Boston for families is the perfect merger of history, culture, and vibrant atmosphere. Family fun can be found around every corner. But let’s talk the three essentials: where to eat, sleep and play! From fun things to do in Boston like whale watching and Duck tours, lobster and cupcakes, and a historic boutique hotel, our family’s Beantown vacation is one we’re still talking about.

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

Swans, whales and lobster are some of the things to do in Boston, Massachusetts. Photo by Sherry Boswell, Melodious TravelingMom.

Boston for Families: Where to Eat, Stay and Play

Boston MA for families is an amazing destination to soak up history, try new experiences, and eat some fab food. Our family, which includes a teen and a tween, had a glorious week-long summer vacation in Boston. While Mom and Dad had been there before, the kids had not, and we were super excited about introducing them to this dynamic, vibrant city. Without a doubt, this was one of our favorite vacations EVER.

Boston for Families: Where to Eat

Boy, did we eat well in Boston! Between the lobster, crab legs, and oysters on the half shell, we were seafood fanatics. Our favorite food finds were The Barking Crab and Island Creek Oyster Bar.

The Barking Crab

The Barking Crab is self-described as offering “the casual atmosphere of a coastal clam shack in a funky urban setting.” They nailed it on the description! Considering its picturesque view of the Charles River and delicious seafood, I could totally understand why people have been digging The Barking Crab for 20 years. And our teen simply DOVE into the lobster. (We’re definitely raising a girl with expensive tastes!)

With a diverse menu ranging from New England clambake, mussels, clams, crab, fried seafood, lobster roll, and lobster mac & cheese, The Barking Crab will put your tastebuds in overdrive. Prepare to use your hands and wear a bib, because you’ll be bathing in the lobster dunked in butter. My mouth is watering just thinking about it!

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

Lobster for everyone. Photo by Sherry Boswell, Melodious TravelingMom.

Island Creek Oyster Bar

At the opposite end of the dining spectrum but still brimming with seafood is Island Creek Oyster Bar, a well-located restaurant near Fenway and attached to the Hotel Commonwealth. Island Creek embraces the farm to table concept, only this time it is the oyster grower and harvester. This place was on my must do list for Boston before we left. It’s clearly a popular destination. We had to go with a 5:30 reservation, and the place was PACKED!

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

Shellfish galore! Photo by Island Creek Oyster Bar.

After perusing the menu, most of us decided that this evening’s focus would be oysters. Our server recommended several varieties and we went to town on 3 or 4 dozen oysters over the course of a few hours. The seafood is fresh from nearby Duxbury Bay, and the decor is upscale and contemporary. My favorite touch? The wall of oyster shells being repurposed if you will. 

I will say this selection is much more upscale than The Barking Crab. My kids are adventurous eaters so we loved it, but Island Creek is not for the mac and cheese/chicken fingers only set. It is for those craving a deliciously fresh, seafood inspired meal.

Other Noteworthy NomNom Locations in Boston

As coffee and tea fans, we gladly skipped the Starbucks and stumbled on Wired Puppy. Let’s be honest: my kids couldn’t resist the name, so we had to check it out. As cute as the name, it’s a delightfully quaint coffee shop with baked goodies, tasty beverages, and outdoor seating.

Georgetown Cupcake was like stumbling onto a sugar fantasyland. My teen and tween preferred Ben and Jerry’s, but this was Mom’s guilty pleasure. The salted caramel cupcake was ooey gooey goodness!

Boston where to eat, stay and play collage of food

Honorable mentions for food: Wired Puppy, Georgetown Cupcake, and Red Lantern. Photo by Melodious Traveling Mom Sherry Boswell.

And a special shoutout for Red Lantern, where we noshed on sushi and the shared plate of whole roast duck with Peking pancakes. Made me think of that scene in A Christmas Story where they have duck for Christmas dinner at the Chinese restaurant. Fortunately for us, Red Lantern already removed the head!

TravelingMom Note: Don’t miss the Copley Square Farmer’s Market Tuesdays and Fridays 11:00 AM to 6:00 PM from mid-May to late November.

Boston for Families: Where to Stay

Our plans changed from a business trip tagalong to a week long family vacation, so when we searched vrbo.com to find accommodations, we came up short. I was really thinking we were going to get the “screw me” rate, and Boston is NOT a cheap city! In desperation, I stumbled onto hotwire.com to find some special deals. The only catch? We wouldn’t know which hotel we had booked until we paid in full up front. We only knew the general area/neighborhood it was in (in this case, Back Bay). Hey go big or go home, right? Our gamble paid off in a HUGE way!

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

The Lenox is one of the nicest, most friendly boutique hotels around. Photo by Sherry Boswell, Melodious TravelingMom.

