Don BucoloIf we could go back and book our very first cruise again, knowing everything we know now, we’d change how we plan the whole thing from the very start. Because after more than 100 cruises, we’ve learned what actually makes a cruise better, and what just isn’t worth your money or your time.
We’ve spent more than 20 years cruising just about every way there is to cruise. Over that time we’ve made all the cruise planning mistakes so you don’t have to. These are the 15 things we’d do differently if we were booking today. This list is about the choices that shape the vacation long before you step up the gangway, because those are the ones that make or break the trip.
1. We’d Decide What Kind of Vacation We Actually Wanted First
When most people picture their first cruise, they’re probably thinking about somewhere warm. A week sailing around the Caribbean or a quick Bahamas getaway. Beaches, pools, tropical drinks, and a few days relaxing in the sun.
There’s absolutely nothing wrong with that. In fact, that’s how a lot of people get introduced to cruising. But if we were booking our first cruise today, we wouldn’t automatically start there.
Because one of the biggest things we’ve learned is that a cruise isn’t really one type of vacation. An Alaska cruise is almost the opposite of a Caribbean cruise. You’re booking it for the scenery, the wildlife, the glaciers, and the ports. A Mediterranean or Northern Europe cruise can be even more destination-focused, where you wake up in a different city almost every morning and spend eight or ten hours ashore before coming back to the ship. And then there are cruises where the ship itself is the destination, with water parks, dozens of restaurants and bars, and enough to do that you could barely get off the ship and still have a great vacation.
So if we were starting over, our first question wouldn’t be, “Which cruise line should we book?” It would be, “What kind of vacation do we want?” Do we want to relax, explore, see wildlife, visit several cities without packing and unpacking, or spend the week at a huge resort at sea? Figure that out first, and every choice after it gets easier.
2. We’d Match the Destination and Season to That Vacation
Once we knew the kind of vacation we wanted, we’d make sure the destination and the time of year actually delivered it. You can book the right style of cruise and still end up disappointed because the where and the when didn’t fit.
Book the Caribbean during hurricane season and you’re accepting a real chance of itinerary changes and rough weather. Book a port-intensive European sailing during the middle of summer and you might spend your vacation exhausted and frustrated from the heat and the crowds. Or, plan to cruise to Alaska during shoulder season and you may miss the very thing you came for — wildlife.
If you’d prefer to relax by the pool or on the beach, a Caribbean or Bahamas cruise probably suits you better than the Mediterranean. If you want to be outdoors and active the entire trip, Alaska or maybe even a destination like the Galapagos is the right choice.
So we’d be sure to line the destination up against the vacation we pictured from the start. You don’t sort out what to do in a destination after picking a cruise. It’s part of choosing the right cruise in the first place.
3. We’d Research the Ship, Not Just the Cruise Line
Once we figured out the type of vacation we wanted and where we wanted to take it, we’d spend a lot more time researching the actual ship. Because when you’re new to cruising, it’s easy to think you’re booking the same Royal Caribbean, Carnival, Norwegian, or Princess experience regardless of which ship you choose.
After cruising for more than 20 years, we’ve learned that two ships from the same cruise line can deliver completely different vacations. Take Royal Caribbean. You could book one of its newest mega-ships with multiple pools, dozens of restaurants and bars, waterparks, huge entertainment venues, and enough activities to keep you busy for a week. Or you could sail on one of the line’s older, smaller ships with a fraction of those amenities. They’re both Royal Caribbean cruises, but they’re certainly not the same vacation.
You’ll find those differences across most of the major lines. Newer Carnival ships have features and dining venues you won’t find on many of the older ships. Norwegian‘s newest ships can feel very different from the smaller ones that have been in the fleet for years as well.
That doesn’t mean newer and bigger is always better. A smaller ship might have fewer attractions, but it could be easier to navigate, feel less crowded, and get into ports the biggest ships can’t visit. On a destination-focused cruise like Alaska or Europe, those things might matter more to you than another waterslide.
So today, we wouldn’t just watch a video about the “best cruise line.” We’d look at the exact ship. How old is it? When was it last updated? Which restaurants are actually onboard? What entertainment does it have? Does it have an adults-only area? Choosing the right cruise line gets you in the ballpark. Choosing the right ship is what gets you the vacation you actually wanted.
4. We’d Look for Value, Not Just the Lowest Price
Once we found a few ships we liked, price would obviously come into play. But if we were booking today, we wouldn’t automatically book the one with the lowest advertised fare.
Cruise pricing has gotten a lot more complicated. Depending on the line, you might have a basic cruise-only fare or a bundled fare that includes drinks, Wi-Fi, specialty dining, gratuities, or onboard credit. And sometimes paying more upfront actually saves you money.
If we know we’re going to buy Wi-Fi, have a few drinks every day, and eat at some specialty restaurants, we’d compare what those cost separately against the line’s packages or bundled fares. To be honest, these packages, like NCL’s Free at Sea, Princess Plus, or Holland America’s Have It All, didn’t exist when we started cruising.
But the opposite is true too. If we barely drank, didn’t care about Wi-Fi, and were perfectly happy eating at the included restaurants, we wouldn’t spend hundreds of dollars more just because a package sounds like a better deal.
