To Heel or Not to Heel….


Tracy's White Stiletto

Hi guys!

I know it’s been a spell since my last post but I’ve been a bit busy planning vacations and destination weddings for my awesome clients.

Currently, I’m in St. Maarten staying at the beautiful Sonesta Ocean Point Resort with my Couples Group and we’re having a great time. However, I do have a question for my female readers. To heel or not heel on vacation?

Anyone who knows me can tell you that I live in a sexy stiletto or wedge shoe. The only kitten you will ever catch me with is a pet! I do however own a few cute pair of flat sandals and two pairs of sneakers but on the norm my everyday shoe is a 3-4 inch wedge or stiletto heel.

Check me out to the far right as you see I’m the only woman wearing heels the other ladies are in their comfortable vacation flats.  Which leads me to my point about heels on vacation.

Couples St. Maarten Getaway All White Welcome Dinner

Ok, this picture looks great right…..what you didn’t see is my heel getting caught between the slats in the deck.  Also, there was some distance for us to walk from our room to the restaurant and since it was our first time staying at the resort we got a little lost finding it and those are not the “walk all night” heels.

Luckily, for me my husband was able to rescue my heel from the deck without it being ruined, and ladies we all know that can blow your night because who wants to walk around with a torn heel.

Tracy at Azul Rooftop Bar at Sonesta Ocean Point Resort St. Maarten

Needless, to say I changed out of those cute but impractical heels that I didn’t need to bring into my comfortable flat but stylish Steve Madden Gladiator sandals. So for me heels don’t serve a purpose while I’m on vacation my super cute flat gladiators or Coach sandals that I packed will do.

Heels on vacation are great if you’re attending a wedding, if you’re the Bride, Bridesmaids or you’re attending any other special destination occasion.  Other than that pack your cute but stylish flats or wedges if you must have a heel and enjoy yourself.  Believe me when I say no one cares what you wear on vacation it’s not a fashion show it’s VACATION.

You can contact me at or for more travel tips.


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Tracy, is a Destination Wedding & Honeymoon Specialist and Owner of Rich Events, a boutique travel agency located in Delaware, that specializes in Luxury Destination Celebrations, Curated Group Travel and Couples Vacations

2 thoughts on “To Heel or Not to Heel….

  1. Well I love to be comfortable wherever I go, and if the occasion calls for heels I will be ready. However, my vacation footwear will always to flats. Especially good for me on those tipsy nights!!

    Liked by 1 person

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