Weekend Trip to Boston: Best 3-Night Getaway Guide

Whether you’re from New York or Rhode Island and taking the train into town, or you’ve found a cheap flight, Boston is a great city to visit for a weekend trip. Bostonians are rightfully proud of its history, culture, and great food.

With our travel tips, you can put together the perfect Boston itinerary. Here's what to do for three nights in Boston.

• Best for seeing historical sites and grand architecture - Back Bay
• Best for immersing yourself in this historic city - Beacon Hill
• Best for baseball lovers and art aficionados - Fenway

• Best for a romantic night out - North End
• Best for families with young kids - Seaport District
• Best for pairing food and history - Downtown Boston

• Best for art, relaxation, and nature - Cambridge
• Best for nature lovers looking for cheap activities - Brookline
• Best for a boozy tour through history - Boston’s Speakeasies

If you’re only planning a weekend getaway in Boston, these are some of the most popular neighborhoods to visit.

When visitors think of Boston, they think of cobblestone streets, history on every corner, and grand architecture — and they’re often picturing the Back Bay and Beacon Hill. Fair warning: in the busy summer season the sidewalks will be crowded, the tours will be full, and the restaurants require a reservation.

• ‌Perfect for:‌ Seeing historical sites and grand architecture
• ‌Highlights of the‌ ‌Back Bay‌‌:‌
  • Boston Public Library
  • Copley Square and Trinity Church
  • Newberry Street

Back Bay is one of the largest hubs of Boston. Clustered around Copley Square, you’ll find the Boston Public Library and Trinity Church, two important historical sites. At the library, you can take a walking tour and admire its grand architecture and long history (you’re not, sadly, allowed to reenact Beauty and the Beast on the rolling ladders).

If you’re hungry after the tour, stop into one of the great restaurants that line Newberry Street for a bowl of clam chowder or a lobster roll. This long thoroughfare is the place to go to see and be seen in Boston. It has designer stores, outdoor cafes, and great people-watching. For many, it’s the Rodeo Drive of the East Coast.

If you’re taking public transportation, the blue line MBTA (“T” to locals) connects to the green line at Government Center. Once on the green line, you can get off at Arlington or Copley Square and you’ll be in the Back Bay.

This cute, clean Newbury Street Airbnb puts you in the heart of it all. Light and airy, it has one bedroom and a functional kitchen if you want to save money on your day trip and cook.

Bringing Fido? Check out pet-friendly Clarendon Square Bed and Breakfast, conveniently located on the outskirts of the Back Bay and also close to Fenway. Relax in the elegant library or rooftop hot tub. You’ll be staying in an elegant brick rowhouse, the quintessential Boston experience.

• ‌Perfect for:‌ Immersing yourself in this historic city
• ‌Highlights of‌ ‌Beacon Hill‌‌:‌
  • Boston Public Garden and Boston Commons
  • Massachusetts State House
  • Park Street Church

Many of the most popular areas in Boston are within walking distance of each other. Beacon Hill borders both Back Bay and Downtown, so if you’re trying to fit a lot into a day trip you could see highlights from each area.

Beacon Hill encompasses the Boston Public Garden, home of the Make Way for Ducklings Statues, and the Boston Commons. These feature large, green spaces with a children’s playground, outdoor ice skating rink in the winter, and beautiful flowers — but if you visit during the spring and summer, they’ll be packed. My favorite time of year is fall, when the leaves turn the pathways into carpets of red, orange, and gold.

Follow the same directions as those for Back Bay, except get off the green line a little earlier. Exit at Park Street, or just walk over from Government Center.

If you need a lot of room, this Vrbo has four bedrooms in addition to a lovely outdoor space, sweeping staircase, and history in every architectural detail.

The Liberty is the place to stay if you want a hotel with amazing ambiance. Set in a former jail, you take an escalator up to the open "yard," with walkways all around. Dine in the "Clink" with open cell doors, or enjoy the bar in the rotunda.

