Five Rooms I Take Clients To — And Why Each One Works

By one of our London companions

Most men who book me already have a restaurant in mind. The cigar lounge is always my suggestion, somewhere between the second course and the moment when neither of us is ready for the evening to close. Five years of evenings like this. I've learned which rooms earn that extension and which ones don't.

These five earn it.

Birley Cigars, 5 Hertford Street

Red door. Bell. Nothing else visible from the street.

I brought a client here who'd spent fifteen years working in Mayfair and had never been inside. His reaction — someone who knows this city that well, genuinely caught off guard — told me everything I needed to know about the room.

Spanish cedar humidor built by craftsman Massimo from DeArt, all 27 Cuban brands stocked, five cigar master sommeliers working the floor. Before you choose anything, the conversation covers duration, what you ate, whether you want something mellow or something that actually registers. The Cohiba 50th Anniversary box sits in the humidor at £450,000. Behind a separate door, 260 private climate-controlled lockers hold members' personal stock as it ages — oldest deposits running back to 2003 vintages untouched since arrival.

Membership requires a proposer, a seconder, a committee vote. The cigar shop beside it runs separately — public, weekday afternoons, bell only, no reservation. Mick Jagger is a regular. DiCaprio. Princess Eugenie. The room is aware of this and doesn't mention it.

Men who come as clients tend to apply for membership within three months. I've watched it happen more than once.

The Connaught Cigar Merchants

Ten seats. Carved oak ceiling, wood panelling running floor to ceiling, and an air system that pushes filtered air upward through the floor itself — smoke rises away from you, jacket stays clean when you leave at midnight after an evening that started at seven.

Adam Lajca, Master of Havana Cigars, built the humidor personally around limited editions and vintage stock. Bespoke requests go directly to Lajca, not through staff. Spirits include the Karuizawa 1972, which most bars in London keep behind glass rather than open.

Staff here read a table without being asked. Arrive with a companion, drinks appear, cigars are cut, everyone disappears. No return visits to confirm satisfaction.

No reservations. Some evenings you get the last seat. Other evenings the door is already full and there is nowhere to wait. I arrive early or I don't come.

Boisdale of Belgravia

Ranald Macdonald opened this in 1986 coming out of the wine trade. He is the eldest son of the 24th Chief and Captain of Clanranald, which explains both the plush tartan running wall to wall and the complete absence of apology for it. Dry-aged Aberdeenshire beef on the menu, Hebridean seafood, Jools Holland as Patron of Music. The combination shouldn't hold together.

The cigar terrace seats 40 — sofas, armchairs, outdoor heaters in November, cashmere blankets from Scotland when the temperature drops below ten. Sommelier Jay runs the terrace with a written menu separating Cuban and New World options by column. I order the Juan Lopez Selection No.2 with a whisky sour without opening the list. Clients who've been before do the same without asking.

First-time visitors miss the secret Negroni bar almost universally — it's through a door that gives nothing away. Jazz carries through from the restaurant Monday to Saturday nights and Sunday lunch. Book the terrace. Tell Jay how long you're staying. He paces the evening around that answer.

Ten Trinity Square, EC3

Tower Hill postcode. It filters the room — everyone else finds it quieter and considerably easier to book than anything in Mayfair, which is precisely the point.

Monthly members-only events at the cigar lounge run to Cuban rolling masterclasses, Macallan pairings, a Churchill birthday session where members smoke in his honour using stock from that year. Full dinner menu alongside the cigar service — unusual in London, where most lounges stop at spirits and send you elsewhere to eat.

I use this room for evenings that need to stay in one place. No transitions between dinner and cigars, no logistics breaking the rhythm. Some clients specifically need that containment. They don't always know it until I suggest it.

Oscuro at The Arts Club, Dover Street

Limited editions and vintage cigars sourced internationally, members keeping personal stock in dedicated keeps available after dinner or during afternoon terrace sessions. Ruinart Blanc de Blancs by the glass. Rare whisky. Cocktails from a bar that doesn't explain itself.

Arts Club membership has the least theatrical application process of these five — real criteria, no nomination ceremony, no waiting list performance. On any given evening: creative industry, international money, considerably less interest in being observed than anywhere north of Piccadilly. Oscuro runs until the last person is ready to leave. Nobody comes to check.

This is the room I suggest last. It's where a nightcap turns into two hours neither of us planned for, the kind of evening without an obvious closing point and no need for one.

That quality is rarer in this city than it should be.