Everything I Wore on a 5-Night Caribbean Cruise

Today I’m sharing everything I wore on a 5-night Caribbean cruise on the Ritz Carlton Yacht Collection.

As you may know, because I’ve been blabbing about it non-stop, Jim and I went on a 5-night Caribbean cruise.

I find it much easier to pack for warm weather vacations.

That said I was a little nervous about traveling on Ritz Carlton’s Yacht Collection for the first time.

Would other guests be dressed to the nine’s?

The answer, I’m happy to report, is no.

While everyone was beautifully and appropriately dressed, their ensembles were casual and comfortable.

And I felt really good about everything I packed.

Let’s discuss.

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Woman standing on balcony overlooking Atlantic Ocean wearing striped sweater and ivory shorts.

ENROUTE

Thank goodness the days of ‘dressing’ for travel are behind us because I like to be comfortable. I also try to avoid looking like too much of a schlub. It’s a fine line. For this trip I went with my usual lightweight joggers, a white t-shirt, cashmere sweater and denim jacket.

Woman taking mirror selfie in airport bathroom.

I wore Hokas, my workout shoes, because I thought I might visit the fitness center on the ship. Wishful thinking. I brought along my Medina Market Basket, a sturdy tote, with a dust bag inside so the contents stay put shoved under the airplane seat. Inside the tote is my Everywhere crossbody to keep phone and passport readily accessible. Also in the tote my favorite plane socks.

Woman leaning retrieving something from straw tote sitting on roller bag in airport.

 

Anyone else procrastinate when it comes to packing? Oh good, sit down next to me.

When I finally start to panic get serious about packing, I pull out my trusty rolling rack. I can’t sing its praises enough, as a packing and planning tool, and wish I’d gotten wise to the genius of it sooner. This is everything I wore on the cruise …

Rolling rack of clothes ready to be packed for Caribbean cruise.

Notice I said this is everything I wore. It does not represent everything I packed. Which was way too much and I only wore half of what I brought. Jim did the same. We weren’t really sure what to expect, now we know.

BON VOYAGE … BOARDING OUTFIT

Day One – San Juan, Puerto Rico –  The outfit I put the most thought into was my boarding outfit. Ha! I know … seriously. I’m not sure why … it just seemed important. And turns out it was one of my favorites of the trip. I bought the J.Crew trouser shorts last summer with the cruise in mind. They’re so versatile and can be pared with just about anything. I could really have leaned into the cruise them with my Veronica Beard navy blazer. Think Julie McCoy. Or, more realistically, Mrs. Howl.

I carried a Tony Bahama open weave raffia tote that Jim bought for me a few years ago. I spent way too much time trying to track it down on resale sites … no luck.

Woman standing on balcony overlooking Atlantic oceans wearing striped sweater and shorts.

 

DAYTIME – ONBOARD AND ASHORE

Our 5-night itinerary had us in a port everyday (no at-sea days). Most days were spent partially on the ship and partially onshore. Shorts, tanks and lightweight blouses, sundresses and of course bathing suits and coverups made up my daytime ensembles.

Day Two – Sandy Ground, Anguilla – I bought my swing dress at Loft a few years ago, it’s perfect for throwing on over a bathing suit. I walked around Sandy Ground looking perfectly respectable, then tossed it over my chaise as we ended our day at a beach bar. Yes, I’m wearing my controversial puffy slides. Can’t stop won’t stop.

 

Day Three – Gustavia, St. Barths – A full-0n beach day at the luxurious Le Barthelemy Hotel and Spa. J.Crew’s linen shirt dress-style cover up (currently on sale!) is perfect for traipsing around uber chic island towns and stunning beachside resorts. Not to mention being perfectly respectable while lunching at their lovely French restaurant. I’m wearing my J.Crew one-shoulder suit underneath.

Woman wearing shirt dress beach cover up walking on beach at St. Barths.

 

Day Four – St. John’s AntiguaJ.Crew Bermuda shorts and a striped tank were perfect for walking around St. John followed by the most amazing lunch at Casa Roots. If you find yourself in St. John’s, Antigua get yourself to Casa Roots.

 

Day Five – Virgin Gorda, BVI –  We toured the Virgin Gorda Baths which involves traversing caves with the tide rushing in and out. Bathing suits were recommended. And I wore my all-around favorite Tulum one-piece. It was another outing for my J.Crew shorts and a tank.

Couple standing in water under the Virgin Gorda Bath caves.

 

Other things I brought included this lounge set for hanging around our cabin and terrace.

Woman wearing navy blue lounge set on cruise ship terrace.

This sarong is the only thing I bought – you heard that right, the only thing I bought – for the cruise. Don’t get too excited, it’s no longer available. It worked really well with my black and leopard print bathing suits.

Black and tan sarong.

I brought four bathings suites … and wore them all.

 

Workout clothes – I packed workout clothes, but aside from wearing my Hokas on the plane I didn’t visit the ship’s fitness center and could have left them at home. Jim, on the other hand, visited the fitness center twice. Good for him!

