Planning a Family Trip to Boston

Apr 7, 2019

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“Wicked good lobstah!” might be your first thought when planning a trip to Boston and yes, the lobster is good and so is the “chowdah.” But there is much more for a family to see and experience in a city that tells the early story of the Revolutionary War alongside the nation’s first public park, first public school and the first subway system.

How to Get to Boston

The easiest way to get to Boston is to fly into Boston Logan International Airport (BOS). Fortunately, Logan serves most domestic airlines, such as American Airlines, Alaska Airlines, Delta, Frontier, JetBlue, United, Spirit, Southwest and even Hawaiian Airlines. Some of the “sweet spot” redemptions to get to Boston include using your British Airway Avios points for flights on American Airlines, flying Southwest 2-for-1 with the Southwest Companion Pass, having your kids fly free with Frontier and jumping on any JetBlue flash sales.

Once you land, getting into the heart of the city is quite easy. Although the airport is technically located across the water in East Boston, it should only take you 10 to 20 minutes by car, depending on where you are going and the time of day (traffic can be a nightmare at rush hour). Uber and Lyft are readily available most of the time and less expensive than your regular yellow taxi.

AERIALS VIEW of Logan International Airport, Boston, MA
Aerial view of Logan International Airport, Boston, MA.

Or if you prefer, you can take public transportation. From the airport, take either the MBTA (the “T”) Silver Line bus service or the Blue Line subway, depending on where you are going. The Silver Line is your best option if you are heading to Cambridge (including Harvard and MIT) or Downtown Boston (South Station). This free bus will pick you up in front of every terminal and will take you straight to South Station. From there you can transfer (for free) to the Red Line subway, which will take you to Cambridge. Alternatively, if you are heading to Back Bay, Fenway or even the suburbs (such as Brookline or Newton), take the Blue Line subway. To do this, you’ll first need to hop on the Massport shuttle bus that runs from right outside of your terminal to the subway.

Family-Friendly Neighborhoods

Boston is actually a small city, which makes it the perfect destination for kids. It is easy to get around on foot and as long as you stay in Boston proper, you are never too far away from many family-friendly activities.

The area around the Boston Common and Public Garden is the most central location when it comes to staying and exploring with kids. It is also one of my favorite places to let them run around and get their energy out. Here you can ride the famous Swan Boats ($4 for adults, $2.50 for kids 2–15 and free for those under 2) and even feed the ducklings. Just remember to pick up some bread on your way over. Tadpole Playground (free) is perfect for kids of all ages and during the summer months your kids will have a ball in the splash pad. During the winter, there’s an ice-skating rink at Frog Pond. (Admission fees are based on height: 58 inches and taller cost $6 and it’s free if you’re under 58 inches. Skate rentals cost $12 for adults and $6 for kids. Lockers are available for $4.)

Feeding the ducks at the Boston Public Garden. (Photo by Jennifer Yellin /

Once you venture away from this area, you are still close to many attractions. To the north, you can easily walk to Faneuil Hall Marketplace and watch the street performers during the warmer months. From there, you are also close to the New England Aquarium ($10 for adults and $8 for kids 3–11) and the North End, where you’ll find many of the city’s most authentic Italian restaurants, delis and bakeries. To the east you’ll find the Boston Children’s Museum (adults $17, kids 1–17 $17 and free admission for children 12 months and younger) and the Boston Tea Party tours (museum tickets cost about $29 per adult and $17 for kids 5–12). To the west is the Boston Museum of Science (Admission is $28 for adults and $23 for kids 3–11). The Omni IMAX theater and planetarium each cost $10 per adult and $8 for child, if you’re not also attending the museum or $6 as an add-on to museum entrance.

Faneuil Hall Marketplace in Boston, MA. (Photo via Shutterstock)

While some locations might be more ideal home bases than others, as long as long as you stick to staying right in Boston, you can easily get around the city on foot, by using the T or by taking a taxi/Uber/Lyft. Just do not book a hotel in South Boston or East Boston; while technically still in Boston, these properties are in more residential areas and are not great locations for tourists looking to explore the city.

