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Sail San Diego

4.9(849)

About

Sail San Diego offers a distinctive way to host business events with private charters on the Maile, a beautifully restored 50-foot sailing yacht. Ideal for groups up to 22, the vessel provides a relaxed yet polished setting for client entertainment, team outings, or executive retreats against the backdrop of San Diego Bay’s stunning coastline.

Each charter includes a US Coast Guard-certified captain and a full service experience with included snacks, beverages, and attentive crew. The venue’s seamless blend of casual luxury and local character makes it a memorable choice for corporate gatherings looking to escape the ordinary conference room.

Best for

  • Client entertaining with sunset views
  • Team-building sails & group outings
  • Executive offsites on the water

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Custom Package Request

Custom request

Not sure which package fits? Tell us about your event and the venue will work with you to build the right experience from scratch.

What's typically included

  • Space & layout
  • Food & beverage
  • AV & technology

Venue Details

Standout features

Lovingly restored 50-foot sailing yacht
Vessel Quality
Lovingly restored 50-foot sailing yacht
The Maile is a stunning, well-maintained classic yacht that offers a premium sailing experience with beautiful design and ample space for groups up to 22 guests.
Sunset sails with panoramic water views
Scenic Experience
Sunset sails with panoramic water views
Guests enjoy magical sunsets over San Diego from the water, combining relaxing and elevated vibes with spectacular city and bay vistas.
Inclusive snacks, beverages, and cozy amenities
Hospitality
Inclusive snacks, beverages, and cozy amenities
All sails include beer, soda, snacks, and blankets, enhancing comfort and convenience so guests can focus on the experience without extra planning.

At a glance

Rated 4.9 on Google · 849 reviews