15 Romantic Things to Do in Boston (+ Where to Stay and Eat!)

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Boston. A city of history, culture, food, and yes, romance. It’s not surprising that there are countless romantic things to do in Boston.

One of the most iconic New England destinations, Boston, Massachusetts is known even outside the US, drawing visitors from across the globe. Each year, millions of people travel to Boston to experience its world-class museums, amazing historical sites, and thrilling sports scene. It’s not just a great starting point for a New England road trip; it’s a prime destination in its own right.

Among those visitors are couples looking for the sweeter side of the city: those seeking activities for two. Boston is indeed a fantastic destination for couples travel, especially for those seeking luxury combined with a variety of urban adventures.

In early April, we spent our first wedding anniversary celebrating with a weekend in Boston. Having just moved to New England, we felt there could be no better city in which to toast to our first year as newlyweds.

Combing our own itinerary along with research (plus expert advice from some friends who are Boston residents), we have compiled a solid guide for a romantic weekend in Boston. From what to do and see, to where to eat and where to stay, this guide will help you plan an amazing Boston getaway with your significant other.

A Romantic Getaway in Boston – an Overview

A weekend in Boston barely scratches the surface of this city’s gems. But you can pack a lot into a few days (or even just one day in Boston)… especially if you’re traveling around the US by plane. In this case, just fly right into Boston Logan Airport (BOS).

Spending a longer time in Boston? Consider embarking on one of these great Boston day trips: you can see places like Salem, Rockport, and Portsmouth, NH in just a few short hours.

But back to the main attraction: the very best things to do in Boston for couples, including where to have a romantic dinner, where to enjoy luxurious spa treatments, and where to lay your head after a long day of exploring. 

However, we should note that these Boston things to do aren’t limited only to couples.

If you’re exploring solo, you will likely have fun at the vast majority of these sites. But we think couples visiting the city are especially likely to enjoy these suggestions.

Here are some of the highlights, what we consider to be the best couple things to do in Boston.

Romantic Things to Do in Boston

Start your trip off on the right foot with our list of Boston couples’ activities. Some are great year-round, while others are specific to the season. PS: Save money with a Boston CityPASS that includes admission to the top 4 attractions in Boston.

Walk in the Public Garden & Boston Common

There’s something about simply walking together that is super romantic. This may be because it’s such a laidback activity that gives you uninterrupted one-on-one time. And discovering a new city hand in hand is extra special.

In Boston, one of the finest places to go for a stroll is the Public Garden. This is located in the heart of Boston right next to the Boston Common. In fact, the two are so close they feel like one massive park. Walking here is really enjoyable, especially on a beautiful sunny day. We found it to be one of the most romantic places in Boston!

During the late spring and summer, you can ride in one of the famous Swan Boats, which have operated since 1877. These are pedaled by a “driver” around the lake, ferrying passengers on a fun little ride. The boats are made for several passengers, so they are not as romantic as a tiny swan for two might be, but still, you can enjoy the experience together.

Looking for romantic things to do in Boston in the winter? This season offers its own magic. The Boston Common Frog Pond freezes over every winter season and hosts a cozy ice skating rink. See more ideas for Boston winter dates below!

Grab your partner and glide around the ice with city lights twinkling in the distance. Tres Romantique!

PS: Only have 48 hours in Boston? Check out this guide for some ideas!

Sip Wine

Wine is an essential part of a romantic trip to Boston–or any romantic trip for that matter! To include wine on your itinerary, you can go beyond just sharing a bottle at dinner.

Boston has a variety of wine tours you can take, and they are generally centered in one specific area of the city. It’s a blend of food culture, wine, and history on these unique tours, and you’ll get a fresh perspective on this exciting metropolis.

Ideal for two would be this Little Italy Wine Tour, which takes you on a walking wine tour of own of the city’s most special spots in the North End.

Or consider this Back Bay wine tour, which lasts 2 hours and takes you sip wine at to some of this upscale area’s most sought-after restaurants.

Sail on a Brunch Cruise

One of the most exciting parts of New England is its coastline. You’ll definitely want to include seeing it on your list of romantic things to do in Massachusetts. Hop on theBoston Odyssey Brunch Cruise for an awesome way to experience Boston from the water while also indulging in a scrumptious brunch. 

As this is a unique attraction, it’s great for a special occasion, like celebrating an anniversary in Boston!

If brunch isn’t your thing, there are soooo many other cruises in and around Boston Harbor to choose from. Whichever one you select is sure to give you a memorable New England nautical adventure.

Attend the Symphony

The Boston Symphony Orchestra is a cultural staple of the city, and what could make you feel more cultured and refined than attending one of its concerts? Dress up in your best, grab a cocktail at one of the city’s many terrific bars, and then settle in for a riveting performance and romantic evening in Boston.