After all these years, we’ve learned that getting a good value doesn’t necessarily mean spending less. It means not paying for things you don’t want, and getting the best price for the things you do.
5. We’d Choose Our Cabin More Strategically
On your first cruise, it’s easy to assume a balcony is the cabin you’re supposed to get. And don’t get us wrong, we love balcony cabins. But if we were booking today, we wouldn’t automatically pay for one. We’d think about the cruise first.
If we were sailing somewhere like Alaska, where there’s scenery outside practically every day, we’d probably be willing to spend more for that balcony. But on a Caribbean cruise where we plan to spend our days at the pool or ashore and our evenings around the ship, we might save hundreds of dollars with an inside or oceanview cabin. In fact, we did sail exclusively in interior and oceanview rooms for years before we decided to upgrade to a balcony on our first Alaska cruise.
Additionally, we’d pay just as much attention to where that cabin is located. We’d check what’s above us, below us, and nearby. We’d avoid being directly under the pool deck or above a nightclub, since both can be noisy. And if we were worried about motion sickness, we’d look for something lower and closer to the middle of the ship, where you feel the movement least.
So we’d spend money on the cabin when it actually improved the vacation, not just because someone told us a balcony is the only way to cruise.
6. We’d Budget for the Whole Trip, Not Just the Cruise
This one is easy to underestimate when you’re looking at cruise prices online. The cruise fare isn’t what the vacation is going to cost you.
You might still need flights, a hotel before the cruise, transportation to the port, gratuities, drinks, Wi-Fi, specialty dining, excursions, and whatever else you decide to do onboard. Suddenly that $1,500 cruise becomes a $3,000 or $4,000 vacation.
So if we were starting over, we’d set a budget for the entire trip before booking anything. Maybe that means taking the less expensive cabin so we could afford the excursions we really want. Or choosing a cruise from a port we could drive to instead of spending another thousand dollars on airfare. We’d rather book a cruise that comfortably fits our total budget than not be able to enjoy the full onboard and ashore experience because we already spent everything just getting there.
7. We’d Know Everything That’s Onboard
Once you’ve picked the right ship, the next mistake is not knowing everything that’s available onboard. It would be terrible to find something you would have loved on the last night, or to discover the restaurant you were most excited about needs a reservation and is completely sold out.
So today, after we booked the trip, we’d spend time researching and learning what that specific ship actually offers. We’d pull up the deck plans, download the cruise line’s app, and look at sample daily planners to see what a day onboard really looks like. We’d note which venues and activities are included and which cost extra, which ones need a reservation, and what’s top on our to-do list.
This is different from picking the right ship in the first place. This is about knowing the ship you chose inside and out, so you walk on already knowing what you want to experience. Which leads straight into the next one.
8. We’d Lock In Our Must-Dos Before the Trip
We wouldn’t plan every hour of every day. But if there were things we’d be disappointed to miss, we’d reserve those as soon as we could.
Maybe it’s a popular specialty restaurant. Perhaps it’s a show that requires reservations. Maybe it’s the thermal suite on a sea day, or an excursion that only takes a small number of guests. A lot of these open for booking before you board, and the most popular times disappear fast.
The same goes for the basics that are easy to put off: downloading the app, completing online check-in, and booking your dining and shows ahead of time. Our pre-cruise planning timeline walks through when each of these windows tends to open.
So we’d identify our must-dos, lock those in, and leave the rest of the schedule open. Because one thing we’ve learned is that you need some structure to get the most out of a cruise. You just don’t need so much structure that your vacation starts feeling like work.
9. We’d Pack for This Specific Cruise
We definitely wouldn’t bring as much as we did on our early cruises. There are packing lists online that make it sound like you’re preparing to live at sea for six months. You don’t need most of it.
But the bigger mistake isn’t packing too much, it’s packing incorrectly for your particular cruise. We’d check the cruise line’s dress code and theme nights. We’d look at what our excursions actually require, whether that’s hiking shoes, water gear, or something to cover up in a religious site. And we’d make sure anything we’re bringing is actually allowed onboard, because every line has a list of prohibited items that surprises people every week. Admittedly, our bags have gotten flagged in the past too.
Most importantly, we’d pack our carry-on knowing we might not see our checked luggage until later that afternoon. So medications, travel documents, valuables, chargers, sunscreen, and a change of clothes would stay with us.
10. We’d Arrive at Least a Day Early
If we had to book our very first cruise again, there’s no chance we’d fly in the morning of embarkation. We actually did that on our first cruise. In January from the northeastern US. With a connecting flight. And somehow, we made it.
Today, we know how easily that could have gone the other way. One delayed flight, cancellation, mechanical problem, or missed connection, and the ship leaves without you. It does not wait just because you haven’t arrived yet.
So now we’d arrive at least one day early. For an international cruise, or if winter weather could cause problems, we might even arrive two days early. Yes, it means paying for a hotel. But it also means the vacation still happens if something goes wrong on the way there, and that peace of mind is worth far more than the price of a room.
