Cape Town, South Africa
Cape Town Summer Session
Eight days between the mountain and the sea, with long working mornings and the space to think past the next quarter.
· 8 days
This is the trip for the year's first hard decisions. January in Cape Town is long light and warm evenings, and the city is set up for exactly the kind of unhurried thinking that is impossible to do at your desk.
We work in the mornings: properly, with facilitation, on the questions members are actually carrying into the year. Afternoons are the peninsula: the coast road, the winelands, the studios and roasteries and small manufacturers that make this a builder's city rather than only a beautiful one.
It is our most popular trip and the one we most often recommend as a first.
The experience
Room to think, and people to think with.
Structured mornings, open afternoons, and a group small enough to stay one conversation.
- 01
Annual planning, together
Three facilitated mornings working on the year ahead, with a room of peers to pressure-test it rather than a document nobody reads again.
- 02
The peninsula
Chapman's Peak, Cape Point, the Atlantic seaboard. The drive that makes everyone go quiet.
- 03
Builders in the Cape
Hardware startups, a semiconductor lab, and the winemakers doing the most interesting things in the valley.
- 04
Long evenings
Sunset at eight, dinner at nine, and the conversation that runs to one in the morning.
The detail
What's included, and what isn't.
Included
- Seven nights' accommodation, private room
- All ground transport and airport transfers
- Breakfast daily and all group dinners
- Three facilitated planning sessions
- Peninsula day and winelands day, fully hosted
- Photography from the week
Not included
- International flights
- Travel insurance (required)
- Lunches on open days
- Personal spending and optional activities
Day by day
The itinerary.
A rough shape rather than a schedule. The useful parts of a trip rarely happen on time.
Day 1
Woodstock
Arrival
Transfers through the day, then an opening dinner in Woodstock. Slow start by design, because most people have flown a long way.
Day 2
Planning, session one
Facilitated morning on where each member actually is, honestly assessed. Afternoon on the Atlantic seaboard.
Day 3
Cape Peninsula
The peninsula
The full day out: Chapman's Peak, Cape Point, and back along False Bay. Dinner in Kalk Bay.
Day 4
Planning, session two
The year ahead: what you're committing to and what you're dropping. Afternoon open for meetings and work.
Day 5
Salt River
Builders' day
Visits to a hardware startup, a materials lab and a manufacturing floor. Evening with the Cape Town founder community.
Day 6
Franschhoek
Winelands
Franschhoek and Stellenbosch with a winemaker who will explain why the last decade changed everything here. Long lunch, no schedule after it.
Day 7
Planning, session three
Commitments, made out loud to the room. Members pair up for the accountability that carries past the trip.
Day 8
Close and departures
Breakfast together, transfers from mid-morning.
South Africa
Cape Town
Eight days between the mountain and the sea, with long working mornings and the space to think past the next quarter.
Gallery
From previous trips.
Before you book
Important information.
Visas
Many passports enter South Africa visa-free for up to 90 days. We confirm requirements for your nationality on booking.
Season
January is peak summer: hot, dry and windy on the coast. Pack for strong sun and cool evenings.
Pace
The most relaxed trip we run, and the one we suggest if it's your first. Days start at nine and there is real downtime.
Payment
A 30% deposit secures your place; the balance is due 45 days before departure.
Questions
About this trip.
Can I extend my stay?
Can I bring a partner?
Cape Town Summer Session
Eight days between the mountain and the sea, with long working mornings and the space to think past the next quarter.