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Travel Guide: A Romantic Weekend in Boston

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Newbury Street, Boston
Newbury Street, Boston

Experience a Romantic Weekend in Boston

Boston’s cobblestone sidewalks, historic brownstones, and beautiful public parks provide the ideal backdrop for a cozy get-away for two. The city is filled with atmosphere, ideal for couples looking for a romantic weekend.

The Boston Public Garden and Swan Boats - Romantic Weekend in Boston
The Boston Public Garden and Swan Boats – Romantic Weekend in Boston

Here are three itineraries for a short escape to Boston, in neighborhoods packed with hidden spots for great food and drink. Each itinerary is different, and includes suggestions for beautiful and unique accommodations; perfect places to use as base camp for a memorable weekend in the city.


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Buildings in Boston's Back Bay
Buildings in Boston’s Back Bay

Not far from each of these hotels are streets for strolling as well as stops for coffee or cocktails, in case a drink and quiet conversation is the preferred activity. And, of course, the itineraries include restaurants for enjoying a romantic dinner.

Cocktails for two in Boston
Cocktails for two in Boston

Option 1 – A Stroll through Quintessential Boston: Beacon Hill

Charming Charles Street, at the foot of Beacon Hill
Charming Charles Street, at the foot of Beacon Hill

Historic Beacon Hill, one of the oldest neighborhoods in Boston, is full of meandering streets lined by historic brick row houses. This part of Boston is incredibly charming, with many unique landmarks, galleries, boutiques, cafes, and restaurants to explore.

At the edge of Beacon Hill is the Liberty Hotel, a great spot to use as a home base for the weekend. Believe it or not, this elegant hotel was once the Charles Street Prison, and every corner of the Liberty seems to have a story. You can grab a couple of cozy chairs in the brick-lined lobby and enjoy a cocktail, or if you prefer, you can choose to sit at table literally behind bars (their restaurants are aptly named “Clink” and “Alibi”).

The Liberty Hotel
The Liberty Hotel

However, if shopping is in order, it is a treat to wander across the road to Charles Street. Make a point to explore Charles Street’s antique art galleries, like Eugene Galleries, where you can find an antique engraving of Boston to take home as a souvenir of your trip. Also consider stopping at Helen’s Leather to do some boot shopping, an especially good idea if you happen to be coming into Boston in the winter, as nice boots are a must. And, if  you need to warm up, Tatte is a great option for an espresso and snack (their “nut boxes” are famous). Properly caffeinated, explore the side streets that run up the hill and down toward the Charles River. If you walk the length of Charles Street, you will arrive at the Boston Common and the Boston Public Garden, where you will find the Swan Boats in the summer, or ice skating in the winter.

Boston Public Garden in Winter
Boston Public Garden in Winter

For dinner, take a walk along sidewalks lit by gas lamps and head to the backside of Beacon Hill, to an Italian restaurant called Grotto. You will find it in an unique location; in other words, look down – the restaurant refers to itself as “subterranean”.  An elegant and restful night awaits you at the hotel, but don’t forget to make a stop for breakfast the next day at The Paramount before you leave town.

Option 2 – Explore Your Inner Hipster in Cambridge

A Mural in Kendall Square, Cambridge
A Mural in Kendall Square, Cambridge

Cambridge’s vibrant neighborhoods are just across the river from the city, and if your tastes tend to be more on the eclectic side, Cambridge is the place to visit for the weekend.

The Kendall Hotel, located in the historic Engine 7 Firehouse, is a small, cozy, and even budget-friendly place to stay for the weekend. It is also conveniently located next to the Red Line, the public transit system that runs through Cambridge.

The Kendall Hotel
The Kendall Hotel

If you need a quick snack or beverage before you head out to explore Cambridge, right across the street from the hotel is the hipster “unfastfood” stop, Clover, originally a food truck business that exploded with popularity. Or maybe a microbrew is in order before you start your travels, in which case Meadhall is around the corner, with countless bitter IPAs and sours on tap to make even the most discerning beer connoisseur happy.

The Bar at MeadHall Cambridge
The Bar at Meadhall Cambridge

Central Square is the next stop, and if the weather isn’t right for walking, you can grab the Red Line; it’s a quick trip.

Central Square is a grittier part of Cambridge, one with a diverse art and music history. It is a great place for window shopping, or better yet, rifling through some vintage vinyl at Cheapo Records. Make sure you take in the street art that is all over the square, then stop for a craft cocktail at Green Street, hidden down a side street but only steps away from the busier parts of Central Square.

Street art in Central Square, Cambridge
Street art in Central Square, Cambridge

If music is on the agenda, take a peek to see who is playing at The Middle East Nightclub. If a hip venue for dinner is preferred, you can grab a table at the funky, candle-lit tapas restaurant called Cuchi Cuchi. They also happen to have amazing cocktails.

A Cocktail at Cuchi Cuchi
A Cocktail at Cuchi Cuchi

And, if all of the great drinking options lead to a bit of an aching head the next morning, get some fresh air and walk from the hotel to The Friendly Toast for a loaded breakfast. The food is almost guaranteed to cure a hangover.

Option 3 – Get Fancy in the Back Bay

Newbury Street, Boston
Newbury Street, Boston

The Back Bay is stylish. In particular, Newbury Street is a posh destination, filled with designer clothing boutiques and stores selling luxury home furnishings as well as other unusual provisions for those with discerning tastes.

The Elliot Hotel is around the corner from Newbury Street. It is a small, cozy, yet elegant place to spend the weekend.

The Elliot Hotel
The Elliot Hotel

Of course, you don’t come to this part of Boston without doing some serious shopping, so spend the afternoon exploring the stores along Newbury. Arms full of goodies, you might be looking for rest and refreshment after all of your hard work. Tapeo, a lovely Spanish restaurant, has a cozy bar and they serve fantastic sangria. However, if you prefer wander away from Newbury Street for a while, take a walk by Trinity Church, the Hancock Building and the Boston Public Library for some sightseeing.

In this corner of the Back Bay, consider a stop at Flour Bakery for a croissant and coffee. But don’t get too full because the evening plan is an elegant French dinner. Conveniently located across the street from your hotel is a lovely romantic restaurant called Deuxave, one of the best restaurants in Boston. Enjoy, relax, and reconnect.

Deuxave Restaurant in the Back Bay
Deuxave Restaurant in the Back Bay

Boston is a romantic destination, no matter the time of year. Whether your interests lean towards the historical, trendy, artistic, or elegant – the perfect weekend escape awaits you this beautiful city.

A view of the Boston skyline
A view of the Boston skyline

All Photos/Content by Iris Fischer-McMorrow

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