This article is part of our Cocktail Chatter series, where we dive into the wild, weird, and wondrous corners of history to share over a cocktail and impress your friends.

We’ve all been there. You go on a vacation, get over-excited about all of the wine you try, and end up lugging a full box of bottles around, unsure of how you’ll be able to get it home. What starts as a fun shopping spree can end up as a serious hassle: Some wineries aren’t able to ship cases of wine directly and paying shipping fees yourself can be seriously costly, which puts travelers in a pickle. Therefore, many often opt to not purchase wine on trips at all — which can be a bummer if you discover a new favorite bottle.

Well, luckily, Alaska Airlines understands the needs of traveling wine lovers. The airline launched its Wine Flies Free program in 2014 to solve the pesky problem of wine transportation, allowing patrons to check an entire case of wine — yes, up to 12 bottles — completely for free from the Sonoma area. All guests would need to do to participate is sign up for Alaska Airlines’ free Mileage Plan membership, and properly package the wines in a protective shipping container.

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The promotion caught on and became wildly popular for those frequenting wine country, prompting Alaska Airlines to expand the program to all of its wine-focused destinations in Washington, Oregon, Idaho, and California. Now, you can fly with a case of wine for free from a total of 32 cities.

“Wine and food are huge passion points for travelers when choosing their next travel destination,” said Natalie Bowman, Alaska Airlines’ managing director of marketing and advertising. “Our Wine Flies Free program makes it easier for our guests to experience some of the country’s best wine regions and take their favorite wines home.”

Alaska Airlines took its dedication to wine a step further in 2019, when it started hosting wine tastings of local bottles in its Portland Lounge for Oregon Wine Month every May. Then in 2021, the company partnered with both the Washington Wine Commission and Idaho Wine Board to arrange free wine tastings at certain wineries for customers who flew there on Alaska.

So whether you’re revisiting classics in Napa Valley, checking out new producers in Walla Walla, or tasting by the beaches of Santa Barbara, taking advantage of the Wine Flies Free program might be your best bet. And as a bonus, that Alaska Airlines boarding pass might get you some free wine mid-trip, too.