Boston holidays

Where they're always glad you came

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Prepare to have your red sox knocked off

Dive into one of America’s oldest cities, settled in 1630 and a cornerstone of the War of Independence. Today, shiny skyscrapers rub shoulders with beguiling Beaux Arts beauties, but you can still explore 16 key historic landmarks via the Freedom Trail. The city is famed for its passionate sports fans, and its winning teams, the Patriots, the Red Sox, the Celtics and the Bruins, have provided plenty to celebrate lately. Sumptuous local seafood and craft beers are also sure to raise a cheer.

Enjoy an indulgent brunch among the brownstones of South End before browsing Brattle Book Shop, one of the country’s oldest. Raise a frosty one at Cheers, the pub that inspired the sitcom, or for a more stylised libation sip a snapdragon in Yvonne’s, a dimly lit speakeasy accessed via a hair salon where JFK once regaled Marilyn Monroe.

Among Beacon Hill’s pretty red-brick buildings, pause for a snap of photogenic Acorn Street. Shop in Newbury’s designer stores and funky outposts – Rick Walker’s has a resident pet rooster – and remember that purchases of $175 or less are exempt from state sales tax. Catch a show at the Boston Opera House, and pair the best seafood with sublime harbour views in the Seaport District. Local specialities include fresh steamed lobster, oysters on the half-shell and unctuous, creamy chowder. Book your flights to Boston and see if it lives up to its self-appointed strapline Hub of the Universe.

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Boston holiday FAQs

Make the most of your Boston holiday

Wander the city’s leafy parks, gorge on fresh seafood and discover historic buildings, attractions, galleries and museums.

What are the best things to do in Boston?

1. Call in at the Institute of Contemporary Art, arguably a work of art in itself, with its cantilevered contours framing waterside views. Inside its light-filled spaces you’ll find works by Shepard Fairey, Christian Jankowski, Boris Mikhailov and Josiah McElheny among many others. Every kind of artform is catered for here, from paintings to multi-dimensional mixed-media mash ups.

2. Catch a game and tour the home of the Boston Red Sox, Fenway Park. America’s oldest operating baseball stadium has plenty of quirks to explore. Discover the stories behind the Green Monster, the Pesky Pole, the Red Seat and more on an immersive hour-long tour of this storied sports stadium. Book game tickets months in advance or take your chances queueing for hours for limited game-day tickets.

3. Visit Harvard. America’s oldest university dates from 1636 and is one of the country’s most prestigious seats of learning with alumni including Barak Obama, Mark Zuckerberg and Natalie Portman. Roam its leafy lawns and handsome red-brick buildings and be sure to rub the shoe of John Harvard’s statue for some good luck with your academic endeavours.

4. Check out the Christian Science Plaza. It’s home to the Mary Baker Eddy Library where you can learn about the founder of the Church of Christ, Scientist. Inside this Neoclassical building you’ll find the Mapparium. Crafted in 1935 this huge stained-glass globe shows a cross-section of the world as it was then known, giving a unique perspective on the planet.

5. Swing by the Boston Tea Party Ships & Museum. See the spot where rebellious colonists dumped 342 chests of tea into the water in 1773 to protest about taxes, kickstarting the War of Independence. Replica ships, re-enactments and interactive exhibits combine to tell the story of this momentous event. Take a peek at the museum’s sole artefact, the Robinson Half Chest, and you can even throw your own crate into the harbour in tribute to its historical rabble-rousers.

Which holiday type in Boston is right for me?

There are some fine spa hotels in Boston. Mandarin Oriental Boston enjoys a prestigious address on Boylston Street and is home to the state’s only Forbes Five-Star spa. The spacious rooms feature soaking tubs and designer linens. W Hotel Boston, in trendy Midtown, has panoramic views and a Bliss spa. In Back Bay you’ll find the Westin Copley Place, Boston. This offers the Grettacole salon and day spa, and plush room amenities such as a Heavenly bath and bed.

Looking for a city break? Try the great value hotel. Staypineapple, A Delightful Hotel, South End and borrow a free cruiser bike to explore the area. Alternatively, check into Yotel Boston in the bustling Seaport area with its self-service check-in desks, resident robot and rooftop bar. Finally, consider the Omni Parker House, a historic hotel with one of the best locations in downtown Boston – it’s close to the Freedom Trail’s sights.

Where are the best places to stay in Boston?

Back Bay boasts some of the best shopping in Boston. Discover an array of chic boutiques and trendy eateries in bustling Newbury Street. Browse over 70 big-brand and designer stores at Copley Place Mall and then see the treasures in the Museum of Fine Arts. You can also watch the Boston Red Sox in action at Fenway Park or enjoy a tour of the iconic stadium.

Hanover and Salem streets are the hubs of Boston’s historic North End, and they have a distinct Italian flavour. Grab a Sicilian-style cannoli and a cappuccino. Visit Paul Revere’s house and the pretty Old North Church. Next, browse the trendy clothing and jewellery at stylish boutiques and explore the waterfront area. Beautiful Christopher Columbus Park hosts summer concerts under the stars.

Seaport Boston is where the locals go for a drink. Away from the crowds, the sophisticated new cocktail bars of the regenerated Seaport area come with great views over the harbour. The 21-acre Fan Pier has shopping at haute couture retailer Louis Boston and a modern foodie scene, courtesy of restaurants Strega and Gather. The Institute of Contemporary Art has great exhibits, as well as frequent DJ nights. On a sunny day, head to the Lawn on D – one of the area’s many green spaces. It has swings that light up at night.

Beacon Hill is one of Boston’s oldest neighbourhoods has beautiful colonial-style architecture, brick sidewalks dotted with gas lamps, and historic terraced houses with attractive doors and intricate ironwork. Browse the charming antique shops or stop for a bite on bustling Charles Street. Just below Beacon Hill, Boston Common is one of the city’s loveliest spots, whether for skating in winter or pedalos in summer.

Boston’s Waterfront contains a diverse blend of areas. Stroll along trendy Fort Point Channel, with its artists’ studios, renowned restaurants and iconic Boston Wharf Company warehouses. Journey back to 1773 at the Boston Tea Party Ships & Museum, or tour one of the world’s oldest floating warships, the USS Constitution.

This sandy Atlantic peninsula known as Cape Cod, just over an hour’s drive from Boston, contains 15 uniquely charming towns – some have been voted among the happiest places to live in the country. Chow down on fried oysters in Chatham, swing by historic lighthouses in the National Seashore, discover the arty charms of LGBTQ stronghold Provincetown and catch a double feature at the Wellfleet drive-In cinema.

Encompassing six states, New England is a fertile region packed with scenic villages, captivating history, cultural attractions and outdoor adventures. Large parts of it are easily reached from Boston. Frequent spooky Salem, see fishing life in Fall River and New Bedford, sit by Waldon Pond in Concorde, visit the sand dunes of Martha’s Vineyard and see where it all began at Plymouth Rock. Go leaf peeping in the autumn when the area blazes into its full fall colours.


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Boston fly-drives by season

Discover a land of lobsters and lighthouses, or clapboard house and autumnal forests