Summer in Boston; An Insiders Guide

Extended version of piece for NZ Herald Travel Section, March 25, 2019


Boston is one of the oldest cities in America, rich in colonial and maritime history, the architecture spans all of the countries eras and the city is littered with momentous locations across the centuries, but less widely known are the modernization, growth, and food scene which have emerged in the recent decade, bringing the best of the old and new side by side. In the summer the city reverberates with festivals, live music, free outdoor activities, farmers markets and endless ways to enjoy the culture. There has never been a better time to visit Boston.

Boston is a great walking city because of it’s relative density of sites and experiences, tackle it by section, bring comfortable footwear and use uber and the subways to break it up. The Boston Harbor Walk is a recent addition to the city and allows you to follow the waters edge, or jump on and off of the Boston Harbor Water Taxis along 43 miles of waterfront, from the Charlestown, to Downtown, the Seaport to North End’s Italian haunts. If you get ambitious you can walk south to the Fort at Castle Island in Southie and take a swim at Pleasure Bay or M Street Beach like the locals do, be sure to stop off for coffees or beers along the way.


The Boston Public Market in downtown is a recent addition to the city, what Faneuil Hall must once have been, showcasing the best artisanal foods of New England, honey, cheeses, beers, chocolates, fruit, fish, and apple cider donuts which tease your nose as you walk in the door to name just a few. Show up hungry as there is great prepared food and plan to bring gifts home with you. Vendors are knowledgeable their craft and can give you a mini culinary tour of New England, its farm and food culture old and new.

Another revamped experience in Boston is the beautiful Boston Harbor Islands National and State Park, a perfect summer activity. Ferries take you from the dock near New England Aquarium and the New England Greenway out to the various islands and forts. Although this has always been a part of the city, in the last decade the Parks created engaging events for adults and children and better access. You can even rent a yurt or campsite on the a few of the islands and stay overnight (book well in advance for weekends, and check out REI Stores for gear rentals.)

The historic register high end Ames Hotel, with its revamped with a modern interior is located in the heart of the city if you are aiming to really dig into the history and heritage of downtown Boston this is a great locale.



The Boston Institute of Contemporary Art’s (ICA) Seaport building was one of the initial buildings to start the redevelopment of the most recent expansion of the city, which seemingly grew up overnight, once a relative wasteland of parking lots and dive bars. Check out Lucky’s which still remains. In 2018 ICA opened the ICA Watershed in East Boston, which can be reached by a ferry ride across the harbor included in your museum ticket. The trip is worth it for the views back across of the Boston skyline alone. While in Eastie you can sneak into the Downeast Cidery and drink some of their free samples. And the Seaport ICA has wonderful live music events on their expansive deck on summer evenings.

If you are feeling hungry, you have great options in the Seaport. Flour is a famous bakery group founded by Joanne Chang with pastries to die for. Drink is a high end speakeasy where beverages are created to one off by kind of liquors you favor and of course there is Lucky’s, the original dive bar of the Seaport. Trillium is one of the highest rated micro breweries in the country with a cult following, the Seaport location is to go only, so check out their summer pop up Bar on the Greenway near South Station. There should be many great food trucks as well representing the cities burgeoning gourmet truck scene. For a serious meal head to local favorite Sportello, Blue Dragon, Row 34, the Coppersmith or new addition Chickadee­­­­­­. Boston’s food scene is pretty fierce so booking on the Open Table app is highly advised.

Evening in the Seaport are great for live music at The Lawn on D. Grab food and beer from the trucks and listen while hanging out on the glowing swings or playing a game of cornhole. Check out the schedule.

Back Bay

Newbury Street, Boston’s famed Back Bay shopping street full of all the big designer names is overrated. Head away head away from the Garden to find the interesting local stores. Ministry of Supply is a successful tech driven local apparel brand-you can 3D print your own garment in the store, Johnny’s Cupcakes is a stellar graphic design experience, Frye boots is an fashionable local brand with its origins in the civil war, Muji’s is a classic everything store and Reformation is a sustainable Californian brand fighting fast fashion.
Boston Museum of Fine Arts is the fifth largest museum in the United States. Grab a coffee in the recently added atrium beside the Chihuly sculpture and check out the photography and fashion exhibits, summer 2019 includes Gender Bending Fashion and Georgie Friedman: Fragments of Antarctica. Best of all is if you are in town during MFA Late Nites, get a ticket and join in the all night revelry in the museum, expect the unexpected, from DJ’s, to artmaking and intriguing food.

If you miss MFA Late Nites, head to Third Thursdays at the Isabella Stewart Gardner Museum just next door. The museum lights up with live music from local musicians, thought leaders and artists in residence, just as it did when the extraordinary building was home of one of Boston’s leading ladies.  

Be sure to head down Clearwater Street to local secret, the Bodega. Even if you aren’t in the market for edgy street fashion the experience of walking into the unremarkable quickie mart and then emerging in the highend boutique behind the shelves is worth the stop, even if only to be able to say, yeah, I knew where the Bodega was.


Beacon Hill

Shakespeare on the Common is a Boston summer long event not to be missed, and like many of the best summer activities it is free. Bring a picnic dinner and a blanket from your hotel, beverages incognito as New England is old school on liquor laws, and relax into a gorgeous evening under the stars. Summer 2019 the troupe will perform Cymbeline nightly, a tragedy which is also purported to be a romance bordering on comedy, check the website for details.

