We’ve done the work so you don’t have to. From the best beaches in and around the city, to local blueberry picking and waterfront dining, we’ve curated the ultimate Boston summer bucket list below. Make sure to keep this guide in your back pocket as you mark things off your summer bucket list! You can thank us in the fall.
1. Take a sightseeing sailing tour of the Boston Harbor
Sail aboard the beautiful Adirondack III, a 80-foot pilot schooner of the 1890s, as it glides through the Boston Harbor waters. You’ll view everything from Spectacle Island to Seaport as your knowledgeable crew takes you on this guided tour at sea! Reserve your sailing adventure today.
90-120 minute tours available Friday-Sunday at the Boston Harbor
2. Enjoy a mystery picnic self-guided foodie adventure
Sure, you could have an ordinary picnic, or you could have a summer picnic of mysterious clue-busting and riddle-solving fun! Every clue you solve takes you one step closer to your gourmet picnic basket. Learn more about this mystery picnic!
3. Go blueberry picking at this local farm
In the fall it’s all about the apples, and in the summer we bring out the berries! This local farm is just minutes from the city and offers endless fields of blueberries and strawberries to pick for your summer snacking.
4. Visit Menemhsma beach at Martha’s Vineyard
Menemshma Beach was voted as one of the best attractions on the East Coast according to Instagram users. With white, sandy beaches and picturesque lighthouses, it’s a quintessential New England summer bucket list destination!
5. Indulge at this 155-year-old waterfront resort that neighbors Taylor Swift’s mansion
Ocean House in Westerly, Rhode Island is one of the most stunning resorts in all of New England, and according to Condé Nast Traveler’s Gold List–one of the best in the world. Set on the unbelievably clear waters of East Beach, the resort has private cabanas, a spa, pool, and delicious farm-to-table summer dining! Oh, and you might even catch Taylor chilling next door!
Ocean House is located on Watch Hill in Westerly, Rhode Island which is both a 2-hour drive or Amtrak ride from Boston.
Find Ocean House at 1 Bluff Ave, Westerly, RI 02891
6. Visit 2 of the top 5 coastal towns in the U.S.
Marblehead and Provincetown were recently selected as two of “America’s top coastal small towns.” We know the summer scene is breathtaking here, so come for food, surf and sun!
7. Enjoy the seaside views at 3 of ‘America’s best front porches’
New England is not only how to some of the best beach towns, but within those towns you’ll apparently find some of the “best hotel porches” to enjoy the fresh air and dazzling views. Watch sunshine reflect offf the Atlantic at Ocean House or find a comforting forest landscape at The Omni Mount Washington Resort in Bretton Woods, New Hampshire.
8. Cool off at a beach just 1-hour or less from the city
You can enjoy a beach “staycation” by taking a dip at Carson or the Boston Harbor Islands. Both provide the salt water you crave without the need for a full-on travel day. You can even kayak or camp at the Harbor Islands for a little adventure!
Alternatively, the North Shore, which is under 1 hour from the city, has some of the best beaches in the state like Wingaersheek and Singing Beach!
9. Escape to Martha’s Vineyard, voted the best attraction in the state
It wouldn’t be a Boston summah without a trip to the “Vineyahd!” Maratha’s Vineyard was voted one of the most “fairly hyped” attractions in Massachusetts.
10. Visit this European vista-style beach in Maine
Some people say that Ogunquit is the closest thing to a European coastal town in New England. If you can’t make it to the Amalfi Coast this year, then this is your best option to traveling local and on a budget! The beach is only 80 minutes from the city and surrounded by cute walking trails, seafood shacks, lighthouses and an acai smoothie store!
11. Shop locally-made resortwear
Riviera Clothing Company is a local woman-owned brand making bright, playful outfits perfect for those New England summers. Delightful prints come in cheeky names like Gators & Roses or Message in a Bottle. Check them out here!
12. Do some yoga with goats at this local farm
Test your flex with another furry, friendly, and jumpy challenge at hand…goats! This farm in Georgetown, MA offers outdoor goat yoga on its massive acreage to help you find your zen.
Goats To Go at Great Rock Farm 201 Pond St Georgetown, MA 01833
13. Dive in to this 21,000-square-foot waterpark
Jellystone added 83 new cabins to the campgrounds and this summer, the new waterpark makes a splash! Glide down a massive spiraling waterslide and dive into the summer fun at one of the state’s largest waterparks!
