Island Jim #2 Connecticut

Recently introduced at TPE 2023 and made publicly available at the Great Smoke 2023 held on March 18th, the Island Jim #2 Connecticut (CT) is a 6×52 Torpedo Vitola and a real beauty to behold. Named the #2 as an homage to the pencil it resembles thanks to the different wrapper used on the open tapered tip, ala LFD Chisel Tip. The cigar also sports a shaggy foot and as the name implies, it is wrapped in a Honduran Connecticut leaf and has undisclosed binder and fillers. The cigar is manufactured by Oscar Valladares Tobacco in Honduras.

Close up of the open cap.

The shaggy foot recalls the cigar’s namesake, Island Jim, with his bearded, easy-going beach-bum appearance and good-natured personality. The band on the #2 CT is attractive and eye-catching with greens, golds, and red used prominently and a portrait of Island Jim smoking a cigar and wearing some shades and a hat. Palm trees adorn the sides, and the Oscar Valladares logo is on the back. Truly a beautiful band and it lends an air of quality to the cigar. Towards the end of my time enjoying the cigar, the band popped off effortlessly with only a slight pock mark in the wrapper where it was adhered to the Cigar. It pulled easily over the foot of the cigar without any further damage.


The #2 CT wrapper had a sweet tobacco aroma, and I did not get anything different smelling the foot. Taking a cold draw didn’t produce much flavor or any hint of spice. A cold draw test did show that the open tapered tip was far too tight for my preference and I opened it up with a Colibri V cut.

After carefully toasting the foot and lighting the cigar, I was really happy with the draw. Right away, the #2 CT had generous smoke production and the flavors were definitely reminiscent of a good CT cigar with the expected bright bitterness. The smoke left a musty flavor on the pallet almost like chewing on a raw mushroom.

Construction was good, exactly what I have come to expect from anything produced by Oscar Valladares. Once lit, the burn was flawless throughout my time with the #2 CT. I admired the golden CT wrapper draped around the cigar. It presented no blemishes, tight seams, moderate veining, with a smooth texture. The cigar was light weight but well packed, and the burn left a nice mascara line around the lit foot.


Any serious cigar smoker knows the importance of retro haling. Doing so with the #2 CT was very smooth with just enough pepper to let you know you’re smoking a cigar; however, it did not inflict any discomfort and reinforced the cigars subdued bittersweet flavors. I brewed some coffee to pair with the cigar and the #2 CT did an admirable job of staying lit in between taking notes, sipping coffee and trying to find something to listen to.

Paired with Coffee and Cream

Nearing the end of the first third, the #2 CT had a good inch and a half of solid ash with nice white highlights, denoting, the tobacco used in the filler was indeed good quality and rich in minerality. I’d like to guess that filler or binder has some Nicaraguan in it. The ash held through a quick shake test and did not fall off. Another observation of note, while looking at the smoke coming off the foot of the cigar, there’s a slight blue tinge in color, which I recognize could indicate the use of mineral spirits, which may also be contributing to the amazing self-combustion the cigar was exhibiting.

Burn Line
Great Burn

I final settled on my Margaritaville playlist and settled in to enjoying the remainder of the Island Jim #2 CT. At about the beginning of the second third, I noticed a slight angle to the ash and feared it was about to fall off. With a slight tap on the rim of my tray, the ash fell off in one solid chunk, and held together in the ashtray. The foot now sported a center peak, which I’ve heard mixed things about, but generally meant that the fillers were not combusting at the same rate as the binder and wrapper, could be I was drawing too quickly.


Where does a Cigar like the #2 CT fit in my smoking rotation? It’s a very easy-going cigar. It burns very well, and the open tapered tip was quite attractive although not very effective on my sample. I can see someone enjoying the cigar on vacation while sitting on the beach with a fruity cocktail or a nice rum. The cigar does not overpower what you’re pairing with it, so you can enjoy your drink and your cigar without being beat over the head with strength or flavor. This would probably be something that I’d hand to somebody first getting into the hobby.

Would I personally revisit the cigar or seek it out remains to be seen. The Island Jim #2 CT is not readily available at my local brick and mortar. For the right price online, I may be tempted to pick up a five pack to have on hand. I’d probably gravitate more towards the Leaf by Oscar or something with a little more body personally. However, I did find it to be a very well-made cigar and as I said earlier, I would recommend this to someone just starting out or if I were on vacation and saw them, I may grab one to enjoy.

Enjoyable to the end

The burn held true throughout the entire experience although my smoking time seemed to pass quickly for its size, I only got about 40 minutes out of it. Another observation I made is that when left resting, the foot of the cigar emitted smoke showing that the combustion was continuing even though I wasn’t actively drawing on the cigar. This could have contributed to the shorter smoking time. The cigar required no touchups, no relights, staying lit after I went inside and made my coffee and left it unattended outside for a few minutes. At no time did I find myself needing to take a second or third puff during a draw. The cigar effortlessly produced ample smoke on each draw and was a pleasure to smoke for this review. I need to try the Natural and Maduro in the future.

The Island Jim #2 Connecticut cigar was part of my Smoke Inn Great Smoke 2023 pack and was purchased at

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