4 Times The Caribbean Cruise Made Me Cry

There are so many fabulous reasons to head off on a Caribbean cruise. See the world. Relax. Get away from it all. Of course, these all top my list, yet on our last journey – I feel that for full disclosure, I need to warn you – I shed a lot of tears.

Don’t get me wrong. Cruises are an amazing experience, and I will definitely be sailing the seas with Windstar Cruises again. Still, I can’t say that my last trip was without waterworks. Tears caused by the ship, the destinations, and even the crew flowed freely.

Here are four times Windstar’s Caribbean cruise made me cry.

The Views

Whether we were spending time looking out from our balcony or meandering the deck of the ship, the sights were majestic. Sometimes the beauty of nature causes my insides to well up with feelings of awe. One special moment during our last trip included the captain taking a small, yet thoughtful, detour to show us the Pitons in St. Lucia as the sun was setting. It was breathtaking.

It was magical to soak in the Caribbean sunsets (and sunrises, although those were minimal since we enjoyed sleeping in!), daytime vistas and nighttime skylines peppered with the lights of island homes.

The Crew Talent Show

One benefit of small ship cruising is getting to know the personalities of the crew, but the talent show brought in a whole new element. With participants such as the ship’s doctor, bartenders, and front desk staff, the show was an unforgettable time of seeing the members of the Windstar Cruises’ crew not only entertain us but share their hearts and cultures.

I shed tears of laughter (literally!) as a junior officer, waiters and sports staff recreated a synchronized swimming routine in the lounge. Tears of emotion streamed as one of our waitstaff sang a beautiful song about love. Waves of pride flooded as we soaked in traditional dances from both the Philippines and Indonesia. The thought that these people would share their talent, traditions and – yes – laughter with us was incredibly moving.

The Signature Sail Away

Need I say more? My first Windstar Cruises adventure was on the Istanbul to Athens route, and although our second cruise was 8 years later (hello, kids!) the sail away was something that flooded me with memories from our first experience years ago. Learn how to pack for a Caribbean cruise.

The song, the raising of the Windstar flag, and having everyone gathered on the deck for the same purpose always brought a tear to my eye. Literally EVERY time I would try to hold it together, but the tears would flow despite my effort to thwart them. If you’ve ever been on a cruise with Windstar, I know you understand!

The Departure (Ours)

I’ll admit, I’ve shared stories about sobbing due to awe, happiness, and gratefulness, but this final one is because I was sad. For me every cruise is a journey of days. I wake up thinking, “It’s our first day,” and then, “We are halfway through,” and eventually, “Oh no, we only have one more day!”

Saying goodbye to crewmembers and thanking them one last time, bidding new friendships adieu, and getting back to life in general definitely created a sentimental feeling as we disembarked and looked back at the beautiful ship that had brought us so many beautiful memories about the Caribbean cruise.

Emotions aside, I’d say that all of the tears – joyous and sad – were worth it in the end. After all, without experiencing a Windstar Cruises journey, there wouldn’t be anything to cry over. My husband and I are already planning – and looking forward to – our next tear-filled adventure with Windstar.

About The Author

Jennifer Prince resides in Lynchburg, VA with her husband, 3 children and a constant rotation of foster kitties. She is a wedding blogger at Hill City Bride, and shares travel tips at Travel Like a Prince. Jennifer thoroughly enjoyed weeping her way through the Caribbean cruise with Windstar.