Freedom Fine Cigars proudly supports

Wounded Veterans Relief Fund

www.wvrf.org

We speak Backgammon

Beer, Wine and Cigar Lounge since 2013 

My wine selections are always changing, let’s talk wines!

Randall

“This is a must visit cigar lounge if you love a good cigar and a place that treats everyone like a wingman. What does that mean? This military themed lounge is more than just decorations...a friendly welcome awaits you here by the owner and veteran Randall.
Good selection of cigars, plus their own handrolled in various form factors. Beer and wine options are perfect for the size and clientle of Freedom Cigars. Randall's knowledge of French wines was especially impressive. Who knew there was a white grenache? I do now.
We look forward to visiting again and bringing a patch to grace the walls of this little gem!” Heather I. April 2021

Price points are very reasonable, and the selection of wines, spirits, and crafted beers are excellent.
Freedom Fine Cigars and Lounge, is well worth your journey even from another part of greater Naples.
Take care and enjoy! BLADE 4 / June 2021

Beautiful cigar bar and the owner, Randall, knows cigars because it’s obviously his passion. Comfortable, not afraid to be patriotic in these crazy times and made to feel at home by the many regulars who welcomed me. My second visit was on a Friday night when he closed late because of live entertainment. I’m terrible with names but the singer/guitarist was excellent. And Randall convinced me to have a glass of Sauternes with my cigar and I (who loves wine) was shocked at how well it paired. I will be back next season. John S. July 2021

Excellent cigar lounge in a very convenient part of Naples. There is a great selection of cigars to meet every palate. They also have a selection of beers, both on tap and bottled along with some very nice choices of wines.
The owner, Randall, is extremely friendly and knowledgeable. He has created a very comfortable and relaxing environment. I'll definitely be back on future visits to the area. David St J. July 2021

Very friendly & accomadating atmosphere between staff and the customers. Great selection of imported cigars & house blends. Deals on cigars and draft beers, a stop for all. Ventilation system is works very good as well. I will definitely be back.

Thank you for your service Randall. Blake S. April 2021

I always check out cigar lounges when I travel. I really like this one! The owner Randall is very hospitable and the place is very comfortable.
Nice selection of cigars, and the prices are reasonable. This will be my regular spot when I come to Naples. I highly recommend it.
Check out their privately rolled private blend Machu Picchu Cigars. Great bang for the buck. Mark H. May 2021

This is a special place. We were in town from North Georgia. The selection is great and Freedom carries lots of one-of-a-kind products that are wonderful. The owner is eager to make sure you enjoy yourself and the regulars are friendly. I won’t ever come to Naples without visiting Freedom. Bill L. April 2021

What a terrific spot to relax over a cigar and beer. Very comfortable and cozy atmosphere. Great selection of cigars. My first time there and felt like I was at a family reunion. What a nice crowd and quality service. I’ll be back for the wine tasting tomorrow. Thank you, Freedom Fine Cigars, for a most memorable afternoon. ✌️ BSJ March 2026

If you’re looking for a true five star cigar bar, this place delivers on every level. The atmosphere is relaxed, inviting, and makes you feel right at home the moment you walk in. Randall offers an exceptional cigar selection and has the knowledge to recommend the perfect smoke for any taste.
It’s the kind of spot where you can unwind, enjoy great conversation, and appreciate a fine cigar.
I Highly recommended for anyone who values quality cigars and genuine hospitality.

Doyle F. February 2026

Randall is absolutely amazing. I immediately felt welcome and had beautiful conversations with people from all over the globe. You can have a drink or a cigar and if you aren't familiar these guys will tell you all about history! What an invigorating experience. This is the new HOT DATE site for a cozy, romantic and fun couples or first dates!

C.E. March 2023

Great selection of cigars. Always a friendly hello and very helpful selecting a cigar...especially for those of us who do not smoke very often. Great atmosphere to sit back, have a beer and cigar.
Regular patrons have always been nice to the occasional visitor.
Always stop when in Naples.

