Boston: city guide. Ivy league universities, the Freedom Trail, excellent shopping and seafood
October 3, 2019 | By: High50
City of Boston skyline

Boston skyline at night

Why go

Situated on America’s East Coast and a six-hour flight from the UK, cultural Boston is the perfect choice for a holiday weekend, or longer getaway. Just 40 miles from Plymouth, where America’s ‘Pilgrim Fathers’ first laid anchor, this is where the American Revolution began with the Boston Tea Party, and its fledging history is here to see in its narrow streets.

What to do
Memorial_Church at Harvard

The Memorial Church at Harvard

A sense of grandeur is maintained – Ivy League Universities including Harvard and Yale plus MIT are in close proximity, oozing elegance from their every brick. The 2.5-mile Freedom Trail will help get your bearings in this easy-on-foot city. You could kayak round the harbour or take a gondola down the Charles River, then head to the esplanade to catch a free film or concert on the outdoor stage of the Hatch Shell concert venue. Fancy a day trip or overnight stay? Massachusetts boasts quaint fishing ports and miles of white sand beaches, and in autumn the scarlet-hued cranberry bogs give way to the spectacle of New England’s autumn colour. There’s even the Sleepy Hollow-style shiver of Salem… if you’re brave.

Where to stay 
Boston Waterfront Hotel

Book into the Boston Harbor Hotel for the best views

The Boston Harbor Hotel is special. You can get a ferry straight from the airport to its oh-so-grand front doors, and the views of sailboats in the historic harbour are the best. If you prefer something quirky, the great value Kendall Hotel is situated in an 1890’s Cambridge firehouse, done up in bright colours and folk art.

Where to eat
Boston Oysters

Don’t leave Boston without sampling the seafood

New England food is fresh from the ocean and mammoth-sized lobster, oysters, and a tasty clam chowder are in order for all. The Union Oyster House and Legal Seafood are famed for what comes out those shells.

Getting around

Take The T! The locals love their rapid transport system, otherwise known as MBTA, and the subway, along with connected buses boats and streetcars, make it quick and inexpensive to get around the city and its historic suburbs. You’ll need to purchase a CharliePass (Like a London Oyster Card) before getting on board.

When to go
Boston common

Boston Common is impressive in spring or fall

Spring is perfect for enjoying Boston Common, but there are few sights in the world so spectacular as a New England fall. Take a trip north to the Mt Washington Cog Railway where the leafhoppers get one of the best views of all. That said, a trip to spooky Salem in Halloween season, or a December visit combining the ski slopes of nearby New Hampshire, would delight as well.

Three things we like
View from Harbour

View across the harbour from the Boston Harbor Hotel

  1. Provincetown: This artsy outpost at the end of Cape Cod’s famous ‘hook’ is the unofficial LGBT of the state. Same sex marriage parties spill out of the courthouse and onto the historic, gingerbread home-lined streets, and you can catch all the action from sidewalk-side eateries or from the local steam train.
  2. Starspotting: Forget Boston Legal and the Cheers bar (yes its still here), celeb spotters head to ‘Hollywood East’ – nearby A-list islands of Martha’s Vineyard and Nantucket. Steven Spielberg, Meg Ryan, James Taylor, plus Tommy Hilfiger and Ralph Lauren live among the quaint century homes.
  3. Shopping: Boston is a shopper’s paradise. The city’s large department stores are Filene’s and Marshall’s, outlet branches are situated in outlet malls The Arsenal Project and The Liberty Tree. TJ Maxx is on another level here, where red-stickered Armani jeans can be snaffled at knock-down prices. And search out overstock purveyor The Christmas Tree Store. As well as seasonal decorations, its a hotchpotch of wonderful finds.
Something we don’t like

Driving! Boston has some of the worst traffic jams in the US, especially on the notorious Interstate 93, and parking rules are confusing.

High50 insider tips
  • Fly to Boston on IcelandAir from certain UK airports for an icy stop-off adventure. Pack a swimming costume in your hand luggage to enjoy a brisk dip in The Blue Lagoon on an afternoon’s bus trip for £61, stopover options are included in your flight price!
  • A nine-day Boston City Pass gives discounted entry to four of the city’s cultural hotspots: choose from The Boston Aquarium, the Museum of Fine Arts, the Museum of Science, the Skywalk Observatory, and Harvard Museum of Modern History. Online adult prices start at $49.
  • Wealthy Bostonians escape the city heat with holiday homes on nearby Cape Cod – where a string of sleepy-eyed townships welcome flip-flop wearing visitors to mile upon mile of unspoilt beaches. Don’t set out for the beach on Friday at 5.30pm!
  • Best not call the city ‘Beantown’. Locals don’t like it.
Don’t miss 

A tour of Fenway Park, ($17 adults, $14 seniors) historic home of the Boston Redsox baseball team. And if you’re organised enough to book ahead between April and October, smell the sizzle of ‘Fenway Franks’ hotdogs as you take in a game. Too late to book? Try Bleacher Bar, situated under the stands

Travelling with family?

Take the tinies to Boston’s public gardens where Mrs Mallard and her eight bronze ducklings are off for a waddle through the park.  Older kids will enjoy a a bike ride along the Esplanade, while a top tip for teens is Codzilla – Boston Harbour’s party tour boat. ($29 Adults, $27.50 seniors)

Autumn visitors should head for Davis Mega Maze, a three-mile walk-in puzzle of tall corn in nearby Sterling, Massachusetts, where you kids can also pick apples and have farm themed fun.

Need to know
  • Logan International Airport is located in the east of the city and is an easy ride by cab or public transport.
  • Boston is five hours behind GMT.
  • The weather in Boston is a ‘four seasons in a day’ city, with hot sticky summers and occasional snowed-in winters, and spectacular storms thrown in.
  • You should feel safe, but usual big city rules apply.
  • You’ll need a US adaptor and plugs with two flat pins.
  • Around 15% on your taxi fare or restaurant bill is fine.