what to wear on a caribbean cruiseLike snowbirds, cruise ships migrate south for the winter, repositioning from San Francisco to Sydney or Vancouver to Miami, among other seasonal switch-ups. In search of aquamarine water and swaying palms, these cities at sea ply the open ocean offering sun seekers a taste of the good life, complete with Broadway-style entertainment, umbrella drinks, chocolate fountains, and a bevy of stops along the way.

Working on a cruise ship, and then cruising on a variety of vessels as a passenger, I’d say I’ve earned my stripes at sea. Not only do I suggest packing Breton stripes and boat shoes, I’ve assembled a fleet of other fashion-meets-function essentials worth stuffing into your suitcase.


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Here’s how to make the gangway your runway:

Carry it
I’m a big fan of the plane-to-pool bag. The embarkation process can make luggage delivery slow, so use your tote to get a head start sunning on the upper deck, packing your camera, sunglasses, hat, and bathing suit. At sea, use it to keep your essentials on hand from the pool deck to ports of call. I like the blue and white striped Baggu canvas tote ($24).


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Essentials
Clasping your cruise carryall (still packed with embarkation essentials), make sure you also include: a travel-sized hand sanitizer, a pashmina – you never know when a gust of wind could cause a chill – and a collapsible water bottle (I like Vapur, $9.99). If you’re with a big group and want to keep track of your brood, bring walkie-talkies, or see if the ship has an app mimicking multi-way communication.

Accessories
Unless you frequent the presidential suite, cabins and closets are efficient, meaning the less-is-more packing methodology is wise on the high seas. To dress up and down your sailing staples, I’m a big fan of accessorizing. Using your basics as a guide, choose whether you’re going to focus on big earrings or statement necklaces, not both. Scarves and pashminas can also glamorize or simplify an outfit without taking up too much space in your bag. At night, cart a clutch filled with your passenger card, lipstick, and blotting papers from dinner to the piano bar.

Basics
For your basics, pull yachting colors from your closet. White, navy, red, yellow, and black are striking at sea. Again, because closet space is tight, color coordinate making sure every garment can be worn twice and updated with accessories. For example, a navy shirtdress can double as a bathing suit cover-up for the pool and a belted dress for port.

Formal
Pick two dresses or mix and match your fancier staples to create a sleek evening look. Rotate pashminas and blazers to switch your look from one evening to the next.

Shoes
There’s no question shoes take up the most space in your suitcase, so choose wisely. I suggest one pair of dinner-to-dancing heels, non-slip flats, sandals, and flip-flops.

Insider Tip: If you choose to cruise the Caribbean during hurricane season (June – November), make sure to bring more than just light sweaters and shorts. Packing pants, non-slip shoes and a rain jacket is advisable.

Would you add any must-haves to this cruise packing list? A captain’s hat doesn’t count.

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