What to Wear on a Caribbean Cruise: Outfit Ideas and Packing List! (2024)

Self-declaring as “not a cruise person,” the opportunity to dig out my chicest resort wear became the saving grace for a 14-day Caribbean cruise I accidentally ended up on.

Yes, accidentally. A week before setting sail on what was supposed to be an adventure sailing nearly the entirety of the Amazon River, thanks to an extremely generous gift from my boyfriend’s grandparents, Viking Cruises canceled the Amazon portion of my Amazon cruise, rerouting the ship to sit in the Caribbean for close to two weeks instead.

Though it wasn’t the trip of a lifetime I expected, I still had a fabulous, memorable time filled with tropical Caribbean cruise outfits, phenomenal people, and of course, a few noteworthy stops in Dominica, St. John, and St. Lucia, amongst others.

As a first-time cruiser, packing for a Caribbean cruise in the winter was daunting, especially as many cruise ship cabins have limited space, to say the least, even when booking with those more giving with space like Viking.

Let my first-hand experience planning Caribbean cruise outfits to the tee (shirt) help you stay stylish when sailing this lush region:

Embarkation Day Outfit

Embarkation day can be a real waiting game, between waking up early to wait to enter the cruise terminal, check-in, passport checks, and security. Once you’re through all that, there’s of course, the obligatory muster drill and waiting period until your cabin is actually available.

Stick with something stylish enough to wear sightseeing after check-in ends but comfortable enough to sit through long waiting periods.

If your port of embarkation is in tropical weather, such as in Florida or Puerto Rico, go for lightweight sundresses or shorts and a cute top paired with cushy sandals or leather sneakers.

If you’re embarking from cooler weather, such as from New York, a sweater dress or cozy top paired with jeans and booties or sneakers might be more appropriate—especially if you’re taking a Caribbean cruise in the winter.

I embarked in San Juan, Puerto Rico, so my Caribbean cruise outfit for the day was a white linen crop top paired with high-waisted white cotton shorts and white leather sneakers. I finished the look with big statement earrings to give it a little extra flair.

Shop Caribbean cruise embarkation day outfit ideas:

• Top: Reformation Lindy Knit Top // Reformation Overland Linen Top // Lovers and Friends Aiden Bodysuit // Cult Gaia Anahita Top
• Bottoms: Zimmermann Lexie Belted Linen Shorts // Aje Agua Embroidered Linen-Blend Mini Skirt
• Dresses: Hill House Home The Elizabeth Nap Dress
• Jewelry: SHASHI Juliette Earrings // Sequin Jewelry Golden Snake Stud Earrings

What to Wear on a Caribbean Cruise During the Day

Trying to figure out what to wear on a Caribbean cruise in the winter is much easier than in other seasons. Pack your trunk for a glamorous whirl around the Caribbean’s blue skies and clear seas. Visiting from December to May, you’ll be greeted with warm weather and mostly dry skies.

June to November leaves more to be desired. The Caribbean, though still warm, enters hurricane season, often seeing turbulent weather, including high winds and heavy rain. Many Caribbean cruises don’t sail at all in these months.

During the day, your Caribbean cruise outfits should include warm-weather staples like sundresses, crop tops or sleeveless shirts, shorts, skirts, and lots of swimwear. While packing, include an oversized linen button-down—the ideal layer over a sundress or crop top and an excellent makeshift swimsuit coverup.

Stick to natural fibers like cotton, linen, and bamboo for breathability in the Caribbean’s thick humidity.

To be honest, most of my Caribbean cruise outfits during the day consisted of swimwear, swimwear, and more swimwear—bikinis, one-pieces, crocheted coverups, breezy sarongs, you name it.

Bring at least one pair of sandals for walking, rubber flip-flops for the beach or pool, and leather sneakers for daytime use.