20 Shoestring Road, Carver, MA 02330
14. Dine at one of these 12 waterfront restaurants serving spectacular views
Dozens of restaurants in Boston are taking advantage of the warmer weather and beautiful waterfronts around the city. You can’t beat the views or the food at these spots.
15. Mingle at a Boston rooftop day or night
Skyline views against the water just never get old. So you know we’ll continue the celebrations at a rooftop! From a Seaport classic to a garden terrace, these are the best in the city!
16. Secure a spot at this secret and swanky ‘diner en blanc’
Diner en Blanc is an annual tradition where cities around the world host a giant get together picnic at a secret location. The dress code is all white and makes for some pristine photos!
17. Catch an outdoor movie
Can’t decide between cozying up with a film indoors and enjoying nature? Why not do both! These outdoor movie spots are serving up classics and new hits (many for free) that you don’t want to miss!
18. Jam out at one of Boston’s music festivals
Kicking off with Boston Calling during Memorial Day weekend, summer is the official start of concert season here in MA! From Fenway to Gillette, you’ll be able to enjoy festivals and tours from artists like Zach Bryan and Ed Sheeran.
19. Pump the adrenaline at one these local theme parks
From rollercoasters to waterparks, these theme parks have everything you need for summer. Copious amounts of carnival food, nostalgic prizes, and scenic landscapes. Make sure to check out the newly expanded Jellystone with 83 cabins and a 21,000-square-foot outdoor water park!
20. Rent a campervan and explore the great outdoors
A huge trend out of necessity during COVID, campervans are here to stay. They provide flexibility and convenience-merging your car and hotel into one. It’s time to take that New England tour you’ve been dreaming about, and here are 12 quaint towns to get started.
21...or take a glamping trip in the Cape
Autocamp Cape Cod merges the nature of camping with the glamour of a Cape Cod resort! Get the best of both worlds on this trip, plus lots of time at sea, land and making s’mores under the starlight.
22. Spend Sunday exploring the 90+ vendors of SoWa
South End’s biggest outdoor market is back! SoWa is perfect for those Sundays where you want to “do the most” but without running all over the place. It’s a one-stop-shop for food, art, mingling, outdoor time, vintage shopping and more!
23. Awe at the stunning summer sunsets
Take advantage of those long summer days and ogle at the stunning sunrises and sunsets of the 617. From the Charles River docks to the more labor-intensive vantage points caught atop the Blue Hills mountains in Milton, here are our vetted spots for sunset chasing.
24. And make a picnic out of it with this local cheese board curator
Summer equals fancy picnic season. We don’t make the rules, just play by them! Take the work out of making a fancy cheese board and leave it to the pros at Chick Cheese Chick! They offer delivery within 35 miles of Needham so get your perfect cheeseboard delivered right to your celebration.
25. Hop on the CapeFLYER train and explore Hyannis
Summer also equals Cape traffic, which as many of us known will suck the joy right out of that Cape outing you’ve been eagerly waiting for. The CapeFLYER runs from Memorial Day to Labor Day weekend and will take you from the city to the Cape sans traffic!
26. Soar through the sky on a private helicopter tour of Boston or the Cape
Live out your Mission Impossible fantasy by taking a helicopter tour above the city! You’ll see everything from Seaport to Fenway and can even take a tour at sunset or over the Cape!
27. Take a free outdoor workout class in Seaport
This summer, Seaport will host a variety of free outdoor workouts! Yoga, HIIT, cardio and more are just some of the options to get fit for free and in a fun environment.
28. Make a splash at this 95,000-square-foot beach resort
Red Jacket Beach Resort & Spa is back for the season, and with brand new pickleball courts! The getaway is just under 2 hours from Boston and sits on a private beach. You’ll be in a New England oasis.
29. Watch cliff divers jump 66 feet off the edge of this famous landmark
Red Bull’s iconic Cliff Diving series tours in 7 cities, and Boston is the only American stop! The city of sports welcomes some of the top divers to jump from a platform suspended 66 feet in the air into the Boston Harbor!
30. Eat the ‘world’s best lobster roll,’ as deemed by experts
The experts voiced their opinion-Maine’s The Clam Shack is home to the “world’s best lobster roll.” Try it out for yourself this summer and you be the judge!
