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City Breaks

The Best Of Boston In The Fall

A visit to this historic American city is always worthwhile, but visiting Boston in the fall is a particularly phenomenal idea.

The brisk air and colourful foliage sets the perfect backdrop for layering your favourite fall outfits, and snapping gorgeous photos for your social media feed. And, as if that wasn’t enough, there are more than 40 universities in the Boston area who are back in session, bringing new life to an already vibrant city.

Whether you’re a history buff, a seafood aficionado, or a culture vulture with a yearning for impressive art and entertainment, this city by the sea is the place to be this autumn. Here’s how to see it in style.


The Four Seasons, One Dalton

There’s a unique low-key decadence felt throughout The Four Seasons in Boston, with a laidback luxury vibe exuded by each and every staff member – from the valet to the GM. But don’t be fooled, there’s also extravagance a plenty: from the multi million-dollar art collection chosen by David Bowie’s private curator to the delicious afternoon tea, and the bedrooms with oversized tubs and floor-to-ceiling windows offering incomparable views of Boston landmarks. On the seventh floor, enter into a zen state of mind – the entire floor is dedicated to wellness and includes a small but impressive spa, and a bright and airy lap pool – also with floor-to-ceiling windows giving you an ideal, autumnal bird’s-eye view of the sea of orange, yellow and brown trees below. Be sure to book a meal at contemporary Japanese hot spot, Zuma, and feast on divine craft cocktails, 70 varieties of sake (including one developed specifically for the restaurant), and robata meats, seafood and veggies, or nosh on their world-famous sashimi and maki.


Mandarin Oriental Botson

This stunning luxury property is set in the heart of the Back Bay neighbourhood of Boston, just steps away from the Boston Marathon finish line. The award-winning holistic spa is the city’s best, inspired by Eastern healing methodologies. The Himalayan Salt Stone Massage is a favourite, featuring warm, hand-carved salt stones from the Himalayan Mountains, and designed to balance the central nervous system and nourish depleted cells. The hotel’s recent multi-million-dollar makeover saw the addition of Ramsay’s Kitchen, an all-new dining concept by multi-Michelin-starred Chef Gordon Ramsay. Nearby you’ll find shopping Mecca Newbury Street, or browse the small boutique in the hotel lobby for fall-inspired accessories including scarves, kaftans and handbags from designers such as Dee Ocleppo, Mae New York and Rani Arabella. The lobby is also an ideal space for end-of-day downtime, complete with a fire place, cosy vibes and dimly lit corners — perfect for sipping complimentary hot cocoa or warming up with a flute of bubbles.


O Ya

The omakase menu at O Ya in Boston has been wowing guests since 2007. Everything here looks, feels and most importantly, tastes like a culinary work of art. As one of the city’s priciest restaurants, be prepared to pay for the experience – but unlike other posh restaurants that have come and gone over the years, O Ya is worth every penny.


Krasi Meze and Wine Bar

With a delicious lineup of Greek-style cured meats, dips blended table-side, and shareable mezze bites straight from a Greek-style rotisserie, Krasi’s traditional fare takes you to the Greek islands. The aesthetic here is modern, but the vibe is warm and intended to make you feel like you’re dining in a friend’s home, offering an especially cosy feel during the autumn months. The entirely Greek wine list is delicious, and all selections are natural and biodynamic.


Neptune Oyster

This tiny spot in Boston’s famous Italian neighbourhood always has lines around the corner – but the wait is definitely worth it. Once inside, slurp down local oysters, get up close and personal with a New England classic Maine lobster roll, or enjoy a spicy seafood stew with saffron rice.


Charles Street

Historic and charming Charles Street is the perfect setting for an afternoon stroll and a bit of shopping. Situated in Boston’s posh Beacon Hill neighbourhood, the area is filled with the tree-lined cobblestone streets and brownstone buildings that this city is famous for. This is also the place for an autumn-inspired photo session – wear your finest fall looks to visit, or pop into one of the many indie boutiques that pack the area for some seasonal shopping. Stand-out boutiques include December Thieves (this October marks 10 years of the store), plus the uber-chic women’s clothing boutique French + Italian. Refuel on homemade, savoury and sweet baked treats at Tatte Bakery & Cafe or pop into Peregrine in the chic Whitney Hotel for a glass of wine and a Mediterranean snack. 


The Boston Seaport

Heavily developed over the past two decades, this bustling neighbourhood doesn’t offer Boston’s historic charm but does offer contemporary architecture, delicious dining spots, watering holes galore, and plenty of entertainment. Get a dose of culture at The Institute of Contemporary Art Boston, situated along the water’s edge. Peruse contemporary works in their various exhibitions or simply contemplate life whilst staring out to the sea from their architecturally-iconic wooden steps, found along the backside of the museum. It’s a great spot for catching the vibrant, ombre fall sunset at around 7PM.


The Isabella Stewart Gardener Museum

This Venetian-Style palazzo once played host to some of America’s most famous writers, artists and glitterati. Its founder, Ms. Gardner, was a world-travelling, eccentric art lover who loved to entertain. View thousands of Gardner’s personal collection of art, collectibles, furniture, ceramics, and more, while taking in the whimsical setting that transports you back to her glamorous life. Gawk at stunning works by the likes of Botticelli, Raphael, Titian, and John Singer Sargent. Designed by Renzo Piano, the newer (by about a decade or so) wing plays host to events and exhibits by contemporary artists and musicians.


The Freedom Trail

Hear the story of the American Revolution via a walking tour for the ages. At only about two-and-a-half-miles, the tour takes you through famed roads, churches, museums and neighbourhoods, including Park Street Church, King’s Chapel and Massachusetts State House (pictured). Take a self-guided version, or book a professional dressed in 18th-century garb. Pro tip: sneak off tour whilst in the Italian North End and indulge in a cannoli from Mike’s Pastry.


Boston Common and Public Garden

Contessa at The Newbury Boston

Contessa at The Newbury Boston

These iconic, adjacent parks date back to the 1600s – in fact Boston Common is the oldest public park in the United States, dating back to 1634. The two beautiful green spaces act as a city oasis, and as a playground for residents and tourists alike. If you’re lucky to be in town when the leaves are turning and falling, this is a dynamite spot for fall photo opportunities. Stroll through and enjoy the gardens, flowers, sculptures and fountains before taking a breather in the form of an aperitivo at Contessa, atop the The Newbury, one of the city’s chicest hotels. 


The Emerald Necklace

For more leaf peeping, dreamy sunsets and outdoor fun, check out this chain of parks designed by famed landscape architect, Frederick Law Olmsted, over one hundred years ago. In the heart of Boston and extending into the area’s suburbs, the park system serves as the backyard for city residents and a beautiful destination for more than a million visitors each year.

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