4-Day Weekend in Boston: History, Sailing, and Seaside Eats

The country’s oldest city, Boston is an obvious destination for history buffs who can follow its famed Freedom Trail to learn about some of the most important events to occur to our then-burgeoning nation. The Bay State capital is so much more than just its past, though. It’s a charmingly small (in square miles) yet lively city, with a vibrant nightlife scene, accessible sailing opportunities, and a thriving sports culture. In our Boston travel guide, we'll cover the best places to stay, play, and dine on your next trip.

How to Get to Boston

For those flying into Boston Logan International Airport, your best bet is to grab a taxi or rideshare. The drive from the airport to most areas of the city proper is around 15 to 30 minutes, depending on traffic. Alternatively, there are Silver Line buses that regularly go between the airport and South Station.

How to Get Around Boston

Once in the city, Lyft and Uber are quick and easy ways to get around, or you can pick up a CharlieCard—a reusable card for taking advantage of Boston’s public transportation system, the MBTA. There’s both a metro and a commuter rail, the latter of which can take you out to the city’s different suburban areas. The metro itself has four lines—red, blue, orange, and green—and provides an affordable way for getting around the city during your stay.

Considering its postage stamp-sized land area, a four-day weekend spent in and around Boston is the perfect amount of time to get fully acquainted with the city. It also helps that where Boston lacks in public transit, it makes up for with supreme walkability. We suggest picking one neighborhood to explore each afternoon, and fully immersing yourself in everything it has to offer.

Best Neighborhoods in Boston

• South End: Elegant and charming, this residential neighborhood is revered for its Victorian-style houses. There are plenty of local shops and exciting eateries. South End is also home to the Boston Ballet and several galleries you can pop into at your leisure.

• North End: Peruse the smaller streets of Boston's "Little Italy." You can do a self-guided Freedom Trail tour and hit hotspots like Paul Revere's house. Make sure to drop into a deli for a roast beef sandwich or grab a cannoli to keep energy levels high.

• Seaport: The quickly expanding Seaport District is the perfect meeting place of modern day Boston and its rich history, where you can find the Boston Tea Party Ships and Museum as well as some of the city’s most exciting bars and restaurants, not to mention the Institute of Contemporary Art.

• Back Bay: Brick townhouses, luxury shopping, and top-rated restaurants are the main draw of this neighborhood. It's got a mix of smaller boutiques, larger fashion houses, and art galleries.

• Cambridge: Cambridge is home turf for MIT and Harvard. Mosey around Harvard Square; pop into the four-story Harvard Coop book store and get your caffeine fix at either Peet's or Bluestone Lane before walking through Museum of Fine Arts, Museum of Natural History, and/or Isabella Steward Gardner Museum.

Certain areas of the city, namely Somerville near Harvard’s campus, are also going through somewhat of a cultural renaissance. There, boutique shops, cool new wine bars, and farm-to-table restaurants are turning it into a destination in and of itself.

Where to Stay in Boston

The Whitney Hotel, Beacon Hill

Modern in design, The Whitney Hotel is a charming boutique property that manages to blend right into the townhouse feel of the neighborhood. The structure it's housed in was actually built back in 1909—part of Massachusetts Eye and Ear, a specialty hospital, before eventually becoming a bed and breakfast. Now, the property features a stunning lobby with high ceilings, tall bookcases, and a fireplace. Out back you'll find a hidden garden-like courtyard where you can unwind. Rooms are minimal, clean, and classy, some with prime views of the Charles River. Make sure to grab breakfast at Peregrine, their Italian-inspired restaurant located just off the lobby, before heading out for a day of adventuring. The hotel is located a few minutes’ walk from the river, boutique shopping on Charles Street, and the Public Garden.

The Newbury Hotel, Back Bay

Located in the site of the original Ritz Carlton Hotel, The Newbury Hotel in Back Bay can be found on the bustling (and beautiful) corner of Newbury and Arlington Streets, looking directly onto the Boston Common, America’s oldest public park (and still among its most majestic green spaces). Rooms here are light, bright, and minimal. Try to score a room with a view of the park. During your stay, grab a book to read in the library, stocked by the Boston Public Library, enjoy afternoon tea at the Salon (you can also imbibe something stiffer in the Street Bar), or head up to dinner at Contessa, the buzzy rooftop restaurant. Just be sure to make a reservation in advance.

Where to Eat and Drink

1928 Beacon Hill, Beacon Hill

It’s unsurprising that 1928 Beacon Hill is owned by a former antiques dealer. Despite only being open since 2022, the speakeasy-style restaurant somehow feels like it's been there for decades—thanks to vintage and historic furnishings and a deeply lived in, neighborhood-y feel. The menu is classic New England, featuring comforting dishes such as a stuffed veal chop and pan-seared scallops with pancetta. Attracting celebrities and local regulars, it's the perfect tucked-away date spot. We suggest grabbing dinner here, then staying a while to enjoy some of the Prohibition-era cocktails.

