Overview
Alaska Airlines has run Wine Flies Free since 2007, and Oregon is the only state where every airport the airline serves participates. If you’re flying home from Portland, Eugene, Medford, or Redmond, a case of wine goes in the hold at no charge.
The terms are straightforward. You need to be 21 or older and a member of Alaska’s loyalty program, which is free to join, and your membership number has to be on the reservation before you get to the airport. A case means one box holding up to twelve bottles and weighing 50 pounds or less. You can buy all twelve from one winery or mix bottles from a dozen different stops — as long as they’re packed in a single container, they all fly free. Anything beyond the first case gets charged as normal baggage.
Packing matters. The wine needs a proper shipping box with cardboard dividers, styrofoam, or bubble wrap. Most tasting rooms keep these on hand and will pack for you if you ask. TSA prefers the box left unsealed so it can be inspected, so don’t tape it shut before you get there. Check it with an agent at the Alaska ticketing counter rather than at a kiosk.
The part fewer people know about is the other direction. Show your inbound boarding pass along with proof of membership at any of more than 300 participating Oregon wineries and your tasting is complimentary. The pass has to be recent — within ten days — and free tastings are often suspended on holiday weekends and during special events. Check this site to see who is participating: oregonwine.org/wineries/?feature=oregon-wine-flies-free
Note: I’m not sure how “stale” this list is so it might be a good idea to reach out to anyone specifically.
Over a three-day trip with two tastings a day, that’s real money before you’ve bought a bottle.
