Planning Our First Mediterranean Cruise
There’s something deliciously ironic about planning a first anything at this stage of life. We’re seasoned now—well marinated in responsibility, careers, carpools, and college tuition—but there’s still plenty of youth left in the curiosity department. Enough, at least, to look at a map of the Mediterranean and think: Yes. That. Let’s finally do that.
This trip is our bucket-list celebration: a milestone birthday, a meaningful anniversary, and a long-imagined Mediterranean cruise—11 days at sea, bookended by time on land. Three days in Barcelona before the cruise to ease into the rhythm, and three days in Italy afterward to linger, wander, and decompress before heading home.
But dreaming is only half the fun. The other half? Research. Planning. Thinking ahead so the trip feels joyful, not rushed.
Here’s what I’m learning as we plan.
Why a Mediterranean Cruise (and Why Now)
A Mediterranean cruise is ideal for a “seasoned with youth” traveler. You unpack once, visit multiple countries, and still have the comfort of returning to the same cabin every night. For a first cruise, it’s especially appealing—structured but not rigid, adventurous without being exhausting. Well, it maybe exhausting as we want to see everything there is to see.
The Mediterranean also offers incredible variety: ancient history, coastal villages, world-class food, and landscapes that feel both cinematic and deeply human. It’s not one experience—it’s many.
And celebrating a big birthday and anniversary? That deserves something expansive.
Timing Is Everything: Booking 18 Months Ahead
Booking this far ahead gives us the luxury of time—time to research each port, figure out what’s actually worth seeing, and avoid the classic mistake of trying to “do Europe” in six hours and a panic. This isn’t a trip we take every other weekend, so we want to squeeze every possible ounce of value out of it. Booking early also comes with excursion credits, and you can be sure we intend to use every last one. Free money is still money.
Mostly, we want to explore at our own pace, on our own terms—without being herded around with a paddle and a flag. That said, we are very committed to making it back to the ship on time. Romantic sunsets are great. Missing the ship? Less so.
After far too much research (and a few late-night “just one more article” moments), one thing became very clear: booking 12–18 months in advance is often the sweet spot for popular itineraries like the Mediterranean.
Why?
You get first dibs on cabins—and yes, location matters more than I ever expected
Early-booking perks like onboard credit (aka justification for nicer wine)
Plenty of time to stalk airfare and hotel prices without breaking into a sweat
Far less stress—planning becomes part of the fun instead of a full-blown crisis
Cruise prices generally rise as ships fill, and while last-minute deals do exist, they’re a gamble—especially for milestone trips tied to specific dates. This is not the vacation to leave to fate, luck, or a flash sale at 2 a.m. Some trips deserve a plan.
Choosing the Right Itinerary (Not Just the Ship)
It’s very easy to fall in love with the ship—and yes, the amenities are lovely—but the itinerary is what really runs the show. A floating hotel is nice. Knowing where it’s actually taking you? That’s the point.
Things we’re paying close attention to:
Port balance:
Too many sea days can feel endless; too many ports and suddenly you’re speed-walking Europe with a map and mild panic. Let’s be honest—we want to see everything, so there will be some speed walking. Comfortable shoes aren’t a suggestion; they’re a survival tool.Port depth:
Longer port stays mean less “wave at the city from the bus window” tourism. Not all ports are close to the places you actually want to see. Trains, regional rail, and early morning alarms quickly become the norm—and once you accept that, it actually adds to the adventure.Embarkation and disembarkation cities:
These quietly shape your trip more than you might expect. Do you want to spend time exploring before boarding, or are you ready to jump straight into cruise mode? The same question applies at the end—rush to the airport or squeeze in one last coffee, walk, and moment of denial before heading home.Transit reality check:
Mediterranean ports often involve real logistics: tenders, traffic, train schedules, and the occasional “are we sure this is the right platform?” moment. Build in buffer time. Missing one attraction is far better than missing the ship.Energy budgeting:
Back-to-back port days look amazing when you’re planning. In real life, they can lead to museum overload and sitting in cafés purely to recover. Choose your must-sees, leave room to wander, and remember—sometimes the best part of the cruise is doing absolutely nothing on board.
