Winston's Cigar Lounge & Bar

What Winston's Cigar Lounge & Bar does

Winston's Cigar Lounge & Bar is a privately held, founder-owned cigar lounge and sports bar operating two physical locations in Orange County, California — a flagship in San Juan Capistrano (opened 2024, ~4,100 sq. ft.) and a second site in Yorba Linda (opened 2025). The company is led by founder Rick Collins ('The Guv'nor') and his partner Deb, who positioned the brand as a modern, 5-star hotel-inspired alternative to traditional dark, dated cigar lounges, featuring a smoke-free upscale bar, custom Italian bar stools, a large humidor, humidified cigar lockers, VIP rooms, a wine retail center, and a signature cigar. The company serves two primary segments: individual cigar enthusiasts and socializers seeking a premium cigar, cocktail, whiskey, bourbon, and sports-viewing experience, and corporate clients in Orange County seeking upscale entertainment and event venue capacity.

The company's revenue model combines recurring membership subscriptions with transactional F&B and retail. Membership tiers include Elite ($75/month), VIP ($225/month), Churchill ($900/year), and Guv'nor ($2,700/year), plus Corporate plans ranging from $250/month for 1-4 employees to $1,750/month for 11-20 employees with custom quotes for 21+. Each tier unlocks escalating discounts on cigars, wine, and retail purchases, access to private rooms, and exclusive access to 'The Winston's Vault' for hard-to-source cigars. Transactional revenue is generated through walk-in bar traffic (open to the public, non-smoking), private event bookings (birthdays, bachelor parties, corporate events), ticketed tastings (whiskey, tequila, cigar) and music events, retail cigar and wine sales, and a wine club subscription program. The technology stack is intentionally lightweight: PassFactory powers membership sign-ups, tier billing, loyalty points, and event ticketing; Company iStores powers the online merchandise storefront; Google Maps supports location discovery; and Instagram and Facebook drive community engagement. The company has no proprietary software, no AI capabilities, no disclosed funding, and operates with a reported 5 employees.

GTM is direct-to-consumer via the company's website (thewinstonsclub.com) and online membership portal, supplemented by community-driven word of mouth through the 'Brotherhood of the Leaf' member community, schooled pre-launch interest of 'hundreds' of prospective members, email/newsletter marketing, and social media. Private event and corporate account sales are handled through direct outreach supported by the website contact form. Founded in 2023 after Collins' 2023 London research trip, the business is at a very early stage with both locations opened within the past 24 months.

Name

Winston's Cigar Lounge & Bar

Legal name

Winston's Cigar Lounge LLC

Website

https://winstonscigarlounge.com

Company type

Private

Founded year

2023

Operating status

Operating

Headcount range

1–10 employees

Short description

Winston's Cigar Lounge & Bar is a founder-owned, premium cigar lounge and sports bar operating two locations in Orange County, California, serving individual cigar enthusiasts and corporate clients through tiered memberships, a wine club, private events, and on-site retail.

Ownership category

akta.pro rank

Headquarters

HQ city

San Juan Capistrano

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Infrastructure, Marketing or Sales, Technology or R&D, Supply Chain, Others

Revenue model

1. Membership Subscriptions: Monthly, annual, and corporate membership tiers providing recurring subscription revenue. Includes VIP and Guv'nor tiers with premium perks, plus corporate plans for businesses of various sizes.
2. Food & Beverage Sales: The lounge operates a full-service bar with high-end cocktail options, craft cocktails, premium well spirits, whiskeys, bourbons, and tequilas. Non-smoking bar is open to the public.
3. Private Event Hosting: The Winston's Room and Big Beautiful Bar are available for private bookings including birthdays, bachelor parties, corporate events, meetings, and community events. Revenue generated through venue rental and bar services for events.
4. Retail Cigar & Wine Sales: In-house humidor and wine retail center selling cigars, cigar boxes, and wine to members and the public. Discounts on retail purchases are tiered by membership level.
5. Wine Club: A dedicated wine club program offering members exclusive wine selections, tastings, and member pricing on wine purchases.

Pricing tiers

Go-to-market motion1 record

Distribution channels5 records

Marketing channels5 records

Core offering

Winston's Cigar Lounge & Bar operates two physical cigar lounge and sports bar locations in San Juan Capistrano and Yorba Linda, California. The business sells tiered monthly and annual memberships (Elite, VIP, Churchill, Guv'nor), offers a full-service smoke-free bar with craft cocktails, premium spirits and wine, houses an in-house humidor and wine retail center, hosts private events in dedicated rooms, operates a Wine Club, and runs ticketed tastings and live music events.