Eric G. May 2026

We’d love to share an amazing experience with Freedom Cigar Lounge. Many thanks to Randall for his personal approach. We highly recommend his own brand, Machu Picchu Cigars, which we smoked. We’ll gladly return at the next opportunity. Thanks for all.

David & Zdenek May 2026

I walked into the shop to everyone saying, “hello, and welcome in!” The service was outstanding and felt very welcoming. I enjoyed my first experience so much that I went a second time later in the week and had the same experience if not better! 4 beer taps, wine and nice range of cigars to choose from. If you’re in the Naples area stop in and support a local Air Force Veteran.

Robert C. April 2026

Trying to find a local place to have a casual cigar in good company. This is the place. Randall was such a great host. Loved his cigars Machu Picchu Cigars Great Beer on tap definitely recommend this place!

Joe L. 👍🏻👍🏻 March 2026

First time visitor from Michigan and this place immediately felt like my backyard porch.

Never judge a book by its cover.

What you find inside is one of the most authentic cigar experiences Anywhere. Randall Denman is the real deal. His knowledge of premium cigars, the history behind them, and the people who make them is obvious the moment you start talking with him. More importantly, he runs the lounge the way a great cigar spot should be run, welcoming, relaxed, and built around camaraderie.

Randall’s background shows. The level of hospitality here is something you usually only see in the great cigar lounges in Major Markets.

Also, don’t sleep on the Machu Picchu Cigars. Outstanding construction and flavor through all three thirds. Easily one of the best values I’ve found.

If you enjoy premium cigars and good conversation, this place is worth your time. I’ll absolutely be back the next time I’m in town.

Joe C. March 2026

Found this place by chance while visiting family here in Naples and I couldn't have been happier I did. Cigar selection is excellent, atmosphere is great, and it will be a recurring stop every time I'm in town. The owner did a fantastic job making me feel at home despite being 1,400 miles away. He's got something special with this place. It is well worth stopping in for a good cigar and staying for great company.

Michael B. March 2026

Randall is the man. Darn good cigars, drinks, music, and conversation. My new spot in town! :)

Andrew E. February 2026

I live out of state but have made a habit of coming by for the owner’s own line of cigars, Machu Picchu Cigars, for the past several years. Great cigars, great shop.

Max O. January 2026

Perfect respite between daytime and nighttime activities. Don made us feel at home. We enjoyed a cigar, a few games of backgammon and wine/beer.

Jessica B. May 2025

Anytime I come down to Naples this is my favorite lounge just to kick back, relax, blast a fine cigar and get away from it all. Randall makes you feel right at home and treats everyone like family, doesn’t matter if you’re a first timer or regular, the vibe has that very homey welcoming feel. Great place to watch a game, sip some suds, have a laugh or two and make some new friends. Randall also gives back and contributes a lot to veteran organizations/charities. This establishment is one of Naples hidden gems. Can’t wait to comeback, thank you Randall.

Peter M. April 2025

Randall has created a very relaxed inviting lounge with a nice cool vibe. Naples is lucky to have such a great hangout. Freedom cigar has a great selection with some nice rocky patel, acid and other great brands and Randall's nice house brand cigar Machu Picchu Cigars. We love the ice cold Stella Artois in the chalace glasses. See you soon Randall!

Franco T. May 2024

draft beers

A Destination

Discover what makes Freedom Fine Cigars unique; 

• Premium Cigars

• Beer & Wine Bar

• $2 Tuesdays $2 draft beers all day……

• Wino-Wednsedays;

  all wines half price.

• Machu Picchu Monday;

  (buy 3, get 1 free!)

• Large comfortable lounge

• Multiple flat screens TVs

• Backgammon Tournaments

• Cornhole Tournaments

• Customer service with smile!

Premium wines by the glass

Premium Draft Beers

"Best Cigar Bar in Naples!"

It’s only getting better

I think you’ll like it, Randall

For this family I am grateful…

Make someone smile today.

Gift Certificates available,

call 239-207-9070