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Fly yourself – and your wine – for free with rewards points

There's more than one way to have a wine flight – and rewards can help you accomplish it at no additional cost

Summary

What’s better than the credit card benefit of free luggage, or the rewards benefit of free flights? How about complimentary wine tastings and taking home a case of local wine at no additional cost?

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I’ve had a busy summer in Portland, Oregon. While I haven’t been on too many international trips the last few months, I’ve been out and about road tripping the Pacific Northwest.

I’m racking up points for the big trips I’m planning for the fall – and playing hostess for way too many friends who have discovered that Oregon’s wine country is an amazing domestic holiday destination.

If the mountains, waterfalls and beaches of the upper left coast aren’t enough to garner interest in Oregon, Washington and Northern California, maybe another reason is: free wine for frequent flyers.

Yes, I realize there are “regular” ways for frequent travelers to get free wine when they travel – like lounge passes and first-class upgrades. However, I’m talking about free wine that you get to drink outside of the airport.

See related: 5 reasons to use your rewards points for travel now

Fly your wine for free

Since 2013, Alaska Airlines has been helping the world fall in love with West Coast wines through a program called Wine Flies Free.

The two most important benefits of this program that you should know are:

  1. Mileage Plan members can taste wine for free at over 300 Oregon and Washington wineries when you show your inbound Alaska Airlines boarding pass.
  2. You can check a case of wine – with no baggage fee – when you depart from one of 30 West Coast wine destinations (Washington, California, Idaho, Oregon) on an Alaska Airlines flight.

While Wine Flies Free is by no means a new benefit for frequent flyers, I was reminded of this great program when my friend, Jenee, a fellow points lover from Washington D.C., came to visit and announced that wine tasting was on her list of things to do in Portland.

Pondering over a Pinot Noir tasting at Cana’s Feast – one of my favorite Willamette Valley wineries – I got to thinking.

To take advantage of Wine Flies Free, you don’t need to have a paid ticket. Rather, if you use reward points to book your travel to your wine tasting destination, then both you and your wine can fly home for free!

Surprising savings

As I thought about it more, I realized that by combining free wine benefits with free rewards flights, you could easily rack up some powerful rewards savings on a wine tasting vacation.

Since I was spending a week in wine country with Jenee, we decided to see how many grapes we could save on travel and tastings by combining all the benefits into one vacation.

Here’s how it all added up:

  • Alaska Airlines return flight (DCA-PDX): Saved $612 by using 25,000 Mileage Plan points earned on the Alaska Airlines Visa Signature® credit card.
  • One night at the Holiday Inn Express Newberg Wine Country: Saved $190 by using 20,000 points from the IHG® Rewards Club Premier Credit Card (because you can’t drive home after four free wine tastings).
  • Checked baggage two ways: Saved $60 with Alaska Airlines Visa Signature free bag benefit ($30 each way for first bag).
  • Checked case of wine one-way home: Saved $40 with the Wine Flies Free program.
  • Wine tastings atfour Willamette Valley wineries: Saved $60 with Alaska Airlines Boarding Pass for Mileage Plan members.
  • Wine Tastings at two Portland Urban Wineries: Saved $30 with Alaska Airlines Boarding Pass for Mileage Plan members.

Jenee’s savings added up to $992.

Tips to save on your own wine-and-fly adventure

Want to trade miles to try some Columbia Valley Malbecs for yourself? Here are my top tips on planning a West Coast wine holiday with Alaska Airlines.

Alaska flies into dozens of small airports with easy access to wine country. While regional flights to small towns like Walla Walla, Washington tend to be pricier than flights into a hub city like Seattle, you can often add a leg into the rural airport for no extra mileage cost when you’re booking the ticket as a reward.

You’ll not only save money, but you’ll also save yourself the three-hour road trip – and leave yourself more time for sipping Syrah.

You can expect to pay 12,500-20,000 Alaska Mileage Plan points each way for a domestic flight to West Coast wine country, regardless of your point of origin.

If you don’t have Alaska Airlines Mileage Plan rewards points (because you didn’t know before that Alaska Airlines is awesome), you still have two rewards options for getting your wine adventure on:

  • You can join the Alaska rewards game now (no matter where you live) by adding the Alaska Visa Signature credit card to your repertoire. Even if you don’t live on the West Coast or fly west often, the points are still valuable for international travel on 18 partner airlines. With the current Alaska Airlines Visa Signature card sign-up bonus of 40,000 miles (after you spend $2,000 on purchases in the first 90 days), you’ll easily have enough points to vacation for free and get your wine (and yourself) home.
  • If you aren’t sold on adding an additional card to your wallet, you can use the flexible points you earn in a program like Chase Ultimate Rewards (from spending on your Chase Sapphire Reserve®) to purchase a reward ticket on Alaska Airlines.

What if you’re not into wine? (Why are you still reading this?) Check back here when the snow starts falling. Alaska Airlines also has a program that lets you ski free at 13 different resorts across eight U.S. states and Canada – with a same-day boarding pass! Also, pineapples fly free on Alaska when you’re traveling from Hawaii.

Cheers to free flights and free wine!

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Credit Card Rate Report Updated: October 16th, 2019
Business
15.18%
Airline
17.11%
Cash Back
17.25%
Reward
17.13%
Student
17.29%

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