Find casual Caribbean cruise outfits for the day:

• Tops: Agua by Agua Bendita Zilia Open Crochet Crop Top // Farm Rio White Delicate Garden Sleeveless Crop Top // Cult Gaia Ase Top
• Bottoms: Agua By Agua Bendita Arroyo Floral Crochet Midi Skirt // Zimmermann Junie Embroidered Short
• Dresses: Agua by Agua Bendita Lima Embroidered Linen Mini Dress // Silvia Tcherassi Balerina Embroidered Mini Dress // Johanna Ortiz Spec Wilderness Tie Back Maxi Dress
• Swimsuits: Tularosa Akira Bikini Top and Bottoms // Lovers and Friends Take Me Away Bikini Top and Bottoms
• Swim coverups: superdown Keva Wrap Maxi Skirt // Luli Fama Ocean Queen Long Caftan // Zephyr Floral Crochet Sweater and Shorts

Caribbean Cruise Formal Night Outfits for Women

Depending on your ship, your Caribbean cruise might include one or more formal nights—your excuse to go all out with your Caribbean cruise outfits.

Shimmering ball gowns, crisp tuxedos, and the like are in order for this black-tie dress code. Your ship’s formal night may also allow for elegant co*cktail dresses or a simple suit if more relaxed.

A black-tie look isn’t one you’re likely to find on shore when sailing the Caribbean islands. Plan your formal look in advance, including a floor-length gown or formal jumpsuit, statement jewelry, high heels, and minaudière.

Discover Caribbean cruise formal night outfit ideas:

• Gown: Cult Gaia Renata Gown // Mac Duggal Ruched Tiered Criss Cross Spaghetti Strap Gown // Mac Duggal Asymmetric Metallic Pleated Ball Gown // Camila Coehlo Isaura Maxi Dress
• Shoes: Alexandre Birman Clarita 90mm Block Sandals // Aquazurra Galactic Flower Leather Sandals
• Jewelry: Miranda Frye Jasmine Earring // Elizabeth Cole Suzie Earrings

Caribbean Cruise Outfit Ideas for Excursions

Being an accidental Caribbean cruiser, I underestimated just how important it is to book excursions for most ports of call—and book them in advance.

Snorkeling, scuba diving, catamaran sailing, island tours, hiking, cooking classes, and visits to beach clubs at large resorts are among the most popular Caribbean cruise excursions.

Casual, leisurely excursions, like a cooking class or island tour by car, are easy to plan for—if there’s no active component, wear one of your daytime Caribbean cruise outfits.

More active excursions, such as hiking or cliff jumping, require a little more planning. Pack activewear such as a sports bra, leggings, and gym shoes, in addition to appropriate swimwear and a swimsuit coverup.

As I learned the hard way, the rainforests in the Caribbean are havens for bugs. If you’re venturing into the rainforest on an active excursion, pack longer clothing, such as full-length leggings, rather than running shorts or bike shorts to minimize bug bites.

If your cruise is during shoulder season when the Caribbean receives rain, bring gear such as a packable poncho, rain jacket, and waterproof shoes to stay dry during your shore excursions.

Cruise shore excursion outfit inspiration:

• Tops and sports bras: lululemon Align™ V-Neck Bra // Athleta Elation V-Neck Longline Bra // Alo Yoga Goddess Ribbed Cropped Racerback Tank
• Bottoms: lululemon Align™ High-Rise Pant with Pockets 25″ // Alo Yoga Aces Tennis Skirt
• Shoes: APL Techloom Pro // On Cloud 5 Sneakers

Caribbean Cruise Outfits for Sea Days

I didn’t understand why so many cruise enthusiasts selected itineraries specifically for precious sea days before setting sail on my first Caribbean cruise.

The pure sailing days offer a unique experience to lay back, relax, and enjoy the ship and its excellent service—it’s truly luxury, especially if you’re used to a fast-paced lifestyle.

Maybe it’s a trip to the spa followed by a co*cktail by the pool or shuffleboard on the sports deck followed by a night hiding out in the theater. Sometimes, ships plan for special activities on sea days, like when Viking Cruises hosted a poolside barbecue with the ship’s band on my Caribbean cruise.

