● A Note on Itineraries Going Forward
As I start sharing itineraries here, each one will open with a little context: when the weekend happened and who it was planned for. And each one will close with what I’d do differently. This one’s a little silly, but it was a real snafu at the time. From here on, you’ll always get the backstory, plus one thing I’d change to make the weekend even better.
● The Weekend
This was one of my very first weekends hosting in the city: five best friends sharing one 700-square-foot apartment. There was a pull-out couch, an air mattress on the floor, and girls piled into the bed with me (my husband, bless him, graciously timed a boys’ trip for the same weekend). We were squished, but thankfully, one entire wall of that apartment was a mirror, which made it perfect for a girls’ weekend of getting ready together.
It was seriously one of the best weekends of my life. Since moving to New York, having the people I love travel to be with me has become one of my love languages. So planning this itinerary and getting us all around the city was my way of giving that love right back to them. We were young, wild, and free, and I truly had the time of my life.
● Best For
A long weekend for your closest girlfriends — shopping, a little culture, and with this crew, of course, a few cocktails. This one leans into early fall in the city: lots of time outdoors (day and night), a little glamour, and plenty of room for spontaneity.
● Day One
Soho Shopping & Rooftop Drinks
- A morning spent digging through vintage racks
- A stop at Studs in Nolita for a spontaneous ear piercing
- Sunset cocktails at Mr. Purple
- Dinner at The Tyger
- A nightcap and dancing at Le Bain in Chelsea
● Day Two
Blow-Outs, Ladurée & the Harbor
- Coffee and a slow morning
- Blow-outs at New Ocean Salon
- Pastries at Ladurée in Soho
- An afternoon at the Whitney Museum
- A sunset harbor cruise with Classic Harbor Line
- Sushi dinner at Momoya Chelsea
● Day Three
Central Park & a Little Team Spirit
- Cocktails and live music at Tavern on the Green
- A picnic in Sheep Meadow under the fall foliage
- Cheering on the Vols at Printer’s Alley
- Dinner at Rosie’s
● What I’d Do Differently
Get to the boat early. We missed our Classic Harbor Line sunset cruise, and the kicker is we just barely missed it. They wouldn’t let us on, and I stood there watching them untie the boat from the dock. I won’t divulge just yet why we were those few minutes late. I’ll just say this crew has our own idea of fun, and the five of us have some pretty wacky traditions. So we had to come back for a later departure, and in the meantime we walked to happy hour in the rain, looking like absolute crazy people in matching slicked-back buns. (Would I change the buns? Probably not. In twenty years we’ll look at those photos and wonder what on earth we were thinking, and I’ll still love them.)
By the time we made it back to the pier, our sunset cruise had turned into a nighttime cruise. And honestly? Lady Liberty lit up against the dark harbor was one of the prettiest things I’ve ever seen (that’s her in the Day Two photo). Still, the sunset was the whole plan, so give yourself a real cushion to get to the pier and check in. This city has a way of swallowing the last fifteen minutes regardless of who you are with.
Here’s to the girls who make the trip, and to the next reason to get us all back together. Tell me your favorite girls’ trip memory below.
Xx,
Caroline
Leave a Reply