We’re also looking beyond this trip. Once you start researching cruises, you realize they’re not just vacations—they’re gateways. This first one may very well set the tone for how (and where) we travel next.
We embark in Barcelona and disembark in Trieste, which means three days on either side of the cruise. That gives us time to properly explore Barcelona—its neighborhoods, its food, and its general joy of life—and then Venice and Rome, which feels like a once-in-a-lifetime experience I’m already counting down to. I booked this cruise a year ago, and now it’s officially time to make sure we actually see what we want to see.
Then came hotels. And let’s be honest: hotel options range from “should I keep my shoes on?” to ultra-luxury where the pillows probably have a backstory. But how much time do I really want to spend in a hotel room? I just want it clean, safe, and close enough that I don’t need a spreadsheet to get around.
So we started by researching neighborhoods—because location matters more than thread count. Once we narrowed that down, we looked at hotels and landed on solid mid-range options: comfortable, well-located, and not requiring a second mortgage. Doing the research ourselves saved money, gave us better choices, and let us spend where it actually counts—on experiences, food, and getting lost on purpose.
Pre-Cruise: Three Days in Barcelona to Adjust and Absorb
Arriving three days before the cruise isn’t indulgent—it’s smart.
It allows time to:
Adjust to jet lag
Explore without a clock
Protect against travel delays
Start the trip grounded, not groggy
Make sure we are there in plenty of time to get to the ship
Hotel research matters here. We’re prioritizing:
Location: Walkable neighborhoods near key attractions or cruise ports
Feedback: Consistent reviews over flashy photos
Price vs. value: Comfort and convenience beat luxury at this stage
Being close to public transit or major landmarks saves energy—and energy is currency when you want to enjoy every moment.
Post-Cruise: One day in Venice and 2 in Rome (to absorb culture)
After 11 days of movement, schedules, and stimulation, ending the trip with three days in Italy feels very intentional. Rome is an invitation to linger, to breathe, to sit down and actually be in the city instead of racing through it like it’s a scavenger hunt.
Here’s what we’re looking for:
A well-located hotel (again—location is everything)
Space to wander without an agenda
Cafés, piazzas, and unplanned afternoons
Pasta and gelato (obviously)
Rome isn’t a checklist city. It’s a sit-down-and-look-around city. Ending the journey here gives the experience room to settle, allows the sights to sink in, and gives us a moment to celebrate having survived the past 11 days of organized chaos. Honestly, it’s also a perfect excuse to practice our “I’m pretending to know Italian” smiles while eating gelato for breakfast.
Research, Reviews, and the Very Serious Bathroom Plan
We used booking sites to look for hotels, but let’s be clear—photos mean nothing without reviews. I want to hear from real people who stayed there, walked the neighborhood, and survived the experience. Recent reviews are especially important. A hotel can look charming online and still be located somewhere that feels a little too adventurous after sunset. Reviews saved us time, money, and potential regret.
My husband does his research a different way—YouTube. Lots of YouTube. And as much as I hate to admit it, it’s incredibly useful. We’ve found a few favorite travel influencers who actually walk through neighborhoods, explain transportation, and show what things really look like without strategic camera angles. Try it. You might fall down the rabbit hole too—and come out oddly prepared.
Thanks to this deep dive, we’ve picked up some excellent tips. For example, using an eSIM in Europe so we can have data without selling a kidney to our phone provider. We’ve also started pinning locations on maps ahead of time—restaurants, landmarks, cafés—so we don’t end up standing in the middle of a plaza debating options while everyone else looks like they know exactly where they’re going.
And then there’s my contribution to the planning process. Being a woman over 50, I’ve asked him to pin public bathrooms—and yes, note whether they cost money. I do not want to be taken short in Europe, nor do I want to discover at a critical moment that I need exact change. This is not the kind of surprise I enjoy while traveling. Some people plan for museums. I plan for bladder management. It’s called experience. Priorities, people—priorities.
What I’m Thinking About (That I Didn’t Before)
Planning this trip has reminded me how travel priorities evolve—or maybe it’s just that over-50 brains work differently.
