Flight Club: Annie On Her Way To (A Beachside) Heaven On Earth

Style editor Annie Georgia Greenberg's favorite season is summer. Her second favorite season is a tie between fall and spring, because they're closest to summer (any guess what her least favorite is?). Always heading to some beach, rooftop, or opportunity to get that vitamin D, A.G.G. is the queen of warm-weather vacays. Her latest trip to Martha's Vineyard might be her sunniest one yet.
Where are you coming back from?
I am coming back from my first-ever trip to Martha's Vineyard. It was actually a very harrowing travel story, mostly on the way out. I got stuck in the cluster of delays when the system went down in Washington. My flight got to Boston safely. And what started out as an hourlong layover turned into an 8-hour stint in the Boston airport. Despite my anxiety-prone personality, when I'm traveling, I tend to take it easy. There's only so much you can do, after all. So my boyfriend and I checked our carry-on bags on the second leg of our flight, left the airport, got some lobster at a Yelp-recommended dockside spot and returned to the airport for about five more hours of eating junk food and playing travel chess. Checkmate! What’s something that happened that you will never forget?
We got to our rented house (where we stayed with my boyfriend's family) in the dead of night due to all of the flight delays. We had no concept of where we were, much less what the house looked like. Waking up early the next morning was something like arriving in heaven — especially after the previous day's travel hell. The house was adorable: all natural light, birds chirping out our window, white linens, and wicker furniture everywhere. But the best part was walking through the still-silent kitchen out to the porch and realizing that our house was directly attached to a farm next door. There were three horses grazing yards away from us and we were able to feed them carrots as we sipped our coffee. Definitely a serene memory I'll call upon in the months to come. What’s something that happened that you want to forget, ASAP?
I really like playing tennis. Unfortunately, tennis also likes playing me. Like a fiddle. I talk a big game and play with people far better than me. But I'd really like to forget those defeats so that I can carry on with confidence on the courts.
What’s in your carry-on?
One book, one journal, one computer. Sneakers, two pairs of sandals, flatforms, a week's worth of bras and underwear, two mini remote-controlled helicopters, candy, two magazines, toiletries, and travel chess. And that's just the tote under my seat.

What's your favorite outfit in your suitcase and where are you wearing it?
When I was in Seattle with Paula, I bought the most adorable, nautical vintage jacket. Truth be told, I bought it specifically for this trip. It has these horn-and-rope toggle buttons that I love. I wore it over this floaty and easy-to-pack Tibi dress with hand-me-down Prada platforms from Christene. Well-rounded, comfortable, and perfect for the lobster cookout I wore it to.

What are you wearing right now?
Mother Denim high-waisted jeans, a vintage Harley Davidson T-shirt with no bra, vintage Gucci slip-on flip-flops (kind of like the new Future song), a vintage straw hat, and a red bandana.
What are you doing in your seat right now?
One of my favorite contemporary poets, Richard Siken, just came out with his second book. The more I read, the more I write. And Siken is so good I try to read it slowly. I try to savor it so that it lasts longer. I'll read one poem then write a little on my own or play chess. Or request more mini chocolate chip cookies — JetBlue, baby! What souvenir are you looking to bring home?
I always hope to come home with some kind of content as a souvenir. My boyfriend is a director/videographer, so we aim to make a video wherever we go. Either that or, let's be honest, some great vintage. What’s your best packing secret?
Your carry-on bag is your best friend. I put all my shoes, undies, workout clothes, and sleep clothes in my tote bag, so it frees up space in my roller carry-on. I also use soft totes to hold toiletries and bring various bandanas that can double as blindfolds on flights and make repurposing the same outfits feel different.

More from Travel

R29 Original Series