Summer Fever: Things to Do in Boston in Summer

May 19, 2023 | ,
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Summer Activities To Do in Boston

It’s getting hot in hereee, so…please, we beg of you, don’t take off all your clothes BUT do enjoy this list of fun things to do in the swelter of a Boston summer. This New England city is packed with great summer activities for all different preferences from boozy to out doors-y, well, let’s be real, back to boozy. Use this as a check list for your best summer yet and don’t forget your sunscreen; it’s gonna be a hot one!

26. Set Sail with Boston Lux Cruises

Photo Credit: Boston Lux Cruises

Get the party started this summer by setting sail this with Boston Lux Cruises. There will be plenty of booze to keep you afloat and some of the best vibes in town as you cruise around jamming to your favorite playlist. This small company started up several years ago offering curated cruises for groups big and small whether you’re celebrating something specific or just celebrating summer and being on a boat. Oh and get this, they’ll be welcoming new tiki boats to their fleet this summer. Ahoy!

25. Check Out Boston Open Market on Boylston Street

Photo Credit: Boston Open Market

Take a stroll through this beautiful open market at their new location on Boylston Street where you can meet the makers behind the amazing products and artwork that catches your eye along the way. New England Open Markets aims to support the New England arts and small business communities by creating inclusive market experiences that connect the public directly to makers and micro businesses. At all of their markets you’ll find a wide range of woman-owned, POC-owned, and LGBTQIA+ owned businesses, showcasing the breadth of unique artisans the region has to offer. They have curated a space that is accessible and meaningful for both vendors and shoppers, fostering connections and bringing local arts and goods to the public directly from the makers themselves.

24. Take a Neighborhood Food Tour with Bites of Boston

Hands down one of the best ways to experience a neighborhood is through its food. And food is best enjoyed with company. So grab your friends, family, significant other, or random person from the street, ok maybe too soon for that, and join us for a walking neighborhood food tour! You’ll explore the landscape and history of one of Boston’s most unique neighborhoods, enjoying the summer weather, while getting to learn about it from the lens of its amazing food. All of our tours include both sweet and savory tastings so come ready to eat, experience, and explore! To learn more about what a food tour is, check out our blog post: Eat, Explore, Experience: What to Expect on a Bites of Boston Food Tour.

23. Feast on Summer Seafood at The Barking Crab

Photo Credit: Brian Samuels Photography

At the top of our list of celebrating summer in Boston is eating alllll the lobster and fried seafood we can get our hands on. While we might have to keep some Tums handy, we’re committed! We love The Barking Crab for both its food and its atmosphere, which is why it has become a favorite eating and meeting place for Bostonians since it opened in 1994. Located on Boston’s historic Fort Point Channel at the gateway to the Seaport District, The Barking Crab will satisfy all of your summer seafood needs from steamed to fried. It gives that clam shack vibe but with city style. Oh yeah, and whatever you do, don’t miss out on the lobster roll, bursting at the seams with fresh lobster meat. It’s an all summer long MUST!

22. Stroll the Rose Kennedy Greenway

Photo Credit: Rose Kennedy Greenway

The Rose Kennedy Greenway is a mile and a half stretch of contemporary parks in the heart of Boston. It’s a beautiful place to grab a slice of nature in the bustling city and it always has something fun going on. It’s the host of festivals and markets, a beer garden, carousel, fountains, and rotating art installations. Boston is a food truck city so if you get hungry on the Greenway, like we always do, then grab a bite at one of the many food trucks that you’ll find parked there. They have a daily schedule of rotating vendors so you’re sure to find what you’re looking for from sweet to savory. Let’s just say you could get carried away and spend the whole day there!

21. Bring your Pup to the Bully Boy Cocktail Garden!

Photo Credit: Bully Boy Distillers

If you want to spend some quality time with your best friend this summer, aka your pup, then head to the Bully Boy Distillers Cocktail Garden for a refreshing sip and fun time with your fluff. The city of Boston is now allowing dogs in outdoor restaurants and beer gardens throughout the city and they jumped on getting a permit. So now you can enjoy Boston’s first distillery since Prohibition with the company of your dog. They’ve built a Cocktail Garden right in the lot of their barrel house. Think of it as an Industrial Tiki Oasis. The regular menu will be offered along with rotating frozen drinks and tropical additions added weekly. Everything is made with fresh juices, house-made tinctures, and local ingredients with each cocktail showcasing a different Bully Boy spirit.

