Packing for a two-week Mediterranean cruise with nothing but a carry-on sounded like a perfectly reasonable challenge when I first started planning what I’d wear on this trip. I travel often, I know what I actually wear, and I’ve learned that shlepping an oversized suitcase through airports, hotels and cruise terminals can take some of the joy out of traveling.
At this point in my life, I want my travel days to feel easier. I don’t want to struggle with a heavy suitcase, wait at baggage claim as I miss my suitcase that went by on the carousel, or worry that my luggage might not make it to Athens when I do (which happened to my husband in Alaska). But, at 72 years old (and 5′ tall) I also have to be realistic about what I can comfortably lift into an airplane’s overhead bin.
So, of course I planned everything meticulously.
I chose pieces that could be mixed and matched using my favorite toddler method of packing. I coordinated my colors. I thought about warm days in Greece, cooler evenings on the ship, sightseeing, dinners and the long flights back and forth. I even thought out how many times I could wear each piece without feeling as though I were wearing the same outfit over and over again.
I had it all figured out.
Then they threw me a curveball.
You see, I didn’t have the entire itinerary until after I had laid it all out and suddenly, the itinerary included a cocktail party with “cocktail attire” and a gala at the foot of the Acropolis where evening dress is required.
Well, that changes things!!!
It’s one thing to create a small capsule wardrobe for sightseeing and casual dinners, adding a nice top to go with a simple skirt like I always do for dress-up nights. It is quite another to fit a cocktail dress and something worthy of an evening at the Acropolis into the same little carry-on.
I sat and pictured formal gowns, evening shoes and all the accessories that usually go along with them. I was excited to be going and at the same time worried that I’d have to ditch my usual way of traveling and actually check my big suitcase. Then I reminded myself that I don’t need a different dress for every occasion. I just need the right pieces and a bit of creativity.
Related: I’m a 72-Year-Old Cruise Expert—Here’s the ‘Toddler Method’ I Use to Pack a Carry-On
One Cocktail Dress, Multiple Evenings
My first solution is to pack one cocktail dress that I can wear to the cocktail party and any dressier evenings onboard. That’s right. I’m not afraid of wearing the same dress more than once. As a matter of fact, with a ship with thousands of passengers, the only one who’s going to notice is ME and I’m perfectly fine with that.
PRETTYGARDEN Women's Summer Satin Maxi Cocktail Dress Black
Check PriceTruthfully, most people don’t look at what you’re wearing, only you do. And, even if someone notices, changing the jewelry, wrap, shoes, or even your hairstyle can make the same dress feel different. Besides, I would much rather repeat a beautiful dress than carry three dresses that each get worn for only a few hours.
The key is choosing a cocktail dress that feels special without being bulky. I want something that looks polished, photographs well, and doesn’t require me to shimmy into uncomfortable shapewear (something ELSE to pack, and the thought of being miserable as I adjust and readjust is out of the question). It also needs to pack easily and come out of the suitcase without looking as though it has been folded into a carry-on for several days.
One dress. Several occasions. Very little suitcase space.
This Elegant Bubble Skirt Does Double Duty
Bubble Skirt and Off the Shoulder topZippy Sandler
The other piece which is something I was already planning on bringing is a bubble skirt.
Now, a bubble skirt might not be the first thing that comes to mind when you think of practical travel clothing, but this one gives me options because it’s floor-length. Paired with an off-the-shoulder top, statement earrings, and gold sandals, it is dressy enough for that gala, a special dinner, or an evening event.
Hanpceirs Women's Bubble Maxi Skirts Long Skirt with Pockets White M
Check PriceMine is white, and I usually wear the same skirt with a simple T-shirt or striped top for a completely different look. That takes it from dressy to casual without adding another bottom to my suitcase.
This is exactly what I look for when packing light. Every piece needs to have more than one purpose. If something can only be worn one way, I have to think very carefully about whether it deserves space in my bag.
The bubble skirt does.
It gives me yet another dressy option without having to pack a full dress. I can even wear it during the day, depending on how I style it. That versatility makes it so much more valuable than an outfit that’s simply for evening.
From Beach to the Ball in Gold Sandals
olegbreslavtsev / Getty Images
From years of experience as a cruiser, I can tell you that shoes are usually the fastest way to lose the carry-on packing battle.
They make your suitcase heavy, are awkwardly shaped, and take up an unbelievable amount of room. If I had someone to carry my suitcases for me everywhere – to check in, from the carousel, to the ship, and to the cabin I’m one of those people who’d pack an entire suitcase just filled with shoes for every occasion, but even an extra pair can turn a carefully planned carry-on suddenly impossible to close.
My solution is to skip the heels and pack flat gold sandals.
DREAM PAIRS Women's Flat Ankle Strap Sandals,Gold,7
Check PriceAt 70+, I have nothing to prove by wobbling across cobblestones or standing through a cocktail party in uncomfortable shoes anyway. I want to enjoy the evening, not spend it wondering when I can sit down or spending the next day looking for blister patches.
The right pair of flat gold sandals can take me from the beach to the ball…literally. They work with a sundress, the bubble skirt, my cocktail dress, and even a more casual pair of pants. The metallic gold makes them look festive enough for evening, while the flat sole keeps them practical for travel.
Comfort does not have to mean giving up style. In fact, I think that walking into a gala in beautiful flat sandals looks much more elegant than wobbling in a pair of heels that hurt.
FYI, I always make sure to wear my sneakers on the plane because they are the most awkward to pack. That leaves room in the suitcase for the sandals and possibly one additional lightweight pair of either sandals or flats, but nothing that only works with a single outfit.
