Winter Sails

Our Ever Popular 3 Hour Sailing Trips

Closing in on the City

We are currently offering our adventure day and beautiful sailing trips leaving four times daily.

We also love to customize trips for you and will make your dream sail come true!
Includes complimentary beverages including: chilled beer, wine, a selection of non-alcoholic beverages, and snacks to enjoy while under sail! Everything is Included

Boats are also stocked with all of the extra polar fleece jackets, blankets, hats, binoculars, sunscreens, sunglasses, wind-gear and much more!For Summer we have added our new and fun rum runner sail, our drop-off and pick-up dinner sail.

Call for times and details.

Price is $85.00 per person

Call for private and larger corporate chartering prices.

Open Sailing in the Pacific Ocean

Times: 4 trips daily
Trip times vary usually starting at 10:00AM (times are flexible for our guests needs)

Duration: Three hours
You can book the boat for longer, look further down the page.

Our charters are designed for our guests to relax and take in the sights of beautiful San Diego.

Rum Runner Sailing Trip

Your Favorite Drink included

The Rum Runners Sail is a unique way to witness the San Diego Bay and investigate a few of San Diego’s favorite bar/restaurants and their signature drinks.

The ladies having a great time on the Barchlorette Party

The Rum Runners Sail is a unique way to witness the San Diego Bay and investigate a few of San Diego’s favorite bar/restaurants and their signature drinks. We will make 2 stops on two islands and have a concoction at each, then sail off to investigate another of the Captain’s favorite haunts.

This is a great way to celebrate a Bachelor/Bachelorette, Birthday, and anniversary! Plus, you can check out some of San Diego’s premier restaurants with outstanding food and views.

Lots of room in the cockpit

This will be a 3 ½ hour expedition where we will sail from our dock for parts unknown… OK, maybe they are known but definitively notorious. Call for times and details! This is considered a private sail where we will sail to a Coronado restaurant/bar (Candelas) to smuggle a little Captain Morgan in ya. From there we sail to one of three other bars; C- level lounge on Harbor Island for a shot/ drink to head off the spins Or sail west to the Bali Hai to for the world famous Mia Tia or Jimmy’s world famous Gastro pub where we will try not to get “3 sheets to the wind”. After you have sampled your fill, we sail back to our slip to finish off one more successful Rum Run through smugglers Corridor. So grab your friends and head out for a underhanded adventure. Bars are subject to change while on the trip, or maybe not. You will have to go to find out.

Cost $115.00 pp includes a drink at each bar, gratuity not included. For the designated driver price is only $85 pp

An Engagement never to be forgotten

What better way to say "YES"

Looking for a way to “Pop the Big Question? Sail San Diego has the perfect idea. We are offering a 3 hour sail with focus on you and the one you love. We can Pretend to do sailing lessons, Find a message in a bottle, Have flowers hiding on board with Champagne as well as congratulation sign ready at the quick. Give the captain you Camera and he will do his best to capture the surprise. If you can think out something unique This trip includes beverages and snacks for you two to enjoy. If you like an audience bring up to four friends with you! Price: $480.00 for the boat privately Call for times and details.

Did She say Yes a few years back? this is a great way to celebrate the date. Anniversaries are always fun aboard A sailing vessel. Bring some friends to join in the fun.

Point Loma Lighthouse

Lots Of privacy on the bow in the cozy bean bag chairs

All Day Sail for your group!

See all of the Bay as well as a few hours in the ocean. Sail up the coast or into Mexico, as we try to reach the islands of Los Coronados

The Mexican Coronado Islands

This trip is for the more experienced sailors who want a full day on the water as we look for sea loins, dolphins, and if weather permits, make it to the Coronado islands. or you can plan the trip anyway you like. Sail Up the coast to La Jolla or sail down to the Coronado Cays inside the bay then out to the pacific. Call for details!!

Minimum of 4 passengers, cost $185pp

Gourmet sandwiches and of our all the usual amenities are included