• ‌Perfect for:‌ Baseball lovers and art aficionados
• ‌Highlights of Fenway:‌
  • Fenway ballpark
  • Isabella Stewart Gardner Museum
  • The Museum of Fine Arts

If you’re coming up from NYC, you might want to skip Fenway. The rivalry between the New York Yankees and the Red Sox is one of the oldest in Major League Baseball. But for other baseball lovers, a trip to Fenway Park could be the highlight of your Boston weekend. This famous ballpark is the oldest in the country (though fans complain the seats are showing their age!).

My son and I took the guided tour of Fenway Park last summer and loved it — it’s a great behind-the-scenes look at both baseball and the Sox’s importance to Bostonians. You can visit the locker rooms and pretend you’re a radio announcer in the booths.

If you’re not a baseball fan, the Fenway area also features the Isabella Stewart Gardner Museum and the Museum of Fine Arts. Take a cab or an Uber over to the museum and the driver will share the story of the famous art heist at the Gardner. Bostonians are almost prouder of getting robbed than they are of its world class art collection.

Blue line from the airport to the Green Line at Government Center (in case you haven’t guessed by now, public transportation is the way to go in Boston. Parking is astronomical and hard to find, and if you’re unfamiliar with local rules you could wake up to find your rental car has been towed). Get on the D line to Riverside and get off at Fenway. Follow the crowds of people if you’re going to a game.

Modern, functional, and close to Fenway’s attractions, this Airbnb condo also gives you access to the building’s amenities (like a pool!). It’s a corner unit, so you’ll have plenty of sunlight, and a kitchen for cooking if you want to save some money.

Prefer to stay in a slice of Boston’s history? This Airbnb, built in 1896, features gorgeous carved woodwork, rich carpets, and the air of old money. It’s also close to the famous Citgo sign and a short walk to Fenway Park.

These cool and unique areas of Boston each cater to a different type of weekend traveler — from a couple in search of romance to a family that wants to tire out their kids, we’ve got you covered. If you have only 3 nights in Boston, be sure to see at least one of these spots.

• ‌Perfect for:‌ A romantic night out
• ‌Highlights of the‌ ‌North End‌‌:‌
  • Fabulous Italian restaurants that line Hanover Street
  • Picturesque cobblestoned streets
  • Rose Kennedy Greenway

With plenty of places that offer dinner lit by candlelight, exposed brick walls, and soft music, the North End is a perfect spot for couples in search of a little romance. Known as “Little Italy” and famous for the Italian restaurants and gelato shops that line Hanover Street, if you’re searching for a European feel you’ll find it in the North End.

Don’t forget to stop in a Mike’s Pastry for an after-dinner cannoli — their blue and white boxes have been a North End tradition since 1946 (but bring cash, as they don’t accept credit cards).

The Rose Fitzgerald Kennedy Greenway, technically at the southern end of the north End and stretching down to the Leather District, was built on top of the Big Dig. What was once a loud, obnoxious highway cutting through the city is now the site of green grass, fountains, and beer and wine gardens. Take a ride on the carousel or hop on a swing built for two. In the summer, there are artisans markets, arts, and cultural events.

Parking in the North End is limited to cars with resident stickers only. Therefore, it’s another area of the city where we advise public transportation.

From Logan Airport, take the blue line to Aquarium (the New England Aquarium isn’t in the North End, but it’s a close walk). Walk up to the North End from there.

This amazing Vrbo puts you right in Little Italy. Enjoy the harbor views from the roof deck or walk to the more than 50 restaurants nearby. It’s also close to the Freedom Trail and TD Garden.

Want a truly unique stay? Rent a houseboat on Boston Harbor. This Airbnb houseboat is a bed-and-breakfast with outdoor seating and views of Boston Harbor and is only steps from the North End.