Your Caribbean cruise outfits for sea days should be casual and comfortable. You can wear something similar to what you would wear onshore during the day or take an even more laid-back approach with breezy elastic waist linen pants or chic lightweight loungewear.

Find sea day outfits for Caribbean cruises:

• Tops: Hill House Home The James Shirt // Hill House Home The Paz Nap Top
• Bottoms: Hill House Home The Livie Nap Shorts // Hill House Home The Paz Skirt
• Lounge sets: Piyama Lounge Set // Piyama Leni Lounge Set

Best Shoes to Pack for a Caribbean Cruise

My cabin looked like something out of Carrie Bradshaw’s closet during my Caribbean cruise.

That’s right, I felt the need to bring all the footwear options, and I don’t regret it in the slightest.

Two pairs of espadrille wedges, one pair of high-heeled sandals, one pair of flat leather sandals, a pair of rubber flip-flops, white leather sneakers, and gym shoes went into my suitcase for my two-week-long Caribbean cruise, and I wore all of them multiple times, some nearly every day.

Okay, maybe I tend to overplan my shoes, but what can I say? My shoes are Choos and I hardly leave home without fabulous footwear—a friend once asked if I was sick when I tried.

Stripping away my penchant for footwear options, at a minimum, pack the following shoes for a Caribbean cruise:

• A good pair of walking shoes
• Rubber sandals for the beach or pool
• Nice sandals that can be dressed up for dinner
• Gym shoes if your walking shoes are not
• Formal shoes, like high heels, if your cruise includes a black-tie night

Caribbean Cruise Dress Code

Dress codes are not created equal in the Caribbean—they vary widely by ship both in standards and enforcement. Study up on yours before packing for your cruise.

As a general rule of thumb, most ships keep to a casual dress code during the day. Casual clothing may be allowed at night, or the ship may enforce a slightly dressier standard. The dress code may fluctuate by restaurant if you’re on a large Caribbean cruise ship with several dining options.

Many ships have at least one restaurant where casual clothing is allowed at night if you’re not one for dressing up.

In addition to standard day and night dress codes, some ships have formal nights with black-tie dress codes or special event nights with separate standards entirely. For example, Virgin Cruises does an iconic Scarlet Night on their adult-only Caribbean cruises, during which the whole ship is ordered to dress up in their best bright red looks.

On my Caribbean cruise, casual clothing was allowed during the day and at the buffet restaurant for dinner. Activewear and swimwear were not allowed anywhere on the ship besides the pool deck or gym.

For dinner, shorts, jeans, and flip-flops were strictly off-limits in all restaurants except for the auxiliary buffet restaurant. Men needed to be in a collared shirt and slacks, while women could wear a nice blouse with trousers or a skirt, or a dress. The dinner dress code was strictly enforced, while the daytime dress code tended to be lenient.

Caribbean Cruise Packing Tips

How to Plan Caribbean Cruise Outfits

For long cruises over 10 days in length, packing enough daytime Caribbean cruise outfits while working with limited cabin space is a delicate art.

Cut down on the amount of clothing you need to bring by ensuring that most of your clothing can be paired with at least two other separates (i.e., one top matches two pairs of shorts, and one skirt works with at least two tops).

Doing Laundry on a Caribbean Cruise

While packing your Caribbean cruise outfits, consider whether your ship has laundry. If your ship includes free laundry as an amenity, you may get away with packing less.

If your ship does not include free laundry, doing laundry can be pricey. To save space, consider packing clothing that can easily be hand-washed in your room’s shower or bathtub instead.

Keep in mind that some items, like swimwear, will take longer to hang dry than others. Bring at least three to four swimsuits to wash and rotate through your cruise, so you’ll never have to wear one that’s still wet.

Pack with Travel Organizers

My suitcase was a jumbled mess of clothing, jewelry, shoes, and toiletries before begrudgingly giving travel organizers a try.

Now, I’m a believer (though I hate to admit it).

