Turning a destination wedding into a relaxing vacation can be a difficult challenge, especially when you and/or your travel companion(s) are part of the wedding party.

When I first found out that my dear friends and expats to Grand Cayman would be getting married on the island they now call home, I was over the moon.  When I found out their wedding would be on a Wednesday, I felt a little less enthused.  A Wednesday wedding on an island would mean an entire week off of work.  My husband would be a groomsman, so with no way around it, I quickly changed my demeanor and decided to embrace #WeddingWednesday.  With a bit of planning (and a bit more planning after that), I was ready to embark on a fabulous vacation jam-packed with exciting activities, a breathtaking wedding, and of course amazing friends to share the adventure with.

After landing on Saturday, we checked into our beautiful waterfront home with four bedrooms, four bathrooms, a massive deck, and a pool overlooking the ocean.

We were excited to see the bride and groom-to-be, so we made our way down the street to their home and helped them prep for the groom’s bachelor party.  While the guys went wild that night (and when I say wild, I mean they went out and had a couple of drinks), the girls stayed in, ate pizza, drank some cocktails, and of course, watched Pitch Perfect.  Traveling can be exhausting so this relaxing evening made for the (pitch) perfect first night in Grand Cayman.

Luckily, our friends, the bride and groom, are awesome hosts!  Yes, they were just days away from walking down the aisle, but they still wanted to make sure their guests were having a great time.  After a day lounging on the beach, we were warmly welcomed by The Westin for wedding week welcome drinks!  Sipping on margaritas as the sun set over Seven Mile beach was a dream.  We chatted with friends, old and new, and before we knew it, 60 or so wedding guests began to feel like family!


My husband, Ryan, and I ducked out of drinks a few minutes early to head over to the wildly popular Camana Bay for dinner. Camana Bay is a waterfront community where you can eat and shop to your heart’s content.  The beautiful landscape allows anyone to explore the grounds, relax on a hammock, and be inspired by all of the natural surroundings.  Ryan and I enjoyed the most delicious dinner at Mizu, dining outside on the waterfront.  This stylish Asian-inspired restaurant and bar, focuses on finely tuned flavors and fresh, local ingredients for an authentic Pan-Asian menu.  Ryan and I sipped on wine and dined on vegetarian spring rolls and delicious pork belly on a bed of kimchi.  I salivated as I ate seared tuna steak and Ryan scarfed down his pan-fried sea bass in a matter of seconds.  As we were about to roll out of the restaurant, we decided to complete the meal with a life changing molten chocolate lava cake.

On Monday, our favorite bride and groom organized a boat trip for their wedding guests.  Due to inclement weather, the plan was changed,  however, 40 guests still boarded a boat and we all made our way in what started as sunshine to Grand Cayman’s Rum Point.  By the time we arrived at our destination it was raining (possibly hailing?), but that didn’t stop us from enjoying the crystal clear waters and stingrays ready to be played with.  As the rain pelted down, I held and fed a stingray, she gave me a massage and sealed the deal with a kiss.  It was definitely love at first sight.  After wading to shore, I shook from the cold as goosebumps raised on my arms.  But, the risk of frigidity was worth the yummy reward.  After hitting the sand, I was able to sample Rum Point’s world famous mud slides.  Officially freezing, I made my way back to the boat and back to Camana Bay where I shared dinner with lots of friends at Brooklyn, an American inspired Italian Restaurant.

The following days were filled with snorkeling, sunbathing and plenty of wedding activities.  The wedding, held at The Grand Old House was stunning.  The bride and groom were beyond thrilled, as were their guests.  I wore my favorite destination wedding dress, which I picked up last year from Anthropologie.  Once again, it was a hit.  I swear this dress never disappoints!

The evening after the wedding I took part in my very first Bioluminescence Tour run by George’s Watersports.  As we sailed out into the night, I couldn’t help but feel both nervous and excited as the sky darkened and the boat picked up speed.  Our crew consisted of two very knowledgeable young men who told us everything we needed to know about Bio Bay and dinoflagellates.   I jumped in the water in my snorkel gear and was instantly amazed as I watched my hands and arms light up in endless bright sparkles, illuminating the water surrounding me.  Not only did the sea sparkle, but so did the sky.  Coming from New York, the only star I ever see in the sky might just be an airplane passing overhead.  Being able to escape all the light pollution out on the water allowed me to gaze at more stars I have ever seen in my life.  This entire tour felt like a once in a lifetime experience, and is, I believe, worth every penny.

After a late night under the stars, it seemed only natural to spend the next day at the spa!  My best friend, Ashley, and I made our way to the Kimpton Seafire Resort & Spa for a little R&R.  And boy did we rest and relax.   While Ashley enjoyed a facial, I experienced my very first Hammam Beauty treatment.  This decadent beauty ritual transported me to a faraway land … in which I may have fallen asleep while indulging in the radiant heat of the Hammam.  The treatment is described as:

A volcanic black soap cleanse rich in moisturizing olive oil and calming eucalyptus is followed by a dual exfoliation using a traditional kessa mitt for buffing and a soothing tea infused apricot oil bamboo scrub to prepare for a rhassoul clay masque envelopment. A signature massage using a black tea infused rich balm with hypnotic scents of ylang ylang and jasmine follows.

I emerged feeling radiant and renewed.  I don’t ever remember my skin feeling so soft as I made my way to the relaxing pool, champagne in hand.

The rest of our destination wedding turned vacation was divine.  We enjoyed Pina Coladas on the beach, swam in the sea, and enjoyed downtime on the sand.  PS – Can we discuss my sun hat below?  I’m kind of obsessed with the Do Not Disturb embroidery by Life Has Just Begun.  The hat has magical powers – people really did leave me alone while it sat daintily on my head!

Sometimes destination weddings can feel hectic, but it is so important to take advantage of the time you have away and make it into a vacation that will be remembered!

Where are some of you favorite destination wedding locations?


This post was sponsored in part by Camana Bay, George’s Watersports and The Seafire Hotel & Spa.  As always, all opinions are my own.








Great blog right here! Also your web site a lot up fast!

What host are you the use of? Can I am getting your associate link to your host?
I wish my web site loaded up as quickly as yours lol


What an adventure. The snorkeling at night with the bio-lums…I would LOVE to do that. The stingray was amazing too- she needed a goodbye kiss huh? It sounded like you had a terrific time, and you always had a terrific sense of style throughout the whole thing. That dress what SO awesome (you know which one), I almost wanted to wear one myself. Keep going Shelby. You got a beautiful thing here.
As for wedding destinations? I like cold spots. There is A LOT of formal wear associated with weddings, so I would pick areas with cold climes, or areas where lighter clothing would not be out of the ordinary. I thought your wedding with snow was lovely in its own way.


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