Island Jim #Two Barber Pole Review

Hey guys! Just left the barbershop. My barber John is also a cigar geek, so the conversation flows easily. With my hair on point, there’s nothing more pressing than grabbing the recently released smoke we talked about. I head to my local shop and pick up the Island Jim #Two Barber Pole, a 6 x 52 torpedo. At $13 a stick, its spiral Connecticut and Corojo wrappers catch my eye. I light it up to see if this vibrant cigar lives up to its bold look.

Let’s dive into this unique smoke.

The Roots

Island Jim Cigars is the brainchild of Jim “Island Jim” Robinson, a Pittsburgh tobacconist known for his colorful style and Leaf & Bean Strip shop. Partnering with Oscar Valladares Tobacco & Co. in Danlí, Honduras, Robinson first hit it big with Leaf by Oscar, a cigar wrapped in a raw tobacco leaf that became a national favorite. The Island Jim line followed, with the #Two Barber Pole as its fourth release, launched at PCA 2025. This 6 x 52 torpedo ($13 per cigar, $273 for a 21-count box) features a barber pole wrapper of Honduran Connecticut and Corojo, an undisclosed Honduran binder, and proprietary Honduran fillers, offering a medium-bodied smoke with a playful pencil-tip design.

Recipe Pairing

Vanilla-Spiced French Toast with Honeyed Almonds

Ingredients:

4 thick slices brioche bread
2 large eggs
1/2 cup whole milk
1 tsp vanilla extract
1/2 tsp ground cinnamon
1/4 tsp ground nutmeg
2 tbsp unsalted butter
1/4 cup sliced almonds
2 tbsp honey
Pinch of kosher salt

Instructions:

Whisk eggs, milk, vanilla, cinnamon, and nutmeg in a shallow dish.
Soak brioche slices in the mixture for 1 minute per side.
Heat butter in a large skillet over medium heat. Cook soaked bread 2–3 minutes per side until golden brown.
In a small pan, toast almonds over medium heat for 2–3 minutes. Add honey and salt, stirring until almonds are coated.
Serve French toast topped with honeyed almonds.
Pair the creamy vanilla and spiced notes with the cigar’s cereal and pepper profile.

What the Pros Say

For the Island Jim #Two Barber Pole, halfwheel gave an 86/100, noting it’s “pleasant, well-constructed, approachable… not wildly complex but enjoyable”. Cigar Aficionado has not rated this vitola but reviewed the original Island Jim #Two at 87/100, citing “sweet wheat, cedar, and mild pepper”. Reddit users rate it ~8.25/10, praising its “visually stunning and consistent flavor”. Fine Tobacco NYC, reviewing the original #Two, noted “graphite, earth, and a creamy finish” with “cherry wood and cedar” in the final third . 86

The Smoke Stats

Name: Island Jim #Two Barber Pole
Vitola: Torpedo (6″ x 52)
Wrapper: Honduran Connecticut & Corojo (Barber Pole)
Binder: Honduran (Undisclosed)
Filler: Honduran (Proprietary)
Origin: Oscar Valladares Tobacco & Co., Honduras
Release Date: April 2025
Price: $13/cigar, $273/box of 21

The Experience: From Start to Finish

First Look: Pre-Light Impressions

Back home post-haircut, I admire the Island Jim #Two Barber Pole. Its Honduran Connecticut and Corojo wrappers spiral tightly, creating a candy cane effect. The shaggy foot exposes filler tobacco, and the pencil-point cap is sharp, like a freshly sharpened crayon. The band, with Island Jim’s sunglasses and hat, adds flair. The wrapper aroma offers hay, honey, and cereal grain, while the foot hints at cedar and wheat. The cold draw is snug but smooths out with a straight cut, delivering vanilla and mild pepper.

I light it up, I’m ready for it!

Foot to Cap: The Flavor Journey

The first third kicks off with warm donut dough and toasted wheat, like a bowl of plain Cheerios with a honey drizzle. Creamy vanilla and soft cedar emerge, with mild black pepper on the retrohale. The smoke is silky, and the light grey ash holds to 1.5 inches with a sharp burn. Compared to the Leaf by Oscar Connecticut, it’s sweeter and less earthy.

In the second third, the creaminess persists, joined by nutmeg and cinnamon baking spices. White pepper and sweet cedar balance the sweetness, creating a complex interplay. The smoke thickens, and the burn stays even, though a minor relight may be needed. The draw is smooth, rivaling the consistency of a Davidoff Winston Churchill but with more spice.

The final third shifts to a doughy, cracker-like note with charred wood and a peppery tingle. The sweetness fades slightly, leaving a cool, smooth finish with no bitterness. The burn holds steady to the nub, lasting 70 minutes. It’s milder than the Island Jim San Andrés but crisper than a Macanudo Café, ideal for a relaxed session.

Build & Burn: The Craftsmanship

The #Two Barber Pole’s construction is stellar for a barber pole cigar. The dual wrappers are seamless, with no tearing, and the pencil-tip cap is precise. The shaggy foot ignites easily, and the draw is medium, slightly snug at first but opening with a cut. The burn is sharp, with light grey ash holding 1.5 inches, though occasional relights may occur. At $13, Oscar Valladares’ craftsmanship delivers boutique quality.

Flavor Deep Dive: What’s Cooking

The #Two Barber Pole starts with donut dough, toasted wheat, and creamy vanilla, accented by soft cedar and black pepper. The second third introduces nutmeg, cinnamon, and white pepper, with sweet cedar adding depth. The final third shifts to cracker-like dough and charred wood, with a peppery bite and smooth finish. It’s less complex than the Island Jim San Andrés but more dynamic than a mild Macanudo, offering a medium-bodied, approachable smoke.

Strength & Body: The Power Within

The #Two Barber Pole’s medium strength delivers a gentle nicotine hum, accessible to all smokers. The medium to medium-full body produces thick, creamy smoke with cereal, spice, and cedar notes. It’s less intense than the Island Jim San Andrés but more robust than a Leaf by Oscar Connecticut.

Perfect Pairings: Elevate the Experience

These pairings enhance the #Two Barber Pole’s 70-minute vibe:

Drinks: Medium roast coffee with cream (matches vanilla); Belgian witbier (complements cereal notes); light rum (enhances sweetness).
Foods: Almond biscotti (echoes nuttiness); honey graham crackers (pairs with sweetness); vanilla custard (boosts creaminess).

Perfect for an unwind with coffee or dessert.

Value: Worth the Price?

At $13 per cigar ($273 for 21), the #Two Barber Pole offers solid value. Its unique barber pole design and balanced flavors compete with pricier boutique cigars, and Oscar Valladares’ craftsmanship ensures quality. The 70-minute smoke make it a standout compared to $15 sticks like the My Father Connecticut. Occasional relights don’t detract from its appeal.

Our Rating:

The Island Jim #Two Barber Pole earns a Refined rating. Its creamy cereal, spice, and cedar notes deliver a 70-minute, medium-bodied smoke with stellar construction. At $13, it’s a visually striking, approachable cigar, though minor relights and limited complexity keep it shy of great.

Final Thoughts

As the #Two Barber Pole’s nub fades, I’m impressed by its smooth, creamy profile and vibrant design. This 70-minute smoke delivered donut dough, spices, and cedar, backed by Oscar Valladares’ craft. Its playful aesthetic and balanced flavors make it a great treat, perfect for sharing with friends.

Own the Smoke: Make It Yours

The Island Jim #Two Barber Pole is for smokers craving a medium-bodied, visually unique 70-minute smoke with creamy and spicy notes. Pair it with coffee or biscotti and enjoy the moment.