This Is How Locals Sail San Diego

A classic 50ft sailing yacht. A rad crew. Room for groups up to 22.

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How It worksExperiencesAdd-OnsFAQs

Achieve Next-Level Local Status.
Even If You’re Just Visiting.

Lock In Your Sail

Pick your time. Tap your phone. Boom. You’re the hero now.

Invite Your People

Bring up to 22 – friends, fam, or just your ride-or-dies.

Make it Yours

Upgrade with bar drinks, catering, and celebration extras.

  • Easiest Cancellation in Town: Get a full refund if canceled up to 72 hours prior to your sail.

Meet Maile, she’s a 50ft classic

Newly restored like the legend she is. Teak accents that gleam like it’s 1977, cushy seating, and a wide-open deck with more soul than your playlist. Your party pics will be scroll-stopping.

  • Room for up to 22 of your favorite humans. 
  • Includes drinks, snacks, and a fun captain + crew. 
  • Upgrade with catering, bar packages, and more.

Maile is waiting. Are you in or what?

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"A unique and memorable experience for all our family and friends that visit us in San Diego!"

— K.G.

Your Sail, Your Way

Lock in your dates, then tell us how you want to sail. Pick your experiences at checkout.

San Diego Bay Sailing

Smooth sailing with the best views of downtown San Diego. Catch the landmarks, and get some great shots to show off at home.

2 hours

Open Ocean Sailing

Head past Point Loma and into the wide-open Pacific. Salt spray, big water, and maybe even some dolphin sightings!

3-6 hours

Anchor & Swim

Our captains know the best spots to drop anchor and cannonball in.

3 hour minimum

Add-Ons

You’re Kind of a Big Deal. That’s Worth Celebrating.

Level up your sail with drinks, swag, and delicious catered snacks.

Catering + Bar Packages

Enjoy gourmet bites from one of our catering partners and add a bar package at checkout with a variety of beers, hard seltzers, and wine.

Capture the Moment

Make the memories last forever with photos and videos from our preferred professionals. Note that photographers count toward your guest limit.

a map of a city

FAQs

Skip the Yacht Club. Our Captains Are Real Sailors.

Are there bathrooms on the boat?

Sure are. And they’re really nice, too.

What if it’s cold, windy, or rainy?

Dress in layers and you’ll be golden. Plus, there are blankets on board. We don’t let a little May-Gray get in our way. But if the weather is truly rotten, we’ll reschedule or refund.

Do I have to help sail the boat?

Nope, your USCG-certified captain and crew are there to do all the sailing. But, if you’re into it, you can definitely take the wheel if you really want to. 

Are my friends going to get seasick?

The Maile is big, super stable, and the waters in San Diego Bay are usually pretty calm. Plus, we won’t go out if the weather is too rough.

Can we bring food and drinks?

Sure! We include snacks and drinks, and you’re welcome to bring more food if you like. If you really want to go all out, you can upgrade with a bar package, and we’ll hook you up with one of our amazing catering partners.

Booking’s Easy. Regret Is Not.

Weekends fill up fast. Lock in your sail now. Or if you have more questions, reach out and we'll be in touch right away.

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