Product overview

Winston's Cigar Lounge & Bar is a luxury cigar lounge and sports bar offering a modern take on the traditional cigar experience. The business operates two locations (San Juan Capistrano and Yorba Linda) and provides a portfolio of membership tiers (Cigar Enthusiast, VIP, Churchill Member, Guv'nor Member, and Corporate Membership) that grant access to different amenities including smoking rooms, lockers, discounts on cigars and wine, and The Winston's Vault for exclusive cigars. The product suite includes the core lounge experience, a Wine Club, Premier Events Center for private parties and corporate events, ticketed events (cigar events, whiskey/tequila tastings, weekend music), and an online merchandise shop. Named spaces include The Churchill Room, The Guv'nor Room, and The Winston's Room for VIP and private events.

Differentiator

Problem solved

Functional benefit

Products and services

• Cigar Lounge Membership Program Recurring membership program offering access to the cigar lounge, smoking rooms, humidified lockers, retail and box discounts on cigars (10-30%), loyalty points, special event invitations, and access to The Winston's Vault for hard-to-source cigars. Tiers include Elite ($75/month), VIP ($225/month), Churchill ($900/year), and Guv'nor ($2,700/year). Annual memberships include a free Winston's Hat and Membership Pin.
• Corporate Membership Plan Business-tier membership program extending Winston's membership privileges to employees. Tiered pricing covers 1-4 employees ($250-$375/month), 5-10 employees ($500-$950/month), 11-20 employees ($950-$1,750/month), and 21+ employees on custom quotes.
• Wine Club Wine membership program providing access to hard-to-source wines, member pricing on cases of wine (25% over cost for Guv'nor Members), and wine tasting events.
• Premier Events Center (Private Events) Private event venue rental hosting pre and post wedding events, birthdays, bachelor parties, corporate functions, business meetings, and community events. Includes full liquor bar, advanced audio-visual equipment, world-class mixologists, and professional event planning support.
• Ticketed Events Special paid events including cigar events, whiskey tastings, tequila tastings, and weekend music performances. Tickets sold through the PassFactory event platform.
• Online Shop (Merchandise) E-commerce storefront selling Winston's branded merchandise and signature cigars via the Company iStores platform, available to members and the general public.

Segments2 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration5 records

Feature3 records

Partnerships

One partnership is on record.

• PassFactorycoreTechnology or IntegrationPassFactory provides the membership management platform and event ticketing system for Winston's Cigar Lounge. The platform handles membership sign-ups, tier management, loyalty points, and ticketed events including cigar tastings, whiskey tastings, and other special events. All membership links on the website direct to PassFactory.

Scale indicators3 records

Recent moves9 records

Expansion highlights10 records

Broad incumbents

• Soho House: Global members-only club business combining food, beverage, and curated hospitality experiences — comparable in its tiered membership model and experiential positioning, though far broader in scope than Winston's cigar focus.
• Nat Sherman: Historic tobacco retailer that operated flagship cigar lounges (Townhouse) combining retail and hospitality — a broader industry incumbent whose lounge-retail hybrid overlaps Winston's core offering.

Direct peers

• Davidoff of Geneva: Operates premium cigar lounges and boutiques globally that combine retail cigar sales with hospitality and bar service — directly comparable format to Winston's, though at a far larger international scale and with proprietary cigar brand supply.
• Tinder Box: Franchise network of cigar retail shops and lounges across the U.S. offering walk-in humidor retail and lounge seating — comparable cigar retail + lounge hybrid, though typically less premium than Winston's positioning.
• Casa de Montecristo: A U.S. chain of upscale cigar lounges and retail shops offering walk-in bar service, humidor retail, and member-style amenities — the closest direct competitor in terms of cigar lounge + retail + bar model in the American market.
• Club Macanudo: Long-running members-only cigar lounge in New York paired with a full bar and dining program — a direct analog for Winston's tiered membership structure combined with upscale cigar and beverage hospitality.

Others

• Total Wine & More: Large-format alcoholic beverage retailer that overlaps Winston's wine retail and Wine Club product offering, though without the cigar/hospitality experience layer.
• Cigar Aficionado (Cigar Club events):

Regional players

• Capital Cigar Club: Regional members-style cigar lounge offering lockers, humidor access, and bar service — comparable format to Winston's membership tiers in a different U.S. geography.

Emerging players

• Laithwaite's Wine: Subscription-based wine club with curated allocations and member pricing — closely comparable to Winston's Wine Club program in mechanics, though operating as a pure-play wine subscription rather than a venue-based experience.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key risks6 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/winstonscigarlounge

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Winston's Cigar Lounge & Bar