What to Pack for a Fabulously Sunny New England Staycation (Our Chic Spring Outfits!)

Oh, my dearest style adventurers! Sometimes, a girl (and her equally chic family!) just needs a little escape, doesn’t she? Not necessarily a mad dash across continents, but a charming, restorative New England staycation to sprinkle a little magic into the everyday. And so, with visions of salty air, picturesque harbors, and perhaps a lobster roll or two dancing in our heads, we set our sights on the utterly captivating Gloucester, MA this past May.

We were simply thrilled when the wonderful folks at Discover Gloucester and the ever-so-lovely Atlantic Vacation Homes decided to collaborate with us on this little jaunt – and darlings, I have so much more to tell you about those fabulous partnerships very soon, so do stay tuned!

Now, packing for Gloucester MA in early May can often feel like a bit of a stylish gamble. Typically, the May weather in New England can be a tad unpredictable – one might expect cool sea breezes, a touch of mist, and the need for cozy layers. However, the travel fairies must have been working overtime for us, because we were blessed with the most glorious stretch of sunshine! Imagine, darlings: clear blue skies and temperatures delightfully fluttering between the high 50s and low 70s Fahrenheit. It was absolute perfection for exploring historic streets, breathing in that fresh ocean air, and, of course, debuting some rather fetching spring outfits Gloucester simply adored (or so I imagine!). Get ready for a peek into our Gloucester style diary!

New England Staycation Night 1

For our stylish jaunt up the coast and a simply divine dinner at Tonno’s on our first night, the girls were utter perfection in their matching Pixielane Glitter Tank Super Twirl Dresses in Pink Glitter Ice Cream – honestly, could they be any more adorable? Meanwhile, I opted for a wonderfully comfortable yet chic Knit Mini Ballet Dress from Target’s A New Day™ line in a lovely Coral hue. To ward off any potential evening chill (and add a dash of panache, naturally!), I topped it off with a treasured old Anthropologie jacket – a true classic! You can find a similar look here – I have had it in my cart but have yet to pull the trigger!

New England Staycation Morning 1

And oh, that first morning! There’s nothing quite like waking up to the promise of a beautiful day in a new place. I’ve recently made a rather brilliant decision, if I do say so myself, and permanently added this divine pair of pajamas from Room Service in Pink Palm to my travel repertoire. They are, without a doubt, the perfect spring and summer travel pajamas – so incredibly soft and comfy, darlings, you simply must investigate! The girls, ever the coordinated duo, were looking royally sweet in their Disney’s Sleeping Beauty pajama sets (a gift from their godparents), complete with removable tutus (because why not?). Though, I must confess, little Aurora was far too excited about the day ahead to curl up with me in bed for long! 

New England Staycation Afternoon 1

That afternoon, bathed in the most glorious New England sunshine, we embarked on a mini-tour of some of Gloucester’s most iconic sights. The girls were the epitome of seaside chic in the most adorable matching sets (complete with the cutest sunglasses!) that I snagged at TJ Maxx – you can find a similar look for toddlers here and for older girls here. As for yours truly, I twirled about in a darling matching top and skirt set from St. John’s that was on a super sale (a true fashion miracle, darlings!). You can find a similarly fabulous vibe here or here. I must say, we received compliments all day long – it seems Gloucester appreciated our stylish efforts!

New England Staycation Night 2

And the fun didn’t stop when the sun went down! That night, we had an absolute blast at Cape Ann Lanes for some cosmic bowling – and darling, the girls were literally glowing! They looked too sweet for words in their Pixielane Simply Soft Short Sleeve Be Happy Dresses in the Rainbow Cupcakes print. I kept things a bit more casual but still fun in a comfy pair of jeans and the Aurora baseball jersey my sister so thoughtfully picked up for me on her last Disney World adventure. You can’t snag that exact Aurora one anymore, but I hear they still have a few in the Cinderella version here if you fancy a bit of princess power for your next casual outing! 

New England Staycation Morning 2

For our final day, we embraced a wonderfully relaxed and casual vibe. The girls looked utterly charming in their comfy jeans paired with matching Minnie and Daisy tee shirts – a fabulous find from Costco (you can get a similar adorable tee for your littles here). And can you believe it, I just stumbled upon an almost matching tee for myself here which I might just have to snap up for future twinning moments! For my own casual-chic ensemble, I turned to my absolute favorite Wooden Ships sweater, the one that cheerfully declares “Beach Babe” in pink, paired with some perfectly relaxed We The Free Brette Cropped Wide-Leg Jeans from Free People. It was the ideal comfy-cool look for soaking up those last lovely Gloucester moments. 

And just like that, our darling little Gloucester getaway came to a sun-kissed close! From stylish dinners to cosmic bowling and simply soaking in that charming New England air, it was the perfect reminder that adventure (and fabulous outfits!) can be found just around the corner. 

A huge thank you once again to Discover Gloucester and Atlantic Vacation Homes for helping make this sweet escape so memorable. Can’t wait to share more with you! Until our next stylish sojourn, darlings, keep exploring and always, always pack something fabulous!