Building the Rest of the Wardrobe
Kostikova / Getty Images
The easiest way to make a small travel wardrobe work is to choose a color story and stay with it. I do not pack random tops, pants, and skirts and hope they somehow work together when I arrive. Each top needs to coordinate with more than one bottom (a skirt, slacks, shorts, a skort, or even as a cover-up over my bathing suit). Every layer should work with several outfits. My shoes should go with almost everything.
My color story is usually black, white, and a few coordinating colors that make mixing and matching easier. A striped shirt can be worn with the bubble skirt one day and a pair of pants or a skort another day. A simple white or black T-shirt can work for sightseeing, lunch, or underneath a cardigan at night.
Accessories will keep the outfits from feeling repetitive. Scarves, jewelry, and a belt take up very little room (and can be tucked INSIDE your shoes in the suitcase so they don’t take up any room), but they can completely change the way an outfit looks. And, if it’s one of those cruises when photos are part of the trip, and I don’t want Monday’s outfit to look like Tuesday’s.
Related: I Was Panicking About a 2-Week Cruise With Only a Carry-On. Then, I Remembered My Cruise Loyalty Perks.
Planning for Mediterranean Days and Cruise Ship Evenings
For certain regions, like a Mediterranean cruise, you’ll need clothes for different types of experiences. There will be warm days, walking tours, ancient sites, seaside stops, meals onboard, and nights when the breeze off the water may have you running for that cardigan. There may also be churches or historic sites where shoulders and knees should be covered out of respect.
Lightweight layers solve many of those problems. A scarf or wrap can cover my shoulders during the day and become an evening layer later over my cocktail dress at night. A lightweight cardigan works on the plane, in air-conditioned restaurants, and on the ship. Simple, comfortable slacks can be dressed up for dinner but still work for travel days.
Rather than packing for every imaginable situation, it’s more important to pack pieces that are easily adaptable to whatever the situation is. That is the real secret to carry-on travel.
Related: The Golden Rules of Stress-Free Cruising, According to a Lifelong Traveler
Packing for Reality, Not Fantasy
Zippy Sandler
One of the biggest packing mistakes I have made in the past is packing for a fantasy version of what I think I want to look like when I travel.
The imaginary me changes outfits three times a day, wears every beautiful pair of shoes I own, and somehow never spills anything on a white blouse. I also don’t mind carrying a suitcase that weighs twice as much as I do.
The real me wants to be comfortable. I repeat my favorite outfits. I reach for the same shoes and crossbody bag because they’re comfortable and easy to walk in. I’d rather spend the morning enjoying Athens than standing in front of my hotel room closet deciding between six nearly identical outfits. So, I pay attention to what I truly wear when I travel.
I don’t need a different outfit for every dinner. I do not need several “just in case” dresses. I don’t need heels simply because the words “cocktail attire” and “evening dress” suddenly appear on the itinerary. I need clothes that make me feel attractive, comfortable, and appropriate for the occasion.
The Beauty and Toiletry Edit
Kostikova / Getty Images
But as women, we know that clothing is only part of the carry-on challenge. Toiletries and beauty products can quietly take over an entire bag if I let them.
So, I bring smaller sizes of the products I actually use and leave the extras at home. This is not the trip for six lipsticks or three different face creams.
One or two good lipsticks, a few multipurpose makeup products (for me that’s a bronzer that doubles as a blush and even eye-shadow), and travel-size skincare will cover most situations. The same makeup can work during the day and become evening-ready with a stronger lip color or a little more eye makeup.
I also use whatever the hotel and cruise ship provide when it makes sense. I never bring a full-size bottle of something that will already be waiting in the bathroom, like soap, shampoo, or conditioner.
Related: Is a Balcony Cabin Worth the Upgrade? This Cruise Expert Says It Depends on One Thing
Leaving Room for the Unexpected
The hardest part of packing a carry-on is resisting the urge to fill every available inch. But I know myself. I will probably find something during the trip that I want to buy. It might be a scarf, a piece of jewelry, or something small from one of the ports (I love Greek jewelry and clothing, so I’m already planning for this to happen).
If my suitcase is bursting at the seams when I leave, I will have no room for anything I discover along the way. I use packing cubes to help keep everything organized and compressed, but my goal is not to stuff them until the zippers beg for mercy. I want to know where everything is, and I want to be able to repack without sitting on the suitcase.
The Carry-On Test
aquaArts studio / Getty Images
Before I leave, I do a final test.
Everything has to fit in the suitcase. I need to be able to lift it. Every piece of clothing must work with the plan, and anything that makes me say, “I might wear this,” gets tossed. “Might” is dangerous when you are packing for two weeks in a carry-on.
If I cannot think of at least two ways I’m going to wear something, it probably stays home. The exceptions are the cocktail dress and any truly essential specialty item. Even the cocktail dress, however, will be worn more than once.
The goal is not to pack the smallest wardrobe possible, but to prove to myself that I can. The goal is to bring enough to enjoy the trip without letting my luggage become a burden.
The Glamour Still Fits
Packing light does not mean giving up glamour. I will still be properly dressed for the cocktail party. I will still have an evening look worthy of a gala at the foot of the Acropolis. I will still have outfits that make me feel like myself.
I will just not have a completely different wardrobe for every hour of the trip.
My cocktail dress will step in for multiple elegant evenings. My bubble skirt will go from an off-the-shoulder top at night to a simple T-shirt or striped shirt during the day. My flat gold sandals will carry me from the beach to the ball, without leaving my feet aching before the evening is over.
That is how I am handling the curveball.
At this age, I have learned that style is not about how much you bring. It is about knowing yourself well enough to bring the right things. If I can walk onto that plane with one manageable suitcase, arrive in Greece without worrying about lost luggage, and still feel fabulous, I will consider this packing challenge a success.
Related: 8 Fall Carry-On Essentials Every Traveler Needs
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