20. Explore the Charles River with Paddle Boston

Photo Credit: Paddle Boston

If you enjoy being active and wanna get out on the water without leaving the city then take a ride with Paddle Boston – guided or on your own. They offer Charles River kayak and canoe tours as well as paddle board, kayak, and canoe rentals. They have several different locations to start from and you can rent by the hour or the day. Their last boat goes out at 7pm so enjoy a day on the water or a quiet evening. Plus, you don’t have to sit in the traffic to get out of the city since it’s right here!

19. Cool Down with a Sweet Treat at Honeycomb Creamery

Photo Credit: Honeycomb Creamery

Enjoy one of summer’s favorite activities (and one of our year-round favorites) — EATING ICE CREAM — at one of Boston’s best small-batch ice cream spots. Honeycomb Creamery has quickly become a local favorite with flavors like salted chocolate truffle birthday cake and brown sugar vanilla. They are also throwing a cooler curveball, they’ve brought back the beloved Choco Taco, but theirs is homemade! Every (Taco) Tuesday they feature a different flavor from their rotation. Is it Tuesday yet?!

18. Grab Food & Drinks at Lookout Rooftop & Bar

Photo Credit: Lookout Rooftop & Bar

For a breath taking view of Boston, head to the Lookout Rooftop Bar in the Fort Point neighborhood, bordering the Seaport for food, drinks, and unmatched views. The Lookout Rooftop Bar is located on the top floor of the Envoy Hotel and offers stunning views of the city and the harbor. It’s the perfect place to spend a casual afternoon or watch the sunset over dinner. The atmosphere can get club-y at night, especially on the weekend where you can book private couches, in case that is or isn’t your vibe but during the day is pretty chill.

17. Take an Outdoor Fitness Class with Seaport Sweat

Photo Credit: @bostoday

While Boston likes to party it also loves to exercise! These days you’ll find all sorts of fun workout classes in all sorts of unexpected locations spanning across the city. We absolutely love the summer workout program that the Seaport neighborhood offers called Seaport Sweat. Oh yeah, and did we mention that it’s FREE. It’s Boston’s biggest free workout series and it’s heading into its eighth season, running from May through September. This year, the community driven series will offer a variety of new classes and instructors on Seaport Common and special weekend classes. The 2023 class schedule features the city’s most popular and award-winning instructors from years past, while also introducing exciting newcomers.

16. Enjoy a Scenic Walk Through the Arnold Arboretum

Photo Credit: Arnold Arboretum

For a scenic walk right in the city head to the Arnold Arboretum of Harvard University. It’s a museum of trees teaching the world about plants and providing a beautiful atmosphere to spend a summer afternoon smelling the flowers. The community is made up of researchers, volunteers, professors, educators, artists, gardeners, caretakers, and everyone in between. The Arboretum is a 281-acre preserve in the heart of Boston that stewards one of the world’s most comprehensive and best documented collections of temperate woody plants, with particular focus on the floras of eastern North America and eastern Asia. A beautiful and educational place for a peaceful summer stroll.

15. Eat on Oleana’s Garden Patio

Photo Credit: Oleana

Oleana has arguably one of the best patios in Boston, well technically it’s in Cambridge, but we still say best in all of Boston. This magical garden hideaway is tucked behind the restaurant from which you’ll find the most stunning and delicious Eastern Mediterranean dishes coming from a teeny tiny female-run kitchen. This place is the full package from flavor to ambiance to service and it’s a nice little local getaway for a summer meal. Be prepared to wait a bit as the patio is first come first serve, but trust us, it’s worth it.

