There’s something about Boston that works for families. It’s walkable, packed with history, has plenty of kid-friendly food options, and somehow still feels manageable with kids in tow. We just spent Memorial Day weekend with Alex’s family, including four boys aged 5, 9, 12, and 14, and everyone had a great time.

And the best part? It’s a surprisingly great city to visit using points and miles. Flights to Boston are easy to book with points from all over the country, especially if you plan ahead. Alex used Delta credits to fly from SLC, and we used some United credits to fly from Denver.

We both stayed at the Hyatt Regency Boston, which is walkable to just about everything. We spent 23K points per night at this Category 5 hotel and used Hyatt Suite Upgrade Awards to get more room. Our Globalist breakfasts covered us for $35 per person off the menu or the buffet (which was very good)! There are a ton of hotel options in Boston, though!

 

 

 

One thing we love about Boston with kids is that you really don’t need a car. Once you arrive, you can walk, take the subway, or even hop on a ferry. That saves money and reduces stress right away.

Some family favorite Boston activities include:

• Walking the Freedom Trail and letting kids see history come alive. Alex booked this tour, and it was fabulous for kids (and grandparents).
• Exploring the Boston Tea Party Ships & Museum. This was so much fun, and the boys enjoyed it a lot. The staff are great!
• Catching a Red Sox game at Fenway Park. It was a little rainy the day we went, but the family loved it. Noah wanted a baseball cap so he could “always remember the day.”
• Spending time at Boston Common. Perfect for throwing a football around and watching Noah chasing squirrels.

 

 

 

Boston also works well as a points-and-miles hub trip. You can combine it with places like Cape Cod, Maine, or even New York City—with just a short train ride—for a longer East Coast adventure.

 

Bottom Line

If your family likes adding educational moments into vacations without making it feel like “school,” Boston is honestly hard to beat.

And if you’re newer to points and miles, Boston is actually a great beginner redemption trip. You don’t need complicated international flights or huge point balances to make it happen. Sometimes the best family memories come from simple domestic trips where everything just feels easy.

Boston may not always be the first city people think about for a family vacation, but it should be. History, food, walkability, sports, and incredible memories? That’s a pretty great combination.