Boston With Kids Recap: Taking a Bite of Beantown

Boston with kids doesn't have to mean one long trip — after two separate weekend visits in the same year, here's what's worth doing, where to stay on points, and the one expense that caught us off guard. In this episode 50 recap, I compare two Hyatt Regency stays booked on free night certificates, share the Alaska Atmos points trick that got us into first class for less than economy, and break down where to eat, tour, and skip the rideshare surprise that cost us the most.

In this episode:

• Why we're recapping two different Boston trips — one with our daughter last summer, one solo-parent-turned-family-reunion this year — in a single episode
• Booking first class on American Airlines for just 9,000 Alaska Atmos points each, because airfare spiked and economy award seats disappeared
• Hyatt Regency Boston vs. Hyatt Regency Boston Harbor: same category 4 free night certificate, two completely different trips
• Boston Tea Party Museum and a guided Freedom Trail walking tour — why paying for a guide beat doing it ourselves in our 20s
• The surprise expense
• Getting around Hyatt Regency Boston Harbor without a car: the shuttle, the $2.40 ferry, and why weekends are trickier than weekdays
• Who Boston is best for, from toddlers to a no-kids weekend away

Boston travel resources
Boston Tea Party Ships & Museum
Freedom Trail guided tour 
Duck boat tour
Hyatt Place Boston/Seaport

