It is permitted to check a case of wine at the airport when flying. 

Esther is on vacation this week and asked if I would take over her newsletter. A conversation we shared before she left ended up inspiring this piece. - Jess Lander

Travel is finally rebounding after two years of staying (mostly) close to home. Travel reservation website Expedia has gone as far as to label 2022 the year of the GOAT — Greatest of all Trips — following survey results in which 65% of respondents said they planned to “go big” on their next trip. 

So, this seems like a good time to share my greatest air travel hack: wine.

I rarely travel without it. If it’s a quick trip over a couple of days, I wrap two bottles in jackets and jeans and stuff them in my luggage — I consider myself very lucky to have not broken a bottle yet — but for anything that’s five days or longer, I bring either a six pack or a whole case. 

I’ve found that wine can be just as useful and necessary as underwear in a number of travel scenarios, including family trips (for obvious reasons), girls trips, weddings or really any situation where you’re sharing a space with a group of people and spending time "hanging out." 

Bringing your own wine saves money and time at the store when you arrive at your destination. It’s also the only way to guarantee you’ll have something on hand that you enjoy drinking. Major cities are bound to have some quality wine shops around, sure, but more remote or far-away destinations, like National Parks and tropical islands, often lack a wide selection. What they have is usually marked up significantly. 

Still, most people seem surprised, or even amused that I go to the trouble, usually because the idea never occurred to them or they didn’t realize it was permitted on airplanes. That makes sense given most airlines banned alcohol on their planes altogether during the Pandemic. But not only is flying with wine permitted, you can do it for free.

One of my favorite, little-known travel facts is that Alaska Airlines has a Wine Flies Free program that covers travel to and from 32 West Coast destinations, including San Francisco. You can access it by signing up for the airline's free mileage plus program. This means you can travel with up to one case of wine (weighing 50 lbs or less) in addition to your regular baggage allowance. Alaska has hubs near many wine country destinations, including San Luis Obispo and Washington's Woodinville and Walla Walla, making it both easier and cheaper to bring home any wine purchased during a trip. Shipping wine is incredibly expensive; if you're curious why, Esther dug into that in this piece from 2020.

But you don’t actually have to be visiting Wine Country to take advantage of Alaska’s program. Use it for a bachelorette party in Palm Springs, for instance, or an extended remote work stay in Los Angeles. 

If you’re not flying Alaska, you can still check wine on any trip, similar to checking skis or golf clubs, onto a plane. When allotted a free checked bag — sadly, a rarity these days — I stuff everything else in my carry-on and save my freebie for a case of wine. In the event you have to pay for it, it’ll still be cheaper than shipping, or purchasing new bottles on your trip. A checked bag typically costs $30-40, while shipping a case of wine in the U.S. can cost roughly $50-100, depending on the destination. Note: It’s prohibited to mail wine as an individual; you have to purchase through a winery or online retailer and then pay for them to ship it. 

You can purchase a wine suitcase (like this one) that will properly protect your bottles and give the impression that you’re the kind of person with a cellar full of rare and expensive Burgundy. These suitcases typically cost a few hundred dollars — Alaska offers some at a 20% discount through its program — but are great investments if you travel often. Personally, I go the less-attractive, yet proven box route. For less than $15, my local packing store in Napa sells wine shippers, six or 12-pack boxes with protective foam inserts. Before each trip, I pack one up with a selection of wines — and maybe even a couple of bottles of liquor or an extra pair of shoes (how would they know?) — curated for the itinerary and weather. I tape it up, then sharpie “fragile” on all sides. 

Alternatively, you could use old boxes from past wine purchases (I always save mine for this very reason), or ask a local winery or wine shop for one. The most difficult part of the whole endeavor is carrying the box to and from the airport, but it fits on the top of most suitcases, and if all goes well, you won’t have to take it home.