San Diego Sailing Tours

Worlds Top Travel Agents Agree

Kyle and his team Restore each of the Beautiful Sailing Yachts from the 1960’s and 1970’s.

All this is done by Hand

San Diego Sailing Tours has Generated Millions of Dollars in Revenue and Taken Thousands out to Experience the Majestic Feeling of Sailing.

A Vision Driven by Inspiration and Motivation = SUCCESS

Kyle Corbett Started this company with $6,500 and a Dream Just after Graduating from Chapman University with a Degree in Social Psychology.


About US

Whale Watching = Kyle’s…
…Fun Way to make a Living

Come enjoy a relaxing tour of the San Diego bay and surrounding area! We offer luxury tours that include complimentary beer, wine, and snacks. Whale watching, fishing, sunset cruises and more!

Experience the San Diego Bay and Beyond on a Luxurious Sailing Tour. San Diego is a city set on the water with the magnificent San Diego Bay that stretches for miles. This amazing water front is home to harbor seals, sea lions, pelicans, cormorants, sea gulls, and much more marine wildlife. While Sailing on the wonderful waters of San Diego, you can enjoy a Mediterranean style climate nearly year round. Whether you prefer a relaxing cruise on the bay, a gorgeous sunset sail on the Pacific Ocean, or want to experience an awesome Whale Watching Tour, we’ve got you covered! Our goal is to make your perfectly custom tour full of excitement and stress free. Whether you’re here on a vacation, or live here permanently, a Sailing Charter with San Diego Sailing Tours is the perfect getaway!


Private Sails

$100 OFF
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Group Sails

20% Off

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Plan Your Perfect Trip With Us

Step aboard one of our classic sailing yachts and feel the outside world melt away. Close your eyes. Feel the sun on your face. Breathe in the fresh sea air. Listen to the wind fill the sails and feel the waves slap against the hull.

A sailing tour offers a unique and special experience you won’t find anywhere on land. See San Diego from a new perspective.

Our Yachts

Kyle and his team Restore each of the Beautiful Sailing Yachts from the 1960’s and 1970’s.





Signature 2 Hour Sail

Set sail from Harbor Island to see the great San Diego Bay and all its beauty. Sit back and enjoy two full hours of pleasure aboard a beautiful classic sailing yacht.

Private Sailing Tour for Up to 6

The vessel and Captain are there just for the two of you. This is an unbeatable date! – not to mention…This private sailing experience for two passengers is offered at an unbeatable rate!

Wild Life Tour

This 4HR tour includes lunch and a complimentary alcoholic beverage. Experience California’s Wonderous Marine Wildlife! Includes a boxed lunch from our deli as well as unlimited water, sodas, and snacks.


Will I Get Seasick?

Seasickness is a reaction to unfamiliar motion while aboard a vessel. While most of our guests do not experience seasickness, a small percentage of people may be prone to seasickness.  In our experience, this often includes people susceptible to other forms of motion sickness. If you do get seasick, it’s OK! Alert a crew member and we can help you overcome it. 

To help reduce your chances of becoming seasick:


  •  Stay above deck and breathe fresh air
  • Look to the horizon, instead of into a phone or book
  • Avoid the restroom and cabin area
  • Get plenty of shade and avoid direct sunlight
  • Sail on a full stomach, and avoid foods that may upset you
Where Are You Located?

Our yachts are docked at Cabrillo Isle Marina, located at 1450 Harbor Island Drive in San Diego (between the two Sheraton buildings on Harbor Island). Secure outdoor parking is available through the Marina. Vouchers may be obtained at the main gate for $10 – $15.

Guests are asked to arrive at least 15 minutes early for their scheduled departure. Please gather at the large sea-lion fountain, located within the marina. Your captain will perform final boarding call ten minutes before departure.

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Group charters are available, as well as sailing charters for corporate retreats and bachelorette parties. Our group charters can accommodate up to 12 guests. Group rates are based on total number of guests and duration of charter. Contact us for more information on creating a memorable, group sailing experience.

Are Life Jackets Required?

California law requires all vessels over 16 feet to carry enough life jackets for all passengers and crew members. Additionally, all guests under the age of 13 are required to wear life jackets for the duration of the charter. Crew members review all safety procedures before setting sail.