Confessions of an Overpacker: What NOT to Bring on a Two Week Caribbean Cruise

Confessions of an Overpacker: What NOT to Bring on a Two Week Caribbean Cruise


“I can’t do it! I tried. I really tried but I just couldn’t do it! I’m not good at this! I’m definitely going to have to pay extra this time!” I frantically cried into the phone in an Uber on my way to the airport; my poor mom on the receiving end of yet another dramatic spiral.

Overthinking the obvious over-packed luggage for my upcoming 2 week Caribbean cruise, I was new to the cruise scene and completely blind to the do’s & don’ts of cruise ship packing. That’s when I decided I was going to take a few lemons and turn them into some much needed vacay tequila shots!

May thy mess be thy message!

A blog: Confessions of an Over-packer and an inventory of what was never needed on my sunshine, sea- sailing vacation.

Of the 50 items packed - not including toiletries, undergarments, workout gear, swimsuits, jewelry and accessories, only a grand total of 34 garments were worn - which doesn’t seem all that bad, however, the extra physical & emotional baggage could have been more than left behind. Needless to say, I completely missed the boat on the cruising needs and went a little overboard (see what i did there) in the evening gown category.

Fun Fact About Me: I love fashion, I love pulling pieces together and I love creating an outfit. Even better if I have some kind of mood or theme to follow. Also Note: I have never met a nautical stripe I didn’t love. If there is a navy and white anything within a 10 mile radius I will find it and I will buy it. I am by no means a fashion expert, just a girl who loves to razzle dazzle. I know most people never remember what they wore let alone remember what others were wearing, but I am not one of those people. I ALWAYS remember. I can even remember the black and white velvet polka dot Christmas dress I wore when I was 6 and how obsessed I was with it until it was obvious that it no longer fit or was seasonally appropriate. So for someone like me, you can see how packing outfits for a trip is absolutely a BIG deal and can get a bit overwhelming. Other Fun Facts: I don’t like keeping things I’m not in love with so if it’s in my closet it means I’m in love with it. I still love playing dress up and I never want a fabulous garment to feel left out of a good party!

What I Learned on my First Cruising Adventure:

  1. There aren’t as many designated formal nights as I thought

  2. You can make any night a formal night depending on your evening plans

  3. Formal and Casual are both open for individual interpretation

  4. Cruising days are comfort days

  5. Hats are tricky. Cruising is windy

  6. Spills happen

  7. If you forget anything the ship will have it for you…at a cost

  8. Food is everywhere. High-waisted swimsuits and flowy dresses will be your lifeline for the second half of your trip

  9. No one is going to remember what you wore

By the end of my trip, I honestly felt much better about my packing skills and really didn’t bring anything completely outrageous. In-fact, my man suggested I invest in a larger suitcase and that mine was considered to actually be quite small - I knew there was a reason I fell in love with him #hesakeeper. Aside from an unworn pair of heels, a dozen too many outfits and some random wrap around belts, I’d say I did pretty well.


Time now to tie this all up in a pretty little Tiffany bow as I give you a rundown of must-haves for your next cruising adventure.

Michelle’s Cruise Travel Must-Haves

  1. All toiletries should be ravel size making for lighter luggage and more space

  2. Walking shoes/ runners/ flips and 1-2 pairs of heels that work with all evening outfits

  3. Mix and match pieces i.e: dresses, blouses, pants that can go from day to night and paired with multiple different accessories to create several new looks.

  4. 1-2 comfy sweaters or cardigans for cooler cruising days (of course this depends on your starting point and destination)

  5. If pools and beaches are on the itinerary swimsuits are a must + at least 1 cover up

  6. Large sun hat and over the top black sunglasses

  7. Casual comfort wear for breakfast, lunch and port days

  8. 1 clutch & 1 wrap that work with multiple outfits

  9. Classic jeans & white t-shirt (can wear with flips, runners or heels)

  10. Statement piece jewelry

  11. 2 formal gowns/dresses

  12. 2 sets of pajamas and a pair of black leggings

  13. Appropriate undergarments + 1 nude & 1 black bra + 1 strapless if your wardrobe requires (also bring safety pins……I snapped a bra at dinner & didn’t have a safety pin)

  14. 1-2 good books or your e-reader of choice

  15. Deck of cards or small fun game (I forgot mine)

  16. Journal, selfie-stick and camera to log all the fun (I will be investing in a GoPro moving forward)

  17. Backpack/ beach bag or crossbody purse

  18. Workout gear to burn off the buffet

Travel is meant to be fun and a time to explore, relax and connect. Remember to keep it simple and you can enjoy the full roster of cruise wear outfits in my InstaStory Highlights should you feel so inclined.

Safe Travels!


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