Suitcase accessories like packing cubes and compact jewelry organizers can make unpacking and repacking your luggage a breeze in a tight space. They can also help you stay organized during your cruise.

For example, this clothing organizer can be removed from your suitcase as-is and hung up in your cabin’s closet. When your cruise is over, it folds back down to be neatly tucked away back in your luggage.

My favorite travel jewelry box is now a must on all my trips—it’s small and lightweight but sits perfectly on a dressing table, keeping all of my favorite baubles easy to see and tangle-free.

Use packing cubes to separate all of your clothing by type. When you’re loading clothing into your cabin’s dresser, unpacking will become mindless as you won’t need to sort.

Bringing a curling and flat iron cover is necessary for packing your hair styling tools. A quality one will have a heat-resistant lining that lets you put your tools back in while still hot. It sounds unnecessary, but during my cruise, it was a massive help for saving valuable bathroom counter space while getting ready.

Save Money by Purchasing Everything in Advance

Most cruise ships have general stores with essentials like sunscreen and feminine hygiene products for those in a pinch, but these come with a steep price tag.

On my cruise, a small bottle of sunscreen was $30 USD, and aloe vera was even more. Sunscreen in our ports of call was cheaper but very low quality and a premium compared to stores at home.

Though we had to give in and buy an $8 bottle of awful sunscreen in Grenada, we luckily bought aloe vera from CVS in San Juan before the ship left port, saving us some money after sailing all day in Saint Lucia left us burnt to a crisp.

In addition to your toiletry essentials, consider buying extras like snorkeling gear and water shoes before leaving home. In my experience, water sports gear is surprisingly tricky to come by on some of the Caribbean islands, and when you do, it is pricey.

Pro tip: If your Caribbean cruise is embarking in San Juan, Puerto Rico, a well-priced Walmart (with $12 snorkeling gear, sunscreen, and other necessities) is an inexpensive Uber ride away from port.

Complete Caribbean Cruise Packing List

Clothing

• Crop tops
• Sleeveless shirts
• Linen button-down shirt
• Lightweight sweater
• Sweatshirt
• Shorts
• Skirts
• Linen pants
• Casual dresses (mini or midi)
• Maxi dresses
• Formal gown
• Swimwear
• Swimsuit coverup
• Sports bra
• Leggings with pockets
• Rain jacket or packable poncho
• Bras
• Underwear
• Pajamas
• Gel petals
• Theme night outfits

Shoes

• Flat sandals comfortable enough for walking
• Neutral heels
• Espadrille wedges
• White leather sneakers or walking shoes of your choice
• Rubber flip-flops
• Athletic tennis shoes

Jewelry and Accessories

• Sunglasses
• Simple stud earrings
• Beachy statement earrings
• Necklaces
• Bracelets
• Travel jewelry organizer
• Small crossbody bag
• Beach bag

Toiletries

• Makeup
• Face wash
• Shampoo
• Conditioner
• Shaving razor
• Nail clipper
• Tweezers
• Skincare routine (toner, moisturizer, serum)
• Sunscreen
• High deet bug spray
• Aloe vera gel
• Toothbrush
• Toothpaste
• Travel toothbrush protector
• Glasses
• Lens cleaner
• Contacts
• Contact solution
• Hairbrush
• Hair straightener
• Hair curler
• Curling and flat iron cover
• Hair spray or styling gel
• Feminine hygiene products
• Needed prescription medications
• Ibuprofen
• Pepto Bismol
• Dramamine or motion sickness patches
• Imodium

Miscellaneous

• Phone charger
• Earbuds
• Power bank
• Chargers for all electronics (camera, laptop, power bank, tablet, etc.)
• GoPro
• Camera
• Extra SD card for your camera
• Turkish towel, such as a Sand Cloud
• USD in cash
• Passport
• Driver’s license
• Location tags such as AirTags
• Small pair of scissors
• Wet bag for swimwear
• Snorkeling equipment

Caribbean Cruise Outfits: FAQ