Pirate Ship Reduces Shipping Cost and Complexity

As a Type A personality, I find the process of shipping packages stressful. Is my item small enough to put in my mailbox, or must I make a special trip to the post office? Would I save money with UPS? Will scrimping on shipping fees add weeks to the delivery time? Because I dislike extra in-person errands, I try to answer these questions online—and the USPS and UPS websites aren’t great.

Last October, I saw a plug for the Pirate Ship service among the six weekly recommendations in the Recomendo newsletter written by tech publishing veterans Kevin Kelly, Mark Frauenfelder, and Claudia Dawson. Pirate Ship is a shipping platform with an elegant interface that allows users to access discounted shipping rates from USPS and UPS with no subscription fee. I’ve used it a handful of times for mailing packages, and it has been brilliant. TidBITS contributing editor Glenn Fleishman has also shipped hundreds of packages with Pirate Ship over the past few years and swears by it.

Pirate Ship is a clever name, to be sure, and the company has fully committed to its schtick, from the big “Yarr, log me in” button to the Support site’s heading, “Lost at sea, matey? Find answers below or send us a message.” Even customer service reps reply with a bit of jaunty swagger. But while you may occasionally feel as though Groundhog Day (the movie) is taking place on September 19 (Talk Like a Pirate Day), the banter is charming and doesn’t detract from the interface.

And, oh, what a lovely interface! Click Ship in the sidebar, and Pirate Ship lets you jump right into addressing. If you have sent a package to the recipient before, it helpfully offers to autofill their name and address. Provide an email address, and Pirate Ship can send them a message with the tracking number and other shipping details. You can even choose when the message is sent, which might be welcome if you can’t drop off the package for a day or more.

I especially like using the time-saving Paste Address field, which allows you to paste an address copied from elsewhere rather than manually entering the data in each address field. Be careful, though: if the address contains anything other than a building number and street, like a mail stop, make sure Pirate Ship translates everything correctly—it sometimes gets confused. Pirate Ship also offers a pop-up with alternatives if it can’t make an exact match against its address database. Check those suggestions, too, since Glenn almost shipped packages to the wrong state several times.

When addressing is done, scroll down to provide package weight and other details, and click Get Rates. I mostly reuse shipping envelopes and boxes I’ve received, but Pirate Ship also calculates rates for standard USPS and UPS envelopes and boxes. You’re warned if your package is too big (the maximum length plus girth—twice the width plus twice the height—is 165 inches) or heavy (150 pounds). It’s good to know about carrier limitations before getting too far into the process. Extra services include signature confirmation, return labels, extra insurance, media mail, and irregular package shapes. You’ll also need to answer questions about hazardous items and fill out customs forms for international packages. You can save your settings if you expect to send this package repeatedly.

When you click Get Rates, Pirate Ship suggests the best option, but links let you switch to the least expensive options for USPS and UPS. A tip at the bottom of the currently selected option tells you how much more the other carrier is, which you might choose if it means a free pickup at your home instead of a trip to drop it off. Clicking the downward-pointing arrow shows you all the options, in the event you want to pay more for faster delivery.

For each option, Pirate Ship shows estimated delivery dates and how much you’ll save over the retail cost at a counter. USPS and UPS offer slight discounts for printing labels online through their sites, but it’s a small savings. Pirate Ship has negotiated corporate-level discounted shipping rates of up to 89% off retail and passes most of those savings on to customers. For shipping something heavy, Glenn has seen international shipping prices that run about $200 on UPS’s site, while Pirate Ship’s rate was about $60.

That slight arbitrage allows Pirate Ship to avoid the monthly subscriptions that make no sense for all but high-volume shippers—Stamps.com charges $19.99 per month plus postage, for example. (On the flip side, Stamps.com net rates can be lower than Pirate Ship’s, and Stamps.com lets you print standard USPS stamp-like postage in addition to USPS and UPS package shipping labels.)

Once you’ve selected a service, scroll down to see the total and buy the label. Pirate Ship lets you pay using a debit or credit card, of course, but you can also pay using PayPal or connect your bank account for automatic ACH withdrawals and save 3%—likely worth it for a higher-volume shipper. You can also fund your account with more than you need to reduce the number of receipt emails.

If you’re just testing the waters, you can start by getting a rate quote from the Rates page. You provide the destination country and postal code, choose a type of packaging, enter the package dimensions and weight, and review options. The information is the same as when creating a label, but it’s presented in a way that makes comparison easier. If you see a rate you like, click Ship Now to create a label.

The Ship page also lets you upload a spreadsheet or import from integrations with a wide variety of ecommerce hosts like Etsy, PayPal, Shopify, and Squarespace. Once, for the Finger Lakes Runners Club, I needed to send race medals to 11 people who hadn’t received theirs at the race. There were two couples on the list, so I had nine packages to send, two of which were twice as heavy as the others. Since I had to extract all the name and address information from our race registration system anyway, it was easy to create a spreadsheet with all the details—including different weights—and generate nine labels in a single order. That was far more efficient than creating nine individual labels and submitting nine separate credit card expenses to the club’s bookkeeper.

The End of Day, Schedule Pickup, and Print Selected Labels buttons on the Ship page are aimed at helping higher-volume shippers. The End of Day button lets you print an entire day’s worth of USPS labels and a single barcode that lets the postal worker scan them all in at once. Schedule a Pickup lets you request a pickup, which is free from USPS (and you can tell them you’ll leave the package in your mailbox, which is what I do for nearly everything) but costs $25 from UPS. Print Selected Labels is helpful if you’ve created many labels and want to print them all in a batch.

Pirate Ship optimizes paper usage and will print labels two-up on an 8.5×11 piece of paper. If you regularly print shipping labels, you can buy adhesive ones, like Avery 8126 labels, which put two labels on a letter-sized sheet and are compatible with both ink-jet and laser printers.

Whenever you ship a package, Pirate Ship emails you a receipt with a link to your account and the Reports page. It shows you how much Pirate Ship saved you, provides total shipping costs, and more. There’s even a map showing your top states and countries, plus a complete transaction history. As an individual, these stats are purely amusing, but I could imagine a company being interested in the details for budgeting and business planning.

Pirate Ship’s support pages are also outstanding. They’re concise, informative, and well-designed, with only a modicum of pirate puns. They also contain helpful information about shipping in general, such as explanations of why USPS and UPS sometimes change the amount of postage Pirate Ship estimated because they disagree with you about the size or weight of your package (and how you can apply for a refund), what to do about packages that arrive late or damaged, and how to deal with oddly shaped items like tubes.

Although I’m delighted with Pirate Ship, it has competitors that might be a better fit for others. You might consider them not so much for cost savings but because you’re outside the US or need to ship through FedEx, DHL, or other carriers that Pirate Ship doesn’t support. Other shipping services may also offer additional integrations that could be important to your workflow. But for an individual or small business with relatively straightforward shipping needs, Pirate Ship’s pay-as-you-go approach with highly discounted rates and an excellent interface make it well worth trying.