Comfort matters—but so does curiosity. You can’t fully appreciate a new city if your feet are staging a rebellion. Slower can be richer than faster. Those two extra hours wandering a piazza? Priceless. Paying a little more for location can save a lot of energy. Experiences matter more than souvenirs (though gelato is always an exception). And perhaps most importantly: anticipation is part of the gift. Researching, planning, imagining—it’s all a form of travel before the travel.
Ship Life
The ship itself is practically a floating city—and yes, it’s geared toward seniors, or at least that’s the reputation. We’ve booked the drink and specialty dining packages because a vacation without at least one glass of wine in hand feels irresponsible. Onboard, we’re thinking about what to enjoy: spa treatments, the quiet lounges, maybe a game of shuffleboard (or at least people-watching). Sea days are for lingering, reading, napping, and sampling the restaurants without the guilt of missing ports. Booking dining in advance ensures we get our preferred times and avoid the “hangry at sea” scenario.
Excursions and Ports
Then there’s the fun but slightly overwhelming part: planning what to see in each port. Excursion research has become a full-time hobby. Which sites matter most? How much walking is too much? Which small cafés and gelaterias are worth the detour? And timing is everything—if we miscalculate, we risk missing the ship, and I refuse to live through that kind of midlife panic.
Balancing structured excursions with wandering on our own gives us the best of both worlds. We’ve also started pinning everything on maps: sights, restaurants, bathrooms (always bathrooms), and hidden corners that only locals know. This way, each stop has flexibility without becoming chaotic.
Consideration: What to Wear in Europe
Ah, the eternal question: what does one actually wear for three weeks in Europe in September without turning into a walking laundry basket? This isn’t just fashion—it’s logistics, strategy, and survival.
We’re talking 3 weeks out of a suitcase, multiple cities, cruise life, and city exploration. Layers? Absolutely. Comfy walking shoes? Mandatory. A little flair for photos? Obviously. And don’t even get me started on deciding whether to pack for summer, fall, or “who knows, let’s just hope for sunny days.”
Enter the modern miracle: cruise laundry service. Wow. These ships think of everything. My plan: use laundry service the first few days on board, somewhere mid-cruise, and again just before disembarking. This should drastically reduce the amount of dirty laundry I lug home—and hopefully jet lag won’t involve a mountain of socks and underwear waiting for me.
Then there’s my husband’s YouTube friends’ latest advice: merino wool. Yes, apparently you can wear it for days on end without cleaning it. Not sure I’m brave enough to test that after hours of walking through cobblestone streets, but I’m willing to try it… cautiously. The selling point? It’s easy to wash, which I suspect will be my preferred method.
We each bought one merino item for Christmas so we can experiment before committing (and breaking the bank). I’m a little skeptical, but hey—this is part of the fun: testing, planning, and occasionally looking ridiculous in the name of comfort.
Packing for Europe at our age is part art, part science, and part negotiation with your suitcase. But thanks to a little strategy, a dash of curiosity, and a hint of merino wool, I think we can survive—and maybe even look cute doing it.
Looking Ahead
We still have eight months before this cruise, and plenty of planning ahead of us. This is my first cruise, which means I could either fall head-over-heels for the cruise life—or politely retire it in favour of other adventures that don’t involve putting my luggage in a tiny closet. Either way, it’s part of the fun: imagining, planning, and debating whether a shuffleboard tournament counts as a “must-do activity.”
This Mediterranean cruise isn’t just a celebration of years lived—it’s an investment in years to come. Proof that even with experience behind us, there’s still so much ahead worth discovering. New cities, new food, new gelato flavors, new people to laugh with, and yes, maybe even new ways to navigate Europe without losing coins for the bathroom.
Seasoned, yes. But still hungry for what’s next. And honestly? That might be the best part. The thrill isn’t just in being somewhere new—it’s in knowing that, after all these years, curiosity still wins over comfort (most of the time).
Eight months may seem like a long countdown, but it’s actually just the perfect amount of time to dream, research, plan, and overthink… and then finally go and live it.
