About Head Case Cigars

Based in the Historic Port of Portsmouth, UK. the Head Case family deliver experiential retail therapy.

Our Motto is “Never Knowingly Normal”, so you can expect the unexpected!

About Our Shop

We’re committed to offering experiential retail therapy in a relaxed, and informal atmosphere. Please visit us and see how lovingly we look after our cigars and what we can advise for you.

Checkout our reviews on Tripadvisor and Google. These have all been gratefully received: we are consistantly rated 5* and the comments are genuinely independant.

Based in the historic port of Portsmouth, Hampshire, UK. The Head Case story began in 2015 with a curiosity style shop however since Covid locked us all down for a while, the direction has changed dramatically and we are now officially Head Case Cigars.

We began ‘at the top’ by selling fine, hand-made Cuban Cigars and have swiftly expanded our range to include many New World Cigars. Pre-Covid we had 5 types of cigars and now in 2024 we currently have over 200 different options for you to choose from in the Ultimate Pick & Mix.

In 2025 we achieved recognition for Tonys hard work and dedication by gaining Habanos Specialist status.

NB: NOT all cigar shops have this – we are one of the few who can access the rarer Cuban cigars and if there is something you are looking for, please ask and we will do our best.

Go To Shop

Buyers and sellers of Humidors, Cutters, Lighters, etc

Head Case Cigars was created from Tony Dukes passion & knowledge in fine cigars, however when you visit you will notice we are not your traditional cigar store!

We guarantee your visit will be memorable for the right reasons – see our testimonials and feedback for reassurance.

Retailers in fine Cigars

Head Case Cigars stock the accessories you’ll need to store & enjoy your cigars.

Our cigar customers are offered a complimentary soft drink during your visit; we also have tables outside to relax, enjoy a cigar and socialise if you wish. If we are a bit busy we invite you to have a seat, enjoy a drink and checkout our Cigar Menus and our Drinks menu.

We provide our visitors with a broad assortment of ever-changing items, the only thing that remain the same are our honest prices, truthful/carefully considered advice and excellent customer service.

    
 
 
       Posted on Tripadvisor  
   
   Alistair H 
 
 
 
 Verified A place where you can find true peace and stillness in a bustling city.
Whilst working in Portsmouth I discovered Headcase thinking it was a coffee shop. I went inside and met the owner Tony and discovered the world of cigars. Tony is very friendly and very knowledgeable. Whatever your background he will guide you to the right choice and never sell you anything that you don’t specifically ask for. This weekend I revisited the shop and was pleased to see that it has gone from strength to strength. You will find everything from cheap starter cigars to those rare gems we only read about. Through visiting the shop I have made a good friend in Tony and you will find lots of like minded people there always happy to talk and smoke a cigar in good company. Headcase Cigars truly is my happy place. If you’re in Portsmouth for the weekend then it is a must visit. Take a bit of time back for yourself and relax with a good quality cigar.
  
 
      Posted on Tripadvisor  
   
   Karen R 
 
 
 
 Verified A must do visit in Southsea!
My partner decided to take me in on the spur of the moment, neither of us being cigar smokers but curious about it, especially as the shop front is so alluring and everyone we saw in there during our many strolls past seemed very friendly and happy so in we went. Tony greeted us immediately and effortlessly matched our tastes to suitable cigars. He is hugely knowledgeable which added to our pleasure and hosts a fine selection of rums especially O’Donnell’s Moonshine which is out of this world! If you haven’t ever been in you must! One of Southsea’s finest shops.
  
 
      Posted on Tripadvisor  
   
   uchiha b 
 
 
 
 Verified 100% would recomend, lovely staff, very knowledgeable
Staff were friendly and service was exeptional. He was very knowledgeable about cigars and cigar care. 100% going for beginers and veterans alike.
  
 
      Posted on Tripadvisor  
   
   Tom Hamer 
 
 
 
 Verified So knowledgeable and friendly!
As someone who doesn’t smoke going to a cigar shop to buy presents can be quite daunting. Not at Head Case. As soon as I walked in a warm welcome from the owner who was more than happy to help understand what I was buying it for the habits of the person who will be smoking to then make recommendations based on this. It was also good knowing he doesn’t just push the expensive stuff on you but actually explains the price points and using analogies to make you understand the differences that relate more to the buyer. Top notch experience and customer service will be back.
  
 
      Posted on Tripadvisor  
   
   vickydetmold 
 
 
 
 Verified Cigars- wine- beer wow!!
We come here for our cigars, Tony ( owner) will talk you through he is the Dr of cigars, now he has an alcohol license you can have a wine/beer/ whiskey with your cigar
  
 
      Posted on Tripadvisor  
   
   Max J 
 
 
 
 Verified Doesn’t matter if you’re new or experienced with cigars you should stop by..
I can’t rate this place enough, me and my mate first gave this place a visit in January to have a look and get some recommendations and we weren’t disappointed. Tony is a genuine guy who takes the time to ask you questions relating to your taste to pick and choose the right cigar for you which is great for people like us who don’t have much experience with cigars and at no point did we feel pressured to buy anything.. if you’re new to cigars stop by and you’ll learn a few things and get some great recommendations to your own tastes, if you’re experienced then stop by and take a look at the great selection of cigars at a great price, there is also rum, coffee and beers to enjoy with your cigar, I’m looking forward to my next visit!
  
 
      Posted on Tripadvisor  
   
   Sam L 
 
 
 
 Verified Excellent customer service and cigar expertise.
We came here to select cigars for our wedding and we couldn't have been treated better. The owner has an incredible knowledge of cigars for all occasions and helped us select the perfect cigars. We would highly recommend this store for any cigar needs and we can't wait to come back for an evening.
  
 
      Posted on Tripadvisor  
   
   Liam C 
 
 
 
 Verified A must see for eclectic tastes and great cigars.
Tony and his shop are a fantastic addition to the high street. Tony is friendly, knowledgeable and clearly very passionate about the cigars he sells. He caters for all budgets without the often judgy vibe you can get from cigar shops. He stocks a wide range of fantastic cigars from around the world, and knows about every single one. Tony’s shop is filled with the weird and wonderful and it can cater for any taste. My most recent purchases include some cool CDs and of course some new cigars to try. This store is exemplary!
  
 
      Posted on Tripadvisor  
   
   Chubby A 
 
 
 
 Verified Excelente
Once in a blue moon you walk through a shops door and are taken a back by the Aesthetics and decor. This is one of them. The owner was there to tailor what cigar you wanted by your own personal taste. Most cigars here are hand rolled and high quality. Prices vary from low to high to very high they have you covered.
  
 
      Posted on Tripadvisor  
   
   Dean c 
 
 
 
 Verified Happy smokes
This the best cigar shop in Portsmouth,and probably the best cigar shop I have ever visited, Tony the owner will do his absolute best to make you feel welcome,the stock he has it excellent,if your new to cigars or experienced,he will guide you to the next level,keep up the fantastic work at Head Case curious and cigars