Cigar Buying Guides

2018 CA Report: 10 Ways to Splurge On Your First Cigar

Reading Time: 6 minutes

Top Beginner Picks: 10 Ways to Splurge on Your First Cigar

By Fred Lunt

“You’re ruining your palate!” Time and time again, we’ve heard old smokers steer the uninitiated toward the bargain bin for their first cigar. Well I say enough is enough: it’s time greenhorn smokers reclaim the top shelf and experiment for themselves.

At some point in our lives we’ve all been victims of this toxic mentality and it’s not just limited to cigars. My own story goes all the way back to my first beer but has since grown to include various hobbies I’ve thrown myself into, including scotch, craft beer, bourbon, and may others.

Why should I start with the good stuff for my first cigar?

Getting a foothold in a new activity takes a lot of time, patience, and practice. Picking up cigars is much like drinking wine or learning how to camp- it’s all relative. But isn’t it that much better when your first time is a memorable one? Spending a few dollars more on a better smoke is taking one small step toward ensuring your first cigar experience will be a good one. Enjoying a fine cigar is usually a special occasion, no matter if you’re celebrating a wedding or simply surviving the week.

As we redraw the lines of a ‘good’ first cigar, or a first ‘serious’ cigar, we need to keep some of the general rules (more like guidelines really). First, let’s keep the price range comfortable but still in a good quality range – think a reasonable $6, to a self-righteous splurge of about $20. Secondly, try not to max yourself out with an overly complex or strong cigar; you want consistency and flavor to be your key goals.

To get things started, I’ve pieced together a highly flavorful list of great first-time cigars. Smoke them yourself or recommend them to a friend!


Romeo y Julieta Reserva Real

choose first cigar romeo y julieta reserva real cigarsRomeo y Julieta is one of the oldest cigar brands and has a long-standing reputation of making consistently flavorful and quality cigars. While most aficionados may direct newcomers to a House of Capulet or 1875, I suggest kicking it up with a Romeo Reserva Real. A knockout blend of vintage Nicaraguan and Dominican fillers, encapsulated in a Nicaraguan binder and sealed with the luscious kiss of an Ecuadorian Connecticut wrapper.


Fonseca Vintage Selection

choose first cigar fonseca vintage cigarsNot to be confused with its Cuban cousin, the Quesada Family has been proudly producing the highly acclaimed Fonseca brand since 1963. While the Serie F and Classic often reign supreme as most popular, the Vintage line holds the same mellow qualities in a special aged blend. Superb in quality and flavor, the Fonseca Vintage Selection entails a high-grade, carefully aged blend of Dominican fillers and binder in an ultra-smooth Ecuadorian wrapper- aged for 5 years before even hitting the shelf. An affordable cigar with top-shelf quality, one first-rate starter cigar.


Macanudo Vintage 2006

choose first cigar macanudo vintage cigarsWhile Macanudo is on the move lately with its hit Inspirado line, there’s nothing wrong with starting on a classic. Their Café line brought Macanudo international acclaim, but the Vintage 2006 is its top-shelf cousin. Blessed with a perfect crop of Connecticut Shade wrapper, this ultra-fine crop was sorted into bales wrapped in palm leaves and aged to perfection. With a customer rating of 90, this is a highly sought-after cigar, perfect for a special occasion or a quiet night in.


Drew Estate Java

choose first cigar java cigars drew estate

Many cigar smokers cut their teeth on flavored or infused cigars, ranging anywhere from a Black & Mild to ACID Blondie. The Java offers a chance for flavored smokers to cross over and is often enjoyed by most regular cigar smokers as well. Java features a loaded blend of coffee infused Nicaraguan tobaccos wrapped in a sumptuous Brazilian Mata Fina wrapper. This cigar oozes rich flavors of mocha, cocoa, espresso, earth, and sweet woods- pure aromatherapy for any cigar smoker.


Montecristo White Vintage

first cigar montecristo white vintage cigarsMontecristo is, without a doubt, one of the more highly regarded cigar brands. The Monte White is a must-smoke for the newly-initiated, and in itself is a fantastic cigar – but we’re going to the top with the Montecristo White Vintage. A flavor-filled blend of Peruvian, Nicaraguan, and Dominican tobaccos wrapped in a vintage 2008 US grown Connecticut Shade wrapper. While mellow, this cigar delivers on toasty, rich flavors that smokers and collectors alike go gaga over. Expertly made and presented, Monte White Vintage is always the right choice.


San Lotano Connecticut

choose first cigar san lotano connecticut cigarsIf you’re just getting your start in cigars now, expect to hear a lot about AJ Fernandez. The Cuban exile, now residing in Nicaragua, has made a huge following for himself by creating full-bodied and hearty cigars. However, this wasn’t the case when he bought back the rights to San Lotano, an original Cuban brand his grandfather created. Considered ‘luxury class’, this premium cigar is brimming with mellow creamy, woody, and toasty notes.


