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.

This article includes affiliate links; if you click on a shopping link and make a purchase I may receive a commission. As an Amazon Associate, I earn from qualifying purchases.

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.

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.

 

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 …

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.

 

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.

 

Day Four – St. John’s Antigua – J.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.

 

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

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.

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 …

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.

 

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.

 

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.

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.

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.

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.

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.

 

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

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

Are you a subscriber? Sign-up here and have new posts delivered directly to your inbox.

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

Until then, cheers from Snowberry!