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I always tell people, spend at least one day on the water when vacationing in the Caribbean. Nine times out ten, it will turn into their favorite part of the entire trip. Always a highlight for this Castaway.

One of the perks of attending the Castaway Winter Beach Bash at Bolongo Bay Resort was a sunset cruise board their catamaran, the Heavenly Days. Motion of the ocean, pushed through the waves by the power of the wind and a rum punch in hand; yes this was going to be a grand time.

Bolongo Bay St. Thomas

Heavenly Days at rest in front of Bolongo Bay

Saturday night arrives on St. Thomas, the skies are clear, the sun is falling and a 50 foot catamaran sits waiting at the end of the dock. We board the Heavenly Days and the crew have a buffet of finger foods and rum punch waiting for us as we step on board. Heavenly day indeed.

All the Castaways and other island passengers quickly board and grab their boat drinks. We were a little worried about one person, Scott. He stayed up to the wee hours of the morning the night before drinking rum on the beach with a few of us and was still a little sluggish come cruise time. He finally boarded Heavenly Days and even had a Team Cocktail “Rum” t-shirt on. Now that’s how you roll.

Bolongo Bay

Castaway Scott ready to go!

We were introduced to Capt. Dan, first mate Matt and 2nd mate Jolene. They were a fantastic crew and not a single drink went dry the entire sail.

Capt. Dan pointed us out to sea and set our course for Charlotte Amalie, downtown St. Thomas.

St. Thomas

Charlotte Amalie, St. Thomas USVI

There’s just something sexy about being under sail power. Even the raising of the sails is a powerful moment. You watch the canvas climb skyward and the boat begins to react, biting into the breeze and plowing through the waves. It’s a feeling I hope everyone reading this gets to enjoy at least once in their lives.

We enter Charlotte Amalie harbor just as a large cruise ship is leaving port. It’s amazing how big these things are. They are engineering marvels, but I wouldn’t have traded spots with anyone on that beast for a million dollars. Paradise was happening on Heavenly Days.

Cruise Ship

Capt. Dan takes us right up to the water front as Jolene gives us a little history of the downtown area. We listen, enjoy our boat drinks and then hear a faint buzz from behind us. As we turn around to pin point the growing sound, someone points the sky as a airplane was coming into the harbor and heading straight for us. Of course the seaplane was going to hit us but it did catch a bunch of us by surprise. Here’s a great video that BigKahunaBrew shot of the Seaborne Airlines plane coming in for a landing.

After the excitement of the plane landing, we sail past Water Island and back out into the Caribbean. The sun was setting and we had front row seats.

Caribbean Sunset

The sun dipped below the horizon and the Capt. turned the Heavenly Days east back towards Bolongo Bay. The seas had grown a bit and the sleek cat was slicing through through the swells with ease. I was sitting up front, taking a good bit of salty spray to the face. Didn’t bother me in the least. Jimmy Buffett was playing over the speakers, a cold drink was resting in my koozie, I was surrounded by great friends and the Virgin Islands were the backdrop; Heavenly Days indeed.

Boat Drinks

If you’re on St. Thomas and looking to get out on the water, contact Bolongo Bay Resort. They take the Heavenly Days out for day trips to St. John and of course sunset sails. It’s an experience not to be missed.


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About the Author: RumShopRyan

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty. To learn more, visit our About Us Page.