Somebody has been asked to plan the offsite. The date is roughly agreed, the budget is set, and the last two were a conference room with better sandwiches. This year the brief is something people will actually remember.
A day on San Francisco Bay does that reliably. It is outdoors, it is a short trip from downtown, and once a group is on a sailboat everyone is doing the same thing at the same time, which is more than most offsites manage. Here is how to plan one that works, from the first headcount to the walk back up the dock.
Start with the headcount
The number of people decides the boats before anything else does. Our largest boat, Yukon Jack, takes up to 20 guests on her own. Past that, the group splits across several boats, and the most we put on the water for one event is 44.
- 44 people on the water at once, across several boats
- 20 on Yukon Jack, our largest boat
- 6 to a boat in a big boat regatta, 4 in a small boat one
A split is not a compromise. Several boats on the same water is what makes a regatta possible, and a crew of four or six is small enough that nobody gets to hide at the back. Every boat in the fleet is a sailboat we own, and every one comes with its own licensed skipper.
Decide what kind of day it is
Corporate days on the Bay tend to go one of two ways, and it helps to know which you are planning before you ask for a quote.
A team regatta puts the group to work. Each team gets a boat and a skipper, there is a marked course and a starting horn, and the boats race each other. It suits teams that like a bit of competition, and it does something useful along the way: there are only so many jobs on a sailboat, and somebody has to take each one. The team building page lays out the formats and how the jobs on board divide up.

A relaxed sail is the other way. One big boat or a few smaller ones, a route along the city front or out under the Golden Gate, food and drink on board, and time to talk. It suits a leadership team, a client day, or a group that has just shipped something and deserves an afternoon off.
How a regatta day runs
The details change with the group, but a regatta has a recognizable shape.
- Before you sail Everyone meets at Pier 40, at least thirty minutes before departure, and crews are matched to boats.
- Leaving the dock The skippers teach as they go: who trims which sail, who calls the turns, who steers. Nobody needs to have sailed before.
- The racing A short course and several races back to back. Bragging rights are the actual prize.
- Back at Pier 40 The boats come in, and the arguments about who won start before the lines are tied.


A big boat regatta runs as a half day of four hours or a full day of seven; a small boat regatta runs three hours or six. If this is the team's first time on the water, the half day is a comfortable place to start.
Food and drink
You can bring your own food and drink and the crew will serve it, or let us cater: salads, wood-fired pizza, sandwiches and breakfast spreads, with beer and wine served on board. Plenty of groups do some of each. The options are on the catering page.
Two house rules: no red wine and no hard liquor aboard, and wine carries a corkage fee. If the day is a regatta, plan the food for after the racing rather than during it. It is hard to trim a sail with a slice of pizza in one hand.
Timing, and the Bay's moods
For most dates, four to six weeks ahead is comfortable. Fleet Week, the Fourth of July and New Year's Eve book much earlier, and the larger boats go first.
The time of day matters as much as the date. In summer the afternoon westerly fills in through the Golden Gate and makes the Bay lively, which a regatta crew will love and a client lunch may not. Mornings are usually calmer. Our guide to the Bay's wind and weather explains the pattern, and how tides and currents work on the Bay covers the other half of the story. Tell us what kind of day you want, and we will suggest a time that suits it.
What to tell your team
- We sail from Pier 40 at South Beach Harbor, beside Oracle Park. Not Pier 39. Directions and parking are worth sending round.
- Arrive at least thirty minutes before departure, and allow extra time to park on Giants game days.
- Bring more layers than seem sensible. The Bay is colder and windier than the city: here is what to wear on the Bay, by season.
- Nobody needs experience, and nobody has to steer. Anyone nervous about the motion can read our honest guide to seasickness on the Bay.
Questions planners ask
Does anyone need to know how to sail?
No. Every boat has a licensed skipper who teaches as you go and keeps it safe. The people who want to drive will get the helm, and the people who would rather sit in the sun and heckle can do that instead. The boat goes just as fast.
What if the weather turns?
San Francisco sails through most weather, and wind is part of the fun. If conditions are genuinely unsafe, the captain makes the call and we reschedule.
How is it priced?
Per boat, by the hour, with the skipper included, and the rate drops from the third hour. The current figures are on the rates page.
Can we invoice the company?
Yes. Add the company name when you request a quote so we can invoice the right name.
Plan your offsite
Send us the headcount, a rough date and whether you want racing or relaxing, and you will have a tailored quote back within one business day. Request a quote, or call 415-543-7333 if it is easier to talk it through.
Somebody on your team will swear they are not a boat person. Offer them a turn at the helm anyway.