14. See Shakespeare on the Common

Photo Credit: Commonwealth Shakespeare Company

For an evening of theater outside of the theater attend one of the free showings of Shakespeare on the Common. Yes, theater that’s free! It’s dinner theater with a twist — the twist being that you pack your own dinner. Picnic anyone? Commonwealth Shakespeare Company presents professional productions of Shakespeare to Boston audiences outside in Boston Common during the summer when local theatre companies tend to be on hiatus from their regular seasons, but when there are record numbers of people in the city. Now entering its 27th season, CSC’s Free Shakespeare on the Common has become an annual Boston tradition, modeled along the lines of “Shakespeare in the Park” in Central Park and the many other free outdoor summer Shakespeare events throughout the city. They present plays of the highest artistic caliber that celebrate ideas and language to create dialogue around compelling issues of our time. To see, or not to see? That is the question.

13. Have An Allergy-Friendly Scoop at FoMu

Photo Credit: FoMu

FoMu is a local company making earth-inspired desserts for the allergy-conscious that are freaking DELICIOUS. They specialize in small-batch, scratch-made, super flavorful, plant-based ice cream with flavors like lemon meringue pie, birthday cake and chocolate pudding. They also offer other sweet plant-based treats like cookies, which they make into ice cream sandwiches and ice cream cakes. This ice cream is honestly so creamy and flavorful you will not miss the dairy, so cool off this summer with a cone from FoMu at one of their several locations and bring a friend who might be skeptical, we guarantee they’ll be on board after trying it.

12. Shop Local at SoWa Open Market

sowa market

Photo Credit: SoWa

SoWa Open Market is one of the South End’s most beloved weekend spots that celebrates the best of the best when it comes to local artisans, farmers, food trucks, brewers, and musicians. Plan to spend a lot of time there because this huge open market has a lot to explore. Get to know the makers behind these local products as you bop from tent to tent with different goods catching your eye as you stroll. The market is open every Sunday from May to October and is dog friendly!

11. Go on a City Scavenger Hunt with Cashunt

scavenger hunt group

Photo Credit: Cashunt

Beantown becomes your game board with the scavenger hunt series hosted by Cashunt. They offer a ton of different hunts in the city of Boston specialized for different groups and occasions and have been operating here for 23 years. This unique activity allows you and your group to explore the city while letting your silly side out. And yes, for those of you who are super competitive, there are prizes!

10. Hang Out at Lawn on D

Photo Credit: Lawn on D

Lawn on D is an interactive outdoor space that has been warmly welcomed by locals since it opened nearly 10 years ago and has now become a city mainstay. It’s a 2.7-acre space for both public and private events that encourages community engagement. I’m sure you’ve seen pictures of people in the cool light-up sphere swing-chairs. Well…those are at Lawn on D! They have lounge chairs and games like bocce, ping pong, and corn hole, and sometimes they have live DJs performing. Head over there and grab a drink and hangout in Boston’s back yard. It’s guaranteed to be a fun time!

9. Fun in the Sun at Castle Island

Photo Credit: @willscitylife

Castle Island is always a great local day trip for some summer fun in Boston. Whether you live down the street in Southie or have to commute it’s full of summer vibes. From the harbor walk to the beach to the historic sites there you can easily fill an afternoon. And don’t forget about the grub! Sullivan’s is legendary for their fried seafood and snacks so refuel there before enjoying the rest of your fun in the sun.

8. Drinks & Chill at the Rooftop Pool at the Colonnade Hotel

Photo Credit: Colonnade Hotel

Who says you can’t enjoy a pool day in the city? Not the Colonnade! Their rooftop pool is one of the most unique summer spots in Boston. It’s an urban oasis with an awesome bar serving food and drinks, and offering private cabanas and daybeds to rent. Sun yourself with a cocktail in hand while towering over the bustling city streets, not something you’d usually consider, but give it a try. The pool is first come first serve so be sure to get there early to secure a spot!

7. Enjoy Seafood & a Summer Night on the Mare Patio

Photo Credit: Mare

Enjoy a summer night out at Mare, a modern Italian seafood restaurant and oyster bar in Boston’s North End, offering a plentiful variety of options from the sea. They have one of Boston’s best patios for sure with tons of fire pit tables to get a little city side campfire going. There’s nothing like sipping bubbly and shooting oysters on a summer night by a fire and Mare offers all of the above!