11. We’d Book Earlier and Get Help Doing It
Honestly, if this really were our first cruise again, we wouldn’t try to figure all of this out ourselves. There are dozens of cruise lines, hundreds of ships, and countless cabin categories, fare types, packages, promotions, and itineraries. We know how to sort through all of that now. But when you’ve never cruised before, you don’t even know which questions you’re supposed to ask.
We’d also book earlier than feels necessary. Booking well ahead usually gets you a better fare and a far better choice of cabins, and it gives you more time to pay the cruise off before the final payment date. While we were at it, we’d read the fine print on that final payment, along with refund and cancellation policies.
That’s where a good travel advisor really helps. They can match you with the right cruise line and ship, explain the different fares and cabin options, and sometimes have access to group rates, onboard credit, or other perks. And best of all, you aren’t paying extra to use them. Even after 100+ cruises, we book our cruises with MEI-Travel. So whether this is your first cruise or you’re just trying something different for your next one, you can request a free, no-obligation quote from their team.
12. We’d Check Document and Entry Requirements Early
This is the mistake that doesn’t seem urgent until it’s too late to fix. It’s not about forgetting your documents. It’s about not checking, months ahead, what you actually need.
For most cruises, the safe bet is you need a passport, and most want it valid for at least six months beyond your travel dates. There are certain closed-loop cruises where you can sail with a birth certificate and government ID, but we still wouldn’t recommend it. And passport renewals can take weeks or months, especially in busy seasons. If you wait until a few weeks before the sailing to look into it, you can find yourself paying for expedited processing, or worse, unable to sail at all. Beyond passports, some countries have additional entry requirements.
So the moment we booked, we’d confirm the document and entry requirements for our specific itinerary, check that every passport in our party has enough validity left, and start any renewals right away.
13. We’d Splurge on One or Two Great Port Experiences
If we were booking our first Caribbean or Bahamas cruise again, we wouldn’t feel like we needed an expensive excursion in every single port. Instead, we’d pick one or two experiences we’re really excited about and spend our money there. Maybe that’s zip-lining through the jungle, an adventure park in Mexico, swimming with stingrays, or a great snorkeling or catamaran tour. Something we’ll remember long after the cruise is over.
If we were cruising to Alaska, the Mediterranean, or another bucket list destination, maybe we’d splurge on a few additional tours. But we’d still balance the experience so we weren’t running ourselves ragged with full-day tours every single day or breaking the bank with a $500 shore excursion in every port.
Then we’d make the other port days different. At one stop, maybe we’d just explore on our own, walk around, try some local food, and experience the place without following a numbered paddle all day. And depending on the itinerary, we might even stay onboard in one port. That’s something we never would have considered on our first few cruises. Back then, if the ship stopped somewhere, we felt like we had to get off. Now we know that staying onboard while most passengers are ashore can give you an almost completely different ship, quiet pools and short lines included.
When booking excursions, we would also consider all available options. Back in the day, we booked all our tours through the cruise line because we didn’t know any better. We overpaid for something we could have gotten cheaper through a local provider or third-party vendor like Shore Excursions Group.
14. We Wouldn’t Try to Do Everything
Modern cruise ships can have dozens of restaurants and bars, multiple entertainment options, trivia, game shows, pools, waterslides, live music, parties, fitness classes, and activities running from early morning until well after midnight. You could turn your entire vacation into a checklist. We know, because we’ve done it. The FOMO is real!
The mistake starts in the planning, when you look at everything a ship offers and quickly decide you’re going to fit all of it in, somehow. If we were starting over, we’d go into that first cruise knowing we’re going to miss things, and we’d be okay with it. We’d pick the experiences we care about most, leave room to try a few things we’ve never done, and then deliberately leave time to do absolutely nothing. Downtime isn’t wasted time on a cruise. It’s part of why you booked one.
15. We Wouldn’t Write Off Cruising After One Cruise
If we took our first cruise today and didn’t love it (which clearly didn’t happen!), we wouldn’t immediately decide that cruising wasn’t for us. We’d ask why. Because after sailing on so many different ships and cruise lines, we’ve learned there’s no single “cruise experience.” When we hear people say that cruising isn’t for them, we immediately want to jump in and say “you just haven’t found the right one yet.”
Maybe you booked a huge mega-ship but you’d be happier on something smaller and quieter. Perhaps you booked an older ship for the price when what you really wanted were the attractions on the newer ships. Maybe you didn’t love the Caribbean, but you’d be blown away by Alaska. Or maybe you spent every day sightseeing in Europe but what you really wanted was a week by the pool to just relax.
Cruise lines are different. Ships are different. Destinations are different. And sometimes the cruise you thought you’d love isn’t the cruise that’s right for you. So if we could go back more than 20 years and give ourselves one last piece of advice before that first cruise, it would be this: don’t stress too much about finding the perfect cruise. Find the cruise that seems right for you, enjoy it for what it is, and pay attention to what you liked and what you didn’t. That’s how you make the next one even better.
Comments
Have you made any of these common cruise planning mistakes? Do you have any other words of wisdom to share with first-time cruisers? Drop us an anchor below with your top cruise planning tips and advice.