 

Other essentials for daytime on the ship and ashore … a hat. Of course. I wore mine every day. It’s getting pretty beat up and I may have to invest in a new one soon. Jim ordered a similar style from Amazon last year, he kept the plastic mold it shipped in for packing. He put my hat inside on the mold, his on top and turns it upside down in his bag, packing other things inside. He always has more room in his suitcase (and he packs better). Otherwise I would wear mine to travel and use a hat clip. I didn’t know about hat clips until last year when I bought this one for our trip to Italy. It works great.

Hats on a countertop in Signature Suite on Evrima yacht.

Sunnies too are essential and who leaves home without them. I packed and wore two pair. And bags, I always bring too many and smart travelers would probably get by with one for day – a tote or some such – and one for night. I traveled with this market tote and also used it for our day trip in St. Barths. Otherwise, for going ashore I took my trusty J.Crew woven tote. I also like this La Pliage open knit as a beach bag and took it with us to Mexico last year; it takes up no room in suitcase.

I wore OluKai flip flops for most of our ashore adventures. On the ship I wore nicer sandals …

Flip flopped feet on old brick path at St. John's Cathedral, Antigua.

And of course a jacket. I wore my cropped denim jacket for travel but didn’t need it during the cruise. It’s no longer available which is such a bummer because it’s a favorite. But I’ve linked a few similars below.

Denim jacket hanging on took in entryway to cruise ship cabin.

 

DINNER AND EVENING ATTIRE

Here’s where things get dicey … and I contemplated not writing a what-I-wore post because my wardrobe was very casual and nothing spectacular. I was not the best dressed person on the ship. And I wasn’t the worst dressed either. Not by a long shot.

The Evrima yacht has is no main dining room and there are no formal nights. Yes, some guests got more gussied up than others, but the majority were low key and elegantly casual. I neglected to take photos of all my evening ensembles, and the two I missed were … are you sitting down … dresses I bought at Target several years ago. I didn’t pack either one with the intention of wearing them in the evening. But once I got a feel for the ship’s atmosphere … it felt perfectly fine.

That said, had we been traveling with friends or family I would probably have felt more motivated to step it up a bit in the evenings. I did pack several nicer dresses that didn’t get worn. I won’t tell you how many because … I already said, I overpacked.

On our first night on the ship we attended a Welcome Aboard cocktail reception on the Observation deck. I wore a floaty, black, tiered dress and threw my striped sweater over my shoulders.

Woman wearing black dress and striped sweater on cruise ship deck.

 

After the reception we went back to our cabin to change but were pressed for time, so I stuck with the tiered dress replaced my sweater with a Vince shirt-style jacket. I adore Clare V. ‘s basket bag with bamboo handles and use it every change I get. And it’s easy to pack, I just stuff underwear or a t-shirt, things like that, inside.

Woman wearing black dress and white jacket in cruise ship cabin.

I meant to change into my Tori Burch slides for these block heeded slides, but forgot. Oops.

 

The next night I brought out a favorite floral embroidered silk dress by Michael Kors … it’s sort of caftan-esque. My floral slides are Michael Kors too. I carried J.Crew’s Portofino straw clutch. I’ve gotten so much use out of it, I consider it summer wardrobe staple.

Couple standing on cruise ship suite deck.

I found the dress on eBay in XS. I’m wearing a small but it’s generously sized. And if you have tiny feet, here are the slides in ivory, and in cognac size 10. Here’s a white t-strap version size 9, and in red size 6. I could be up all night tracking these down on resale sites, but we’ve got to move on.

 

Here are the two Target dresses I wore.

Two summer dresses from Target.

On the left, Universal Thread seersucker striped maxi dress, is beautifully made and I wear it all the time. It’s easy to throw on and can be dressed up or down. I found it on Poshmark in an XS (here), Small (here) and Medium (here). For reference my dress is a small. The photos in all the listings are dreadful. On the right, A New Day spaghetti strap, smocked dress. Also seersucker and striped. There are quite a few listings on Poshmark for this dress too … XS (here and here), Small (here), Large (here and here).

 

And my last evening’s ensemble is a Rails wave print dress I bought at the end of last summer … and I’ve worn it over and over again. Of course, it’s no longer available because that’s the story of my life with this post. Because it’s a little chilly inside the ship, I wore a billowy white shirt as a sweater or jacket … a look I really love. And my favorite Jack Rogers sandals. It’s seems Jack Rogers no longer makes a neutral sandal in the original style which is irritating. I didn’t wear heels once on this trip. Even though I packed several pair. Sigh.

Woman wearing blue and white summer dress standing on cruise ship balcony.

Here’s the dress on Poshmark in a xsmall and large (I’m wearing small). And here’s a short swing, style in the same fun fabric (small and xsmall, and large) that would also be great for a Caribbean adventure. And just for fun here’s my same dress is a really wild print in a small.

 

While it’s warm outside, it’s cool inside the ship … so lightweight sweaters, jackets or wraps are a must when going sleeveless. I brought my Vince shirt-style jacket which of course is no longer available. Here’s an xsmall and  medium  and large on Poshmark.  I also brought an oversize white shirt which works well over dresses. And you can’t go wrong with J.Crew’s light cashmere wraps.  oversize white shirt.