6. Take a Beach Yoga Class in Southie

Photo Credit: @crg__photography

Head to Pleasure Bay in Southie to get your summer yoga fix…on the BEACH! You’ll get your workout and your beach time all in one with the added bonus of being zenned out. Not bad right? It’s a great way to celebrate summer in Boston so join Morgan of Daisy Face Flows as she hosts beach yoga for the sixth season. All of the classes are geared towards both advanced practitioners and beginners so all are welcome! Classes are on Saturday mornings at 10am and Wednesday evenings at 6pm. You can pay $20 in cash or Venmo and mats are available for rental if you need one or don’t want to get yours sandy. So really there’s no excuse to not get your beach yoga on this summer!

5. Dine, Drink & Shop at Bow Market

Photo Credit: Bow Market

Bow market is a hidden gem where you could easy spend a summer day frolicking, and by frolicking we mean eating, drinking, and shopping, duh. From your first cup of coffee to your last round, and every meal and errand in between, Bow Market offers award-winning choices, right in the neighborhood and a lovely seating area to rest in between. Bow Market has quickly become a hub for the area’s most creative and collaborative. From chefs and comics to DJs and designers, it’s a must-stop-spot for the best in small business and local entertainment.

4. Have a Luxury Picnic with Pop-Up Picnics

Photo Credit: Pop-Up Picnics

If you’re looking for a truly unforgettable summer experience in Boston then let Pop-Up Picnics take the reins! They are a local company owned by two best friends who met in college. Alissa and Chenoa turned their passion project into a business venture (born after a few glasses of wine) in the Spring of 2022 and now are hosting the most Insta-worthy picnics all around Boston. Here’s how it works: Pick from one of their highly curated packages based on decor or celebration type and build from there. No matter which of their unique and carefully crafted concepts you choose, all of their picnics include a standard set-up complete for any gathering include custom place settings and tons of cushy pillows. You can upgrade to add games, food, balloons and more. Their team will arrive on-site prior to the start of your designated time and complete the picnic set-up. After greeting you, they will leave you to enjoy your time and come back once your picnic is over to deconstruct and clean-up. Pick from a number of scenic locations and picnic like you’ve never picnic-d before!

3. Have a Sweet & Colorful Treat at Sweet Waffles + Boba

Photo Credit: Sweet Waffles + Boba

Looking for a sweet and refreshing pick-me-up in the summer swelter? Head to Sweet Waffles + Boba in Boston’s Chinatown, right near the gate (PS this is a great photo op spot). This sweet shop started up in 2019 serving t0-die-for handcrafted Belgian liege waffle pops and delicious drinks such as boba, lemonade, tea and more. They always have a flavor of the day but just to tempt you with a couple of their mainstay waffle pop flavors how does churro crunch and strawberry shortcake sound? Yeah, we know. SO GOOD.

2. Land Ho! Lounge at The Tall Ship

Photo Credit: Tall Ship

This is one of Boston’s coolest hangout spots and it’s ON A BOAT…well, sort of. The Tall Ship is a 245′ vessel turned floating oyster bar moored on Pier One in East Boston. The docked ship features three custom built mahogany bars for guests to enjoy food, drinks, and uninterrupted views of the city skyline and harbor. There is also a big open area with picnic tables and games like giant chess and Jenga. This spot is perfect to set sail without the Dramamine, ha! Enjoy one of summer’s last warm nights there before the chill sets in. To make this place even cooler, they offer a free water shuttle service between their sister restaurants – Pier 6 and Reel House. They take bar hopping to a whole new level.

1. Grab a Drink and Stay Awhile at Cisco Brewers Beer Garden Seaport

Photo Credit: Cisco Brewers Seaport

Aaaand we’re back to drinks. I mean are you surprised? Beantown boasts a ton of local brewing companies but one of the favorites is absolutely Cisco Brewing Company. They started on the island of Nantucket and have since made their way to the mainland bringing brews and smiles. Someone once called them “the happiest place on earth” and it stuck. They’ve brought that happy to one of Boston’s most bustling neighborhoods – the Seaport – with a huge beer garden serving up drinks, games and entertainment. So for a true Boston summer experience grab a brew at Cisco in the Seaport and stay awhile!


Editor’s Note: This post was originally published on July 24th, 2018 and has been updated and revamped for accuracy and fresh content.

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