Cigar Lifestyle: Destination Herf 2023 – Miami, Florida

Well it is that time again, the start of the new year and the beginning of a years worth of exciting cigar events, festivals and trade shows. The 2023 cigar calendar kicked off with the 2nd Annual Destination Herf – Miami cigar event. As in the past, the event was primarily sponsored by Caldwell Cigars and of course the swag bags were filled with a fine collection of Caldwell cigars. The event was also sponsored by Uncle Nearest Premium Whiskey, Casa Caraballo Cigars, and Konscious Cigars,

As the name notes, attending the event, would mean a trip to sunny, warm Miami, FL. Not this year though. It was sunny, but old man winter got the best of us here in Florida. The chill was in the air and the wind brought it down even colder, not to mention the dampness that cut to the bone. Regardless though, it did not deter the many dedicated cigar enthusiasts from descending on Miami, Florida for a long weekend of food, drink, dance, and of course…cigars.

The non stop weekend started with a Meet & Greet at City Cigar Lounge Thursday evening January 12th. This is the kickoff event and sadly I never can make this as I have to drive down to Miami and my work schedule is just too tense at the start of the year. This was followed up on Friday afternoon with a Smoke Easy Social – Sip and Smoke event where attendees got to experience pairing cigars with locally produced wines and spirits. It was held at the roof top lounge at The Citadel. As much as I wanted to make it to this event, traffic heading south was not having any part of it. A simple 3 hour drive ended up taking me close to 5 hours.. ouch!. From the posts I saw on Facebook, it looked like both events were a fun time; as I would expect from Destination Herf organizer Jay Ferg.

With time a little bit on my side now, I ended up heading straight to my AirBnB – The At Mine Tree House Hotel – in Little Haiti and got freshened up and went straight over to the second Friday event – the Destination Herf Awards Dinner. My room was just a simple 4 minute drive to the event, which I did get to ahead of schedule. Imagine that, on time and ready to enjoy the evening.

Destination Herf Awards Dinner

This years awards dinner was held in the same location as last year – Magic City Innovation District. It is most definitely a little oasis in this part of the city. The dinner is held outside in the courtyard of an old building with its large reflection pool and old banyan tree and various palms and other tropical foliage.

Once I got settled in, I spent some time talking to Kevin King Brown, the owner of Konscious cigars. Kevin introduced me to his latest creations and you will hear about them in the coming weeks for sure. I also made my over to the bar to see what was available. There was plenty of beer, wine, spirits, and cocktails to be enjoyed. As for me, I went with some tequila to get my juices flowing and to warm up to the chilly evening. Then I met up with Mario Caraballo – owner of Casa Caraballo Cigars.

Meet & Greet

With a drink in hand and camera ready to shoot, I spent the start of the event snapping photos of the guests as they entered the venue. Folks loved posing for photos which was just alright for me. Click on any photo to see a slide show of each gallery.


Once the guests had arrived, and meet an greets slowed down, it was time to partake in evenings gastro delights. The menu was served buffet style and included BBQ chicken, rice, collared greens, salad, and dinner rolls. This gave me time to relax and enjoy some conversation with a number of fellow enthusiasts including premium sponsor, Robert Caldwell.


After dinner, it was awards time, as that is why we were here in the first place. Every year, Jay Ferg and his Destination Herf team select members of the industry to receive awards. This years honorees were:

  • Rookie of the Year – ATL Cigars
  • Hustler of the Year – Drunk Chicken Cigars
  • Accessory of the Year – Phat Ash Collection

Sadly, only ATL Cigars was present at the dinner.

Music and Dance

As the night drew on, the music was spun by the sounds of D.J. REDD and the guests took to the dance floor to dance the night away. I got a few laughs as I tried to do a dance but as my wife says, Jimmie you ain’t got rhythm! So I did what I like and took some photos and watched the show.

With the late hour upon us, the crowd thinned out and eventually departed to their hotels or wherever they decided to go.

Magic 13 Brewing Company

As for me, I was a wee tired, but decided to head across the street to a brand new brewery – Magic 13 Brewing Company – that I found just opened up this same week. I met the brew master and had some of his craft and I gifted him a Caldwell Cigar which he said he is big fan of. The brewery has a beer garden in the back and a live music stage. They also do private events. Checkout them out of you are in the Miami area.

That was it for Friday as I headed back to my hotel to get some rest before the main event on Saturday afternoon.

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The Main Event – Virginia Key

Like last year, the main event was held at historic Black Beach on Virginia Key. The beach and park rests right on Biscayne Bay and is steeped in history as it was the only beach a person of color was allowed to go back in the day. The bathrooms, dance pavilion, and concession stand are the same structures from back in the 1940s. Though it is easily accessible today, “Virginia Beach, a Dade County Park for the exclusive use of Negroes” was only accessible by boat from a downtown dock on the Miami River, in 1945 when it officially opened on August 1, 1945. The beach and park are a great place to have an event and Jay Ferg knows this. The all access pass got you entry to the event along with drink and food tickets. There was a VIP section under a tent over the historic dance pavilion and a few vendors spread out around the grounds.

The event started at noon and went on to 5 PM. DJ REDD spun the tunes and Grill Daddys BBQ Pit was serving up the ribs and chicken. Casa Caraballo were present showing off their craft and Oliva Cigars were selling sampler packs, where all proceeds went to schools in Nicaragua. I purchased a sampler of Melanio cigars which included a rare lancero. LVD Lifestyle was also at the event selling cigar accessories for the Ladies of the Leaf. You could also purchase Destination Herf Merch and even talk to a law group if you needed hep with an accident or other legal issues.

The crowd was about the same size as last year but the cooler than normal weather seemed to have an impact on attendance. It was fun to meet old friends and make new ones as that is what cigar herfs are really all about.

The Midnight Burn

After the main event ended, people had time to get back to their hotels and dress in their party clothes again then head over to what is known as the Midnight Burn. This is where we all gather at a another unique place in Miami, this time it was the classic Dunns Josphine Hotel in Overtown. This is a beautiful old boutique hotel that is apportioned with art, sculpture, and even a piano. It has a outdoor courtyard that includes numerous patio couches and tables to relax and enjoy a Miami evening. Everyone in attendance got a special Caldwell cigar to light up and burn in the late night.

The crowd is always smaller at the midnight burn event but those that came had fun relaxing and enjoying each others company. There was food, desserts, and an open bar.

With Sunday morning coming upon me, it was time to head back to my room, pack and set the alarm for an early wakeup to head back to Melbourne, FL The trip back was easy and free flowing with no traffic, no accidents, and less than three hours compared to the almost 5 hours it took to drive down.

I would like to thank Jay Ferg and his Destination Herf team along with the sponsors and vendors, Caldwell Cigars Uncle Nearest Premium Whiskey, Casa Caraballo Cigars, Oliva Cigars, Konscious Cigars, Grill Daddys BBQ Pit, LVD Lifestyle, and D.J. REDD for a terrific cigar weekend and great start to the 2023 cigar event season. I will be seeing you all soon.

~Peace and Love – Boston Jimmie

3 thoughts on “Cigar Lifestyle: Destination Herf 2023 – Miami, Florida

  • Destination Herf Miami 2023 was soooooo much fun, even though the weather wasn’t playing fair lol. I stayed until Tuesday and got some good warm weather. It was really nice seeing you this year. Very good article Jay Ferg did an amazing job on the venue selections, food was delicious all weekend and to get the pleasure of smoking Long Live The Queen before anyone gets it was special. I will be back next year…

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