ShippingEasy vs ShipStation vs Pirate Ship: Which Shipping Tool Fits Your Store?

ShippingEasy vs ShipStation (and Pirate Ship) is a common question once a store ships more than a few orders a week. All three let you buy discounted USPS and UPS labels, but they suit very different store sizes. I ship orders every week for clients, so here is a practical comparison with real prices.

Quick Answer

• Just starting or shipping under 25 orders a month? Pirate Ship or ShippingEasy’s free Starter plan.
• Selling on several channels with growing volume? ShippingEasy Growth, for its simple dashboard and unlimited stores.
• High volume, many carriers or a warehouse team? ShipStation, for advanced automation, users and inventory tools.

ShippingEasy

ShippingEasy imports orders from your stores and marketplaces, compares discounted USPS and UPS rates and prints labels in batches. The dashboard shows new, shipped and unshipped orders and any exceptions to review.

• Starter: free, up to 25 shipments a month and up to 3 stores.
• Growth: from $19.99 a month, with unlimited stores, CSV uploads, branded tracking, reporting and phone, email and chat support. Higher tiers cover up to 10,000 shipments a month.
• 30-day free trial on paid plans.

ShipStation

ShipStation is built for scale. It connects unlimited stores, compares rates across carriers and offers deep automation rules.

• Starter: from $14.99 a month (50 shipments), 3 users, rate shopping, return labels and basic automation.
• Standard: from $29.99 a month, 10 users, unlimited automations, combined and split orders, your own carrier accounts and basic warehouse tools.
• Premium: from $349.99 a month, with advanced inventory and warehouse management.
• 30-day free trial, no credit card needed.

Prices rise with shipment volume, so check the tier that matches your monthly orders.

Pirate Ship

Pirate Ship is a free shipping tool for USPS and UPS labels. There is no subscription and no markup on labels, because the company is paid by the carriers. It offers deep discounts off retail rates and supports spreadsheet and batch shipping, plus integrations with popular store platforms.

It is ideal for small sellers and side businesses. As volume and the number of channels grow, a dedicated multichannel tool usually saves more time.

Side-by-Side Comparison

Prices checked on the official websites in October 2026. Always confirm current pricing before you subscribe.

How I Use ShippingEasy for a Client

For a US retailer selling on several channels, my daily shipping routine was simple:

1. Check new orders downloaded overnight and any order download exceptions.
2. Compare rates and buy USPS labels in one batch.
3. Confirm tracking was sent back to each store.
4. Review unshipped orders before the cut-off time.
5. Keep postage balance topped up so labels never fail.

See all the tools I use on my tools page.

Which Shipping Tool Should You Choose?

Count your monthly shipments and sales channels first. Under 25 orders and one or two channels: start free with Pirate Ship or ShippingEasy Starter. A few hundred orders across Amazon, eBay and your own store: ShippingEasy Growth is easy to run. Thousands of orders, a team and warehouse needs: ShipStation’s automation pays off.

Whichever you pick, a virtual assistant can handle the daily routine of buying labels, checking exceptions and answering “where is my order?” messages.

Frequently Asked Questions

Is ShippingEasy better than ShipStation?

ShippingEasy is simpler and cheaper for small to mid-size stores, with a free plan up to 25 shipments. ShipStation is better for high volume, many carriers and advanced automation.

Is Pirate Ship really free?

Yes. Pirate Ship has no subscription or label markup. You only pay the discounted postage for each label.

How much does ShipStation cost?

ShipStation starts at $14.99 a month for 50 shipments on the Starter plan, with Standard from $29.99 and Premium from $349.99, rising with shipment volume.

Does ShippingEasy have a free plan?

Yes. The Starter plan is free for up to 25 shipments a month and up to 3 stores.

Can a virtual assistant manage my shipping software?

Yes. A virtual assistant can buy labels, check exceptions, confirm tracking and answer delivery questions every day.

Conclusion

In the ShippingEasy vs ShipStation vs Pirate Ship decision, volume decides. Pirate Ship is perfect for small sellers, ShippingEasy is a simple step up for multichannel stores, and ShipStation suits high-volume teams that need automation. Start with the free options and upgrade when the time saved is worth it.