The Complete 2021 Small Business Guide To Holiday Shipping: Deadlines, Prices, & How To Save

The holiday season is upon us! For many small businesses, this is the busiest time of the year for sales and shipping. How busy? So busy that UPS reports having delivered more than 32 million packages each day during the 2019 holiday season. This year, with 68% of Americans expressing concerns about their health and the safety of in-person shopping, the effect of Coronavirus on online shopping remains to be seen. But it seems safe to bet that more people will be shopping online than ever before. In fact, so far, almost half of Americans say they plan on doing more shopping online this year.

What’s more, online shoppers are now fully accustomed to inexpensive and fast shipping, so making a holiday shipping plan is essential if you want to keep up. But how do you prepare for such a busy season? As a business owner, what are your best shipping options? And how do you get the best rates to make your customers happy and compete in a space with Amazon and other two-day shipping providers?

Heading into the holiday season blind, without information about shipping rates and times, is an expensive mistake you can’t afford to make. It’s important to understand:

1. What customers want in shipping rates.
2. The shipping methods customers prefer.
3. How to navigate general holiday busyness.

In this post, we’ll answer all these questions and more to help your business handle holiday shipping with ease. Here is everything you need to know about holiday shipping 2020.

The Best Holiday Shipping Options For Your Business

Shipping choices are an integral part of your overall business strategy, and never more so than during the holidays. Even though the small business holiday season starts with Halloween, don’t let your shipping start with a scare. Learn what shipping options you have ahead of time so you can be prepared and ease the stress of doing business during the holiday season.

In today’s small business world, you have more shipping options than ever, whether you outsource or use software apps and software. That means the holiday shipping rush doesn’t need to be crazy. Still, when it comes to shipping options, there are really three major contenders: The United States Postal Service (USPS), United Parcel Service (UPS), and FedEx.

We’ll explain what services each provides, how much they cost, and which is the best to use for your shipping needs. And, if none of these fit your needs, we’ll also cover the best shipping software and outsourcing options.

USPS Holiday Shipping Overview

Best for affordability and saving money when packages don’t need to arrive quickly.

The United States Postal Service, better known as USPS, is the undisputed king of shipping. USPS can be a great option for holiday shipping, and it’s competitive with private companies in terms of options and prices. It is still the preferred method to ship to military bases or PO Boxes. With free pick-up scheduled at residences and businesses all over the United States, small businesses can save money on shipping using USPS, especially if you ship:

1. Heavy and small objects
2. Light and bulky objects

You may get a commercial shipping price if you are a business that qualifies, and the USPS also has sales reps who can come out to your business and help you make shipping plans.

USPS Services

You have several shipping options with USPS. Here is a basic rundown of each option:

• USPS Retail Ground®: This is a shipping service for packages, thick envelopes, or tubes that do not exceed 70lbs. Cost is based on weight, size, and location of the shipment. The speed for Retail Ground is between 2-8 days, depending on the distance the package needs to travel. This shipping method is deliverable to PO Boxes and military bases. It is available for purchase only in-person at a US postal office.
• First-Class Mail®: This is for standard size envelopes weighing up to 3.5oz or small packages that weigh up to 13oz. Cost is based on weight, size, and location. The speed for First-Class Mail is 1-3 days, and it is only available for purchase in-person at a US postal office.
• Priority Mail®: This is a shipping service for packages that has a flat-rate, regional rate, and retail rate. Priority Mail regional and retail rates are based on weight, size, and zone. However, the flat-rate covers up to 70lbs without a need to weigh. Mail arrives between 1-3 days, and you can purchase this option in-person or online.
• Priority Mail Express®: This is the USPS option for overnight guaranteed shipping of packages under 70lbs. It also includes free pick-up at your home or office. That overnight shipping is guaranteed, or your money back, and includes insurance. (Although, for the holiday season, there is some fine print: the money-back guarantee is only applicable if the package hasn’t been delivered after two business days if it’s mailed between December 22 and December 25, due to the volume of mail.) The rate is based on weight, size, and location of the shipment destination. You can purchase this option in person or online.
• Media Mail®: If your business sells items that classify as media items then you might be able to use Media Mail® to ship items as an economical option. This is for videos, books, CDs, etc. This isn’t the best option for time-sensitive material as it takes anywhere between 2-8 days for delivery. It is available only in-person at a post office.

How Much Does USPS Holiday Shipping Cost?

The USPS website has a useful and easy-to-navigate shipping calculator. You can use it to get an estimate for your shipping rate. If your shipping method is available via their Click-N-Ship® option, you can sign in to your account, select shipping type, pay, and print your label. Small businesses can use Click-N-Ship® to create batch shipments or order flat-rate boxes to be delivered directly to your home/place of business. Pick-up at residences and almost all business locations is free. For international shipping prices, visit the USPS business prices page.

Prices listed below are up to date as of October 28, 2020.

*USPS also has flat-rate prices for their priority mail service. With flat-rate boxes and envelopes, weight and destination do not affect pricing. If you can fit it in, it’ll ship for a pre-determined price. Prices listed below are up to date as of October 28, 2020.

When To Use USPS For Holiday Shipping?

If you are a low-volume merchant, USPS offers free pick-up, and you can use the Click-N-Ship® method for the shipping services available. The entire process is quick and simple. Click-N-Ship® is the most economical, it reaches all households/PO Boxes, and it can be a great option this holiday season when time isn’t of the essence. USPS overwhelmingly provides the best experience for most small businesses and eCommerce merchants. UPS and FedEx can’t compete with the prices and speed for lightweight (under 2lbs) packages. If that applies to your shipments, then this is your best choice.

UPS Holiday Shipping Options

Best for fast deliveries with guaranteed shipping, package tracking, and no peak surcharges.

We recognize those trademark brown vans anywhere. UPS (United Parcel Service) is a favorite among merchants because of their amazing customer service, package tracking abilities, and reliability. However, it is the most expensive option whether you ship from a regular pick-up or from a retail shop. Be aware, too, that amid Coronavirus disruptions UPS is adding peak surcharges this year, though it will apply only to higher volume and overseas shippers.

UPS Services

Unfortunately, UPS does not offer free pick-up or Saturday delivery, but it does have top-notch tracking and excellent uniforms. Reliability and ease of tracking are two of the positives of using UPS for business shipping.

Here is a rundown of shipping options available at UPS:

• Ground: This is the most economical option. Using Ground, a package will arrive between 1-5 days. Pricing is based on the weight, size, and package destination.
• UPS 3-day Select®: This option promises that your package will be delivered by the end of the third business day. Pricing is based on the weight, size, and package destination. (An AM option is also available for a fee; your package will be delivered by the morning of the third business day.)
• UPS 2nd Day Air®: This option promises that your package will be delivered by the end of the second business day. Pricing is based on the weight, size, and package destination. (An AM option is also available for a fee; your package will be delivered by the morning of the second business day.)
• UPS Next Day Air®: As it sounds, this option delivers a next-day/overnight shipment. (An AM option is also available for a fee; your package will be delivered by the morning of the next business day.)
• UPS Express Critical®: Details aren’t posted, but if you need a critical rush, UPS is dedicated to helping you get your package where it needs to go. This assuredly-not-cheap option can involve a private charter or courier to deliver your shipment.

How Much Does UPS Holiday Shipping Cost?

UPS also has a handy calculator to determine shipping costs. Prices for shipping are different for daily rates or retail rates. Daily rates are for businesses with a scheduled UPS pick-up. Retail rates are the shipping rates you will pay if you go into a local UPS retail location. The fees for scheduling a pick-up start at $5.80, if scheduled in advance.

Here’s a breakdown of UPS’s shipping by service. Prices listed below are up to date as of October 5, 2020.

When To Use UPS For Holiday Shipping?

UPS has great tracking. If you have a package you need to be delivered fast and you want to keep a close eye on its travels, then UPS might be worth the extra cost. Tracking and guaranteed speed are the two reasons to choose UPS over USPS. While some small businesses have amazing relationships with their UPS drivers, other small businesses and eCommerce sites will hesitate to pay the pick-up fees or the increased rate prices you’ll find when you head into a store.

FedEx Holiday Shipping Options

Best for fast deliveries with package tracking and Saturday shipping.

Our Merchant Maverick shipping expert makes the claim that the differences between UPS and FedEx are negligible. For what it’s worth, like USPS, FedEx does offer Saturday delivery, and they tout a more involved tracking system, too. There are fewer FedEx stores in the United States, so locations are limited, and that could add time to delivery for remote locations.

FedEx Services

Screenshot of FedEx webpage, captured 10/2/2020

FedEx offers several shipping options, which vary depending on how quickly you need your packages to arrive.

• Ground: Prices for Ground shipping are based on package weight, size, and destination location. Shipments will arrive between 1-5  business days (up to 7 days to Alaska and Hawaii). Ground shipping is available only for Monday-Friday delivery.
• FedEx Express Saver®: Prices for the FedEx Express Saver® shipping are based on package weight, size, and destination location. Your shipment will arrive within 3 business days. 
• FedEx 2Day Air®: Prices for FedEx 2Day Air® are based on package weight, size, and destination location. Your shipment will arrive by the end of business on the 2nd day. (You can also purchase 2Day® AM to make sure your package is delivered by the morning.)
• FedEx Standard Overnight®: Prices are based on package weight, size, and destination location. Your package will arrive by the next business day. 
• FedEx Priority Overnight®: Your package will arrive by mid-morning the next business day. (Early delivery, by 8, 8:30, or 9 a.m. is available to most areas, for an extra fee.)

How Much Does FedEx Holiday Shipping Cost?

For the holiday 2020 season, FedEx does have peak and surcharge fees. Surcharge fees start at $4.90. You may also need to pay a fee for a package traveling to a remote area. You can use their rate calculator here and view a breakdown of their pricing details below. Prices listed below are up-to-date as of October 28, 2020.

FedEx also has flat-rate prices, known as One Rate. When you use FedEx boxes and envelopes, weight and destination do not affect One Rate pricing. If you can fit it, it’ll ship for the pre-determined price. Prices listed below are up-to-date as of October 28, 2020.

When To Use FedEx For Holiday Shipping?

If you are close to a FedEx store or need a very detailed tracking provider, this is a solid choice. Pricing between UPS and FedEx is similar and inconsistent (some years one is more economical, the next year the other one is; it’s impossible to tell you which one is the best option). So, this comes down to your own preference. This year, FedEx has added peak/surcharge pricing for the holiday season, and the pricing differences between UPS and FedEx are negligible.

Using Shipping Software For Holiday Shipping

Best for streamlining your shipping process and integrating with your eCommerce site.

As your holiday sales increase and shipping demands become cumbersome, it might be time to look into using shipping software to help with some of the details. Shipping software is a helpful tool to streamline the shipping aspect of your business. If the information above on shipping prices and options made your head hurt a little, that’s okay. If you don’t have the time or inclination to do shipping calculations yourself, finding shipping software that works for you can cut time off your precious holiday work hours.

What can shipping software do? It can give real rates, print labels in bulk, manage shipments, and work with your eCommerce site. But are some of the top choices you should look into?

Best Shipping Software For The Holidays

Merchant Maverick’s top-rated shipping software is a great place to start to find a shipping software that will work for you. Here are a few of the top merchants we recommend:

• Shipping Easy: Shipping Easy is, you guessed it, easy to use, and its pricing is excellent. That makes it one of our favorites at Merchant Maverick. A bonus of partnering with Shipping Easy is its partnership with USPS, making it an affordable option for low-volume merchants.
• ShipStation: ShipStation is one of the leaders in eCommerce shipping, and it offers integrations for UPS, FedEx, and USPS. Read our full ShipStation Review.
• Ordoro: Ordoro has great dropshipping options where you can send packages directly from a supplier, which might be an amazing step for the holiday rush.
• Stamps.com: Stamps.com works directly with USPS. This is a flat-rate service; you pay a flat monthly fee no matter how many packages you ship. With free pick-up from USPS at almost all residences and businesses, Stamps.com is a great choice for companies looking for a reliable economical option.

How Shipping Software Can Help For The Holidays

Shipping software takes some of the labor of shipping and moves it into a streamlined process. Time is money, and time is limited. If you can assign a dedicated person to work on shipping, that’s amazing. Still, human error is bound to happen, and shipping software helps take some of the uncertainty out of your shipping process.

Here are the top reasons you should invest in shipping software:

• Saves you time
• Reduces chances for error
• Simplifies your shipping craziness
• Streamlines your shipping process
• Keeps shipping information in a single location

These shipping software companies are prepared for the holiday rush and they can help you, too. Anytime you can economically outsource, you should.

Is it worth the cost? Keep on reading!

How Much Does Shipping Software Cost?

Shipping software is an expense, and rates vary. However, many of these shipping software companies provide shipping discounts and cheaper rates for their clients, and that makes the differences in price negligible compared to not using shipping software.

If you acquire help via a shipping app that is saving you up to 40% on shipping costs, it’s worth it to pay a monthly fee for that type of discount — that fee is absorbed by savings on shipping costs. When you look at the bottom line, you can’t go wrong with a shipping software company if your company ships enough products to benefit.

Read our post on the advantages of shipping software to learn if this option is right for you.

Outsource Shipping For The Holidays

Best for business owners who are too busy to handle shipping themselves.

If shipping your products takes up a lot of time and a lot of space: Outsource it.

Outsourcing means your product ships directly to your customer through a warehouse. And when you outsource your shipping, you can reach new markets, reduce your shipping hassles, and cut shipping costs all in one fell swoop. Start the process by looking at where you ship, how often you ship, and what those shipping rates look like, and then give a company permission to take charge of shipping your products for you. By outsourcing shipping, you allow a third-party company to manage and ship your inventory. Outsourcing shipping is really just the act of saying, “Let’s not hassle with this craziness!”

You might be a smaller merchant who is hoping to rise to the level where you can outsource. The savings threshold is 25 orders a day. If you fulfill more than 25 orders a day, you could benefit economically from outsourcing. (And we’re cheering for you to get to that level or above!)

One important thing to consider: Third-party shippers are better equipped for dealing with the holiday shipping madness, and it’s nice to hand a difficult task off to someone else.

Best Options To Outsource Holiday Shipping

Finding a way to keep yourself as hands-off as possible is a small business owner’s dream. Fortunately, you have multiple options to outsource your holiday shipping. Here are a few options for holiday outsourcing:

• Fulfillment By Amazon (FBA): Best for businesses already selling on the Amazon Platform as one part of their eCommerce strategy
• Fulfillrite: Best for businesses that sell bundles or kits of items commonly sold together
• FedEx Fulfillment: Best for businesses that have already determined FedEx is a close competitive selection for your shipping needs
• Shipwire: Best for businesses that ship orders around the world

How Outsourcing Shipping Can Help For The Holidays

Outsource your shipping, and you could gain the freedom to focus on all your other important business issues during the holidays. After all, timely customer service is still a huge part of consumer decisions. When choosing whether to outsource, ask yourself:

• How quickly am I able to fulfill orders?
• What are my plans for returns/refunds?
• Can I respond to situations immediately?

If the answers to these questions are inducing a heart attack, stop right now. Outsourcing may be the cure you need.

How Much Does Outsourcing Shipping Cost?

To set up an outsourcing system for your company, you will need to find an outsourcing company and set up an account through them. There are initial set-up fees and fees based on use and inventory. Costs for outsourcing vary. The average industry cost for outsourcing shipping is under $3 per order, with negotiated rates.

When To Outsource Your Holiday Shipping

If you are struggling with just the thought of shipping your holiday orders, outsourcing is a no-brainer. Here is the best way to assess if you need to outsource. Close your eyes. Imagine that you don’t have to worry about fulfillment regulations, inventory space, the time spend on shipping, training staff to ship, or where you’ll keep holiday inventory. If this vision has you relaxing for the first time since the Back To School supplies hit the shelves, then you need to find a way to outsource.

Remember: in general, if you send out more than 25 shipments a day, you may find it cost-effective to outsource.

Holiday Shipping Schedule for 2020

As a small business, it’s important to fulfill your shipping promises. Knowing the shipping deadlines and understanding the holiday schedule will help you plan and set your own shipping costs and let customers know when to expect their items. We’ve all had one or two close calls with holiday packages … including those packages that came just a few days too late.

Deadlines listed below are up-to-date as of October 28, 2020.

USPS Holiday Shipping Deadlines

With USPS, the last day to ship a package and have it arrive by Christmas is December 23. However, for cheaper shipping options, you’ll want to send your packages well before this date. See the deadlines below:

UPS Holiday Shipping Deadlines

With UPS, the last day to ship a package and have it arrive by Christmas is December 23. However, if you don’t want to be stuck paying for Next Day Air, you’ll want to use another one of UPS’s shipping services and get those packages in sooner. See the deadlines below:

FedEx Holiday Shipping Deadlines

With FedEx, you could choose to ship a package on December 25 and still have it arrive by Christmas Day. But if you want to save a lot of money, and save a poor soul from having to work on Christmas, you’ll need to send your packages a little sooner. See the deadlines below:

5 Tips To Make Holiday Shipping Easier For You & Your Customers

Shipping is a crucial element of eCommerce. Customers buy your products because of what you promise to deliver, and shipping can make or break the sale. According to a recent study, up to 63% of customers navigate away from a shopping cart because of questions and concerns about shipping. It’s gut-wrenching to bring customers to that final click and then lose them because of shipping speeds and prices.

With that in mind, how can you make holiday shipping easier for both you and your customers? It’s easy! Think about your own needs as a customer in today’s holiday market and try to meet those needs for them. Here are a few tips:

Tip #1: Keep Your Inventory In Stock

This should go without saying but here goes anyway: Keep inventory in stock during the holiday season. Nothing creates a headache like running out of an important item during the busiest time of the year. (Is this the appropriate place to incorporate an anecdote about the time I worked for a chain restaurant famous for ribs, and a man actually threw a pitcher of water at me one day when we ran out of those ribs? Stay in stock, people!)

Waiting for a shipment yourself definitely slows down the shipping process. Be ready to ship as soon as you can after receiving a customer’s order. That’s what most customers expect.

Tip #2: Make Shipping Work For Your Business

Whether this involves free shipping options or putting effort into tracking packages, shipping needs to be not an afterthought but an integral part of your business plan. Instead of feeling like shipping is interfering with your business, make a shipping plan to boost your business.

Maybe that involves utilizing all shipping options (USPS/UPS/FedEx) to get the best price and delivery options for each customer. Maybe you promise free ground shipping, knowing you can absorb the cost. Research your business and know what your customers expect for holiday shipping options.

Tip #3: Provide Shipping Information In Your Meta-Data

It’s the year 2020. We don’t quite have those fully automated flying cars we all were promised, but we do have a robust internet that is an incredible resource for small businesses.

If customers are looking for your product and a way to ship fast or free, advertise and capitalize on your ability to give them just what they want.

Tip #4: Make Shipping Information Clear For Everyone

Customers who go into a sale with clear expectations are often the most satisfied. Whether the shipping takes one day, three days, or 14 days, as long as the customer has that information as part of the decision-making process, they can be happy with the results.

Will you provide tracking information? Do you have a ship-by date? When will packages arrive? Transparency is the number one most important quality in a business. If you advertise certain shipping speeds, make good on those promises. Whenever you make a promise, stick with it, and keep customers informed.

Tip #5: Prepare For Returns

No matter how you ship, it’s inevitable that someone will need or want to return a product.

Do you have a return policy? How will customers return incorrect or damaged items? These are critical components of the shipping process. Implementing an automated return process is integral. Also, customers may be looking for information on returns before making a purchase, so communicate your return policy in a clear, public location.

Get Started On Your Holiday Shipping

Shipping is the key to eCommerce success during the busy holiday season. If you and a competitor are equal in all other things, you’d better make sure you have superior shipping options. How do you do that? By knowing your inventory inside and out, including how much it weighs; by checking prices between the carriers and deciding on a shipping plan to utilize during the holiday season; and by understanding whether outsourcing or using a shipping service is the right choice.

The holiday shipping rush starts now. People are already thinking about holiday purchases; make it easy for them to choose your business. Check out our other articles on shipping to make sure you are prepared for the holiday rush.