Planning a trip to Boston? 10 surprising things to know before you go
Tucked between a row of gleaming glass skyscrapers, Boston’s Old State House stands its ground, a dignified landmark in a city that never stops moving. It’s easy to miss, unless you’re looking for it, but that’s Boston summed up: layered, surprising, full of stories waiting to be unearthed. In this historic city, past and present rub elbows on every corner.
And that’s exactly what makes it such a brilliant city to explore. If you’re looking for unexpected things to do in Boston — beyond the famous attractions — this article is for you. And with our great value direct flights from Dublin and Shannon, and US preclearance before you board, it’s one of the easiest and most rewarding American cities to visit.
This summer, we’re highlighting ten surprising experiences that reveal a different side of Boston, from floating stages to indie bookshops, hidden green spaces and some excellent food. Read on to find ten reasons why you should book your Boston flight today.
1. You can island-hop from within the city
Boston has its own series of harbour islands and they’re just a short ferry ride from downtown. Spectacle Island offers scenic hikes and skyline views, while Georges Island is home to the 19th-century Fort Warren, with its shadowy tunnels and ghost stories. The boat ride alone is epic, especially with a lobster roll from James Hook & Co. in hand. Pack a picnic and a sense of adventure, and you’ve got yourself a full-day expedition (no car required).
Boston’s harbour islands are charming and easy to reach
2. The food? Some of the most exciting on the East Coast
Boston’s food tradition goes far beyond clam chowder and cannoli. In the South End, you’ll find bistros like Bar Mezzana offering Italian small plates and standout crudo. Over in Cambridge, Oleana specialises in Middle Eastern flavours served up in their leafy garden courtyard. For something more laid-back, head to Bow Market in Somerville for indie food stalls, then a glass of natural wine at trendy Rebel Rebel.
If you’re craving something sweet, Tatte Bakery has locations across the city; its pistachio croissants and coffee are a super combo.
Grab a pastry to fuel your Boston itinerary
3. You can see incredible live music gigs any night of the week
Whether you’re into jazz, indie, punk or trad, Boston’s music scene is rich and satisfying. The Sinclair in Cambridge is known for showcasing rising acts, while The Burren in Davis Square hosts weekly Irish trad sessions. Wally’s Café near Back Bay gives jazzy vibes: it’s a long-running institution, famous for late-night sets in a tiny, neon-lit room that feels straight out of a movie.
In summer, music spills into the streets; especially around Harvard Square, where buskers play everything from folk to funk. If you’re planning a list of things to do in Boston in summer, don’t miss the outdoor concerts you’ll find scattered around the city.
Boston’s striking skyline by night
4. There’s a floating stage for free summer concerts
Each year, the Hatch Shell on the Charles River Esplanade becomes one of Boston’s most popular summer stages. The Boston Pops light it up for Fourth of July, but you’ll also find outdoor movie nights, symphonies, local bands and Shakespeare productions, all completely free. Locals bring blankets, snacks, and sometimes even fairy lights to set the ambience. Collect some snacks from Flour Bakery or a pizza from Area Four and settle in early on a premium patch of grass.
Summer fun in Boston
5. You can spend many happy hours lost in green space
The city may be compact, but green space is everywhere. The Emerald Necklace is a chain of parks and waterways stretching through neighbourhoods from Back Bay to Jamaica Plain. It’s one of the most relaxing places to visit in Boston, especially if you need some rest between museum stops. Whether you’re exploring the Arnold Arboretum or picnicking in Boston Public Garden, you’ll find that nature is never that far away, even in the heart of the city.
Walking the promenade in Boston’s North End
6. It’s a book addict’s dream
Boston is packed with literary history, as well as a thriving modern-day book culture. Drop into Trident Booksellers & Café, where you can eat brunch while dipping into a new novel. Or browse Brattle Book Shop (one of the oldest bookstores in the US), where great value books spill out into a pretty open-air space. Looking for quieter, offbeat Boston attractions? The Boston Athenaeum offers temporary passes to its stunning reading rooms; make sure to snap a photo of its iconic red leather staircase.
Browsing the quirky Brattle Bookshop in Downtown Crossing
7. The city’s art scene is bold and beautiful
Boston’s art institutions aren’t afraid to break boundaries. The Isabella Stewart Gardner Museum, modelled on a Venetian palace, has eccentric, daring vibes (and you can view the empty frames from a famous 1990 art heist that still hang in place). Across town, the Institute of Contemporary Art juts out over the water and features both global names and provocative new voices. For something more interactive, the SoWa Art + Design District opens its studios to the public on weekends; this is a great way to meet the artists and find unexpected treasures.
The beautiful courtyard of Boston’s Isabella Stewart Gardner Museum
8. The city is built for walking
You don’t need your own car to enjoy Boston. From the cobbled alleys of Beacon Hill to the café-lined streets of Back Bay, this is a city made for wandering. The Freedom Trail connects key historic sites via a red brick path, but a detour into Beacon Hill Books & Café will secure you a pastry and a peaceful browse. Over in the North End, pop into Bricco for handmade pasta or Modern Pastry Shop for dessert (some locals say it’s better than Mike’s).
Walking through Boston’s Little Italy neighbourhood
9. You can swim in the Charles River (for real)
Once too polluted to go near, the Charles is now clean and swimmable. Locals take part in the City Splash each June, but even just watching is a joy. You’ll also find kayak and paddleboards for hire at spots dotted along the river, especially near Kendall Square. It’s a relaxing way to see the skyline from a new angle — and you’ll earn that second helping of cannoli later.
Boston’s Charles River brims with summer activities
10. Getting here from Ireland is easy
Our direct flights to Boston from Dublin and Shannon are smooth and enjoyable. With US customs and immigration cleared before you leave Ireland, you’ll land as though you’re a domestic passenger — meaning you’ll have extra time for exploring, not queueing. Whether you’re flying in for a long weekend, visiting friends and family, or mixing business with a little sightseeing, it’s one of the smoothest transatlantic routes going.
Ready to book Boston?
From outdoor swims and concerts to late-night jazz and espresso in tiny bookshops, Boston is designed for the curious. It’s a city of contrasts — old-fashioned but modern, laidback but full of energy. And with direct flights from Ireland to Boston, getting there couldn’t be easier.
