4 Key Elements to Key West Success

Discover the bustling, cigar smoke loving, rum drinking city at the southern most point of the US.

CIGAR REVIEWS: NeverAsh Torpedo (7.8) & San Cristobal Papagayo XXL (6.7)

GADGET REVIEW: Cigarmedic's "HumidiMeter"

SPECIAL REVIEW: Papa's Pilar Rum (9.3)

One of my top 3 favorite cities to smoke a cigar is Key West, Florida. For more than 12 years, my wife's family has ventured to the bustling beachside town 90-miles from a cigar smoker's Mecca (Cuba) to celebrate the New Year. There is no better place to celebrate the most overrated holiday. You just know what you are going to get with Key West and it never disappoints. I just hit my 7th consecutive, annual visit and have perfected the experience.

1. Day Drinker's Paradise

The first thing to know about Key West is that it's a day drinker's paradise. You need to accept that before you step on the plane. Because the second you step off that plane, it's go time. The first bar you see is a stones throw from the tarmac, hitting you with wafts of rum and sugar immediately upon entrance to the KWY baggage claim. It's a (very) small airport and the bar takes up 2/3 of the baggage claim area. If that doesn't get your juices flowing then you are in the wrong city!

For me, day drinking and smoking cigars goes hand-in-hand. That's why I love Key West. I average around 2.5-3 smokes a day ranging from a number of different blends and wrappers. This year I brought down ~15 of my own smokes via my Fox Cigar Bar + Xikar 15 count travel case. They ranged from NeverAsh Figurado/Torpedoes (photo below) to Puerto Rican hand rolleds my buddy Johan sent me from the island. I like to stay as authentic as I can while in Key West and try to only smoke Caribbean hand rolleds.

CIGAR REVIEW: The Torpedo by NeverAsh (7.8) is a beautiful hand rolled cigar from the Dominican Republic. Tom and Steve started this local Chicago cigar label in 2020 working directly with a DR cigar factory to import high-quality cigars to the Chicago area. They have a great line of sticks with the Torpedo being one of their more fuller body cigars. This smoke is smooth from start to finish and has a great price point of ~$12. Highly recommend for formal events or golf rounds to share with family and friends.

Oh! And do not slack on Happy Hour. These island goers thrive off of the ~3pm-9pm deals littered across the city. You can eat and drink your way from the Dante's to the 90 Mile sign with ~$40 in your pocket, a handful of 2-for-1 tickets from the airport, and will to find a deal. Places like Schooners Warfe start their HH as early as 9am!

2. Smoke as you Please

The second thing you need to know about Key West, and the reason I love it so much, is that you can smoke absolutely anywhere you please. Some places frown upon the indoor toke, but most of the bars have an indoor/outdoor vibe so you are free to enjoy yourself as long as you don't bother others around you. (No sniveling!)

Some of my favorite cigars I have ever smoked in the states were hand rolled from the Key West. My guy one-eyed John from the Key West Cigar Shop used to hint that the tobacco in his hand-rolleds fell off the back of a boat due south for Cuba. My brother-in-law and I would smoke nothing but those torpedoes for a week straight. Sadly, the shop did not make it through Covid and closed down in 2020.

This past year we were on the southern side of the island for dinner one night and stumbled upon a great tiki bar - Tipsy Rooster. They had a live acoustic act, outdoor games, homemade rum concoctions and the entire outdoor scene was covered in sand. It was the perfect place to kick your shoes off, sip some Pilar Rum and light up after a good meal.

The most unique part of this place is that it is actually a liquor store. They sold this Legacy Edition of Papa's Pilar Rum for the most affordable price on island ($89). I had toured the Papa's Pilar Rum distillery just hours before (an annual occurrence for the 3 free shots), which charged $105 for the same bottle and no leather case. Typically, I am a blender of the dark and lite Pilar rums, but this Legacy Edition is something special.

SPECIAL REVIEW: Papa's Pilar Rum (9.3) is my absolute favorite rum in the states. It's a taste of the island, from the island. This delicious liquor, named after Earnest Hemingway's hinckley, is distilled and bottled in Key West, FL. Thankfully it now ships across the US and can be found in your local Binny's. You can easily have it shipped to your doorstep if it's not distributed local. For years I was a bourbon only brown drinker. However, the year I proposed to my wife (in Key West!) her brother and mother convinced me to try this local liquor. I was hooked from the moment it hit my lips. I've been pushing not only Papa Pilar but rum in general on everyone and anyone who will listen. To me, there is no better pairing with a nice cigar. I drink Papa Pilar's rum straight up, or on the rocks. It's that tasty and smooth.

3. Limited Beach Scene

The third thing you need to know is that Key West does NOT have a beach scene. This crushed me the first couple of years because I am a fish. I'm also pretty judgmental on island beaches having grown up on the east coast frequenting Nantucket in the summers. Key West has plenty to offer, but it's not a vacation destination for those looking to enjoy the ocean and sand.

Key West is surrounded by a coral reef so the beaches that do exist are man made, corse and typically heavy with seaweed. The only decent beaches are connected to the hotels. However, there are a few fun locations for beachside drinking. Try Lagerheads Beach Bar for an afternoon Landshark and some of the best fish dip on the island - per the fish dip connoisseur, Keegan F Linza.

4. Be Prepared for a FULL Day Out

It's a race, not a sprint. My recommendation is to take advantage of your mornings. Wake up at your leisure, maybe play a few games while relaxing by the dunking pool, but make sure to get a sweat in early on. Trust me. Because once you leave the house for lunch, or to "walk the town," you are essentially bar hopping for the rest of the day and night.

Get your fanny packs in order! Stuff all of your drink coupons/tickets in. Bring your lighter, cutter and single, double, or even triple cigar sleeve because you are not heading home until it's time to pass out. Make sure to leave a little room for your games and gadgets!

GADGET REVIEW: You will come to learn that I am a big gadget guy. I get it from my momma. Mother Nardone has always spoiled me with phenomenal stocking stuffers, and Christmas 2022 was no different.

This year, my favorite gift was about 4 inches long and could fit in your pocket or fanny pack - the "HumidiMeter" by Cigarmedic's. This fun device provides you with a humidity reading by simply sticking the two medal prongs directly into the front of your cigar. It will pick up readings between 60%-70% humidity. I like my sticks closer to 70% so this devices helps me choose which cigars I take with me for the day vs which need more time in the humidor. This is a great device to use while traveling!

CIGAR REVIEW: San Cristobal Papagayo XXL (6.7). This stick (scroll down for photo ) was in my rotation while I was living in Austin, Texas right after college. I was 21 and just starting to take cigars smoking seriously. I was first attracted to the San Cristobal line because it smokes similar to my father's (and probably yours) favorite cigar - The Ashton. This classic Connecticut wrapper offers new smokers an easy pull and mild body with a solid quality tobacco. The San Cristobal lives under the Ashton family, and is offered at a much more competitive (low) price point. The XXL is a nice touch if you're in the mood for a heavier gauge.

Any Questions?!

In closing, I urge you to visit the keys and make your way down to the southern most point of our United States. I promise you will not be disappointed with your trip. I suggest 3-4 nights for first timers. Feel free to drop me an email with any questions before your trip. Our family has a number of trackers offering tips, tricks and hot spots.

With friends, family and good sticks...namaste.

Thank you for reading and Happy Smoking!

- Bostogian

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Bonus Covid Key West photo from 2021.