 

I packed minimal jewelry, mostly gold toned basics and a couple of cocktail rings. I wore my faux diamond studs for travel and when we went ashore.

 

At night I alternated between a bucket bag and woven clutch.

 

These are a few of my must have packing essentials that probably don’t require an explanation. My hat clip has been discontinued, try this one. I think I’m going to upgrade.

 

A few things I packed and wish I’d worn. This Barefoot Dreams caftan that is the softest most comfortable and can be worn as a coverup or a dress, this Rails linen dress with lace up back detail, and these striped linen pants from Reformation.

 

And finally, some dresses I’ve been eyeing for the cruise and upcoming spring and summer vacations and occasions.

 

Divider graphic.

So there you have it, everything I wore on my Caribbean cruise.

What I Wore on a Caribbean Cruise pin collage.

You’ll find my full review of our Ritz Carlton Yacht Collection experience here.

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And I’ll be back on Saturday when I join Elizabeth and Kim for our weekend roundup.

Until then, cheers from Snowberry!

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  • Cute outfits. I am interested in the suitcase size you use for all your clothes. Like you, I layer on the plane and have the same size carry on and large bag/purse. You took a lot of clothes to Italy. I usually spend five weeks in Europe. Even though I use all the creative packing tips, too much luggage is an inconvenience to tote around. Your thoughts?

    • I totally agree with you, Greet. I wish I was a better packer. One thing I love about a cruise is you only unpack once. In Europe is was more challenging on our last Italy trip one of our hotel rooms was really small and we had big bags! I have a set of hard side Tumi graphite luggage. For the cruise we checked the large and medium and carried on the small. Jim’s a much better packer than I am and tends to travel carry on only when not on vacation with me! xo

  • Juliet what a needed post for someone packing for a cruise. I love how you stayed in the navy and blues sort of which probably made it easier to mix. I love every one of your pieces and all the cute shoes and purses. I am impressed you were able to take so many bags. Loved them all!

    I give you credit for digging up things on Poshmark. It’s no easy feat to find past season things.

    You looked chic and comfy and that is exactly what I want to be on this sort of holiday.. I am going to go now order that cute striped coverup!
    Saving all of this. xo
    kim

    • Good morning, Kim … and thank you! I think my wardrobe was a little boring but it was easy and it worked. And most importantly I felt comfortable. I went overboard on bags for sure! One of these days I’ll master the packing thing. Hopefully. The striped cover up is so you! xo

    • Jane, thanks for pointing that out. It’s a Klipsta, but I can’t find it anywhere. I updated the post with a new link. I actually like the new one better, it looks more secure, and I’m going to upgrade. xo

  • Hi Juliet,
    Fun post!

    I am always curious how other women pack and dress on a trip. I think a cruise is an easy one to pack “more” than a trip where you unpack/repack multiple times, but “too much” is a problem for me; as a slow, ordered packer, getting it all back in to take home can feel burdensome!

    One thing I know: the more frequently you travel, the better you become at packing!

  • Hi Juliet,
    Hey, I really mean this I think you looked fabulous. I think packing is not easy. I think when I first started packing for business world it became a nightmare. I quickly learned. Like you my Honey Bear was an instant pro at it. I was the bring the kitchen sink too. To this day I dread packing but because I’m super duper casual because I have to be. It’s the day when everything changed. Finally it’s become so much easier.

    • Katherine, I think packing is a universal achilles heel … sort of like public speaking! We dread it and don’t always do it well. Hope you have an amazing weekend, friend. xo

  • Hi Juliet,
    It looks like you had all your bases covered with great outfit options for whatever came up while at sea, or on land! You packed some really cute things and looked perfect.
    I always laugh at how many shoes you pack when you travel, I try to keep it down to two pairs, absolute max is three. They take up so much space and are heavy. But I totally get the urge to have options!
    I long to travel someplace new and exciting again, and soon!
    Xo Heidi

    • Oh Heidi, I’m hopeless. If only I could get to the point of packing just two pairs. Sigh. You need to show me. xo

  • I love it all and thanks so much for your great informative tips. I also loved all your outfits however, id never imagined the cruise to be so casual i felt for sure it would be diamond attire etc.. glitzy. You looked very nice anyway, but all good to bear in mind. Oh I do have a question, i love bags and baskets just like you do, i have a solid squarish bag like yours its basket material, I wanted to ask how did you pack those, and your beautiful hats? Please let me know… Id love to pack my baskets and hats too.

  • We’re heading on a Ritz yacht cruise in September. This is so helpful! Curious about your boarding outfit. Did you change from your travel clothes before you got on the ship? (Is that general practice or just your preference?) We’ve never done anything like this trip before, so I am a little stressed (like you were) about what is appropriate to wear. I don’t keep “yacht casual” and “yacht sophisticated” in my regular wardrobe! LOL!

  • Hi, I’m Juliet … welcome to Make Mine a Spritzer where we talk about all things home décor, classic style and more! I’m so happy you’re here!

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