Best Points Hotels in Boston for Families

Sheraton Boston Hotel

The Sheraton Boston Hotel is right in Back Bay, which is one of the more popular areas of the city. Not only does it put you in the middle of the action, the property is also connected to the Prudential Center and the Hynes Convention Center. With this location, you are a stone’s throw away from the shops on Newbury Street and still in walking distance of a baseball game at Fenway Park. This property also features the largest indoor/outdoor pool in Boston — indoor becomes outdoor thanks to a retractable roof during the summer months!

(Photo courtesy of Sheraton Boston)
(Photo courtesy of Sheraton Boston)

This hotel costs 50,000 Marriott Bonvoy points — this means the 100,000 point offers (after spending $5,000 in the first three months) from the Marriott Bonvoy Boundless Credit Card (offer ends May 16), Marriott Bonvoy Brilliant™ American Express® Card and Marriott Bonvoy Business™ American Express® Card (offer ends April 24 for the Amex cards) will get you two free nights. Or you can always use the free-night certificate that you receive annually from the Marriott Bonvoy Brilliant Amex.

Residence Inn Boston Downtown/Seaport

The Residence Inn Boston Downtown/Seaport is the perfect hotel for those looking to stay within Boston but a little bit outside of the hustle and bustle. This property is located in Boston’s waterfront area, which is extremely kid-friendly. Not only are you next door to the Boston Children’s Museum, you are just a few blocks from The Lawn On D. During the summer months, you will find many kid-friendly concerts and activities taking place on the lawn. And, just over the bridge, you can still walk to the Boston Common and Boston Public Garden.

(Photo courtesy of Residence Inn)
(Photo courtesy of Residence Inn)

The real benefit of this property is that all guests receive complimentary breakfast and it only costs 35,000 Marriott points a night. This is significantly less than the other full-service Marriott properties throughout the city and it will also allow you to use a free night certificate from any of the Marriott credit cards (they are capped at 35k points a night). Tip: Do not miss a trip to Flour Bakery, which is right around the corner at 12 Farnsworth St.!

Hyatt Regency Boston

The Hyatt Regency Boston is perfectly situated right in the center of many family-centric activities. The hotel is extremely close to the Boston Common and Boston Public Garden, not too far from Newbury Street and only a short distance from Faneuil Hall. You truly should be able to walk almost everywhere. Aside from the location, the hotel itself is incredibly kid-friendly. From the iPads and life-size games in the lobby to the indoor pool, your kids will be occupied after a long day of exploring Boston.

Playing in the lobby of the Hyatt Regency Boston (Jennifer Yellin /
Playing in the lobby of the Hyatt Regency Boston. (Photo by Jennifer Yellin/

Unfortunately, this hotel recently increased to a Category 5 property in the World of Hyatt award chart, which means it will now require 20,000 points for a free night stay. But based on the quality of the hotel and the location, it could be well worth it. Not to mention, if you have World of Hyatt Globalist status, you’ll receive complimentary breakfast in its restaurant for two adults and two kids, and have the opportunity to be upgraded to a suite if you use one of your Suite Upgrade certificates. Those benefits can be priceless when traveling with kids. The World of Hyatt Credit Card can also earn you up to 60,000 bonus points: 30,000 Bonus Points after spending $3,000 on purchases within the first 3 months from account opening. Plus, up to 30,000 more Bonus Points by earning 2 Bonus Points total per $1 spend on purchases that normally earn 1 Bonus Point, on up to $15,000 in the first six months of account opening. This will give you enough points for two free nights at this property (with points to spare).

DoubleTree by Hilton Hotel Boston – Downtown

The DoubleTree by Hilton Hotel Boston-Downtown is a former high school transformed into a hotel. This historic property is located right in the middle of Boston’s Theater District, just two blocks from the Boston Common and Public Garden. While you can walk to many sites, you also can easily climb aboard the T from the Tufts Medical Center stop. Kids will love the chocolate chip cookies offered during check-in, and parents will be pleased with a Starbucks in the lobby. Guests receive complimentary access to the nearby YMCA that features a fitness center and an Olympic-sized indoor pool.