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

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Transcript

0:01

Hey there, and welcome back to Family Travel Unpacked. I'm your host, Melissa, and in case you're new here, you can find tons of detailed destination guides, travel tips, hacks, and more on my website, thefamilyvoyage.com. And if you've been enjoying the show, be sure to hit follow wherever you're listening so you never miss an episode, and drop a five-star review over on Spotify or Apple Podcasts. It really helps other families find the show. Now I'm gonna give a special shout-out because it turns out this is the 50th episode of Family Travel Unpacked. Whether you're a new listener or you've been here since the beginning, I really appreciate your support. Keep hanging around, keep talking travel with me And I know we're gonna have a great time. we just got back from a Boston weekend, our second one in the last year. Last summer, my husband Ronnie and I flew with our daughter to pick our son up from camp, and we squeezed in a full day in the city before we drove north to Maine. This year, it was just my husband and I back on our own, so we spent Saturday exploring Boston together, and then we met up with our son at the airport and showed him around a little bit before we flew home together. So two trips, two nights each time, but I want to put them together in one recap instead of doing them separately. This episode isn't gonna be the usual deep dive that I like to do on destinations. Because they've been really quick visits, and honestly, we have been so busy traveling this summer, I'm just gonna give you a little recap of some of the highlights and one lowlight of our time in Boston. So the first question is, would we go back? Absolutely, no question. Two short trips in 12 months, we're nowhere close to done with the city. Eventually, we'd love to turn it into a real New England road trip with both kids, maybe pairing Boston with Maine, New Hampshire, and some other stops along the way. If you've never been to Boston, you might be wondering who it's best for, and I would say it's good for basically every age. There's enough stuff to do that it works whether you've got a toddler or a teen, or if you're just on a romantic adults trip. And it's a super easy city to take in a bite-sized chunk like a weekend. I want to give you a quick note about how we got to Boston. If you're listening to this in real time, as you probably know, airfares have gone through the roof due to the current conflict with Iran. Thankfully, we were able to get our flights nonstop on American Airlines, But we booked them with Alaska Atmos points, and they were way cheaper than if we had gone directly through American. In economy, we could have gotten our tickets for just 4,500 Alaska Atmos points each. But at the time that we booked, economy wasn't actually available. The only option for the flight we wanted to take was in first class. now we're not typically front-of-the-plane people. It just doesn't usually fit into our budget. But this is a real sweet spot if you have Alaska points, because you can book those short partner flights, like on American Airlines, for just 9,000 points in first class. Talk about a deal. We walked on at the beginning of the boarding process, and we got to feel pretty darn fancy. I'm not gonna lie, it was definitely worth the splurge, even though economy tickets did eventually become available. It was just my husband and I on that outbound flight, so it was pretty nice to kick back in a huge comfy chair with a glass of champagne before takeoff. So I wanna give you a little bit of color on where we stayed. On both of these trips to Boston, we used our Hyatt free night certificates, which are good for category one through four properties. And both times we stayed at a Hyatt Regency, but they were two completely different properties and two very different experiences. Last summer we stayed at the Hyatt Regency Boston, which is right near Boston Common in the heart of the city, and it's walking distance to almost everything. This year, since we were meeting our son at the airport and we needed easy access, we booked the Hyatt Regency Boston Harbor instead. Same category, both are a category four redemption, so the certificate could cover whichever one you prefer But like I said, completely different experiences. Boston Harbor is a lot less convenient if sightseeing is the priority, but our harbor view room definitely made up for some of that. And this trip, being close to the airport mattered way more than being close to downtown. I would say that both hotels are reasonably nice, but neither one of them is super fancy. That said, cash rates for hotel rooms in the summer in Boston could easily top $300 a night, so I'm happy with anything that's not gonna cost me a dollar out of pocket. If you've got points to spend instead of a free night certificate, I'd also look at the two other Hyatt properties that are in Boston. First is the Hyatt Place in the Seaport District, which is pretty new, and I actually have a friend who stayed there last week. She had amazing harbor views, and she told me there was a great lounge for guests to relax in. So that one is definitely on my list, and the Seaport District is really new and fun and very walkable. There's also the Hyatt Centric near Faneuil Hall, and that puts you in the middle of everything. It's right in the historic district, so it's great for sightseeing. But it's a category six, so it's a lot more points than the other options. Plus, it's kind of busy over there. The point is there are some great values for staying at a Hyatt in Boston, And I definitely found a lot better value with Hyatt than I did when I looked at IHG, Marriott, or Hilton properties in the city. In terms of highlights for a Boston visit I'd definitely say to put history first. Last summer we took Shoshana, who was 11 at the time, to the Boston Tea Party Museum, and she loved it, but so did we. It's a really interactive and immersive kind of experience for visitors of all ages, and it's way better than just reading placards on a wall. I won't spoil too much, but I would say they make great use of everything from costumed interpreters to super, super high-tech stuff. It's perfect for anyone who has studied American history in school, and it makes that history come alive in a way that's a lot harder to get from a textbook. This time, since Ronnie and I had a whole day to ourselves, we did a guided walking tour of the Freedom Trail. You can book some companies with a costumed interpreter, which sounded like a lot of fun, especially if you've got kids. But since it was just the two of us adults this time, we went with a different guide instead, and I've linked to the one we used in the show notes. Honestly, Noah was awesome. We learned so much. We did the Freedom Trail as a self-guided tour back in our 20s, and having a real guide this time made a huge difference. We picked up a lot more history and context than just wandering around on our own gave us. On our second day in Boston this time, we also accidentally caught part of a free tour run by the National Park Service Rangers while we were exploring the city with our son, Jacob, and if the timing lines up with your schedule, that's a great way to get some of that same guided context without spending a dime Now, one of the original plans for this trip was to take Jacob to a Red Sox game at Fenway right after camp pickup. But instead, it happened to be the World Cup final. So we ended up at the High Street Place Food Hall watching the match together with a few hundred of our closest friends. Now, obviously, that's not gonna happen every time you're in Boston, but if you're in that part of town, in the Financial District, High Street Place Food Hall is really cool. There are tons of great options, so you could definitely find something for everybody to eat. There are stalls ranging from burgers and fried chicken to high-end sushi and pretty much everything else. Now, one thing that surprised me and I definitely did not love is how expensive Uber and Lyft rides get. Last summer we only needed one ride share the whole trip, which was from the airport to our hotel because we had rented a car toward the end of our stay to go pick up our son. But this time we were staying on the harbor side near the airport, and We ended up taking a few different rideshares, and every single one was twenty-five to thirty dollars, even if it was just a 12-minute ride. I'm gonna tell you, that added up fast for just a two-night trip, and it really caught me off guard given how walkable and transit-friendly Boston is everywhere else Getting around from the harbor side of Boston without leaning on rideshares all the time definitely took a little figuring out. The Hyatt Regency Boston Harbor does run a shuttle to the Airport T stop in both directions, so you can get out that way. But on the return trip, you have to call the hotel to request the shuttle, and you might wait fifteen to twenty minutes for pickup. Now, what's great is that there is a ferry dock right behind the hotel, and the ferry's just two dollars and forty cents, same as the T. It sounds ideal until you check the weekend schedule. There are only three departures into Boston before noon, compared to eleven that you can get on weekdays. So if you're staying at Hyatt Regency Boston Harbor on a weekday, it should be no problem to get into the city, and then you can just walk around from any of the ferry docks. But on the weekend, it's a lot harder And you're definitely gonna have to plan for it. We did manage to catch the ferry on Sunday morning over to Seaport, and those were 10 beautiful minutes. It's really stunning on a clear summer day to just be out there on the water with the city coming up in front of you. Just don't plan around it on a weekend without checking the times first. Now, as I said at the top of the episode, Boston's great for almost every age group, and that's part of why I like the city so much for families. With younger kids, you could add in the New England Aquarium, which we still haven't made it to, or you can take an amphibious duck tour around the city, and we did that with Shoshana last summer, and she had a blast. Older kids and history-loving teens are gonna get a lot out of that Freedom Trail tour and the Tea Party Museum. And adults have plenty to do on their own, too. Ronnie and I visited the Museum of Fine Arts this trip, and the impressions collection definitely made it worth carving out the time So there's my quick recap of our time in Boston. Unfortunately, right now I don't have a deep dive episode planned just because we haven't spent enough time there. Between the two trips, we've covered downtown and the waterfront. We've done it with a kid. We've done it solo, and we've tried two different hotels. So hopefully this gave you a pretty decent starting point for planning your own trip to Boston. And I promise that in the future, If we get a longer trip as part of a New England visit, you'll hear about it here. Thanks for tuning in to this episode of Family Travel Unpacked. If this made you wanna add Boston to your list, do me a favor and hit follow wherever you're listening, and share it with another family who's dreaming up their next trip. If you've got a question about points and miles, travel planning, or anything else, you can always email me at melissa@thefamilyvoyage.com. I read every message, and I love hearing from you. Until next time, safe travels.