Staycation's All I Ever Wanted

Why I love seeing my home city through my toddler's eyes.

Going into the city was our first big test for family trips. I know Boston well from years of commuting back and forth between the train station and various offices scattered in the downtown area (and from sneaking out for workouts, the cookie truck, or lunches midday.) How many times had I passed that big playground in front of the Children’s Museum? About a thousand. But this country mouse needs peace and quiet, so the idea of wrangling a stroller and feeds and naps on crowded, uneven sidewalks felt scary. (Now there’s a missed opportunity for a Halloween costume, lol. I did see a toddler dressed up as a spooky commuter rail train last night, purple “T” and all.)

Now, we’ve done three staycations, mostly with the same-ish itinerary, and I’d 100% recommend doing one in your own city. We took our first staycation just before my toddler’s first birthday, and since then have been twice more for big celebrations. There is something so magical about going from sightseeing to whooshing up the elevator to your hotel room at the end of the day—that satisfaction from a sense of adventure—that I frankly needed as a new mom, especially a mom who traveled a lot pre-kids.

If you’re itching to go somewhere but not sure you can handle it, try a staycation. You have an easy exit strategy—just go home if it’s miserable!—but I think you’ll have more fun than you’d expect. Here’s how to plan a great staycation with a baby or toddler:

Think of the most tourist-y spot in your city and that’s where you should stay.

I’m obsessed with Boston, actually, because of how historical it is. You’ve got cobblestones and bars where colonial revolutionaries planned major battles mashed up against slick all-glass skyscrapers and four-floor H&M stores. We chose to stay blocks away from the biggest tourist attractions we were interested in doing (the New England Aquarium) rather than trying on a more residential neighborhood.

Our first aquarium visit was SUCH a hit. The awe and wonder!!

We hit alllll the spots I would NEVER have gone to while I was working downtown because “that’s for tourists.” Staycationing releases that sense of being cool (if I ever had it in the first place) so you can just enjoy new sights and sounds and show your little one what their home city is all about.

Pick a hotel that has a pool and a really cool view.

Could you do an Airbnb or home rental in a city? Of course you can! But to me, hotel -= vacation. You’re already in a place where it kinda sorta doesn’t feel vacation-y out and about, so staying in a hotel is a way to access that feeling. (Plus doing hotel things you might not necessarily do when you’re trying to maximize time adventuring, like ordering room service or going to the spa.)

You’re already ahead if you can take the elevator (its own attraction) to the pool. With babies and toddlers, “just add water” always works. I stuff a few small bath toys into my bag and bring them along with our suits and bubble (30+ pounds).

Explore one neighborhood/area per day.

This is general advice for traveling with babies or toddlers, but the biggest benefit of a staycation is you’ve already lived/visited that destination so there’s no pressure to do it all. Choose one “big” activity for the day and that’s it.

We spent the majority of our second staycation at Martin’s Playground in the Seaport and had a BLAST. They have a huge ship in the middle of one of the playspaces. They don’t make ‘em like this in the ‘burbs!

Slowing down and experiencing just one piece of the city worked so much better for us than trying to do it all. For my toddler, the amount of different sights, noises, and cars/trucks to see was already very exciting, so we didn’t need to do much more.

Here’s a sample itinerary from one of our staycations in Boston:

DOWNTOWN/NORTH END DAY

• Drive during morning nap, check into hotel and drop stuff

• Visit New England Aquarium (~1.5 hours) which was MAGICAL for my toddler

• Ride the Rose Kennedy Greenway Carousel

• Order ahead - lunch at Sweetgreen and eat in hotel

• Afternoon nap in the hotel

• Pool time!

• Pasta from La Famiglia Giorgio’s for dinner

• Get the wiggles out at Christopher Columbus Park in the North End

You can see it’s not jam-packed with stuff to do, though there are plenty of exciting historical spots in that neighborhood, like Old North Church (“one if by land, two if by sea”) or Faneuil Hall. We’re also not maximizing all the cool parts of the Aquarium or taking a Duck Tour, which are all things I recommend in this area. We’re just…doing the one thing and then chilling for the rest of the day. Instead of trying to do! all ! the ! things! it made for a really relaxing and fun day.

Build in parenting breaks.

If you’re traveling with a partner, create some alone time for yourselves as part of your staycation. This could be during naptime—one trip I took a stroller walk to an art museum while my toddler napped and my husband took a much-needed rest himself. That same trip, I booked a Barry’s Bootcamp class in the morning for myself which felt like such a treat (It was *significantly* harder than I recall from several years ago which I’m pretending is because of a new instructor and not my postpartum fitness.)

You could book a spa treatment, go take a tour, or just sit by the pool by yourself. Whatever you need to recharge, take it.

Invite friends and family to come hang.

We live far enough from the city that whenever we come in for any reason, we tell family and friends and invite them along. A regular vacation you’d maybe be able to meet up with someone who lives in that city, but a staycation? It’s so fun to all get together for dinner, or a long walk along the Esplanade, or do a bucket-list item like riding the swan boats at the Boston Public Garden.

I’ve found that as much as it’s fun doing stuff as a nuclear family, it’s so nice to add a few aunties and uncles into the mix on our adventures—partially for extra eyes on our toddler, but also for a breath of fresh air. I don’t get to see my friends as often as we’d like, so being able to do things with them is extra special.

