I Sailed the Caribbean for 12 Days: All the Stylish Caribbean Cruise Outfits You Need to Pack

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.

Eva Phan wearing an all-white Caribbean cruise outfit in Viejo San Juan, Puerto Rico.

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:

Casual Caribbean cruise outfit consisting of a crop top, shorts, and statement earrings.
My actual embarkation day outfit for my Caribbean cruise was perfect for the long, hot day. These beachy Sequin Jewelry statement earrings were among my most worn during the trip.

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:

Eva Phan wearing a blue bikini on the beach in Barbados during a Caribbean cruise.
Getting sun at Carlisle Bay in Barbados in the Monday Swimwear Cala Roja Top and Palma Bottom.

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:

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 cocktail 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:

Eva Phan wearing a pink Monday Swimwear bikini as a Caribbean cruise outfit for conversions.
Sailing St. Lucia by catamaran in a Monday Swimwear Maui Top, Byron Bottom, and Mykonos Sarong—one of my favorite Caribbean cruise outfits of the whole trip.

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 bathing suits and a swimsuit coverup.

Consider your excursion itinerary when planning your outfits. When I visited Titou Gorge in Dominica during my cruise, I needed to bring swimwear and regular clothes. Having a wet bag was essential for keeping my soaked swimsuit separated from everything else.

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:

Caribbean cruise outfit for excursions, worn by Eva Phan.
Spontaneous exploration in Dominica while wearing a Reformation knit mini dress and Havaianas flip-flops.

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 cocktail 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:

Casual Caribbean cruise outfit for the day, worn by Eva Phan.
Exploring San Juan, Puerto Rico in Veja Esplar Sneakers and L’Academie shorts.

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:

Eva Phan wearing a blue mini dress, one of the best Caribbean cruise outfits for dinner.
The Michael Costello x REVOLVE Sunny Mini Dress was perfect for meeting Viking Cruises’ evening dress code. I paired the dress with gold espadrille wedges from Jimmy Choo.

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.

Resortwear set by Farm Rio worn on as a Caribbean cruise outfit.
One of my favorite casual Caribbean cruise outfits was this Farm Rio set paired with Sequin Jewelry hoop earrings, worn on a rum tour in Barbados.

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 for your cruise wardrobe 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 cruise wear, 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.

Eva Phan wearing a white bikini while in Grenada on a West Indies Caribbean cruise.
Cruising Grenada on a snorkeling excursion in a Monday Swimwear Sorrento Top and Capri Bottom.

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. We ordered cruise essentials from Amazon last minute, which saved us from having to spend even more.

In addition to your toiletries, 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.

White linen top and high-waisted white lace shorts worn by Eva Phan during a Caribbean cruise.

Complete Caribbean Cruise Packing List

Clothing

Shoes

Jewelry and Accessories

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

Woman wearing a crochet swimsuit coverup set on the beach in the Caribbean.
I wore tons of Monday Swimwear crochet swimsuit coverups during my cruise. Not only are they cute, they’re easy to throw on for excursions that require swimwear.

Caribbean Cruise Outfits: FAQ

What should I pack for a Caribbean cruise in the winter?

In the winter, the Caribbean tends to have warm weather and little rain. Bring lightweight resort wear such as sleeveless tops, shorts, sundresses, and sandals for exploring during the day, plus a few more formal options for nighttime events.

How many outfits should I pack for a Caribbean cruise?

Plan to wear at least one outfit during the day, one outfit at night, and possibly an additional outfit for an excursion per day on your Caribbean cruise. Pack separates that can be mixed and matched with each other. Bring enough clothing for seven daytime and seven nighttime outfits for a week-long Caribbean cruise.

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