Connecticut. Rhode Island. Massachusetts. One bag. No checked luggage fee. I’m calling it a win.
When I booked my Breeze Airways flight to New England, a whirlwind trip that had me visiting my cousin in Connecticut, squeezing in a press trip to Rhode Island, and heading to Massachusetts to watch my brother-in-law perform in a stunning recital — I made a decision that was equal parts thrifty and strategic: carry-on only. Eight days, three states, one bag, and a backpack.
And honestly? I nailed it. So, I figured that I’d let you in on my little secret. I’ve written about how I use a “toddler” method to pack before, but there are always a few items that I sneak in, or add (or subtract) depending upon where I’m going. Since this one spanned not only three different states, but three distinctly different REASONS to be there (CT/visiting my cousin, RI/press trip, MA/a recital), there had to be a bit of a difference in my packing theory…oh, and this was the first time I decided to buy the CHEAPEST seat on a plane (in otherwords…I bought no seat and kept my fingers crossed that I wouldn’t be too squished in the middle as it was less than a 3-hour flight).
Here’s what made the cut.
The Snacks I Was NOT Going to Pay $15 For
Let me be real with you: Breeze Airways is budget-friendly in all the ways that matter until you’re sitting on the plane parched and staring down a $6 bag of pretzels. They do offer complimentary water, coffee, and tea, but beyond that, you’re on your own. So I packed my own, and I did it in style.
I slipped a stash (those are some BIG BAGS) of DM Snacks into my backpack before I left, and if you haven’t tried their coconut curry peanuts, you are genuinely missing out. They are chef’s kiss, just the right amount of heat and crunch, and they feel like a treat rather than sad airport desperation food. Into the front pocket they went, easy access, no regrets.
FYI, I love them all, but those and the Thai Chili Peanuts are my absolute faves.
- Pick them up at DM Snacks
- FYI, they’re less expensive than those little bags on the plane, and they’ll last your whole trip PLUS if you conserve, you’ll have some for the trip home.
The Screen That Made the Flight Feel Luxe
Cheap ticket, not cheap experience. That’s my motto. I also tucked my MobilePixels Fold into my backpack. This genius little portable monitor hooks right up to your phone (or laptop) and is so slim and lightweight you almost forget it’s there — until you’re watching a movie on what feels like a real screen instead of squinting at your phone like you need new glasses. It’s bigger than the built-in screens on most planes used to be, and it folds flat into practically nothing.
But here’s the bonus I didn’t fully anticipate: I had a mountain of work to get through, and plugging the Fold into my laptop gave me dual monitors at 30,000 feet. I got more done on that flight than I do on some full work days at my desk, which meant more time for exploring once I landed. Worth every penny.
- Whether on the plane or at work, this is a lifesaver. Pick one up at Mobile Pixels Fold
The Little Tablet That Saved My Stomach
Speaking of flights (and boats, because Rhode Island), I never travel without Boiron’s MotionCalm tucked into my backpack. It’s a homeopathic remedy for motion sickness and nausea that dissolves right under your tongue, no water needed, which means it works fast and travels easy.
Whether it’s turbulence on the plane or the gentle rocking of a boat in Narragansett Bay, this little tube is my secret weapon. I’ve been a believer in Boiron products for years (like Oscillococcinum, and now I don’t leave home without this one.
- Available at Boiron and local retailers
My Not-Complicated Skincare Routine (That Keeps People Guessing My Age)
I’ll let you in on a secret: my skin looks the way it does in my 70s because I keep it simple and I don’t sleep in my makeup. Foundation? Rarely. Clogged pores? Never, if I can help it.
I packed my Akar Skin bag, already fully loaded with everything I needed, including their Soothe Cleansing Milk, Soothe Moisturizer, Soothe Face Oil, and Nourish Lip Butter – which I use on the plane to keep from drying out from that drying air. Clean, thoughtful ingredients, and it all fits neatly into one organized pouch. No digging through a makeup bag the size of a toaster. Just everything I need, nothing I don’t.
My skin definitely needs soothing when I travel, so it’s perfect. Of course, everyone’s skin is different, so check out their products.
- My suggestion is to start with The Starter Kit and go from there.
The Rain Boots I Refused to Leave Behind
Last year, I was in Boston at this time for the Pride Parade. It didn’t rain. It poured. I was soaked to places I didn’t know I even had, and after that, I swore I’d never be caught without proper footwear again. So this time, in went my Totes Chelsea Ankle Rain Boots. FYI, the trick to fitting boots in a carry-on with everything else? Stuff them.
My socks and underwear went inside the boots, saving precious space and keeping my bag organized. Yes, these are simple black, elegant, rubber boots. And they are, structured enough to look intentional even with jeans, and actually waterproof when New England decides to do what New England does.
- Never be caught in the rain again when you pick up a pair of Totes
The One Pair of Shoes That Did Everything
Here’s where packing gets strategic: I knew I had a formal recital in Boston, dinners out, shopping on Newbury Street, a gondola ride in Providence, and zero room for heels. So I turned to my Tieks in taupe. Those iconic blue soles. That ballet flat that somehow manages to look polished enough for a recital and comfortable enough to walk a city for hours.
Whether I was in basic black or wearing color, this one neutral pair worked for everything, all week. It’s the kind of shoe that earns its real estate in your bag. I know you know them, I know you love them. I know it’s difficult to decide which colors to get (because they have so many). Just make sure that at LEAST one of your pair of Tieks by Gavrielli is in a nice neutral color. You’ll be glad when you realize you have to fit everything into that small bag.
- Go ahead, choose a pair. They’re available at the Tieks Boutiek
The Bag Charms That Changed Cities With Me
I traveled with my trusty small black crossbody the entire trip, but I brought two Theo Grace bag charms to let the bag tell a different story depending on where I was. For Boston, I clipped on the Lucky Me Clover charm because nothing says Boston more than a clover, and I was absolutely leaning into it.
For Providence, I switched to the Fortune Found Horseshoe charm, which felt deeply personal. My family owned racehorses in Rhode Island, and that little gold horseshoe felt like wearing a piece of home.
These charms are the smartest packing hack for your accessories. They take up virtually no space (I hung both from my backpack for the flight), they instantly elevate a bag, and swapping them out makes it feel like you brought entirely different accessories. I’m obsessed.
- Check these and more out at Theo Grace
The Clothes That Worked Hard So I Didn’t Have To
I kept it simple: a sundress, a striped top that works as a dress or styled as a skirt-and-top situation, a pair of jeans, a t-shirt, and my favorite linen overalls. Everything mixed and matched, everything worked with the rain boots and the Tieks. Did I stick to the plan perfectly? Well, I may have wandered into a J.Crew outlet and walked out with a shirt for $12 and a black vest from the clearance rack that gave me full Annie Hall energy, and I have zero regrets about either. Sometimes the outfit finds you.
The Takeaway
Eight days. Connecticut, Rhode Island, Massachusetts. One carry-on, one backpack, zero checked bag fees, and a trip I’m already dying to tell you about in full. There were places I visited, some brand new, some old favorites, that absolutely belong on your New England radar whether you’re planning a trip or lucky enough to live there. That post is coming soon. For now, just know: you can do New England right without dragging a suitcase through cobblestone streets. Pack smarter, not heavier.