The Lenox Hotel

The Lenox Hotel was our reward, a stunner of a boutique hotel located one block away from Newbury Street’s shopping and dining mecca. It’s exactly where we wanted to be location-wise, but we were even more bowled over by the service and attention to detail. Upon arrival, the kids received plush lobsters, and we had a basket of goodies and a handwritten note awaiting us in our room. Quite an excellent start!

While our room was a standard two beds, the hotel itself never felt standard. And its location is superb! One block from the Boston Public Library, the ever-popular Copley Square, Trinity Church, and the Prudential Center. The Lenox Hotel is a stone’s throw away from boutiques, art galleries, sidewalk cafes and restaurants a plenty.

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

The Lenox Hotel had us at hello with goodie basket, stuffed animals, and handwritten note from the staff. Photo by Melodious TravelingMom Sherry Boswell.

TravelingMom Tip: Especially at the Lenox, always ask the concierge for assistance on dining reservations, activities, and other notables like arranging the hotel sedan ride back to the airport which was WAY better than our taxi trip there. Our concierge never once steered us wrong, and for that reason, they always become my new BFF on vacations.

Boston for Families: Where to Play

Discovering a Great Band at Faneuil Hall

Since music is such a big deal in my life  – hey, it’s even my TravelingMom name – I’m always looking for new and inspiring music. What better place to find street musicians than Faneuil Hall and Quincy Market? This bustling marketplace filled with food and souvenirs is also alive with the sound of music.

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

Photo by Sherry Boswell/Melodious TravelingMom.

Our exceptional musical find was the band Cahill. The more they played, the more we liked them. Two guys, acoustic guitars, a foot amp to add special effects, and that was it. But their unique voices really hooked you! You can find them on iTunes. My favorite tune from the set? “Hard to Miss.” Forget America’s Got Talent: THESE GUYS got talent!

Duck Tour

Boston Duck Tours are a delightful way to spend an afternoon sightseeing. This is a land/water tour on a World War II style amphibious vehicle also known as DUCK.  Our “ConDUCKtor” was Flo, who kept us in stitches despite the crazy Friday afternoon traffic. Once on the Charles River, my teen even got to drive! This goofball tour is a perfect overview trip to give you a sense of all that Boston has to offer. Your perspective totally changes as soon as your vehicle becomes a boat and drives headlong into the river.

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

Brace yourself: Your kids might even be able to drive the DUCK (only on the water!) Photo credit: Boston Duck Tours.

TravelingMom Tip: My only advice would be to choose a tour earlier in the day to avoid rush hour traffic.

Boston Garden and the Swan Boats 

No big surprise that my kids loved Boston Public Garden given how much they loved Central Park in NYC. Lots of green space to run and play is like a beacon to them. But the added bonus was the Swan Boats. Families piled on to take the 15 minute sojourn around the lake. The swan boats are powered by pedal propulsion…say that 3 times fast! That means a person pedals like a bicycle and the boat slowly glides through the water.

What an unexpectedly serene moment in the middle of a metro area. I totally forgot that I was in a big city as we watched swans gracefully swim by and the willows hugging the lagoon. The swan boats are unrivaled (as in, you won’t find them anywhere else) and inexpensive to boot. My family of four enjoyed this leisurely cruise for only $ 9.00. Family fun + inexpensive entertainment in the great outdoors=winning!

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

I’m on a (swan) boat! Photo by Sherry Boswell/Melodious TravelingMom.

Whale Watching

On our last day, we decided to do something totally unexpected and unlike anything we’ve ever done. Boston Harbor Cruises fit the bill because they offer whale watching excursions. Seriously? I was down for that! It was AH-MAZ-ING! We went from one mode of water transportation (swan boats) to a giant catamaran that would take us miles away from Boston in search of whales.

When we arrived at the feeding grounds where they had seen whales earlier in the day, we sat there. A minute passed, then two. Then a few more. I’ll admit, when we weren’t seeing anything, I thought, “I rode an hour and a half for this?” As if on cue, a whale emerged from the sea not once, not twice, but at least 30 times while we all gasped and squealed at every leap (the technical term is “breaching”). It was breathtaking and exhilarating and I was so glad we went. Although I’m not sure when or where we might have the chance to whale watch again, that is exactly what made this excursion so memorable and special!

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens

The camera-worthy moment: whale breaching! Photo by Melodious TravelingMom Sherry Boswell.

TravelingMom Tip: CityPASS Includes admission to all 3: New England Aquarium, Museum of Science, and the Skywalk Observatory at the Prudential Center; and either the Museum of Fine Arts OR Boston Harbor Cruises. Good for 9 days from its first use. Depending on what you plan on visiting, this may be a great money saver!

Looking for more Boston vacation ideas? Then Read about Kuleen’s 5 Reasons to Take Your Kids to Boston.

From whale watching to DUCK in the Charles River to jam session at Faneuil Hall, Boston for families means fun! Top things to do in Boston for teens/tweens