Browse our trip notes to find great ideas for Frum trip ideas. Whether you’re looking for Kosher vacation homes, or Chol Hamoed Succot or Pesach trips, just ask the Hippo! We’ll lead you to the best frum family outin! You can even search for attractions that have kosher food and shuls nearby!

Boston, Massachusetts

There’s no shortage of things to do in Boston, Massachusetts, one of America’s oldest cities. History buffs and fun-seekers alike will appreciate the vast array of Boston’s hotels, tours, and attractions. Why put in all that time doing your own research? Just follow the Hippo! 😉


Day 1:

Try to get an early start in the morning, as you have 3.5- 4.5 hours of driving ahead of you if you live in New York or New Jersey. Start in Downtown Boston at the beautiful Boston Common, which is a scenic park where you can stretch your legs after the long drive. If you brought along lunch, you can sit on benches and eat at the park. You can also visit Tadpole Playground and Frog Pond, which features a large, kid-friendly playground as well as a spray plume and wading pool (in the summer; there’s
ice skating in the winter).

When you’ve finished lunch, you can head to the The Swan Boats, which are located right there in the park. The driver takes your family and others on a leisurely, 12-minute pedal-powered boat ride— an inexpensive, relaxing start to your trip that will bring you up close to some of the city’s waterfowl..

TIP: The lines for the Swan Boats may look long, but don’t worry, they move very quickly.

Now you’re ready to experience what Boston is all about on the The Freedom Trail. Don’t skip this major highlight, which starts right at Boston Common. It leads you to all the major historic sites of early America (and there’s a Holocaust memorial located on the trail, too). You can walk the 2.5-mile trail yourself for free, but the Freedom Trail Foundation offers 90-minute walking tours led by guides in 18th-century costumes. Call the Freedom Trail Foundation in advance to book a tour, and remember to print out and bring your tickets. (Cost: adults $12, kids 6 to 12 $6.50, kids 5 and under free.) The Foundation tours only cover part of the Freedom Trail and do not include admission to the Freedom
Trail sites. The Old State House, Old South Meeting House, and Paul Revere House each charge an
entrance fee.

TIP: This walking tour is also baby-friendly. Bring on the strollers — literally!

If you still have energy left, take a trolley ride to The USS Constitution Museum, where you can enjoy a free tour of the oldest floating warship in the world. You can also check out an adjacent warship in dry dock.

You should be good and ready to check in to your hotel by now. If you have Starwood points, the W Hotel downtown is a beautiful and friendly hotel. If not, The Holiday Inn is a lower cost option. Alternatively, you can try one of several charming bed and breakfasts like Sharon Woods Inn, Bertram Inn, and Samuel Sewall Inn, all located a bit further from the attractions, but closer to the shuls and kosher food.

If you have the opportunity to go back out in the evening, you can stroll around Faneuil HallThey have awesome street performers and acts. You can walk around and browse the shops and enjoy some fun people-watching.

Day 2:

If you are staying at a hotel, the nearby groceries generally carry kosher products, so you might want to buy breakfast and prepare lunch to take along, since most of the Kosher restaurants are in Brookline, which is a distance from the attractions. If you are staying at a kosher B&B, then your breakfast is covered of course, and you can pick up some fresh bagels for lunch from Kupel’s bakery.

With the technicalities out of the way, you are now ready for the fun: The Duck Tours are pricey, but there’s a reason that they’re Boston’s number one attraction. The Duck Tours are an amphibious bus that takes you around Boston’s streets — and then becomes a boat that takes you around Boston’s waterways, showing you the whole city in less than 90 minutes. If your kids automatically tune out when they hear the word “history,” don’t worry: The Duck Tour drivers are out-of-work actors and comedians who sprinkle their tour with plenty of humor. You can take the entire tour, or use the boat as transportation, hopping on and off at the three different departure locations. (Cost: adults $42, children ages 3 to 11 $28, children under 3 $10.50)

TIP: You can save money by getting a two-day duck tour pass, or, if you want a very
cheap boat tour, check out the MBTA boats. You can travel for a short ferry ride or all the way
from Boston to Hingham, which takes about 1.5 hours — a real bargain. (Cost: Fare starts at $3.50
one way and increases for longer ferry rides; 2 kids under 12 per adult can ride free.)

If you end the 80-minute Duck Tour at Prudential Center at Boston’s historic Back Bay, take a 13-minute walk or 5-minute trolley ride to the Boston Tea Party Museum. And tell your kids to stop rolling their eyes — this tour’s fun! Grade-school aged kids and up will enjoy watching costumed actors reenacting the Boston Tea Party, bringing history to life.

Your younger kids will love the Children’s Museum, (which Trippo has a coupon for). You can easily spend two to three hours there, and it’s just a two-minute walk from the Boston Tea Party Museum. The Children’s Museum has various areas addressing art, science, play, etc. The construction truck/demolition area and the water tables are always favorites! (Cost: $17 per person. Infants under 12 months are free.)

TIP: You can get your parking fee discounted (from $12 to $9) by parking at 280
Congress Street and getting it validated when you get to the museum.

Or maybe you want to round out the day with an adult activity: the The Sam Adams Brewery Tour. It’s a 25- minute drive (or 30 minute trolley ride), but it’s a unique experience and it’s free. (Suggested donation: $2.)
TIP: This adult outing works for kids too, and it’s even stroller-friendly. There’s free beer sampling, and if you get lucky, they may even be offering free mugs, too. Reminder: Don’t go on Pesach, of course!

Enjoy a dinner at Taam China for Chinese cuisine, or Eilat Café if the kids vote for milchig. You can’t go wrong with either!


