Sailing the Caribbean. Hopping from tropical island to tropical island. Exploring the vast open crystal blue waters of the Caribbean. Images of tropical destinations fill ones’ heart with wanderlust and freedom.

If you’re like me you love the open road or in this case the open sea, the quest to seek and discover the unknown. If you’re like me, you love the quest to discover your next quality cigar. Perhaps it’s a mild Connecticut leaf.

Well if the combination of crusin’ the high seas and smokin’ cigars thrills you then look no further than the “Cigar Cruise”. This annual gathering of cigar lovers, their friends and wives entered its fifth year in 2016.

The cruise is the brainchild of two Kansas boys – Dean Prather and Kendall Culberston and features cigars from Rocky Patel Premium Cigars, Gunslinger and La Sirena. What more could a lover of the leaf ask for? Cigars and the tropical sun!

The eight-day cruise set sail from Miami and since yours truly has smoked a million stogies and never set sail on a cruise ship before, I was excited to discover the unknown. At the end of the trip I would discover new friends, great smokes and the companionship of fellow cigar lovers.


First stop – the Bahamas. Who knew that Carnival Cruise lines has their own private island, but they do. Our ship dropped anchor just off the shoreline of this stunning slice of heaven. Half Moon Caye is everything you have ever imaged a Caribbean island to be. Sugar soft white sand beaches, crystal blue transparent water and a party!

The crew set up shop for the day in its own private beach cabana complete with a hot tub, a fully stocked bar and plenty of cigars to go around.

The beauty of the “Cigar Cruise” is that you are handed free cigar after free cigar. Each day you are given a pack of delightful cigars to enjoy, as well as a few more handed out by your host Dean Prather. If you are even a mild cigar enthusiast; the cigar cruise is for you!

La Sirena cigars was founded in 2009 in New York City. Their founder Aerielle Ditkowich has hand crafted a variety of smokes that are an absolute delight. The name La Sirena in Spanish and Italian means “The Mermaid”. Aerielle is indeed the Mermaid of the enchanted seas of cigars. She casts her magical spell and blends a cornucopia of delightful flavors. Sticking with the nautical theme; her sticks each have names that represent the aquatic life, Porthole, a Sirena, Merlion-Sealion, and Oceano.

Their limited edition Porthole is a masterpiece.  They are hand crafted at the La Zona factory in Esteli, Nicaragua. I was lucky to have one in my daily cigar goodie bag that was handed out. This blend has a limited production annual of only 15,000 cigars.

Our next port of call was the U.S. Virgin Islands and St. Thomas. As others from the cruise enjoyed the sugar white beaches of St. Thomas. Here, eight of our intrepid crew decided that we needed to stretch our legs and enjoy a round of golf, beers and cigars at the Mahogany Run Golf Course.

This splendid track has two signature holes that play alongside the blue waters of the Caribbean. The 13th is a short par 4 that plays in at 327 yards. Her narrow fairway requires pinpoint precision off the tees to find the fairway. Her postage stamp of a green is nestled into the side of a mountain. Her right is protected by a bunker. Her left flank is guarded by another bunker. And the back of the green careens into a tranquil cove that meanders back out into the Sea.

The 14th is a gem of a par 3 at 159 yards. The tee box provides an incredible 180-degree elevated vista of the Caribbean and nearby islands. Your tee shot must cover ninety yards over the cliff-side and then onto a postage stamp green. Her right is flanked by a steep uphill wall of grass. And her left is a small three hundred foot drop off into the Sea.

One amongst us that day was Kendall Culbertson owner of Gunslinger Cigars. What can I say about him – he’s wild, crazy, a lover of mirth and merriment and smart as a whip too. I liked Kendall the second I met him.

If you go to his website, you’ll read in a few paragraphs all you need to know about him, his brand and his lifestyle.

Kendall is a 21st century Renaissance Man. He has his Outlaw cigar shop, he has his own band and writes cigar themed music, he blends his own cigars as well.

I believe he’s a bit of a mad scientist as well. He explained that he spends countless hours in the tobacco fields of faraway lands. There he mixes, matches and blends a variety of leaves in search for the perfect blend.

Let’s take a look at a few of the flavors Gunslinger Cigars offered us during our cruise.

Perdition: Kendall tells us, “Perdition consists of Nicaraguan, Honduran and broadleaf fillers wrapped in a spicy Nicaraguan binder topped off with a San Andreas wrapper. Together this well balanced and complex combination of tobacco delivers a rich and unique flavor profile.

Black Powder: This cigar took three plus years and blending sessions in eleven different factories to find the best factory and tobacco to achieve a truly special cigar. An incredible amount of time and attention has gone into creating the perfect balance of pepper, earthiness, deep rich chocolate and sweetness.

Hangman: The flavor profile begins with cinnamon raisin tones and underling hint of woody spices; each puff brings in a smooth blast of chocolate. The flavors change to a nuttiness as the strength starts to build. Towards the end more and more spice and heat hit the palate in this medium to full body cigar.

Puerto Rico provided the next stop on the cruise. Walking through the streets of the old town and exploring the San Cristobal Fort is a full day’s adventure, but worth every step.

Built in 1783 the fort inspires awe and amazement in a cigar traveler’s heart. As does the history of San Juan. If you love history like I do then the names of Sir Francis Drake, Teddy Roosevelt and the Roughriders conjure and stir the imagination.

(End part one)

By Randy “Tank” Tantlinger

Related Posts