31. Visit Maine’s newest boutique hotel and ‘most anticipated’ according to Vogue
The Longfellow Hotel just opened! Last year, Vogue named it one of the “most anticipated new hotels” in America. With stunning architecture and a central location, we totally understand why.
32. Shop local at this charming outdoor market in Seaport
If you’re a fan of Snowport, you’re gonna love the Seaport Summer Market! 100s of vendors and food options are available at this sunny outdoor market located at the Seaport Common each weekend!
33. Prance through this fairytale rose garden in Fenway
Bountiful roses bloom in pink, blush, fuchsia, reds, whites and more! It’s like stepping through a magical summer fairytale at the Kelleher Rose Garden in the Fenway’s Emerald Necklace.
34. Enjoy dinner with a view on Boston’ floating oyster bar
Tall Ship is Boston’s 245-foot mahogany floating restaurant. It’s a must add to your bucket list if you’re a fan of waterfront dining!
35. Catch a drive-in movie at one of these theatres
Go a little old-school and watch an outdoor movie from the comfort of your car! Go all out with snacks and even set up a cozy seating situation in the tailgate for the ultimate summer drive-in movie experience.
36. Try some of the most unique ice cream in the entire city
Some of the best ice cream shops in the country are here in Boston according to the Thrillist, The New York Times and more-hint, hint- Toscanini’s! And part of the reason why is because they have flavors you certainly can’t find elsewhere like Miso Banana, Australian Malt, and the infamous B3-brown butter, brown sugar, brownie! Check out the funky flavors at Tosc and other shops around the city!
37. Explore the magic of the Revere Beach Sand Sculpting festival
Revere, the world’s first public beach hosts its annual sand sculpture festival this year on July 28-30! It’s one of the largest summer events in the state, so you can’t miss it.
38. Hike the Mohegan Bluffs of Block Island
Block Island is one of the hidden treasures of New England. The tiny island off the coast of Rhode Island and New York’s Hamptons is just gobsmacking-clear blue waters, a hiking trail akin to Malibu, and tall lighthouses.
39. Check out the unreal seafood scene at Nightshade Noodle Bar
James Beard nominee, Chef Rachel Miller, runs the legendary award-winning Nightshade Noodle Bar in Lynn, MA. During the summers they have plenty of seafood on the menu offering refined options of all of your favorites like lobster rolls, fried crab, and clams galore!
40. Learn to surf in Hull or Newport
No need to travel to Oahu, you can learn to surf right here in New England. Two popular surf spots- Hull in Massachusetts and Newport, Rhode Island!
41. Ride horses and ponies on the beach with Rustic Rides Horseback Riding
You can book a beautiful, guided beach ride with Rustic Rides Horseback Riding. There are also pony rides for the kiddos. Rides start at $100 an hour and welcome all experience levels!
42. Rent a scooter and go for an oceanfront ride in Rhode Island
If you prefer that your ride isn’t a living animal but instead a mini car or Vespa, then check out Scooter World in Newport for rentals! You can take a Polaris Slingshot, Scooter, Trek Bicycle or adorable Scoot Coupe and ride around the Ocean State!
43. Explore a famous lighthouse
Nubble Lighthouse is one of the most photographed on the East Coast, and with good reason. Built in 1879, the historic lighthouse sits at the tip of York, Maine.
44. Relax at ‘America’s Best Waterfront Hotel’
If you’re seeking a luxurious waterfront getaway to treat yourself this summer, Cape Cod’s Chatham Bars Inn was named “America’s Best Waterfront Hotel.” It boast expansive waterfront rooms, farm-to-table dining, tennis courts, a spa, and a private beach.
45. Go ziplining through a forest less than 1 hour away from the city
In Berlin, MA, just about 50 minutes driving from Boston, is a ropes course and ziplining park! There are 18 different ziplines and 110 obstacle courses for outdoor enthusiasts ages 7 and up!
46. Stroll through a car-free Newbury Street
Car-free Sundays lead to care-free Sundays! Starting July 2, stroll through an open Newbury Street and explore vendors, “patio” dining and special events every week through October!
47. Go on a New England lobster roll crawl
We asked Bostonians the best place to find a lobster roll in all of New England. We compiled the many responses down to a list of the 40 finest! Make it your summer mission to try as many as you can lobster fans! This Maine seafood shack was voted to have the “best lobster roll in the world” according to taste experts.