Day 3:

If you’re lucky enough to stay over for a third day, you can take the Fenway Park Tour. It is an excellent one-hour guided walking tour at the home of the Boston Red Sox. If you have baseball fans in the family, this will definitely be the highlight of their trip. Challenge: find the green monster at the stadium and discover why it was built.

If you can fit in a Mitzvah opportunity, there are, unfortunately, always Jewish patients at the Children’s Hospital. The hospital is right nearby, just outside of Brookline. Consider making a Bikur Cholim stop, and infusing your fun with meaning.

Drive/trolley 8 minutes to Jerusalem Pita and pick up falafel or schwarma for lunch. Enjoy your lunch at the Larz Anderson Park, 15 minutes away. It’s a nice, shady park in Brookline with beautiful views, a playground, a walking path, and pond. Bring along some kites in the summer and sleds in the winter!

Wasn’t Boston an awesome trip? Who said American history is boring?! Wondering where to go on your next vacation? Just follow the Hippo! 😉

The Trippo Hippo Team

P.S. Follow us on Instagram @TeamTrippoHippo for more amazing Chol Hamoed and anytime frum trip ideas!
And you definitely want to subscribe to our email list- we share exclusive discounts from kosher attractions as we get them! Happy travels!



The Swan Boats

The Swan Boats are beautiful and relaxing. They are right near the Boston Common- which is a really nice park to walk around and is right at the start of the Freedom Trail.

The Freedom Trail

The Freedom Trail sums up what Boston is all about. It brings you to all the major historic sites of early America. Not to be missed! It’s an excellent walking tour, and baby friendly too. It starts at Boston Common.

The USS Constitution Museum

The USS Constitution Museum is not far from Boston Common. It’s the oldest floating commissioned warship in the world. The tour is free.

Boston Tea Party Museum

For more fun historical education, go to a Reenactment of the Boston Tea Party which is educational in an immersive way, and lots of memorable fun.

The Duck Tours

The Duck Tours are pricey, but they are the #1 attraction in Boston. It’s an amphibious bus that takes you around Boston on the streets and then becomes a boat that goes in the water. You can save money by getting a 2-day duck tour pass. You will get to see a bunch of interesting places, as well as have transportation from place to place, all for one fee.

MBTA Boat Ride

Alternatively, if you want a very cheap boat “tour” check out the MBTA website You can go from Quincy to Boston without getting off for 6$ a person and kids ride free! The boat ride takes about 1.5 hours- a real bargain.

Faneuil Hall

Faneuil Hall has awesome street performers and acts. You can walk around and browse the shops in the daytime or evening.

The Sam Adams Brewery Tour

The Brewery Tour is a unique experience, and it’s free- with a $2 suggested donation. It’s a fun outing for the adults that works for kids too, and strollers are fine.

Fenway Park

If you are baseball fans, the guided walking tour at Fenway park,home of the Boston Red Sox, is excellent. It lasts an hour.

Larz Anderson Park

For little kids or for some picnic down time, in Brookline is a nice shady park with a playground, a walking path, and pond.

Children’s Museum

Immersive museum for young kids.

Children’s Hospital

Make a Bikur Cholim stop and infuse your vacation with meaning. Unfortunately, there are always Jewish patients who come from all over the world for treatment at the one-of-a-kind hospital.

Kosher Food

Most of the kosher restaurants are in Brookline, which is a 15 to 20 minute drive from most of the attractions listed. If you are staying at a hotel, the nearby groceries generally carry kosher products, so you might want to buy breakfast and prepare lunch to take along. If you are staying at a kosher B&B, then your breakfast is covered, of course, and you can pick up some bagels for lunch from Kupel’s Bakery. Drive/trolley eight minutes to Jerusalem Pita and pick up falafel or shawarma for lunch — or if you’re in the mood for a dairy restaurant, try Café Eilat. There’s also Rami’s (falafel) and Kupel’s Bakery (bagels). Or you can pick up some food at the kosher grocery, the Butcherie.

  • Taam China– chinese food
  • Rami’s– falafel
  • Jerusalem Pita– shwarma, falafel, Israeli style food
  • Eilat Cafe-Pizza place
  • Kupel’s bakery(for bagels)
  • JP Licks(Cholov Stam)-ice cream chain in Boston shop where everything is kosher, and certain branches also have waffles.

Butcherie– Kosher grocery store


  • Young Israel of Brookline
  • Chai Adam
  • Congregation Beth Pinchas(Bostoner Rebbe)


  • The W Hotel The W Hotel downtown is a beautiful and friendly hotel. Its location makes it convenient to use the
    subway and walkable to many attractions. It’s also a Starwood Hotel, which may make it an attractive
    option if you have points to redeem.
  • The Holiday Inn
    The Holiday Inn in Brookline is a lower-cost option. It has some key-only rooms for Shabbos.
  • Sharon Woods Inn
    A kosher bed and breakfast run by the the wonderful Yarmush family. Located right outside Boston, near shuls and a kosher supermarket. It is on a nice property and beautiful area to walk around.
  • Bertram Inn (and The Samuel Sewall Inn) around the corner, same ownership)
    Charming, comfortable bed and breakfast. Walking distance to the heart of Brookline (Harvard Ave) for kosher food and shuls.



    You can use Boston’s trolley system to get around downtown. Purchase a hop-on-hop-off trolley pass and a harbor cruise ticket. Well worth it — your kids may find the trolley rides the most exciting part of their trip. (Cost: $40 for a one-day pass, $60 for two days. The harbor cruise costs an additional $10. Note that the passes also include free admission and discounts to other Boston attractions.)

Kashrus of any establishment mentioned by Trippo Hippo is not guaranteed and should always be independently verified.


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