Cuban cigars genuinely taste better when smoked in the Caribbean because this is exactly where they’re meant to be enjoyed.

Lighting a Cuban cigar in its home region feels natural because the Caribbean’s climate closely matches the conditions under which these cigars are produced. The consistent warmth, humidity, and soft ocean breeze help maintain the perfect state of the tobacco leaf, enhancing flavour and burn quality. Instead of fussing with uneven burns or constant relights, cigars smoked here burn smoothly, releasing their rich, earthy and woody notes effortlessly. The spice and sweetness inherent in Cuban tobacco also become notably pronounced.

The experience goes beyond the weather. The Caribbean atmosphere naturally encourages relaxation, allowing you to fully savour each moment and each puff. Your mood here is different—less rushed, more content. The people around you matter greatly as well. The friendships built while sharing cigars in such a relaxed setting tend to be deeper and more meaningful, enhancing the entire experience.

This was clear during my recent visit to Aruba for the Caribbean Habanos Days, held on May 30th and 31st. This annual event highlights Cuban cigars and the vibrant culture surrounding them.

Day 1 – Registration

The first morning started at Lucy’s Retired Surfers Bar & Restaurant, an open-air spot with a relaxed, beachy vibe overlooking Oranjestad’s port. With boats gently swaying on the water, approximately one hundred cigar enthusiasts gathered, starting the event with a San Cristobal de La Habana El Principe cigar and some strong, flavourful Cubito Coffee—a perfect combination to kick off the day.

Panama Hats

Early into the seminar, Panama Hats presented their iconic products. Renowned for creating stylish yet practical hats made from Ecuadorian toquilla straw, Panama Hats caters specifically to cigar aficionados, even offering exclusive hats featuring the La Casa del Habano (LCDH) logo. Given the intense Caribbean sun, a Panama hat isn’t just fashionable—it’s essential.

Celebrating Caribbean Champions

A significant highlight was honouring the winners of this year’s Habanos World Challenge. Matthew Edward Castillo and Alexei Vladimir Sleur proudly represented the Caribbean, winning the prestigious competition with expert guidance from their respected coach, Francisco Rojas. Rojas made history by coaching two consecutive winning teams, following last year’s Canadian triumph. Castillo and Sleur captivated attendees as they detailed their rigorous preparation process, their deep dive into cigar profiles, tobacco blends, and pairing methods. Their passionate discussion highlighted the mental discipline and extensive knowledge needed to excel in this intensely competitive event.

Magical Evening at Flamingo Island

The evening transported attendees to the breathtaking Flamingo Island, accessible only by boat. This private paradise featured powdery white sands, crystal-clear turquoise waters, and majestic pink flamingos roaming freely, creating an unmatched tropical ambiance. Guests, elegantly dressed in white, mingled effortlessly as they danced barefoot to live Caribbean music, the vibrant sunset painting the sky in shades of deep orange, purple, and gold. The cigars selected for this special evening were the Romeo y Julieta Línea de Oro Dianas, Romeo y Julieta Churchill, and Romeo y Julieta Wide Churchill, all enhancing the magical experience and effortlessly complementing the island’s natural beauty.

Day 2 –  A Relaxing Morning on the Golf Course

The second day started at the golf course, with attendees competing for a luxurious a Hublot watch valued at around £10,000 for a hole-in-one—a challenging feat that, despite great attempts, remained unclaimed. Even though I didn’t participate, watching others compete was enjoyable, enhanced by the Montecristo Open Regata cigar, explicitly designed for outdoor leisure.

The Montecristo Open series holds special significance in the cigar world, especially for golfers. Specifically crafted to be enjoyed in outdoor settings like golf courses, each cigar in the Open range—Regata, Master, Eagle, and Junior—is blended to provide a lighter, smoother experience, ideal for daytime smoking under the sun. The Regata, with its elegant figurado shape, delivers a harmonious blend of creamy, woody, and mildly spicy notes, making it particularly enjoyable on the golf course. It complements the leisurely pace and casual conversations that accompany golf games, enhancing the overall experience. Lunch introduced the Montecristo Open Slam, the newest addition to this iconic series, notable for its balanced, mild flavour that suits relaxed afternoon enjoyment.

Pairings and the Longest Ash Competition

After lunch, we delved deeply into the complex flavours of the Bolivar Royal Series cigars. Each pairing with various spirits and beverages was carefully chosen to highlight and complement the cigars’ distinct flavour profiles, ranging from bold spice to subtle sweetness. The conversation around the pairings was lively—rum was a common favourite, with a few surprisingly good matches made with dark chocolate and coffee-based cocktails that some participants experimented with informally. This wasn’t just about taste; it was about how cigars interact with other sensory elements. There was a lot of knowledge being passed around, casually but with real insight.

Following this flavour exploration was the much-anticipated Longest Ash competition, using the Montecristo Open Eagle cigar. It’s always a bit of fun, but it also reveals something about the quality of construction. A well-made cigar holds its ash longer, and this particular smoke delivered. Participants leaned forward, focused, trying not to laugh or cough as they balanced growing columns of grey ash over white shirts and summer linen. Laughter, friendly banter, and supportive cheers made this competition genuinely memorable and enjoyable.

Gala Dinner at Renaissance Hotel

The event concluded spectacularly with a gala dinner at the Renaissance Hotel, set outdoors against the mesmerizing Caribbean sunset. Tables were arranged facing the ocean, dressed in white linens and flickering candlelight. Attendees enjoyed a multi-course dinner featuring fresh seafood and Caribbean-inspired dishes, all complemented by top-shelf rum and more Cuban cigars. Conversation flowed naturally, from shared memories of the event to plans for next year.

The evening’s highlight was the auctioning of commissioned Bolívar and Romeo y Julieta humidors, each fetching impressive bids exceeding $50,000, showcasing the attendees’ deep appreciation for Cuban cigar craftsmanship and heritage. Beyond the numbers, it was the reverence for tradition and artistry that stood out—collectors clapped not only for the winners but for the craftsmanship itself. The night was filled with dancing, heartfelt toasts, and meaningful connections, culminating in an unforgettable finale beneath a star-filled Caribbean sky.

Why Caribbean Habanos Days is Unmissable

Caribbean Habanos Days isn’t just another cigar event—it’s an authentic celebration of cigar culture in an extraordinary setting. The natural beauty, ideal climate, and genuine camaraderie among cigar lovers create an unparalleled atmosphere that significantly enhances the cigar-smoking experience. It’s about more than the cigars themselves—though the cigars are exceptional—it’s about the moments they create, the conversations they spark, and the people you share them with.

Attending this event is essential for any serious cigar aficionado. It provides an opportunity to deepen your appreciation and knowledge of cigar heritage, build lasting friendships, and create unforgettable memories in one of the most picturesque locations on the planet. Once you’ve experienced cigars like this, it’s impossible to go back.