments over which bakery carries the best Italian pastries, but you can choose for yourself. Visit Modern Pastry Shop, Mike’s Pastries, and A. Parziale & Sons Bakery, plus any others that you find. Compare your thoughts on the different choices and then walk off your desserts and take in the sites along the Harborwalk.

Explore the Greenway.

The Rose Kennedy Greenway is a beautiful green space in Boston. It winds through downtown with tons of public art displays and gardens along the route. It’s easy to take a bike or train to the Greenway. Once you’re there, you can walk the entire length of the park. There are food trucks and beer gardens to stop along the way and rest and recharge. It’s a great way to get outside and be active together. Ride the carousel, catch a movie in the park, or take a free fitness class. Check the calendar to see what’s happening in the park and plan a fun date day out.

Browse the art at the Isabella Stewart Gardner Museum.

Art galleries are great places for dates. Slowly meander through the galleries and exhibits and chat about the pieces. Every person views art a little differently, so it’s a fun way to spark some conversation and get to know each other a little better. The Isabella Stewart Gardner Museum has contemporary galleries and classics along with beautiful gardens to explore. Other great Boston area art museums include the Institute of Contemporary Art and the Museum of Fine Arts. Grab a bite at one of the museum cafes and decide which paintings and sculptures were your favorite. Maybe you’ll even be inspired to take an art class together for your next date and see if you can tap into your own creative juices.

Go on a Back Bay wine tour and visit some high-end restaurants.

Explore some of Boston’s best restaurants with a wine-tasting tour through the Back Bay neighborhood. You’ll learn some fun trivia about this historic area and sip on varietals and sample food pairings with the wine. A wine sommelier is with you on the journey, so you can ask questions and learn all about the things you’ve tried. Plus, you don’t have to worry about getting a table because everything is set up for you. There will be six different wines to sample, so you’ll definitely be able to find something you love. 

Cruise down the Charles River on a gondola.

Looking for a unique date idea in Boston? Hop on a gondola on the Charles River. This 80-mile-long river winds through Massachusetts, reaching all the way to the Atlantic Ocean. People enjoy the river in many ways. You’ll see people canoeing, rowing, paddleboarding, and sailing. The gondolas offer a special experience. It’s a private tour where someone is guiding you through the waters. Enjoy a glass of wine and snack on the complimentary basket of cheese, chocolates, and crackers. There’s even live music with an accordion or violin. It’s so romantic that it’s been voted as one of the best places to pop the question in the city.

Take a sunset kayak at Mystic River Reservation.

The Mystic River Reservation is a privately owned nature preserve located in nearby Somerville. There are four different riverside parks that make access to the river easy. Kayaking is a popular activity here. Because of its location and beautiful scenery, it’s one of the best places in the area to watch the sunset. Rent kayaks and paddle to a quiet part of the marsh. You can watch for birds and enjoy the peacefulness of floating in nature.

Have a staycation at the Fairmont Copley.

Whether you have a special occasion to celebrate or just want to treat yourselves, a romantic staycation would be a wonderful option for Boston couples. The Fairmont Copley is a historic landmark hotel that offers remarkable elegance. Book yourselves a couples’ massage and then order room service and enjoy the luxuries of this Boston institution. Another popular staycation option is The Newbury. With a special afternoon tea experience or a fireplace suite, there are tons of specialty options to take advantage of at this more modern hotel in the city. There’s just something fancy about spending the evening at a hotel. 

Learn about the witches and history of Salem.

Salem is a famous destination for Halloween lovers and people who are into the spooky, scary stuff, but you can visit and explore all year round. Learn about the 1692 Salem Witch Trials, which led to more than 200 people being accused of actively practicing witchcraft, and see some of the historic sites. Get your fortune told or shop some of the fun gift shops in town. Even if witches aren’t your thing, there’s tons of history to see in this beautiful old town with colonial architecture. Salem is located just a short drive away or a quick ride on the train. It’s a perfect spot for a day trip.

Watch the famous Boston Pops perform.

The Boston Pops is an orchestra made up of musicians from the Boston Symphony Orchestra. They play some of the big holiday events of the year, including an epic Fourth of July show and holiday specials. The shows usually have a theme, like soundtracks of famous movies, or famous singers join them for performances. Check the current Boston Pops calendar and see if you can get tickets for a future show. It’s the kind of date night where you’ll be able to enjoy a quintessential and memorable Boston experience. 

