Afternoon: Marylebone, then west
Marylebone is the gentlest possible start — a high street rather than a landmark, with room to talk. If you would rather browse than sit, Notting Hill is the alternative and takes an afternoon comfortably.
Neither needs booking, which is the point of the first few hours: nothing to be late for while you find the rhythm of the day.
Early evening: the South Bank
The walk between the bridges is the best free hour in the city and works in almost any weather. It also solves the awkward gap between an afternoon and a dinner reservation, which in London is usually an hour longer than you expect.
Shoreditch is the other direction if you want the evening louder and later.
Dinner, and the dress code question
Dinner tends to start between 7 and 8:30pm, and a drink beforehand is close to standard. Dress is relaxed almost everywhere — the exceptions are a few older members' clubs and West End rooms that still hold a jacket rule.
If your venue is one of those, say so when you request availability. Several London companions are used to jacket-required rooms, and arriving correctly dressed is the difference between an easy evening and a conspicuous one.
Getting home, and when to book
The Tube stops around midnight most nights, with the Night Tube on Friday and Saturday on several lines. Black cabs and licensed minicabs cover the gap, so a late finish is never a problem — it just wants deciding in advance rather than at 12:10am.
On timing: summer weekends and the December party season are the two peaks. Wimbledon fortnight, the summer wedding run and the Christmas calendar all pull bookings forward, so leave more room in June, July and December.
Frequently asked questions
Is a companion comfortable at a members' club?
Yes, and it is a common request in London. Tell us the venue and dress code when you enquire — several companions here are used to jacket-required rooms.
How late can the evening run?
As late as you like. The Tube stops around midnight, so agree beforehand whether the night ends before that or continues by cab.
When is London busiest?
Summer weekends and December. Wimbledon, the wedding run and the Christmas season all stretch lead times.