Use it as practice.

Staycations give you a low-stakes way to practice doing all of this travel stuff without going too far. For example, part of why we bought a travel stroller for our first real trip was because we tried to take the Uppababy Vista V2 to the North End, which is basically like the Suburban of strollers…we could barely fit down the sidewalks and had to completely take it apart to get into the restaurant. They parked it at the server’s station and it created a lot of stress for everyone involved.

Better to learn it now than later!

This week’s rapid-fire recs

Disclosure: This newsletter contains affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you. I promise I’ll only ever recommend products I’ve actually used and loved.

1. Are you an aisle or window? (Now I’m a middle, because car seats have to be on the window.)

2. I always love Amelia Wilson’s substack but this issue was particularly relevant to upcoming holiday travel.

3. Love to see it! (NYT gift link.)

4. This is the BEST travel stroller—can handle weird pavement issues and tight tourist attractions, no problem.

5. These no-mess coloring books are one of my go-to travel toys and they’re great for restaurants too!

If you’d like to re-create our Boston staycation…

This is an abbreviated version of my Boston destination guide, which will go out to paid subscribers in a few weeks. If you haven’t already, consider supporting Travel with Toddlers with a paid subscription.

Okay, on to the staycation stuff.

Trip strategy and itinerary:

I think a staycation should be 2-3 days, max. Especially if it’s a place you know super well, staying over is really just a way to make the most of your trip and make it easier by staying overnight rather than schlepping all of your stuff all the way in and out of the city.

Where to stay:

• Hyatt Centric Faneuil Hall (c/o) is in a cool old building—they have the original mail slots and everything, which my toddler loved looking at—and it’s situated right above the Old South Church, super close to Faneuil Hall. (No pool)

• Dagny Hotel Boston (c/o) is two blocks away from the Aquarium and basically on the Greenway. The hotel recently did a renovation so it feels funky and cool. They included toys in our hotel room to borrow for the duration of our stay which was especially nice—definitely one of the most kid-friendly hotels we’ve stayed in. (No pool)

• Renaissance Seaport is way further down in the Seaport and good if you plan to explore that area, tricky if you want to go further into the city. We got upgraded to a suite that had incredible views of the harbor and more importantly for my airplane-obsessed toddler, we could see planes landing and taking off from Logan. (Yes pool!)

Where to go:

We skipped all the important historical stuff that I’d recommend if you’re from out of town and instead had some fun doing the same things we do at home, but City Version (TM) like:

• Stroller walks along the Harborwalk and the Esplanade

• Stumbling into a huge Japanese festival on the Common and watching Taiko drumming

• Sampling multiple cuisines and a free musical storytime with Berklee students at Boston Public Market or storytime at the Boston Public Library

• Playing at Martin’s Playground, Christopher Columbus Park, and Stoneman Park

• Riding swan boats at the Boston Public Gardens and the Rose Kennedy Greenway Carousel for old-fashioned fun

• Visiting touristy stuff like the New England Aquarium. (We skipped the Children’s Museum because tbh I’m too afraid of the mayhem. The Museum of Science is one of my favorite places EVER but it’s not toddler-friendly so unless you have an older sibling (7,8 at the youngest) then skip it.) Tip: If you live in New England, many libraries offer half-price passes to major tourist attractions or museums. We picked up a discount pass from our local library for the Aquarium and saved $50!

• Going to our first art museum! We did the Institute for Contemporary Art in the Seaport—I think contemporary/modern art is more kid-friendly because it often invites interaction in ways that classical/antiquities don’t—we haven’t yet done the Museum of Fine Arts OR the Isabella Stewart Gardner Museum as it’s difficult to move through the galleries with a stroller with weekend crowds, but if you had a baby who likes a carrier, you should definitely check out both of those.

Where to eat:

This is maybe cheating, but our staycation move is to get takeout or DoorDash to the hotel and then eat it in our room or one of the lounges. Dinner is trickier mood-wise for us than lunch, so we do a big sit-down at lunch usually and then quicker things in the evening, like Bartaco in the Seaport. (La Famiglia in the North End counts because we asked for pasta with butter as we were literally sitting down and it came out 5 minutes later, bless them.) I agree with most of this list from Eater, though.

Thanks for being here.

Traveling with toddlers isn’t always rewarding in the moment, especially when they’re barreling toward another baby outside the sea lion enclosure because they’ve got a pouch in their hand and you have to lunge for them (may be a true story…) But every trip gets easier and easier.

This past trip we yelled “TUNNELLLLLLL!” at the top of our lungs in the car every time we drove through. We put our hands in the aquarium’s touch tank and giggled when the rays brushed our fingertips. We named every sound we heard (truck! saxophone! airplane! garage door! walk sign!) as we strollered up and down Atlantic Ave. We ate pizza on a park bench and went down the fastest slide I’ve ever been down about a thousand times. So keep going, friends. The more you travel, the more fun it gets.

Thanks for reading,

Kayla

Thank you for supporting Travel with Toddlers! If you liked this issue, please like it, share it, all the things. It really does mean a lot. I’m just a mom in the thick of the toddler years trying to create core memories for our whole family while minimizing meltdowns—I sincerely hope this helps you do the same.