Saving at by Double Dipping

Thursday, February 7, 2013 is our nation's largest online wine retailer. They're the only national retailer I'm aware of that's gone through the trouble of obtaining a Massaschusetts retailer license so they can legally ship wine to residents here. They've gone to similar lengths in other states and as a result have the widest reach of any online wine retailer.

But their prices are high.

And they're not exactly the most favored of wine retailers thanks to antics like a sting operation targeted at other wine retailers who ship illegally.

So as consumers we interact with them in a "special" way. We'll buy from them if there's a good deal to be had, but we don't exactly "like" them.

One of the central problems, from a consumer's perspective, is how expensive shipping is. This is true for wine in general but seems to be pricier than most. So this post will serve as a description of a way to get their fully loaded prices down out of the stratosphere with their Steward Ship program combined with a little trickery called The Double Dip.

Here's how to do it, step by step.

Step 1: Sign up for their Steward Ship program

Steward Ship is their equivalent to Amazon Prime. It provides shipping for 1 year for a fixed price. It "retails" for $49 but they've been known to offer it for half price from time to time. Go here for more information if you don't have it already, but if you can wait until it's on sale:
Steward Ship shipping for a Year icon

Step 2: Buy a Gift Card through an Online Portal

This is step one of the double-dip. You'll can get "x" % cashback by buying a gift card through an online Portal. I chose uPromise because when I was performing this experiment they explicitly stated they offer 5% back on gift card purchases:

Bonus: When I ordered the gift card I was emailed a code for $10 off my next order of $75 or more.

There are tons of different cashback portals out there. Some of my favorites lately are Ebates and Fat Wallet, not to mention shopping portals associated with credit cards.

There are even sites which try to dynamically compare cashback amounts across the various portals. Try and

Step 3: Redeem that Gift Card through an Online Portal

Once my gift card arrived ( chose to mail a physical gift card out) I went back to to redeem it through a different online portal. I chose SavingsWatch this time because it offered the largest percentage at the time - 7.5%.

I loaded up my shopping card with $75 worth of wine, applied the $10 off $75 coupon I received when buying the gift card, used my Steward Ship benefit that's tied to my account for the year, and applied the $25 gift card. The remaining balance went on my credit card. I was able to find a few wines at good prices I was genuinely enthusiastic about purchasing.

Pro tip: Try sorting on by savings - one time I found a wine being sold for less than $2 on sale. Not that I was enthusiastic about trying that wine but it was pretty amazing they'd conceivably ship it out for less than $2 fully loaded.icon

A few days later the transaction appeared in my acount.

Notice in the image below how each of the 4 bottles I ordered were credited for cashback. The $10 coupon was charged back against that, but the free shipping didn't come into play (nicely) and most importantly the amount I paid for with the gift card didn't negate the cashback. A successful double dip!


Ironically, two things went wrong while performing this experience I didn't expect.

First, uPromise still hasn't credited me 5% of the $25 gift card purchase although their terms explicitly say gift cards qualify. I called them about the missing transaction and they said it can take up to 40 days to process. I'm not so much concerned about the $1.25 of course, but it's annoying chasing these things down. Some portals are better than others. uPromise has frequently failed to credit me for transactions.

Second, my order actually still hasn't arrived. has reliably fulfilled orders for me in the past, and this one has been mostly FedEx's fault, but after missing a couple of delivery attempts and requesting it be routed to a nearby FedEx location the order seemed to go into no man's land. It illuminates one of many ways this is not the most efficient way to get a few bottles of wine delivered.


In all, this technique should save the following on this sample $75 order:
  • 5% back on the original gift card purchase (I did just $25 as a test but you could do more)
  • 13.3% off (thanks to the the $10 off $75)
  • 7.5% back when redeeming the gift card through an online portal (the double dip)
uPromise hasn't paid the 5% back yet, but I think they will if I submit a missing transaction after 40 days have elapsed. Plus the wines I chose were on sale and priced pretty well. The Sanford Pinot Noir sells in the $30s at most online retailers in the country.

Here's the potential net of it:

$75 - 5% - 13.3% - 7.5%
$75 - $3.75 - $9.95 - $5.62 = $55.68
That's a total savings of 25.76%

That's like paying $19.23 fully loaded for that $25.99 bottle of Sanford that sells for $35 and up in most stores. Plus no tax on wine in Massachusetts.

And that doesn't include the cashback/points/miles/signup bonuses you might be getting on your favorite credit card. If you consider that you might call this a triple dip.

The Steward Ship benefit has cost me $25 or $35 per year over the last few years. I typically use it 6-12 times a year. What's nice about it is that you can ship out a single bottle if you like. For example, when the 2010 Cosme Gigondas got 95 points from Spectator I ordered a single bottle and it showed up a couple days later.

Subscribe to The Wellesley Wine Press and I'll mention next time I see Steward Ship on sale. Sometimes Steward Ship also includes a Wine Spectator subscription extension.


The actual amounts you could potentially save using this technique will vary over time, and it's a rather complicated transaction. But I thought it was an interesting exercise that might provide a way to help get more value out of their Steward Ship program.

Related Reading: Wading into the credit card signup bonus game

Question of the Day: Any other tips and tricks for getting the best deals from


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