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Portland the Third: Travel with Four

As I mentioned in my parking post (thanks for all the feedback calling me crazy after I said so myself, btw!), we were back in Portland, Maine, our favorite local vacation spot, to test out traveling with four. Things were definitely different with a 2.5 year and 2.5 month old, but the trip went well and we’re ready for more. Here are some things I observed about traveling with four.


All credit goes to my wife for this one. I’m just recently back at work so I literally gave her a pile of my clothes and she did everything else. With two kids, it’s double the diapers (potty training only half complete), wipes, eating stuff, clothes, baby carrier – all the stuff adds up.

Jess, being a miracle worker, ended up getting all of our stuff into two carry on size suitcases (one is like European carry on sized). All of our clothes fit in one, all the child related accessories fit in another. It helps a ton that we don’t really need to bring toys for M – she loves playing with all the junk in hotels (read: ice bucket) so we banked on that and were rewarded.

Including the backpack that was on my back when I took this, this is everything we brought to Portland
Including the backpack that was on my back when I took this, this is everything we brought to Portland

On top of the two suitcases, we brought my backpack, Jess’ purse, a plastic bag with our boppy in it, and a diaper bag. Plus two strollers (really need to invest in some sort of sit and stand situation). So, technically, we could have gotten onto an airplane without checking any bags. Hey, you can still kinda travel light with two kids under three!

Getting Around

I know I got a lot of flak for not valeting the car, but I ended up only having to move my car once (for the record, even though it worked out very well doesn’t mean I think I made the right decision, but what’s done is done). The reason for this was because two strollers makes a twenty minute walk a much more cumbersome undertaking than it used to be, especially when you factor in stopping to deal with a fussing infant or stopping because a ridiculous toddler insists on pushing her little brother’s stroller.

So we ended up driving to a lot of the things we had walked to in the past, so I was glad to have my car readily accessible. And even though we were there on the weekend I had no trouble finding parking whenever we got back downtown. The hidden cost of having two strollers is it makes everything feel more cramped when you get inside, nobody has any free hands, etc. – so it was often just easier to drive. It might be easier with a sit and stand but like I said that’s next on the research list.


I’ll have a more comprehensive look at our various eating and sightseeing activities later, but eating went pretty smoothly. We skipped Fore Street just because I didn’t want to queue and I didn’t have reservations, but we did make it to Eventide Oyster Co. with both kids. Google has a neat popular times graph that we used to determine when we went (330 PM on Friday), although the graph isn’t quantitative and it’s mostly common sense. Still, a nice feature.

EVENtide popular times

Eventide was so empty it would have been fine although my parents met us there (they decided to come to Portland but stay elsewhere) so that further alleviated any pressure we were feeling. The stroller space situation did come into play though.

Having a 2.5 year old and a 2.5 month old in the same restaurant isn’t too bad – one parent eats and feeds M and then we switch. If M gets antsy whoever’s not eating goes for a walk in the end.

Getting to eat oysters was a real victory and made our vacation a success within the first hour
Getting to eat oysters was a real victory and made our vacation a success within the first hour

Once again, free hotel breakfast came in very handy. Although we hit our usual Portland breakfast haunts, it was great knowing we could get M food as soon as she was up to avoid hangry-ness. Jess says that might be the number one feature we look for in hotels going forward and I am inclined to lean that way as well.


We stayed once again at the Hyatt Place Old Port. Even though we didn’t get upgraded to a suite this time, the room was plenty big. At night we each slept with a kid in separate beds (rotating as necessary for feedings); we requested a pack and play but didn’t end up using it at night.

Big enough
Big enough

M did, however, insist on napping in the pack and play for some reason. I thought it was weird but she went to sleep and we got a good photo op so everybody won. Once again we avoided the tiny pool, but other than that the hotel and staff was awesome. I was at first hesitant to drop the 24K Ultimate Rewards needed for two nights but ultimately decided to just bite the bullet – what am I saving them for, really?

One occupant only, please
One occupant only, please

Final Thoughts

Overall, having a second kid on vacation didn’t create as many logistical problems as I had feared. I think when H becomes a toddler things might change, but for now (and for our upcoming trip to Disney in January), I think we’ll be okay. We’ll see what things are like when the kid starts walking though! More on how awesome Portland is (again) in a later post!

Portland Light

Just an average joe trying to fly his family for less

4 thoughts on “Portland the Third: Travel with Four”

  1. Check out the Phil and Ted’s strollers with doubles kit. Used to be called the Sport, now Navigator. There is one called the Classic on Amazon. Double wide strollers are ridiculously hard to handle in tight spots like stores. Double long ones are way to big. It’s not cheap but, Phil and Ted’s are the best compromise.

  2. did you have any noise issues from bars outside the hotel (or even from w/in)? a good chunk of reviews state noise issues with music and drunken ruckus around 130am ish when bars close and everyone spills out into streets.

    1. The hotel provides earplugs, so it can be an issue. The last time we stayed there (there’s a post somewhere), we were facing Fore Street and it definitely was an issue. This time we were facing the back and I didn’t hear anything, so maybe request a room facing the back?

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