Relax With a Couples Spa Treatment

As you look for romantic things to do in Boston, your itinerary demands a bit of luxury. If you’re aiming to “treat yo’self”  you should book a couples spa session to put you both in a blissed-out state of mind.

The G2O Spa and Salon is the place to go for the best couples massage Boston has to offer. This spa offers many options for massage, facials, and other body treatments. After your side-by-side couples massage, you can retreat to the penthouse roof terrace that looks out on posh Newbury Street–one of the most romantic spots in Boston!

Visit Boston’s Aquarium

What could be nicer than a walk among seals, turtles, and all of the wonders of the sea? Of all the fun things to do in Boston for couples, this one must include the most cuteness!

The New England Aquarium houses a huge variety of sea life, from the beautiful intricacy of the leafy seadragon to the adorability of the little blue penguins (the smallest penguin species in the world). You and your significant other can even pet rays and small sharks in the Touch Tank.

The museum centers around the Giant Ocean tank, a multistory exhibit featuring a Caribbean menagerie of sea creatures. These include Myrtle, a green sea turtle who has lived in the aquarium since 1970! Bond with your loved one over the beauty of nature. SKIP THE LINE by buying your tickets now through Viator!

If you’re planning on visiting the aquarium as well as other attractions, you may also want to consider buying either the Boston CityPASS or the Go Boston Pass to save tons of money on attractions. These are definitely a great money-saver. Not sure which one to buy? Read our article for help deciding which Boston attractions pass is best for you.

Explore Boston’s Museums

Some folks’ ideas of romantic getaways in Boston might not include museums, but we Two Drifters really enjoy them. Wandering around museums is a low-key way to discover something new together and spend some time appreciating art, history, or culture.

Think that most museums are dry and boring? The Boston Science Museum will change your mind. You’ll encounter exhibits and presentations on things such as dinosaurs, the magic of physics, optical illusions, and the natural world, along with trippy planetarium shows.

This place is endless fun–you could spend hours here and still have much more to discover. Strolling through the butterfly garden definitely provides a romantic touch, but for something more “electrifying” hop into the live lightning display.

For art lovers, the Museum of Fine Arts will suit. This institution opened in the 1870s and has grown into one of the world’s largest and most exhaustive collections of art. The museum currently houses more than 500,000 pieces.

With your partner, you can explore the vast collections, which range from Japanese art to landscape photography to centuries-old textiles.

Other Boston museums to check out:

The Isabella Stewart Gardner Museum (This was the scene of one of the world’s biggest art heists, featured on the podcast Last Seen.)

The Boston Athenaeum 

The Sports Museum

The Gibson House Museum

The John F. Kennedy Presidential Library and Museum

The Institute of Contemporary Art, Boston

The Boston Tea Party Ships & Museum

Get Your Sam On

Adams, that is. Sam Adams is the iconic Boston beer. Tour the place where it’s made–the Sam Adams Brewery in Boston–and sample some of what’s on tap. The brewery tours are free (though a small donation is suggested), so you can save a bit of cash. (Though if we’re honest, you’ll probably end up taking home a growler of one of their tasty innovative brews.)

It might not be one of the most traditionally romantic things to do in Boston, but for couples like us, it’s a must! Our friends at Our Escape Clause suggest visiting the brewery in their list of more great things to do in Boston.

Breathe the Sea Air Along the HarborWalk

The Boston HarborWalk stretches some 15 miles along the outer edge of the city. If you want to have a coastal experience, walk any length of the trail. During your weekend getaway in Boston, you may not have to search very hard to find the HarborWalk.

Many major attractions are located along it, including the New England Aquarium, U.S.S. Constitution Museum, and several different hotels. We found the HarborWalk very peaceful and even secluded, which allowed for a happy, intimate conversation as we walked.

Follow the Freedom Trail

History buffs–and especially first-time visitors to Boston–should not miss the Freedom Trail. It’s an essential Boston activity. If you follow the brick line running along the sidewalk, you will find yourself in the midst of the trail.

It stretches 2.5 miles and passes 16 historic sites. If you’re curious about Boston’s Revolutionary history, this trail will be your guide. Guided walking tours are offered as well.

Snap Some Instagrams on Beacon Hill

All kidding aside, Beacon Hill is one of the most photogenic neighborhoods in all of Boston. Set alongside the northern part of the Boston Common, this quaint area is home to shops, cafes, and a bevy of amazing, multi-million dollar residences.

With cobbled streets and brick sidewalks on its many lanes, the area is simply an Instagrammer’s dream! Have a wander in this neighborhood and perhaps stop into Tatte Bakery & Cafe for some coffee and pastries.