48. Check out Boston’s sky lounge
Boston finally has an observation deck! The 3-story observatory, View Boston, has indoor and outdoor viewing platforms in addition to 3 restaurants to mingle and take in the glorious views!
49. Relax at a 20-acre Nordic New Hampshire getaway
The newest New England glamping destination arrives in style this summer to New Hampshire’s White Mountains! Lumen Nature Retreat is a 20-acre property with 35 Nordic-style accommodations and amenities – it’s a pretty magical place to relax in nature,warm up in a sauna, and then refresh (Nordic style) in a cool lake! It’s about a 2-hour drive from Boston or you can take the Amtrak to Lincoln, NH and then it is just an 8-minute Uber!
50. Get lost in a ‘lavender haze’ at this epic farm festival
This blooming awesome farm festival in June and July is a must-see attraction! Rows and rows of lavender line sweeping views of Mount Wachusett for a breathtaking scene. You can also walk the fields, taste fresh lavender honey, snap photos and more!
51. Captain your own boat around the Boston Harbor
Boston Electric Boats has a stellar ‘be your own captain’ boat rental! This summer, grab some friends, snacks, and beats and head out into the harbor for a day at sea! It’s super fun and easy to steer these Duffy electric boats. Reserve your boat here.
52. Groove out at the Newport Jazz Festival
Get jazzed about the return of Newport’s beloved music festival! Running August 2-4 there will be over 50 unique jazz artists and ensembles to enjoy. If jazz isn’t your thing, you can check out the Newport Folk Festival running July 26-28.
53. Enjoy a festive summer brunch at Para Maria
The Latin-inspired restaurant in Seaport is spicing things up this summer season and it’s about to get amplified! On Saturdays and Sundays at Para Maria in Boston Seaport, from 7 AM until 3 PM, catch live music and standout eats!
54. Spend the perfect weekend on Nantucket at the newly renovated The Brant
The Brant, formerly Salt House Nantucket, is the epitome of lodging on the Gray Lady. You have Nantucket’s quaint whaling charm coupled with an ultra-chic, deliciously smelling stay. Plus, The Brant just added a pool by its outdoor hydrangea garden! Grab the new Elin Hilderbrand novel, Swan Song, for a quintessential Nantucket summer.
55. Zipline from Massachusetts to New York at speeds exceeding 55-miles-per-hour
If you thought summer made you sweat, how about this long adrenaline-filled ride across state lines. Would you ride the longest zipline in America?
56. Stay in a coastal cottage in Ogunquit
The newly renovated The Dunes on the Waterfront offers the most idyllic stay in Maine. The new cottages offer charm with adventure at your doorstep. Explore the dunes, go fishing, kayaking, biking, visit the clearwater beaches of Ogunquit, and enjoy some of New England’s best seafood!
57. Check out one of America’s most historic (and romantic) small towns
Neighbors with Ogunquit, Kennebunkport is a popular town to visit year-round. It ranked as one of the most romantic small towns in America, but also makes a lovely summertime destination-no wonder it’s popular for presidential estates.
58. Attend a summer festival in the North End
The popular San Gennaro Feast will return to Boston’s North End this summer from August 30 through September 2. The festival decorates Hanover Street in white, red, and green!
59. Feast at a traditional New England clambake
Find delicious seafood and vibrant community at these seafood-centric summer events:
- Summer Shack Shuck-fest: Sunday, August 4 from 11 AM-3 PM
- Puritan & Co. Clambakes
- Clambake feasts: Sunday July 21 and August 25 at 6 PM ($100 per person)
- Clambakes for one: Every Sunday ($55 per person)
60. Check out Vinyl Nights at the ICA
The Institute of Contemporary Art returns with its Vinyl Nights series! Enjoy live vinyl-only DJ sets overlooking the Boston Harbor. Find live beats on Fridays from 5-9 PM on the following dates:
- Friday, July 12: Keep On with CAKEWALK, Brianna Paon, and Trip Report
- Friday, July 19: Stay Silent with Lefty
- July 26: Music Research Library
- August 9: Kickback with Real P, DJ Knife, and Basi B
- August 16: Social Studies with Alfredo, Sacha, and Azzeddine
- August 23: Slow Gemz with KNSZWRTH, and Mez Wav
- August 30: Infra with Angel Attack, Ntmowen, and Xam76