Last year, I was lucky enough to be invited to sail on the Sun Princess, the first Sphere-class ship in Princess Cruises’ line, and one billed as the reigning “foodiest destination at sea.” While I’d never set foot on a cruise before, I happily accepted the challenge. After all, what’s not to love about a Mediterranean itinerary making stops in Naples, Istanbul, and Mykonos?
After seven days sailing past some of the prettiest coastlines I’d ever seen, I was completely hooked. Between testing out Princess’ new specialty restaurants—from Catch by Rudi to Love by Britto—and experiencing the mind-bending Spellbound by Magic Castle evening, I finally understood why cruising has such a massive, fiercely loyal fanbase. The ability to wake up in a new country every morning, experience world-class dining and completely hand over your stress to an all-inclusive tab makes it an incredible value. For busy working parents in the sandwich generation, it’s practically the perfect vacation.
So, when an invitation arrived to head back to the Mediterranean a year later to cover the biggest ship at sea—Royal Caribbean’s brand-new Legend of the Seas—saying yes was a no-brainer. But this time around, I’m looking at my suitcase with a lot more wisdom. After packing for and surviving 10 more cruises in other destinations over the last 12 months, I’ve realized just how many rookie mistakes I made that first time out.
As I get ready to board my second Mediterranean voyage, here are the major cruise pitfalls I am actively fixing:
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Related: Why Everyone Is Swapping the Mediterranean for a ‘Coolcation’ Cruise This Summer
Over-Scheduling the Port Days
When I set sail the first time, I was completely overwhelmed by the sheer volume of choices. I’d never been to Naples, the Amalfi Coast, Turkey or Greece, and I was desperate to maximize every single second on shore. I fell face-first into cruise newbie mistake number one: booking an all-day, marathon excursion for every single stop.
Whether we were docking in Naples, Istanbul, Crete, or Mykonos, I had an eight-hour tour locked in. The reality? It was exhausting. Every morning became a high-stress race against the clock—waking up at dawn, battling the crowds at the buffet and the espresso bar, scrambling to find the right gangway station, and making sure I had the exact documents in hand. From there, it was straight onto a bus with 40 strangers for an eight-hour tour that left very little time to actually take in the scenery.
While ship-sponsored excursions are an easy, seamless option, I wish I had spent some time researching traveler groups on social media to figure out the true crowd-favorites. This time, I’m keeping it chill. I want the freedom to simply wander through the gorgeous, pedestrian streets of Málaga or slow down for a long lunch in Cinque Terre. Excursions in every port are expensive, unnecessary and generate a ton of time anxiety—which is the absolute last thing you want on vacation.
Treating Ship Excursions as the Only Option
It’s the ultimate cruise conundrum: Do you pay a premium for the ship’s official excursions to guarantee you won’t be left behind on the dock? Or do you venture out on your own via third-party sites—or even just wing it at the pier—to find a cheaper, more authentic local experience?
The answer is that it really depends on the destination. On my first trip, a few seasoned travel creators on board bypassed the ship’s menu and booked a private, third-party horseback riding tour along the coast of Crete, returning with incredible stories of swimming in the sea with the horses. They knew exactly what they were doing, kept the timeline short and right in the middle of our off-shore window, and made it back with hours to spare.
On the flip side, I was deeply grateful that my all-day tour of Pompeii, Sorrento and Capri was booked directly through the cruise line. It was a logistically packed itinerary involving high-speed ferries, massive tourist lines, and multiple moving parts where a lot could go wrong. And on a holiday weekend, it did—traffic backed up, and our tour ran two hours late. Because it was a sanctioned cruise excursion, our guide was in constant contact with the bridge, and the ship waited for us.
For this upcoming trip, I’m doing the homework ahead of time so I can confidently explore the local neighborhoods on foot, while keeping a strict eye on the clock.
Related: This Popular Cruise Line Is Reimagining One of Its Ships to Be Completely Adults-Only
Waiting to Book Restaurants and Shows Onboard
Luckily, I had an experienced team helping me map out my first sailing, but on subsequent trips when I’ve been left to my own devices, I made the mistake of trying to “wing it” when it came to specialty dining and marquee shows. Any veteran cruiser reading this right now is probably shaking their head.
Before you even think about heading to the safety muster station, hitting the welcome buffet or filming a room tour for your Instagram Reels, you need to find a quiet corner, log into the ship’s Wi-Fi, and open the app. The most sought-after entertainment on these mega-ships—like Legend of the Seas’ high-octane Shockwave production or Charlie and the Chocolate Factory, or Norwegian Cruise Line’s massive Elton John tribute shows—will reliably sell out on day one. On a recent MSC Cruises sailing, I ended up going straight to the concierge desk to help me manually piece together a master schedule of dinner times and theater reservations just to cut through the digital gridlock. If your cruise line allows you to lock in these reservations weeks before you fly out, do it the second your booking window opens.
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Overpacking the Wardrobe
The second I found out I was heading to Europe last summer, visions of an effortless, linen-heavy “Euro-summer capsule wardrobe” completely took over my brain. I meticulously planned seven distinct daytime outfits, three separate swimsuit-and-cover-up combinations for the pool deck, more than seven upscale evening looks for formal nights, and an embarrassing five or six pairs of shoes. I wanted to look professional, polished, and like a seasoned traveler who belonged on a luxury liner.
Instead, I ended up dragging a massive, overweight checked bag across the ancient cobblestones of Rome and hauling it through crowded customs lines. It was a total headache, and I spent the week watching smart, stylish passengers breeze past me with a single, sleek carry-on.
After a solid year of traveling on the water, I’ve finally mastered the art of the cruise edit. The trick is to pick a rigid, simple color palette—like crisp white, black and navy—and accent it with one or two fun pops of color. You truly only need a maximum of four versatile bottoms, four tops, four lightweight dresses and two swimsuits. As for footwear? Limit yourself to three pairs max, and make sure one of those is the supportive pair of sneakers you wear onto the airplane. You’ll still have plenty of outfit options, your back will thank you, and you’ll actually have leftover room in your bag to pack a few unique souvenirs from the local boutiques on shore.
Related: How I Pack for a 7-Day Cruise With a Single Carry-On
Forgetting to Protect the Spontaneous Downtime
When you look at the glittering promotional videos for these massive new ships, it’s always the record-breaking features that grab the headlines—whether it’s the high-tech culinary theaters like Royal Caribbean’s Royal Railway or upscale partnerships like MSC’s Eataly. Those marquee experiences are absolutely worth the hype, but some of the most memorable moments I’ve ever had at sea happened entirely in the quiet spaces in between.
It’s the hidden, adults-only infinity pool at the aft of the ship that feels like your own private deck because nobody else stumbled upon it. It’s sitting at the dueling piano bar on Legend late at night, or sharing a great conversation over the best espresso martini of your life in a quiet lounge. It’s watching an impromptu ABBA tribute set that somehow gets everyone from teenagers to grandmothers up and dancing together like no one is watching.
It’s incredibly easy to overschedule your vacation to the point where it feels like a corporate itinerary. This time around, I am intentionally leaving blank spaces in my calendar. Some of the best parts of a cruise are the spontaneous, unscripted moments—the ones your phone never captures because you were too busy simply being in the moment.
Related: Why Everyone Is Swapping the Mediterranean for a ‘Coolcation’ Cruise This Summer