Watch a Killer Sunset from the Skywalk Observatory

We love catching a sunset together. During our visit to Boston, we watched the sun go down as we walked along the waterfront before dinner. That was definitely a beautiful spot. But there are some truly iconic places to see the sunset in Boston.

One of the most highly recommended is the Skywalk Observatory, located inside the Prudential Tower. On clear days, the view stretches for nearly 100 miles as you soak in the vista of Boston from 749 feet in the air. It’s a tad pricey at $21 per adult, but nothing beats a sunset from the sky.

Romantic Things to Do in Boston in Winter

As you might suspect, Boston can get mighty cold in the winter months. Does that mean you shouldn’t come here for a getaway? Nope! In fact, it can be a truly romantic and beautiful time of year, particularly around Christmas. In addition to indoor activities above that would suit the winter season (such as getting a couple’s massage or touring the museums) there’s plenty more to do in this big city. 

Some of the most popular winter activities in Boston that are perfect for couples include:

Ice skating on the Boston Common Frog Pond

Ice skating is one of the sweetest winter date ideas we know. And what more lovely and wintry setting could there be than the Frog Pond right in the middle of Boston Common? As of December 2019, adult skate rentals are $12.00 per person.

Discover Boston’s Literary Sites

Boston is a hub of literature and thought. On a cold winter’s day, why not spend time at some of the famous bookshops, the stunning Boston Public Library, or one of these other top literary sites in Boston.

Grab Afternoon Tea

You know what goes with a good book? A good cup of tea. In Boston, you can enjoy a lovely afternoon tea in many spots throughout the city. Consider the Mandarin Oriental for a particularly luxurious afternoon!

Where to Dine: The Most Romantic Boston Restaurants

Romantic restaurants are a MUST. After your days spent adventuring around Boston, you’ll want to settle in for a romantic dinner for two. While Boston has hundreds of great spots to choose from, here are a few that come highly recommended as Boston’s 

Lolita Cocina & Tequila Bar

We found Lolita on a list of Boston’s “sexiest restaurants” and we knew we had to try it. Boy, does it deliver on that promise! The place pulses with sensuality from the minute you walk in.

A complimentary granita, wreathed in tendrils of dry ice, is offered to you by a gorgeous staff member (seriously, everyone working there was hot!) dressed in clothing that perfectly matched the vibe.

Everything is red, black, lacy, and gothic. Think punk rock meets the Day of the Dead. Following your tequila splashed granita, it’s onto kickass margaritas and small plates of utterly delectable Mexican food.

We devoured everything we ordered (carne asada, fish taquitos, chicken quesadillas) and would absolutely love to go back.

Top of the Hub

This restaurant’s website actually says, “Boston’s most romantic dining experience.” Can’t say no to that! Although we didn’t get to the Top of the Hub on our anniversary trip, a future visit is planned. This sounds like a fabulous place for dinner or even just for cocktails.

This award-winning restaurant is found in the Prudential Tower in Back Bay, only a few floors below the Skywalk. Why not combine a great view with an outstanding meal? Top of the Hub will meet your needs, it seems, with some of the finest dinner-time views one could ask for.

Coming just for drinks? A $25 pp minimum applies during certain hours.

OAK Long Bar + Kitchen 

During our romantic trip to Boston, we stayed at the Fairmont Copley Plaza, which is incidentally home to a terrific restaurant, the OAK Long Bar + Kitchen. We dined here on the evening of our anniversary.

The vibe in here is great, a cross between an old-fashioned men’s smoking room and a trendy, upscale urban eatery. That is probably owed to the blend of classic leather bar stools and unique, expertly crafted cocktails.

This is a lovely place to cozy up together and have drinks and dinner. A candlelit atmosphere levels up the romance, and if you can get a seat by a fireplace, even better.

For our meals, Nathan ordered the half chicken with vegetables, while I opted for swordfish. Both entrees were excellent, but we have to rave most of all about our appetizer. We ordered the hearth-baked bread, a rustic loaf served with honey butter. Oh my goodness. This is one of those things you could eat forever and never tire of.

Almost Anywhere in the North End

While we can’t speak from experience here, we’re told that some of the most romantic restaurants in Boston are those found in the North End. The small, family-owned Italian eateries dotting the area seem to combine true intimacy with unbeatable Italian flavors.

On our next trip to Boston, we’ll definitely be heading to the North End. We hope to report back with some great options. Potential choices include Giacomo’s (a friend tells us the line is regularly out the door), Carmelina’s, and La Famiglia Giorgio’s.