Be sure to look into free yoga all over the city, including Copley Plaza and the Frog Pond on Boston Common, where you will be surrounding by Beacon Hills residents walking their dogs just as their ancient forebears exercised their right to graze their sheep on the shared common land in the early colonies.

For more yoga, farmer’s markets and events, the Boston Magazine online has a Free Things to Do in Boston This Weekend section so you can roll like a local with weekly news, knowing about all the best activities, concerts, local festivals, and exhibits.

Walk along the Charles River, once renowned for it’s dangerously unsafe water quality, now classified so highly that the Charles River Conservancy has a Charles River Swim. The band the Standells made it a point of acclaim with their song “I love that dirty water, Oh Boston you’re my Home,” a beloved classic which echoes around Fenway’s hallowed green stands as fans sing along. A game at Fenway watching the Red Sox, hot dog in handing as twilight drops is a summer necessity in Boston, the worse your seats the better a fan you are.

Near Fenway Park, newly added The Verb Hotel has a funky vibe and an outdoor swimming pool which is a relative rarity in Boston.

Check out the free evening music from Boston Landmarks Orchestra’s Concerts at the Hatch Shell, alongside the Charles River Esplanade. 

If you want to live Bostonian dream stay at the Beacon Hill Hotel on Charles Street, you will literally be in the heart of the original old city, and the prices are shockingly reasonable. Or alternatively nearby the XV Beacon was named Conde Nast #1 Boutique Hotel in 2017. Or check out the new Whitney Hotel, on Charles Street, named one of the Best New Hotels to Check out Around the World by Travel + Leisure, and the in house Peregrine Restaurant, opening to rave reviews in May 2019.

On Charles Street, don’t miss Follain a local all natural group of beauty supplies, Good for locally made home and clothing objects, December Thieves for fashion and jewelry, and Dress to shop for clothing like a modern day Boston brahmin. Bin 26 is a great stop for some wine tastings, Toscano is a classic Italian stop, or if you really want to splash out at the top of the Common Park No 9 is one of Boston’s swankier and best known restaurants.

Another unique hotel experience is the Liberty Hotel. A panopticon style jail built in 1851, the austere granite building was a functioning prison until recently but now provides a high end experience at the top of Charles Street and Downtown Boston. The in house restaurants, including Clink, are a great way to check out the unique building even if you don’t stay overnight.

unsplash photo

unsplash photo


When locals speak of “Boston” they generally mean the greater region, which includes Allston Brighton, Brookline, and East Boston, but also north of the Charles River; Cambridge and Somerville, jokingly known as Camberville. Together this makes up metropolitan Boston.

Be sure to cross the Charles River into Cambridge, easiest on the red line. Check out MIT's Museum which showcases cutting edge inventions and tech from the school’s history and present with interactive opportunities for all ages. On the flip, Meadhall is a great beer stop with much of MA’s best beers on tap, Commonwealth is great for a healthy bite, and if you fancy getting out on the water you can rent kayaks at Paddle Boston in Kendall Square to see Boston and Cambridge from a different view.

If Harvard is on your must see list definitely head there on the red line, but limit your time in Harvard Square’s chain stores, and whatever you do don’t touch John Harvard’s foot. Stop by Harvard’s Museum of Natural History is worth a visit if only to see the Ware Collection of Blaschka Glass Models of Plants, lifelike pieces made from glass, which still mystify scientists to this day. Peek in Hogwarts like freshman dining space, Annenberg Hall, and head to the Richard A. and Susan F. Smith Campus Center to make like a student and get a coffee.

Alden and Harlow Restaurant has a seriously delicious fresh farm to table food with tasty cocktails, the Beat Hotel and the Sinclair for live music and good food. If you want to walk the famed neighborhood, meander to Forage or Formaggio both outside of the square.

Wrap up Harvard and grab an uber or a bike like a local, and head to Union Square in Somerville. This creative square will someday be on the Greenline (someday, ask a local over a beer if you dare) and is home to delicious restaurants and bars like Juliet, Celeste, Back Bar and Remnant Brewing Co. To shop locally made goods check out the Bow Street Market which opened in 2018, as well as Queen of Swords, Loyal and Co, and Janje. Keep an eye out for the world’s tiniest museum.

Further Town

Guests love a visit to World's End Conservation area south of the city in Hingham. The two drumlins landscaped by Fredrick Law Olmstead sit in Boston Harbor and as much of the world as I travel, remain one of the most beautiful places I have seen, and are stunning in all seasons.

To the south Cape Cod is a famed beach destination. Skip and head to vibrant and fabulous artists enclave at the end of the cape, Provinctown (PTown).  You can take the Ferry from Boston, and potentially get your whale watching fix in as you cross Stellwagen Bank National Marine Sanctuary.

Although people say Bostonians are crazy drivers, we believe we are assertive and tactical, but either way the road network here was laid out by cows so save yourself the trouble and use Uber, the subway, trains and ferries as much as possible.

In summer there are loads of bike sharing options and the Minuteman Bike path will take you out of vibrant Davis Square in Somerville through historic Lexington and Bedford and makes a great ride with coffee and ice cream stops along the way.

For days out of town Uber or Zipcar are good, although Amtrak trains run to many key cities and towns as well affording great views of the countryside. Just don’t expect European convenience from our old decrepit network, it will get you there, eventually. And if you really want to splash out and see the city there is always the Boston Helicopter Tours $195 USD per person, $99 for a third.



Boston Magazine online has a Free Things to Do in Boston This Weekend
And pick up the Improper Boston Magazine on stands for free to get a detailed run down of music, shows, openings and events.