(Photo courtesy of Hilton)
(Photo courtesy of Hilton)

A standard room at this property will typically cost 60,000 Hilton Honors points. With the current Hilton Honors American Express Ascend Card offer, you’ll earn enough points for a two-night stay at this hotel. Here’s a rundown of other cards that allow you to rack up Hilton points in a hurry.

Kimpton Marlowe Hotel

If you’d prefer to stay in Cambridge, the Kimpton Marlowe Hotel is a great option. Located in an historic area of Cambridge and right on the Charles River, it’s just a half-mile walk over the bridge into Boston. You’ll be positioned perfectly to visit the Museum of Science (a six-minute walk) or jump on one of the Boston Duck Tours (also a six-minute walk; $43 for adults, $29 for kids 3–11 and $10.50 for kids under 3). You are also only a mile from the North End, where you can eat your way through some amazing pastries. The Kimpton is very close to a T stop, which makes visiting nearby Harvard Square incredibly easy.

(Photo courtesy of Kimpton Marlowe Hotel)
(Photo courtesy of Kimpton Marlowe Hotel)

If you’re not yet familiar with the Kimpton brand, it’s extremely kid-friendly. The Hotel Marlowe has hot chocolate for the kids in the evening (and wine for the adults), welcome bags with toys, Boston-themed books and even babysitting services. To top it off, all guests can use complimentary bikes and kayaks.

Image courtesy of APCortizasJr / Getty Images
(Photo by A.P. Cortizas Jr./Getty Images)

This property requires you to redeem 55,000 IHG Rewards Club points per night, but you might find extremely reasonable cash rates during off-peak times. The current up to 120,000 point offer from the IHG Rewards Premier Credit Card after spending $5,000 total in the first six months, will allow you to stay two nights at this property. Or, if you have a free-night certificate issued before May 2019 from the old IHG Select Rewards Credit Card (no longer available for new applicants), this is a great opportunity to redeem for a free night.

Planning Tips

Best Time of Year to Visit Boston

While Boston has a lot to offer 12 months a year, some times are better than others for a visit. First, Boston can get its share of snow and cold weather during winter. On those freezing cold days, being outside for any length of time can be tough and put a damper on your visit. Some activities, such as the Duck Boat Tours, are seasonal and do not run in the winter. I love the spring and fall in Boston with perfect weather for walking around — not too hot and not too cold.

Image by joe daniel price / Getty Images
(Photo by Joe Daniel Price/Getty Images)

Also, with Boston being the college capital of the US, you’ll want to steer clear during move-in days and graduation. The city is packed with tourists and the families of students and hotel rates can be at all-time highs (and possibly sold out). This means stay away Labor Day weekend and almost every weekend in May. Many schools also host family weekends in October, which can put a squeeze on hotel availability.

Look at the Sports Schedule

If you are a sports fanatic, check the Boston sports schedule if you want to see a game. All the teams play right in the city, which makes it easy to catch a game, but plan ahead because the city is sports-crazy and tickets go fast. The Bruins and Celtics play at TD Garden by North Station, while the Red Sox play at Fenway.

Fenway Park in Boston, MA. (Photo via Shutterstock)

You Don’t Need a Rental Car

Driving in Boston can be a nightmare. It is anything but a grid and the street signs can be extremely confusing. Parking is expensive at hotels and finding street parking can be difficult (and typically limited to those with a resident sticker). If you are staying within the city, there is no reason to rent a car. You really can get around many parts of the city on foot, or for a destination slightly further away, consider taking the subway or a taxi.

Bottom Line

Boston is a wonderful city that offers a ton of activities for all families. While the city can easily be seen in a long weekend, there is also much to do outside of the city. For a longer vacation, you can make Boston just one stop in a trip within New England — south to Cape Cod or north to Portsmouth, New Hampshire — an historical city combined with a quintessential New England beach town.

Keep Planning Your Boston Trip:

Jennifer Yellin is a Boston-based travel blogger who covers family travel deals for TPG and blogs at Deals We Like. Follow her family’s adventures on Twitter and Instagram.

Featured photo by Summer Hull / The Points Guy

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