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How to Choose your Charter Type

a large ship in a body of water

All (100%) of Sail San Diego’s charters include:

  • a fantastic, highly-memorable time aboard a 40-foot modern-day sailing yacht
  • a professional US Coast Guard-licensed skipper/tour guide
  • all beer & wine included, for drinking-age adults
  • light snacks
  • non-alcoholic beverages
  • a restroom or two aboard each yacht
  • departure from / return to our Company’s private marina
  • other amenities
  • straight-forward pricing; no additional taxes or fees

At Sail San Diego, we believe that the items above should simply be a given. Tourist or local, if you’re going to invest in a high-end luxury sailing experience for yourself and/or people that you care about, you shouldn’t have to pay extra for these things.

You’ve already chosen the right sailing charter, San Diego’s top-rated boat tour Company, Sail San Diego. Your next step is to figure out which type of charter you want to do. Sail San Diego offers a wide assortment of sailing charter options to suit your fancy.

Day Sails

Sail San Diego’s day sails offer a 3-hour luxury sailing experience in the San Diego Bay & Pacific Ocean. Enjoy the warm San Diego sun, the vast wildlife including sea lions, dolphins & exotic birds, expert tour guidance provided by your captain, and included libations & snacks. Private & small-group day sails are both available.

Sunset Sails

Sail San Diego’s sunset sails are the same as day sails; they simply occur later in the day, to make sure that you catch the sunset while you’re on the water. Our guests love to watch the “double sunset”, simultaneously enjoying the actual sunset as the sun fades away beyond the horizon, and the sunset as reflected from the iconic Downtown San Diego skyline.

All Day Sails

All-day experiences are available for private parties that want to spend a full 6 hours on the water. These trips also include a nice lunch for each guest from Panera.

Rum Runner Sails

For those desiring adult libations above-and-beyond the included onboard beer-and-wine, Rum Runners are a 3.5-hour private experience in which your captain will stop along the way at two upscale restaurant bars. The first round of cocktails, at each stop, is on Sail San Diego! Rum Runners takes the idea of “bar-hopping” to a whole new (luxurious) level!

Whale Watching Sails

The Pacific Gray Whale migration (annually, from late December through March) offers the spectacular opportunity to witness these majestic sea creatures in luxury and style. Our whale watching trips are 3.5-hours in duration, and our whale watching captains may use the motors of the sailboats to catch up to the migrating whales. (Standard day & sunset sails will usually feature more sailing, less motoring.)

Corporate Sailing Trips

Our corporate event sales manager can arrange an unforgettable team-building experience for your corporation or church. Companies including Google, Amazon, Wells Fargo, Shell, Loomis, Orange Theory Fitness and many others use our top-rated sailing charter services regularly. We also work directly with a gourmet catering Company for delicious lunch, dessert & charcuterie options.

Bachelor & Bachelorette Parties

Sail San Diego is San Diego’s leading on-the-water bachelorette party venue. We offer private-party experiences for brides & grooms to be. For bachelorettes, we also offer special themed party packages.

Still can’t decide?


Call one of our friendly sailing experience experts at (619) 297-7426 and we’ll help you choose the sailing charter type that’s best for you!