Go stargazing at the Coit Observatory.

The Coit Observatory is owned by Boston University and sits on the roof of the College of Arts and Sciences. Most of the time, it’s used to help students with their undergraduate and graduate studies in astronomy. Each Wednesday night, they host a public open night where people can come and experience the night sky through telescopes and truly see the magnificence of the world. It’s a free experience, but you can reserve your spot in advance. Take your date to an evening of stargazing and then cap off the night with dessert or something warm. 

Get a little competitive with a game night out.

Game nights are a great way to get the conversation flowing easily. Challenge your date to a fun game night out at one of the game bars in Boston. A4cade is a perfect date spot for anyone who loves nostalgic games. Play pinball, Mario Kart, Guitar Hero, or one of the other fun arcade games. With a menu of funky cocktails and great snacks, you can hang for hours and battle it out to see who has the better gaming skills.

If board games are more your style, visit Tavern of Tales. With the claim to be Boston’s only board game bar, it’s a great place to grab a table and settle in for some classic gameplay. With everything from simple dice games to complex deck-building games, you’re sure to find something you’ll love in their selection. 

Organize your own food tour at Quincy Market.

Quincy Market might be a tourist trap, but there are some gems hidden in this market that deserve a visit. Plan a day when you come hungry and create your own food tour. Plan to split everything you order so you can sample more items. The Dog House sells the same hot dogs you can get at Fenway Park. Order the Clam Chowder Bread Bowl at Boston Chowda Co and some fried clams from Fishermen’s Net. If seafood isn’t your thing, grab a slice at Regina’s Pizzeria. Finish your tour with dessert if you still have room. Grab cookies at Carol Ann Bake Shop or find the ice cream parlor and pick your flavor. There’s a reason this market is so popular with out of towners and locals alike, so take your date there to find some new favorites.

Cheer on a college hockey team.

New England universities have some of the best college hockey teams in the country (or at least comparable to the midwest). While Bruins tickets can be hundreds of dollars, you can snag college hockey tickets for a great price and see some incredible athletes. Choose between Boston University, Boston College, Harvard, or one of the other 38 college teams in Massachusetts. Grab a beer before the game and pick out some gear for the school you’re cheering for. Maybe your alma mater is playing, or maybe you just want to root for the underdog. The energy of the college fanbase is unmatched.

Walk the Freedom Trail through downtown.

The Freedom Trail is an actual line on the sidewalk through downtown Boston, MA, that takes you on a self-guided walking tour past some of the most important historic sites in the city. You’ve probably taken this route with visitors or as a student, but it’s a different experience if you take a date and just enjoy the people-watching. Bring a camera and take some pictures of some of the lesser-known stops. Try and find a new interesting location or fact together. 

See a show at the Boston Theater.

Boston isn’t too far from New York City, and touring Broadway musicals and plays all make a stop in this city. Check the calendar for upcoming shows and grab tickets. A night out at the theater is fun and entertaining. Make a whole night of it with a nice dinner reservation before the show and maybe some after-dinner drinks. It’s a perfect date night.

Final Thoughts on Date Night Ideas in Boston

With so many ideas for unique and fun dates in Boston, it’s time to get planning. Don’t get stuck in a rut eating at the same spots every date night. Try one of these ideas and introduce some new fun memories into your relationship.

As a bonus, if you’re still wondering about things to do, tour the city with Let’s Roam! You can share laughs together as you set out on a date night scavenger hunt. Choose to go spooky style, artistically, or bar-crawl style.

Which date night are you going to try? What’s your favorite go-to? Let us know in the comments!

Frequently Asked Questions

What are good winter date night ideas in Boston?

For fun winter dates in Boston, go ice skating at the Frog Pond, rent an igloo at the Envoy, or take in a college hockey game. Just dress properly to stay warm (and take hot chocolate breaks).

What’s a good first-date spot in Boston?

Consider activities instead of just a meal. Head to A4cade and play some vintage games or go to a museum. You’ll have plenty to chat about, and there won’t be awkward pauses in conversation.

What are unique gift ideas for Valentine’s Day?

Pick up a gift of experiences for Valentine’s Day so the gift can keep on giving. Try the Adventures From Scratch book, which is filled with date ideas you can scratch off and be surprised by!

Share Post: