The Smartest $100 You’ll Spend Before Your Cruise
Five Small Investments That Can Save You Money, Reduce Stress, and Make Every Cruise Better
I’ll admit it. When Susan and I start looking at cruises, I can spend hours comparing prices. I’ll look at different sailing dates, different cabin categories, and even different departure ports if it means saving another $50 or $100.
If you’re anything like me, you’ve probably done the same thing, as there is just something strangely satisfying about finding a better deal than yesterday.
But over the years, I’ve realized something. Some of the smartest ways to save money on a cruise actually happen after you’ve already booked it.
That may sound backwards at first. Once we’ve committed thousands of dollars to a vacation, it’s tempting to stop thinking about spending money altogether, of course until that final payment is due. But I’ve found that a handful of relatively small purchases before we ever leave home can save hundreds of dollars later, eliminate unnecessary stress, and simply make the entire cruise more enjoyable.
These aren’t luxury splurges, but as I like to call them, travel investments.
1. Travel Insurance: Buy Peace of Mind, Not Just Coverage
If there’s one thing I’ve become more convinced of over the years, it’s that travel insurance isn’t an expense but part of the vacation budget.
The longer we travel, the more I realize that insurance isn’t just about protecting the cruise fare. It’s about protecting everything that surrounds the cruise: flights, hotels, medical emergencies, baggage delays, missed connections, and those unexpected moments none of us like to think about.
One of the biggest lessons I’ve learned is that if you cruise or vacation more than once a year, an annual travel insurance policy often provides far better value than buying individual plans for every trip.
For example, our 2026 Allianz annual policy will cover our three separate vacations for roughly what we would have paid to insure just one of them individually. That makes it one of the easiest financial decisions we make each year.
The funny thing about travel insurance is that the best-case scenario is never needing it. But if something does go wrong, it can easily become the smartest money you spent all year.
Check out our Cruise Travel Insurance Guide.
2. Apple AirTags (or Similar Trackers)
I honestly don’t think we’ll ever travel without AirTags again.
There’s something incredibly reassuring about opening your phone and seeing that your luggage made the same connection you did. We’ve used them on flights, in cruise terminals, inside checked luggage, and even in our carry-on backpacks. Have we ever actually lost a suitcase?
Thankfully no, but we’ve had enough close calls and enough moments wondering where our luggage was, that the peace of mind alone has been worth every penny.
Sometimes the best travel purchase isn’t the one you use but the one you hope you never need.
3. Packing Cubes
If you ask Susan, this might be the best travel purchase we’ve ever made.
I used to think packing cubes were just another travel gadget that people bought because Instagram told them to. Yep, I was wrong.
They keep our suitcases organized, make unpacking into the cabin closets incredibly easy, and somehow make fitting everything into the suitcase seem almost a breeze.
Perhaps my favorite benefit comes at the end of the cruise. Dirty clothes go back into one set of cubes, clean clothes into another, and packing for home becomes surprisingly painless.
It’s one of those products that seems unnecessary, until you actually use them for the first time.
Then you wonder how you ever traveled without them.
4. A Motion Sickness Plan
Every cruise Facebook group seems to have someone insisting that the unlimited drink package is the cure for seasickness. In my younger days, I’ve tried it….and it doesn’t work.
Personally, I’ll stick with Bonine, while others have had tremendous success with the seasickness bands you wear on your wrist.
Even if you’ve never experienced motion sickness, I think it’s worth having a plan before you board. Bonine, Dramamine, motion sickness patches or Sea-Bands, are much easier (and often much cheaper) to buy before your cruise than onboard the ship or in a port where your options may be limited.
Think of it like bringing an umbrella. You don’t pack it because you’re expecting rain, but because it’s nice knowing you’re prepared if it does.
5. A Portable Charger
There are few better feelings on a sea day than finally finding the perfect lounge chair by the pool.
You’ve got your Kindle, your phone, and maybe your iPad. The drink server already knows your name. Life is good.
Then…10% battery. The last thing I want to do is give up the perfect seat just to hunt for an outlet.
A good portable charger solves that problem completely. It also becomes invaluable during long port days when you’re using your phone for maps, photos, and excursion tickets.
It’s one of those purchases you barely notice until the day you’re incredibly glad you packed it.
More Than Just Saving Money
Notice something about every item on this list? None of them make your cruise cheaper, they just make your cruise better. That’s an important distinction.
For years, I thought sailing smart meant squeezing every possible dollar out of the cruise fare and today, well I think it means something totally different.
It means understanding where spending a little more upfront creates a much better experience later. It means buying the things that reduce stress, eliminate frustration, and allow you to spend more time enjoying your vacation instead of solving problems.
Ironically, those smart investments often end up saving money anyway.
Final Thoughts
If someone gave me $100 and asked how I’d improve their next cruise, I probably wouldn’t tell them to spend it onboard. I’d tell them to spend it before they ever leave home.
Because some of the smartest cruise purchases aren’t glamorous and they don’t come with umbrella drinks or specialty dining reservations.
What they do provide is peace of mind, convenience, and a vacation that’s a little less stressful and a lot more enjoyable.
To me, that’s what Sail Smart. Live Large. Spend Less. has always meant.
Not spending the least, but spending wisely.
Bonus: TSA PreCheck or Global Entry
If there’s one purchase on this list that has absolutely nothing to do with cruising, and yet makes every cruise vacation better, it’s TSA PreCheck or Global Entry.
Technically, it’s not going to save you money though it will save you something even more valuable. Stress.
One of the quickest ways to start a vacation on the wrong foot is standing in an airport security line wondering whether you’re going to make your flight. Meanwhile, you’re taking off your shoes, emptying your pockets, pulling out your laptop, and hoping the person in front of you didn’t forget the full water bottle in their carry-on.
TSA PreCheck changes that experience entirely.
Most of the time, you’ll move through security much faster, keep your shoes and belt on, leave your laptop in your bag, and spend far less time wondering if you’ll make it to your gate before boarding begins.
If you travel internationally, Global Entry is an even better value because it includes TSA PreCheck while also dramatically speeding up your return through U.S. Customs.
Is it absolutely necessary? Of course not.
But if you cruise or travel by air even once or twice a year, it’s one of those investments that quietly pays dividends every single trip.
I’ve come to believe that Sailing Smart isn’t just about finding the lowest cruise fare. It’s about removing as much unnecessary stress from your vacation as possible, so your trip begins the moment you leave home and not the moment you finally reach the ship.
