A luxury 48 hours in Boston

Words by Laura Itzkowitz

19 October 2023


Plan the perfect autumn weekend in New England’s charming largest city.

Known for its plethora of universities, colonial charm, and a bit of a rebellious streak, Boston is the largest city in New England and one of the most historic in the US. In the Autumn, when an estimated 250,000 students return from summer vacation, the cultural calendar brims with events, and the colourful Autumn foliage peaks, the city is at its best. We’ve curated the below itinerary to guide you through some of the city’s highlights during a brief stay.


Where to stay

When The Newbury, a member of the Leading Hotels of the World, opened in 2021 right on the corner of posh Newbury and Arlington Streets, it became an instant classic. The design is modern yet timeless, the staff are friendly and attentive, and there’s a cosy library lounge where hotel guests can help themselves to coffee and tea.

The plush Street Bar on the ground floor serves classics like a club sandwich and burger, but it’s the rooftop restaurant Contessa that has Bostonians clamouring for a table. When you book a room, request one with a view of the Public Gardens and ask the concierge to reserve a table at Contessa at the same time.

Enjoy a cosy stay at The Newbury hotel

Sightseeing and a snack

With The Newbury as your perch, Boston’s most charming neighbourhoods are within easy reach. On a nice day, it’s pleasant to stroll through the Public Garden, America’s oldest botanical garden. Stop to admire the Swan Boats gliding along the lagoon and the bronze duckling sculptures inspired by the 1941 children’s book Make Way for Ducklings.

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Explore Boston's Public Garden, America’s oldest botanical garden

When you reach the end of the park on Charles Street, head north, and you’ll be in Beacon Hill, the picturesque neighbourhood home to the gold-domed State House and lined with beautiful red brick townhouses. The stretch of Charles Street that runs from the northern end of the Public Garden up to Cambridge Street is full of boutiques selling everything from antiques and vintage clothes to stationery and gifts. If you feel like having a snack, pop into Tatte Bakery & Café, which makes delicious pastries and savoury sandwiches.

Dinner at Contessa

Return to the hotel for dinner at Contessa. Bostonians don’t usually take kindly to New Yorkers who open restaurants in their city, but they’ve embraced this Italian-inspired stunner by the Major Food Group, which is behind New York hotspots like Torrisi and Carbone. The glamorous design by award-winning interiors master Ken Fulk is the perfect backdrop for dishes like the standout squash carpaccio and crowd-pleasing fusilli Genovese.

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Dine at Contessa, The Newbury's rooftop restaurant


A Gilded Age collector’s Venetian palazzo

If it’s your first time in Boston, you may want to visit the formidable Museum of Fine Arts, but our favourite cultural attraction is the Isabella Stewart Gardner Museum nearby. During the Gilded Age at the turn of the 20th century, European masterpieces were all the rage among America’s wealthiest industrialists. Still, it was rare for a woman to actively pursue art collecting. Isabella Stewart Gardner was an heiress whose marriage to Jack Gardner, a Boston Brahmin, cemented her place in Boston’s high society and ensured that she had the capital needed to acquire priceless works of art.

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Be inspired by history at the Isabella Stewart Gardner Museum

The couple travelled extensively and especially loved Italy – so much so that they decided to build a Venetian-style palazzo on the Fens and fill it with the Renaissance masterpieces and antiques that Isabella collected and arranged. A modern wing designed by Renzo Piano hosts rotating exhibitions, but the palazzo will always be the star of the show.

Lobster rolls and a spectacular library

For lunch, head to the Back Bay for superlative seafood at the Banks Fish House by the team behind the venerated Harvest Restaurant in Cambridge. The menu borrows from many coastal cuisines, with dishes like crispy fish tacos and shrimp po’boys, but when in Boston we recommend sticking to the classics: clam chowder – made here with Berkshire pork belly – and a lobster roll.

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Taste the clam chowder at The Banks Fish House

Afterwards, head around the corner to visit the Boston Public Library, a masterpiece of Renaissance revival architecture by McKim, Mead & White, the firm behind many of the most beautiful Beaux-Arts buildings in New York and other cities on the East Coast. Inside, you can admire John Singer Sargent’s mural series Triumph of Religion as well as other artistic treasures. (Singer Sargent was a friend of Isabella Stewart Gardner and also painted her portrait.) The library offers free art and architecture tours every day except Wednesdays and Sundays.

Think you’ve seen it all? Think again. Our global network of dedicated travel specialists plans one-of-a-kind, tailor-made travel experiences to make every trip your best yet. Find out more about Quintessentially Travel here.

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