• ‌Perfect for:‌ Families with young kids
• ‌Highlights of the‌ ‌Seaport‌ ‌District:‌
  • Boston Children’s Museum
  • Boston Tea Party
  • Lawn on D

Huzzah! Shout along with costumed actors and wave your feather in the air as they describe the events that led to the Boston Tea Party. Tour a replica boat and throw fake tea over the side. My son loved the Boston Tea Party Ships & Museum, located on the bridge across Congress Street on your way to the Boston Children’s Museum.

The Boston Children’s Museum, the second oldest children’s museum in the world, is one of the best children’s museums we’ve ever visited. Four floors mix science, art, literacy, and more in interactive displays that will keep your children running and climbing. Travel tip: don’t make my mistake and try to do both the children’s museum and the Boston Tea Party Ships on the same day. It’s too much for younger kids and we had a meltdown.

Lawn on D is an outdoor area best enjoyed during the summer. Play lawn games like cornhole or challenge your kids to a Jenga game, take a swing on the round “O’s” that light up at night, and exhausted parents can grab a beer and food in a concession tent and relax on lawn chairs while kids play. Lawn on D closes for private events, so check that it’s open to the public before walking over.

The Seaport is within walking distance of South Station (on the Red Line). It’s also accessible by a rideshare or water taxi from the airport.

If you're traveling with kids, you'll want space. This three-bedroom apartment fits the bill. It has great water views, can sleep six, and is within walking distance of the Boston Children's Museum.

Sleeping five, this Vrbo host caters to families — there's even a baby swing on the back deck! Your kids will delight in the built-in day bed by the window, and at night the open floor plan means that you can keep on eye on them in the living room while you make dinner.

• ‌Perfect for:‌ Pairing food and history
• ‌Highlights of Downtown:‌
  • Faneuil Hall Marketplace
  • Boston Public Market
  • Old State House

Come for a weekend trip to Boston and you’ll quickly realize, Bostonians have liked to eat and drink since the 1700s. Faneuil Hall Marketplace is a long, open-air building built in 1742 that stretches several city blocks. Sample food from over 80 vendors, sit in the center rotunda and listen to live music, or enjoy street performers in the open square in front of the marketplace.

If you’re still hungry, nearby Boston Public Market features local and artisan vendors — everything sold there is produced or comes from New England. It’s across the street from the New England Holocaust Memorial. Walk through the six illuminated glass towers etched with 6 million numbers in tribute to the many lives lost.

Boston’s history touches many eras and the Old State House, built in 1713, reaches back to our nation’s beginning. The site of several important milestones on America’s path to independence — from the Writs of Assistance to the Boston Massacre — the first reading of the Declaration of Independence in Boston happened on its historic balcony.

Downtown Boston provides the perfect pairing of great food and American history for your weekend trip.

Downtown Boston is on the Green Line. If you get off at Haymarket or Government Center, you’ll be within walking distance of most major attractions.

As one of the most congested areas in Boston, with little housing available for residents, it’s better to look for a boutique hotel in Downtown Boston. Most Airbnb searches actually put you in a neighborhood like Beacon Hill or Back Bay, which are nearby, but not exactly Downtown.

Try this Back Bay Airbnb studio with great closet space, a small kitchen to save money eating out, and access to laundry.

You can really be in Downtown Boston at the Langham Boston, a stunning hotel in the former Boston Federal Reserve. Marvel at the gorgeous ceilings and marble floors or take a dip in the indoor pool. Travel tip: it’s on the pricier side, but you can often find deals on their website.

Boston is such a popular destination for day trippers from around New England — from Maine to New York — that it’s hard to wander off the beaten path. But even popular sites have hidden gems.

• ‌Perfect for:‌ Art, relaxation, and nature
• ‌Highlights of Cambridge:‌
  • Harvard
  • Cambridge Center Roof Garden
  • Charles River

It may seem odd to put Harvard on a list of Hidden Gems, but many visitors focus on the famous educational institution and miss many of the nearby sites. Don’t just wander past Harvard’s buildings or take a walking tour of the campus, visit one of its three museums, each focusing on a different type of art.

You can get discounted admission to the Harvard Museum of Natural History and others with the CityPass.

