Corporate Sailing Outings in San Diego
Impress your team, wow your clients, and actually enjoy the day yourself.
Get Out of the Office. Way Out of the Office.
Ditch the conference room and give your team a break they’ll remember without adding more to your to-do list.
Time to Chill
Leisure Sails
No trust falls or slide decks. Just quality time together on the water and away from the daily grind.
Time for Thrills!
Team Building Regatta
High-energy, hands-on fun that brings your larger team together with a little friendly competition.
"My team stopped by during a work trip for a mental break and some competitive bonding. The captain did a fantastic job of making the experience engaging for every one of us. Best activity of the week!"
– Drew M.
Your Sail, Your Way. We’ll Bring the Boat.
For groups up to 74 guests.
Tell us where, when, and for how long, and we’ll handle the details.
Choose When You Sail.
It's your sail, on your clock. We’re ready when you are. Set sail on your schedule and stay out as long as you want.
Decide Where You Go.
Stay in the Bay or head out to open water. Either way, our captains know the best spots to see wildlife and great views.
Add Food & Drinks.
A selection of snacks, beer, seltzer, and soft drinks are included, plus catering options & bar packages if you want to go big.
Team Building Sailing Regatta
For up to 100+ guests.
Skip the breakout sessions and slideshows. Get your team racing on the water and working together in a whole new way.
Learn 15 Minutes
Meet your captain and get a quick rundown of the course and your crew roles.
Race 2 Hours
Take the helm, trim the sails, and work as a team to race across the Bay.
Relax 45 Minutes
Win or lose, kick back with drinks, snacks, and a sail around San Diego Bay.
FAQs
Way Cooler Than Another Expensive Team Dinner.
Will this feel professional enough for my company?
100%. Whether it’s an executive outing or a team event, we make sure everything runs smoothly. Your corporate sail will be impressive and well-organized without being stuffy.
Is this too complicated to plan?
Not at all. Tell us your group size, pick a time, and tell us what activities you’re interested in. We’ll handle the rest. No endless emails, no guesswork. Planning will be easy on you and make you look great to the people you most need to impress.
Can you really accommodate a group our size?
Yep. We can take up to 74 guests across multiple boats, and more than 100 with custom scheduling. Big crew? No problem.
What if not everyone in my group is comfortable on a boat?
No worries. Our boats are stable, spacious, and professionally captained. Guests can stay seated, enjoy the breeze, and take it at their own pace.
What happens if the weather is bad?
San Diego is sailing heaven, but if the weather becomes dangerous, we’ll reschedule or refund. No risk, no problem.
Will my boss think this is worth the budget?
Absolutely. This isn’t just a fun day out. It’s a unique, high-value experience that brings teams together, impresses clients, and makes you and your company look like rockstars.
Will this be safe/liability-proof?
Yes. All our captains are USCG-certified, our boats are meticulously maintained, and safety is always the priority so you can relax and enjoy the sail.
First-Class Sailing. No Stuffy Yacht Club Nonsense.
You’ve got a lot on your plate. Planning an office or conference event that’s fun, unique, and impresses all the right people can be pretty stressful. We get it.
Cal & the Sail San Diego Team
What Are You Waiting For? Let's Go!
"*" indicates required fields
Spots are limited. Lock in your dates today!