Boston’s got brains, beauty, and buckets of charm. It’s where American history meets buzzing neighbourhoods, world-class eats, and a waterfront that’s just asking for sunset strolls and lobster rolls.
Why Boston?
You’ve got American history slapping you in the face on every corner, but then you turn around and bam—there’s a rooftop bar, a food truck, or a student debating aliens at MIT. It’s old school meets college cool. Cobblestone streets, fancy brownstones, Irish pubs, and fresh seafood. It’s walkable, it’s loud, and it’s got attitude. Boston doesn’t try to be like anywhere else—it just is.
Getting There:
Fly into Boston Logan International Airport (BOS)—right in the city, no faffing about. Flights from the UK take around 7 hours, direct from London and some regional airports. Once you land, you’re about 20-30 minutes from the city centre depending on traffic. Easiest way in? Taxi or Uber if you’re feeling fancy. Otherwise, hop on the Silver Line bus (SL1) straight from the terminal—cheap, quick, and drops you at South Station right in the thick of it. Or grab the Blue Line subway if you want to feel like a proper local.
TUI Holidays to Boston – TUI sorts your flights, stays and extras all in one go—super smooth, no faff, and top-notch trusted service.
Boston Holidays, OnTheBeach – OntheBeach lets you build your Boston break your way—flights, hotels, extras, sorted. Easy-peasy, flexible, and budget-friendly too.
Things To Do in Boston
You gotta walk the Freedom Trail, even if you’re just in it for the photos. Then there’s Fenway Park—whether you like baseball or not, the vibes are unreal and the hot dogs are elite. Head to Boston Common for a people-watch and a swan boat ride, or pretend you know stuff at Harvard just across the river (yes, it’s technically Cambridge, but close enough). Don’t miss Quincy Market—it’s touristy but buzzing, with street food, chaos and street performers. Round it off with a chill Harbour Cruise or a sunset beer at Seaport.
Escape the city and head to Martha’s Vineyard for the day—no driving, just chilling. Cruise over, snack up, explore the island, or hop on a guided tour to see cliffs, cute towns, and celebrity-worthy views. Martha’s Vineyard Daytrip on Viator
History nerd or not, this Freedom Trail walking tour is a banger. You’ll stroll past big-deal landmarks with a pro guide who knows all the juicy old-school drama. Think rebels, revolutions, and a bit of fresh air with your fun facts. Freedom Trail Walking Tour on Viator
Whale watching? Oh yes. Zoom out on a speedy catamaran and spot actual whales—like, massive humpbacks and finbacks just hanging out. There’s even a guide onboard to tell you which ones are flirting or fighting. Whale Watching Cruise on Viator
Get in a WWII duck boat (yes, seriously), roll past all the top Boston sights, then splash into the river like it’s no big deal. It’s part tour, part boat ride, all hilarious. Your guide will keep you laughing while pointing out landmarks and telling you what’s what. Boston Duck Boat Tour on Viator
Hop on the old-school trolley and cruise around Boston like you own the place. You can jump on and off whenever, wherever—see parks, shops, monuments, even the original Cheers bar. The guides are funny, the views are fab, and the vibes? Amazing. Hop-on Hop-off Old Town Trolley Tour, GetYourGuide
Want to see where presidents were born and where pilgrims landed? Hop on a comfy minibus and head to Quincy and Plymouth. You’ll get coast views, a lighthouse, and visit Plymouth Rock, which is tiny but iconic. Plus, there’s history about rebels, lighthouses, and a very sassy army of two. Quincy, Plymouth, and Mayflower II Day Trip, GetYourGuide
MIT and Harvard in one day? Yes, brainiac! Start with MIT’s pranks, hacks, and weird but interesting facts, then subway it to Harvard Yard to see old buildings, statues that lie, and where George Washington once chilled. It’s all about legends, clever students, and loads of great photo ops—no homework required. MIT and Harvard Walking Tour, GetYourGuide
Fall in New England is unreal—like, full-blown postcard vibes. Cruise up to New Hampshire through forests of red and gold, stop for waterfall hikes, snap leaf pics, eat lunch in a mountain town, and feel very outdoorsy. Fall Foliage Tour, GetYourGuide
Fenway Park is legendary—even if you don’t know baseball, this place is buzzing with history. Tours take you to the Green Monster, dugouts, and the famous pole. Go short and sweet or pre-game fancy. Either way, you’ll feel like part of Red Sox royalty for a hot minute. Boston Fenway Park Tour, GetYourGuide
Top Rated Food Stops
Union Oyster House – Oldest restaurant in the USA, proper Boston vibes, lobster rolls that’ll change your life. Right by the Freedom Trail.
Giacomo’s – Tiny, loud, and full of carbs. Tasty Italian in the North End. Expect queues, carbs, and zero regrets.
Yankee Lobster Co. – Diner energy with big seafood flavours. Fried clams, chowder, and lobster rolls by the waterfront.
Tatte Bakery & Cafe – Instagrammable brunch heaven. Pastries, shakshuka, and oat lattes. Casual, cosy, slightly boujee. Found all over Boston.
Regina Pizzeria – Brick oven pizza that will leave you wanting more. Greasy, cheesy goodness in a tiny North End spot that’s been around since dinosaurs.
The Friendly Toast – Retro diner gone wild. Insane pancakes, tasty milkshakes, and breakfast all day. Found in Back Bay, chaos in a good way.
Practical Tips
Walk loads – Everything’s weirdly close, and parking costs more than your hotel.
Cash for tips – Bostonians don’t mess around when it comes to tipping.
Layers always – It’s sunny, then snowing, then humid. Madness.
Use the T – The subway’s cheap, cheerful and efficient.
North End – Eat everything. Just go hungry.
Visit Fenway Park – Even if you hate sports. It’s a vibe.
Harvard Yard? – Not actually that big. But you’ll still take 50 photos there.
Tours – Check out what Boston has to offer with Viator & GetYourGuide.
CityPASS – Snag a Boston CityPASS to hit 4 top attractions and save up to 46%. Aquarium, science museum, harbour cruise, zoo, Harvard exhibits—your itinerary just built itself. No stress, just scan and go. You get 9 whole days to use it, too. Boston CityPASS, GetYourGuide
From skyline views to seafood feasts and Red Sox games, Boston delivers big city fun with small-town charm. It’s easy to explore, full of surprises, and always worth the trip. Are you sold yet?
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