
Booking your first cruise is exciting and nerve-wracking at the same time. The thought of visiting exotic locations, endless ocean views and savoring new dishes was super enticing to me, so much so that I almost forgot the practical details. Making these rookie mistakes took a little shine off my vacation. Although I had a wonderful time, with a little better planning I could have enriched my trip much more. I’m sharing the exact 5 mistakes I made so you can avoid them and enjoy every second at sea.
- Don’t wait until the last minute to book your cruise. I hear this question all the time. Can I wait for the last minute and get a great deal. Yes, you can get good deals on last-minute bookings but be prepared for a little disappointment if you do. First, if it is a popular cruise during the summer for instance, the price will more than likely go up and not down.
If you do get a great price, the cabin will probably be a “guarantee” cabin. This means the cruise line picks the cabin for you and the location might not be the greatest, for instance below the restaurant or the pool. Noisy locations or so far towards the front that you’ll feel the ships movement much more.
Pro tip: Book 6–12 months in advance for the lowest rates, free upgrades, and your choice of sailing dates and staterooms. Keep an eye on the price, cruise lines will honor price drops up until final payment, after that date they might give extra onboard credit or other freebies.
- Don’t wait to get onboard to buy your drink package. If you wait to get onboard the ship to purchase your drink package, you’ll be paying up to 25% more. That goes for all the other packages as well, WI-FI, Specialty Dining and Shore Excursions. You can wait until just before embarkation to buy the drink packages, just be sure to check the cruise lines’ policies on that subject.
Some cruise lines will have special sales on drink packages before sailing, so keep checking back to see if they do it for your cruise. I honestly believe that drink packages are worth it for longer voyages because even if you’re not a heavy drinker, 1-2 glasses of wine add up quickly on a 14-day voyage. Also, most packages include WI-FI and Specialty Dining at their fine restaurants. I’ve done the math on some packages and found that just using the WI-FI and the Specialty Dining more than make up for the price.
My Tip: Grab the drink package during the booking process or right after final payment. The savings add up fast!

3. Don’t skip buying cruise travel insurance Halfway through my first cruise I caught a nasty stomach bug and missed two ports. Without insurance I was out $800 in unused excursions and had to pay for onboard medical visits. Insurance would have covered everything.
Always buy travel insurance the day you book your cruise. If you need time to do more research, most insurance will let you cancel within a 10-day period, but you can’t purchase it after final payment. Travel Insurance protects against cancellations, medical emergencies, and lost luggage. Make sure to read the policy thoroughly, if you need a “cancel for no reason” clause, that is usually an add-on and extra cost.
4. Don’t overpack or pack the wrong things. Cruise cabins have limited storage. Pack strategically, check the weather in your destination ports, will there be formal nights onboard that you want to attend. Think about what shore excursions you’ll be going on and what outfits will be appropriate. Think about what additional travel gadgets you might find useful. Check out my “Best Travel Tips and Resources”
5. Don’t wait to book shore excursions and specialty dining Popular excursions in Alaska and the Caribbean sold out before I even stepped onboard. I also missed out on the best dinner reservations because I assumed “we’ll just wing it.”
Book excursions and specialty restaurants the moment your cruise line opens the window (usually 90–120 days out). You’ll get first pick and often better prices.
Final takeaway: I still had a blast on my first cruise, but these five mistakes cost me money, time, and a little anxiety. Learn from my rookie errors and you’ll sail stress-free.
Ready to book your first cruise the smart way? Start planning early, grab those packages and insurance, and you’ll create memories that last a lifetime.

