Plan a Romantic Weekend Getaway in Boston

Oct 30, 2019

Boston is the perfect destination for a romantic getaway: stroll down the cobbled streets of the North End, sip on mulled cider while you explore Beacon Hill, and dance the night away to live music. No matter the season, there’s always lots to do in the city, so we’ve put together a few of our favorite activities to help you plan out your own dream weekend in the city with a loved one.

Plan to stay a night or two, and plan to travel with C&J Bus Lines! We make getting in and out of Boston a breeze. Relax, use our free Wi-Fi, cuddle up on our reclining seats, and let us navigate traffic. In just over an hour, we’ll drop you off safe and sound at our terminal in South Station. When you ride with C&J, you can spend more time enjoying your romantic getaway, and less time stressing over travel logistics and high-priced parking rates.

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Wander Through Beacon Hill

Easily the most picturesque neighborhood of Boston, Beacon Hill rests atop the hill behind the Massachusetts State House and reaches out toward the Charles River. Its historic, leafy streets are lined with stunning brownstones and townhouses and small boutiques, restaurants, and cafes are tucked away between the meticulously maintained homes.

When you get off your C&J bus at South Station, Beacon Hill is a perfect first stop. It’s a quick walk from the terminal and an even faster ride on the T. You’ve probably worked up an appetite from traveling so drop into Tatte Bakery and Cafe for an exceptional latte and a buttery, flaky apple croissant. Get your order to go so you can stretch your legs. If history is your thing, you’re in the right place—the George Middleton House, Nichols House Museum, Lewis and Harriet Hayden House, and the John Coburn House are all nestled in the center of Beacon Hill. You can easily spend an entire morning wandering through the picture-perfect neighborhood.

Cozy Up to Some Good Reads

If the weather isn’t cooperating to explore Beacon Hill, hop on the Red Line at South Station and ride into Harvard Square. There are plenty of cute shops to draw you in, but we recommend heading down Mass Ave. to the Harvard Book Store. It boasts an impressive collection of new and used books, hard-to-find titles, and best sellers. We love the shop’s narrow aisles and quiet reading nooks which welcome visitors.

Raven Used Books, about two blocks away, also offers an incredible selection of gently loved books. Here you’ll find a great number of philosophy, social theory, architecture, and history books, so it’s perfect for anyone who’s looking for something more educational rather than a beach read. When you’ve done enough reading, walk over to L.A. Burdick for dessert! They make by far the most delicious hot chocolate you’ll ever try, which is perfect for a cold day. Sit in the cafe for a while, people watch, and enjoy the good company!

Share a Candlelit Meal

One thing you’ll notice about Boston right away is the overwhelming number of restaurants. It seems like every block is filled with about five different eating establishments, all elbowing for your attention. For date night, however, you’ll want to pick somewhere special. For a “traditional” romantic dinner, Mooo is your best bet. You’ll love the mood lighting, cozy atmosphere, and crisp table linens. Mooo is known for serving up some of the best steaks in Boston, so bring your appetite!

If you and your loved one are more adventurous, we recommend Whaling in Oklahoma. Their menu ranges from the familiar (fresh-caught seafood) to unique (spicy rice cakes with duck). Sit outside on the terrace and share your meal as the sun sets!

See a Show in the City

Make the most of your weekend in Boston and go see live music played by some of the city’s most talented musicians. Visit Wally’s Cafe Jazz Club for an authentic jazz club experience—it’s among the oldest jazz clubs in the United States and has live music every single day. It’s a small venue and you may not be able to grab a seat, which is totally fine! You’ll probably want to get up and dance anyhow. If you’d rather sit back, listen to music, and relax, The Beehive right down the street is a great stop. There’s live performances nearly every night and the drinks are excellent.

Passim in Cambridge is an unmissable venue for anyone who loves music. Bob Dylan, Tom Rush, Joni Mitchell, Muddy Waters, and Jimmy Buffet have all performed at Passim over the years. Wind down the evening here to one of the many talented folk artists who play on this world-renowned stage.

Are you ready to start planning your own romantic getaway to Boston? Check out our bus schedules, buy tickets, and see what else is going on in the city! There’s always plenty to do, so you and your loved one can find the perfect activities in our favorite New England destination.

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