Memberships
Memberships at Pirate Cigar at Darkwater Alley
Drop anchor with us and the pot is always on.
Bottomless house drip — all day, every day you come through that door. That is the first thing a membership buys you, before a single cigar changes hands.
Every Ashhole gets:
- ☕ Bottomless house drip coffee — all day, every day you are here. On the house, always.
- 🎭 Monthly member events — no ticket, no guest list. Just show up.
- 🚬 Free cigars or specialty coffees, every month.
- 💰 Deep discounts on everything in the room.
Then choose your rank.
Location: 6850 66th St. N, Pinellas Park, FL
Contact: (727) 317-9799
Email: info@piratecigarlounge.com
What Level Ashhole Are You?
Salty Ashhole Membership
Price: $30/month
Annual Plan: $300/year
Every crew starts somewhere. Nothing about this is a lesser seat.
☕ What’s Included:
- 5 fresh local house cigars or 5 specialty coffees, every month
- 10% off cigars, coffee and merch
- 10% off tickets to special events
- Salty Ashhole T-shirt with the annual plan
🔥 Want a berth for your sticks? Add a 30-count humidor for $25/month.
Officer Ashhole Membership
Price: $60/month
Annual Plan: $600/year
This is where your cigars stop living at home.
Benefits:
- 10 fresh local house cigars or 10 specialty coffees, every month
- Your own 30-count humidor in our wall — locked, climate-held, waiting for you
- 15% off cigars, coffee and merch
- Half-off tickets to ticketed special events
- Officer Ashhole Crew Shirt with the annual plan
Twice the cigars, and a place to keep them. Your stash lives here now. So do you.
⚓ Captain Ashhole Membership
Price: $150/month
Annual Plan: $1,500/year
The run of the room, and a chest with your name on it.
🚬 What’s Included:
- 20 house cigars, 10 brand-name cigars, or 10 specialty coffees — every month, your pick
- Your own 100-count treasure chest, your name on the plate
- A cigar of the month, dropped in your chest whether you’re here or not
- First pick when a limited drop lands
- Free entry to ticketed special events
- 20% off cigars, coffee and merch
- Captain Ashhole Guayabera with the annual plan
🎁 Sign on for the year and we stock your chest to start — a 20-count box of premium cigars, on us.
💡 Best value: the annual plan saves you $300.
Add-On: Locker & Storage Options
Need a secure berth for your sticks?
Officer and Captain memberships come with your own humidor — a 30-count on the wall, or the 100-count treasure chest with your name on the plate.
Anyone else who wants one, member or not: $25 a month.
Ask our team about availability.
Important Terms & Conditions
- All discounts and freebies are only valid during the time of active membership.
- Free items reset monthly and do not carry over.
- Bottomless coffee is our house blend drip. Specialty drinks, espresso, cappuccinos and Kracks are not included — those are what your monthly allowance is for.
- Shirts come with the annual plan.
- Tickets for special events are sold in the lounge or by phone. Online ticket sales are not available.
- Annual memberships do not renew automatically.
- Annual memberships are refundable on a prorated basis, starting from the first day of the next month.
- The annual Captain signing gift is one time, when you sign on — not monthly.
- Discounts do not apply to clearance items.
- All memberships are for individuals 21 and older.
- Veteran and Senior discounts may not be combined with Ashhole Membership discounts.
- Pirate Cigar at Darkwater Alley is not liable for the end of your relationships or bad life choices