–> More suggestions on where to eat in Boston from our foodie friends at 2FoodTrippers. <–

Where to Stay: Most Romantic Hotels in Boston

The Fairmont Copley Plaza

While we’ve got plenty of suggestions on romantic places stay in Boston, we personally recommend one place we’ve stayed at and really loved. That’s the Fairmont Copley Plaza. This hotel is a Boston landmark, having served guests since 1912.

The Fairmont Copley is in a fabulous Back Bay location that makes it very convenient to many of Boston’s major sites, including some of those listed above. (Psst: Lolita Tequila Bar is a mere 3 minutes away.) Luxurious Newbury Street is just two blocks away, while the Boston Public Library is right across the street. It’s also close to a T station so you can easily head to more distant points.

The Fairmont is nothing short of elegant. It isn’t over the top, but has a stately, refined vibe while still feeling accessible and friendly. It’s really a nice choice for couples traveling to Boston and seems to attract guests in their 30s and 40s.

We were really excited to stay at the Fairmont Copley Plaza because we stayed at another Fairmont hotel almost exactly a year ago, during our honeymoon in Lake Louise.  Fairmont hotels are not only grand and beautiful, but they really treat every guest like royalty.

The inside of the hotel is opulent and feels a bit palatial–where Versailles meets Boston. The lobby, pictured above, is a feast for the eyes, and from here you can access the restaurant, ballrooms, front desk, and the OAK Long Bar + Restaurant. When we arrived on a Friday, a friendly staff member was handing out beer samples. Nice!

For a truly romantic Boston getaway, you’ll want to opt for the Fairmont Gold level. This area has some of the best rooms and comes with extra touches for great service. You have access to the Gold Lounge with complimentary evening hors d’oeuvres, a breakfast buffet, and more. But in general, the Fairmont offers awesome service at all levels.

What makes the Fairmont Copley Plaza one of the most romantic Boston hotels is not only its classic luxury and fine service but its guest rooms, which are oh-so-comfortable.

Huge beds with soft white linen beckon you to basically spend all day in bed (a romantic getaway staple for many couples!).

Spacious bathrooms and great views combined with 24-hour room service mean you could stay in your guest room forever and still have an utterly romantic weekend. We would definitely suggest the Copley for those looking for places to stay in Boston. Check prices and book here.

The Liberty

The Liberty Hotel is one of the most popular places to stay in Boston and is just such an epically beautiful property…not to mention the great views over the Boston skyline. 

Gorgeous architecture might be the hallmark of this hotel, combined with its terrific on-site dining and fab location.

The Liberty is at the bottom of Beacon Hill, just a short walk to the Museum of Science, Kendall Square, and Faneuil Hall, so it’s great for those planning to visit some of the most fun and most romantic spots in Boston.

What is unique about this hotel is that it used to be an old jail!  The Liberty has not shrunk from it’s “criminal” past, and so elements of the jail-theme are incorporated everywhere, including the aptly named bar “Clink.”

Want to stay at the Liberty? Click here to check prices and book. 

Other Romantic Boston Hotels

Truly, Boston has many wonderful hotels for couples, including some that are uber-luxurious, and might be considered the finest choices for honeymoon hotels in Boston.

Some of the best romantic hotel packages in Boston can be found at places like The Lenox and The XV Beacon. Click each name for more details about each of these lovely luxury hotels. 

Boston Romantic Getaway Essentials

When planning your list of couples things to do in Boston, make sure you’ve got your suitcases fully stocked with everything you might need. Style-wise, you can’t go wrong in Boston with the classic New England preppy look. Think blue and white stripes, casual button downs for men, and, in the winter months, some L.L. Bean Boots. These classic boots have been made by L.L. Bean for more than 100 years, so you can depend on their quality and warmth.

Good winter footwear is essential in Boston from around November through the end of March. Other good options for snow boots include, for men, this pair from London Fog, which Nathan owns, and for women, this pair from Sorel that has excellent ratings. My own trusty snow boots are the Squall design from Land’s End. They’re both functional and really nice looking. Both of our pairs have served us extremely well and are completely waterproof and comfortable. 

Your packing list for Boston will vary depending on when you visit. While summers can be hot in New England, temps can also be quite cool, even on summer evenings. We recommend packing layers. If you’re going out on the water, you’ll definitely want to have a nice hoodie or sweater on hand, as that sea breeze can be chilly. Keep it New England-style with a sweatshirt like this one or this one.

And of course, for the best possible trip, don’t forget to pack these travel essentials we personally recommend: a convenient hanging toiletry bag, a portable power bank to keep your devices fully-charged on the go,  and a set of packing cubes to take your organization to the next level.

*We stayed at the Fairmont Copley Plaza as sponsored guests. All opinions are, as always, our own. 

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