What you'll do:

You and up to five friends take over a sport catamaran on San Diego Bay for three hours of real sailing, open water swimming, and views of the city skyline that you simply cannot get from land.

Sport catamaran, no crowds: Your group has the entire boat to yourselves, with a bow-to-stern trampoline and padded lounge chairs where the water passes directly beneath your feet.
Sail and swim: Captain Ryan navigates to the bay's best swimming holes, where you can anchor, jump in, and swim toward a secluded beach that most visitors never find.
Real sailing, motors off: Wind Drum relies on wind power and travels 40 to 100 percent farther than a typical motorized charter, giving your group a sailing experience that's genuinely different from a standard bay tour.
Captain who teaches: Ryan holds your group's comfort and curiosity in equal regard, offering sailing lessons and the chance to take the helm yourself if you want it.
Bring your own drinks and food: The boat is BYOB-friendly, so pack whatever makes your celebration feel like yours.

San Diego Bay's wildlife, open water, and city-facing sightlines make this feel less like a boat rental and more like a private afternoon on the water with people you actually like.

Why we love it for your bachelorette or birthday group:

Private booking: No strangers, no shared decks, just your people for the full three hours.
Smooth, stable ride: The catamaran's wide platform stays flat even when the wind picks up, so nobody's white-knuckling the railing.
Photo-ready setting: The trampoline deck, open water, and San Diego skyline create a backdrop that earns its place on your camera roll.
Flexible celebration: Bring a speaker, a cooler, and decorations, and the boat becomes your venue.
Proposals and couples: The experience also books well for romantic occasions, with a setting that handles intimacy as naturally as it handles a group.

About this experience partner:

Fun Cat Sailing Adventures has operated private catamaran charters on San Diego Bay since 2011, led by Captain Ryan, a local champion sailor with deep knowledge of the bay's best anchorage spots and swimming areas. The company runs Wind Drum, a sport catamaran selected for its lightweight design and sailing efficiency, which consistently outsails heavier charter vessels in both calm and windy conditions. Fun Cat specializes in bachelorette parties, birthday groups, photoshoots, couples' sails, and proposal moments.

Additional information:

Capacity: up to 6 passengers
Duration: 3 hours, captain included
BYOB and outside food are welcome; please drink responsibly
Bathroom onboard

By Category

By Party Type

By Top Batch Cities

Plan an Epic Party

By Category

By Party Type

By Top Batch Cities