The Cambridge Center Roof Garden, tucked away in Kendall Square, hosts paint nights, craft activities, free yoga, and dance nights in a green oasis on top of a skyscraper. After a day of sightseeing, you might want a chill break (and did we mention it’s free?).

Kayaking on the Charles River is a unique experience — or you can take a nighttime cruise or walk along the river’s banks and drink in the great views.

Cambridge is easily accessible by the T. Hop on the Red Line and get off at Harvard/MIT or Kendall Square and you’ll be close to most attractions.

Irving House at Harvard is a great family-friendly inn with bright rooms, off-street parking, and breakfast included in your rate.

If you did decide to rent a car, this Airbnb in Cambridge features a rarity in the city: parking. This calming space has touches of old-world charm in the fireplaces and chandeliers. It’s also close to Harvard and MIT.

• ‌Perfect for:‌ Nature lovers looking for cheap activities
• ‌Highlights of Brookline:‌
  • Brookline Reservoir Park
  • Larz Anderson Park
  • Allandale Farm

Brookline, accessible on the green line, is further West of the city’s Downtown. It features numerous green spaces where you can bike, walk, or kayak —and most are free. It's also got some great restaurants and shops, perfect for a well-rounded Boston weekend trip.

The Brookline Reservoir Park has an easy 1-mile jogging/walking track and multiple playgrounds. The Gatehouse, with its arched windows and Greek-style temple front, is a National Historic Landmark. Enjoy the park year-round, in the winter areas are flooded to make an ice rink.

Larz Anderson Park shows off fall foliage in style. Featuring woods, water, and beautiful landscaping, its 64 acres encompass gardens, picnic areas, and an ice skating rink. It’s also a popular sledding spot in the winter.

A farm in the city, Allandale Farm connects Bostonians to the city’s agricultural city. Young kids enjoy events and workshops, such as learning about the farm’s animals, jumping on a hayride, or bird watching.

Public transportation is your best bet for reaching Brookline. Street parking is limited and, yes, I have been ticketed and towed in Brookline. The green line runs out to Brookline and, once there, you can take a ride share to your destination.

Stunning wood-paneled walls give this Brookline loft the feel of a boutique hotel. Located in Coolidge Corner, it’s right off the Green Line.

The Coolidge Corner Guest House is also close to the Green Line. A fun, purple and green-painted Victorian, the bed and breakfast, guests enjoy a hearty breakfast before heading out to explore the city.

• ‌Perfect for:‌ A boozy tour through history
• ‌Highlights of‌ ‌Boston‌‌’s Speakeasies:‌
  • Great craft cocktails
  • History and ambiance
  • A variety of good food

Boston was a hotspot during the Prohibition Era. If you love history, craft cocktails, and want to take a food tour of the city, check out some of its many speakeasies. Restaurateurs have turned historic spaces into some of the city’s hottest drinking spots.

Yvonne’s is a classic. If you can get a reservation in the Gallery, you’ll enter through a hidden door in a bookcase. It’s been open since 1862.

Located beneath the streets of the North End, Stanza dei Sigari is a former speakeasy from the 1920s. The old school cigar bar serves cocktails, liquor, and beer and wine.

If you want to learn how to make your own drinks, take a cocktail class at Brick & Mortar. Voted one of the best bars in Boston, bartenders put on a show shaking craft cocktails to sip at tables tucked against brick walls.

All of these spots are reachable on the Green Line.

You can stay in any central spot in the Back Bay, North End, or Beacon Hill and be close to these bars.

Enjoy a hard-to-find in the city outdoor space with this Airbnb, which features calming blue and cream decor, bright light, and a small kitchen space.

The exposed bright walls, wrought iron, and thick wooden beams of this North End Airbnb are quintessential of the area. It's directly on the Freedom Trail and perfectly located to explore the city.

Now you know what to do in Boston for a weekend. Boston is a city rich in history, culture, and fun. It’s a great weekend destination. With our travel tips, you can plan the perfect day itinerary.