Rum Runner Sailing Trip

Time to celebrate!

RUM RUNNER SAIL 3.5hrs $125 per person
($90 for the designated driver)

The Rum Runner’s 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 at to spots 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:

  • Bachelor/Bachelorette parties
  • Birthday parties
  • Anniversaries of any kind

Plus, you can check out some of San Diego’s premier restaurants with outstanding food and views.

The Rum Runner Cruise is a 3 ½ hour expedition! We’ll be sailing from our dock for parts unknown… ok, maybe they’re known but definitively notorious. Call us anytime for departure times and details! This is considered an awesome sail but we need at least 4 scallywags to book.

Rum Runner

We’ll sail to two upscale restaurant bars: The “Bali Hai” for the world famous Mia Tia (for the brave at heart) or Jimmy’s world famous Gastro Pub where we’ll try not to get “3 sheets to the wind”.

After you’ve sampled your fill, we’ll sail back thru Smugglers Corridor to our slip to finish off one more successful Rum Run! A great time had by all!

So grab your friends and head out for an memorable adventure!

Bars are subject to change while on the trip, or maybe not. You’ll have to come with us to find out!

"We love groups of 6 or more and will accommodate you through our bareboat program. Call for details"

Sailing Tour Information

Tour Includes

  • Free Parking
  • 2 bar drinks included
  • Jackets and blankets provided
  • Ample room- NO standing or sitting on uncomfortable places
  • We'll customize your sail to meet your needs


Sail San Diego is located at one of the closest marinas to the Pacific Ocean so you have your choice of either sailing in the harbor or heading out to the Pacific Ocean to watch the sun as it melts into the sea. You may meet a host of wildlife along the way including: sea lions, seals, dolphins and whales.

Rated #1 in Trip Advisor

Sail San Diego has been sailing guests for more than 30 years & we are #1 on Trip Advisor by customer review out of 185 boat tours & water sports in San Diego.

Spacious Boats

We have 4 of the newest most beautiful, spacious, seaworthy boats in San Diego. Plenty of room to stretch out and be comfortable.

Everything is included

Beer, non-alcoholic drinks, water bottles, and light snacks are complimentary. We don’t give you just one and have you pay for more! Free parking options available nearby!

Safety & Comfort

Due to COVID-19 restrictions, we currently do not provide: Hats, jackets, blankets, binoculars, sunscreen, sunglasses, snuggies, and more.

Over 30 Years Experience

Our Captains are all U.S. Coast Guard-certified. Our hand-selected crew has worked for the best charter companies across the globe and will give you a great experience.

Best Captains

With more than 80 years combined experience sailing, our captains are some of the best & most entertaining. They also like to share the wheel!

Book your Next Trip With Sail San Diego

Ready to book your next Sailing Charter, Fishing Trip, Corporate event, Sailing Lesson or Bachelorette Party?

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2646 Shelter Island Drive, San Diego, CA 92106 | Call +1 619-297-7426 | Email:

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