Avo XO

choose first cigar avo xo cigarsAvo is a world-renowned brand produced by Davidoff and adored by cigar enthusiasts worldwide. Named after owner and musician Avo Uvezian, the Avo XO was his ‘everyday’ cigar. While it’s priced a bit high for most smokers to enjoy daily, it’s affordable enough to have more than every once in a while. The blend is a perfect combination of delicately spicy, aged Dominican grown fillers consummated with an oily Ecuadorian Connecticut wrapper. 90+ customer rated, Avo XO is an unbridled winner and sure to win over the greenest of cigar smokers.


Crowned Heads Luminosa

choose first cigar crowned heads luminosa cigarsLuminosa by Crowned Heads is a surefire hit and way off the beaten of your typical starter cigars. Made at E.P. Carrillo’s Dominican factory, Luminosa stands out as an introductory cigar to one of the brightest boutique cigar companies to date. Owners Jon Huber and Mike Conder, formerly of CAO, blended Luminosa with select Dominican fillers and a silky Ecuadorian Connecticut wrapper to cast a warm, creamy smoke with notes of pepper, wood, and coffee.


Davidoff Aniversario No. 3

choose first cigar davidoff aniversario cigarsThis may be the most expensive cigar on this list, but it’s for damn good reason. Davidoff is one of the most renowned cigar makers in the world, owing their fantastic blends to Eladio Diaz and Henke Kelner. The Aniversario line is pure cigar nirvana, medium in body but captivatingly aromatic, artfully blended, and robust in flavor. The No.3 is universally loved and holds a perfect 100 rating from customers – why not start at the top?


Fuente 858 or Don Carlos

first cigar arturo fuente don carlos cigarsIf you’re new to cigars, Fuente is another brand you’re going to hear a lot about. Aside from the #1 Cigar of the year in 2017, Fuente is renowned for expert blends including the Hemingway line, named after the author and writer. The traditional introductory cigar in their portfolio is typically the 858 or Curly Head due to their affordability; but for a mere few dollars more, the too-often-overlooked Don Carlos line offers much more flavor to a beginner’s palate. Carefully aged vintage and rare tobaccos adorn this premium, which features a delicate, yet flavorful Cameroon wrapper.


My question to the reader: did you dig the bargain bin for your first cigar, or go straight to the top with an ultra-premium? Leave a comment below!

Notify of
Inline Feedbacks
View all comments
Mike Spear
5 years ago

Hard to beat the sweet flavor of a Hemingway!

James Laabs
5 years ago

My ideas, Fuente Don Carlos or Romeo Juliet 1875, depending on budget, are medium bodied with tons of flavor. Oliva O for something a little heartier. I’d shy away from Connecticut shade wrappers, I started with those and almost quit smoking until I tried stronger cigars and loved them.

John Chin
5 years ago

bargain bin but now I know better

Zak Young
5 years ago

I couldn’t tell you what my first three or four cigars were back when….but I can tell you that I discovered La Gloria Cubana Serie R pretty early on and that’s the one that did it for me

Joseph Gadberry
5 years ago

Can’t find a single one on those links.

Adam Gai
5 years ago

Surprised to not see My Fathers Connecticut on this list or any of the My Fathers for that matter.

Fred Lunt

Fred Lunt


Fred Lunt was discovered to be the youngest cigar smoker in his family shortly after setting his crib ablaze; today, he's added an avid whiskey and craft beer appetite to his lineup. Fred has worked in marketing, blogging and communications at boutique PR agencies across New York and has personally had the pleasure of witnessing over four breakdancing shows in a single commute on the NYC subway. Prior to his work in marketing Fred was a student of communications at Temple University and still holds illusions that Temple has a better football program than Penn State.

Show all Fred Lunt's Articles
cigar advisor news – plasencia releases year of the dragon cigar – release – cover

Cigar News: Plasencia Releases “Year Of The Dragon” Cigar

Reading Time: 2 minutes The Dragon occupies the fifth position in the Chinese zodiac and is depicted for Chinese New Year 2024. To celebrate the annual event, Plasencia Cigars has crafted a luxury-class, limited edition Torpedo. Read all about it here.

Read More
cigar advisor ultimate guide to the cigars of summer - cover

Cigar Advisor’s Ultimate Guide to the Best Cigars of Summer

Reading Time: 6 minutes In our guide to the best cigars for summer, you’ll find a handpicked and curated selection of blends to get you through even the most sweltering of days. From full-bodied and meaty to light and breezy, you’ll find a blend or two that’ll provide you with a summer’s worth of cigar smoking bliss.

Read More
cigar advisor #nowsmoking villiger de nicaragua edicion limitada 2022 - cover

NowSmoking: Villiger de Nicaragua Edición Limitada 2022

Reading Time: 3 minutes One year later than expected, the Villiger de Nicaragua Edición Limitada 2022 has arrived and Gary’s got the goods on this all-new blend crafted at Villiger’s Nicaraguan factory. Check out his review here and see if it was worth the wait.

Read More
top new cigars January 20 2020 Cigar Advisor Cover

CA Report: Top New Cigars (Jan 20 2020)

Reading Time: 3 minutes Looking for a new smoke to rid you of the winter slump? Top New Cigars has them all – click here to check them out now!

Read More