Field & Vine, Somerville

Field & Vine is a charming, community-driven restaurant located in the heart of Somerville, led by husband-and-wife duo Andrew Brady and Sara Markey. Find a hyper-seasonal menu rooted in sustainably sourced ingredients from local farms and purveyors, which allows quality produce to shine. The dishes rotate weekly (a sample menu lists grilled bluefish and a hearty cider-brined pork chop), and are complemented by a curated organic wine list. The warm dining room features a bustling open kitchen, light wood furnishings, and an abundance of grapevines and lush greenery.

Rebel Rebel, Somerville

A “no-rules natural wine bar” located in Bow Market in on-the-rise Somerville, Rebel Rebel’s goal is to provide a no-BS space where people can learn about (and enjoy) natural wine. With two James Beard nods under its belt, the spot has a carefully curated vino list worth snaking your way through, whether you’re sitting on the outdoor patio or sitting at the wraparound bar.

Waverly Kitchen & Bar, Charlestown

Sometimes you want to enjoy the full brunch experience on a Thursday or Friday afternoon (especially when traveling), and Waverly Kitchen & Bar in Charlestown is the place for exactly that. A sweet neighborhood bistro with leather banquettes, hanging greenery, and natural light, it’s the perfect choice for filling up on a steak burrito or buttermilk pancakes before embarking on the Freedom Trail or checking out the Bunker Hill Monument—both of which are just steps away.

Drink Seaport, Seaport

Nestled in what was once a wool warehouse (more of Boston’s musty history!), craft cocktail bar Drink has become a beloved fixture of the Boston Seaport neighborhood since it first opened in 2008. The bar’s warm, industrial atmosphere is always buzzing with young professionals, who flock here for the inventive menu—or lack thereof. In lieu of fixed selections, bar staff ask patrons, “What can I make for you tonight?” Based on your preferences, you’ll be served up contemporary twists on Prohibition-era classics.

What to Do in Boston

Learn How to Sail with Community Boating

Hopping onto a sailboat might not be the first activity that comes to mind for an urban itinerary, but it’s one of the things that makes Boston so great. You can glide along the Charles River with the help of Community Boating Inc. The oldest public sailing organization in the United States, the volunteer-driven nonprofit has spent over 75 years teaching locals and visitors alike about the art of sailing. Those who have never sailed before can sign up for Rigging and Shore School lessons before getting on the water, intermediate sailors can get on-water instruction, and seasoned mariners can rent boats of their own.

Ride the Swan Boats in the Public Garden

A very different way to get out on the water, the charming swan boats of Boston’s Public Garden have been in operation since 1877. Regardless of whether you hop into one, or opt for a stroll, the picturesque setting (America’s first public botanical garden), is a must during any trip to the city—centered on a large pond with grand, gently swaying willow trees dotting its perimeter. The lush swaths of green grass also provide the perfect space for afternoon picnics.

Root for the Home Team at Fenway Park

A trip to Boston isn’t complete without a cold beer and a hot dog at the nation’s most famous ballpark. Despite being built over one hundred years ago, the energy during a game in Fenway Park is still as palpable today as ever. Baseball season tends to fall between April and October, so if you’re planning on being in town during those months, make sure to grab tickets in advance to secure your spot. For off-season visits there are also Fenway Park tours, which are available every day year-round, during which you can book to learn about the history of the park and its most legendary players.

Visit the Isabella Stewart Gardner Museum

A unique backdrop for a cultural excursion, the Isabella Stewart Gardner Museum is set in a Venetian-style palazzo. Inside, find the vast and eclectic art collection of its eponymous founder. Before making your way up and around the building, your first stop will be a stunning courtyard full of exotic flowers and marble statues. Over the course of three floors, there are more than 7,500 art objects, 2,700 books and manuscripts, and over 8,000 historic objects—all arranged by Stewart Gardner herself. Though you could easily spend all afternoon here, the museum is also located just down the street from other attractions including the Museum of Fine Arts and the MassArt Art Museum.

Sip Brews al Fresco at Trillium Garden on the Greenway

One of Boston’s top breweries (that’s saying a lot), Trillium is well known for having some of the best hazy IPAs in the game. Besides their three-story location in the Seaport, they’ve also opened a seasonal beer garden in Downtown Boston that’s open until the beginning of November. The perfect happy hour situation for good weather days, we also suggest coming hungry so you can dig into some delicious tacos by Taqueria El Barrio.

Grab Photos on Acorn Street

A tiny strip with big impact, Beacon Hill’s Acorn Street is technically only 200 feet long. Despite that, it draws tens of thousands of viewers every year who flock to photograph it, because it’s just that good-looking. Federal-style row houses adorned with green ivy and gaslit lanterns flank the cobblestoned street. The street was built two centuries ago in 1823. To snap ideal shots, we suggest visiting on the earlier side in the morning, especially during busy seasons like summer and fall, then devoting the afternoon to soaking up the rest of Beacon Hill and nearby Boston Common.