(619) 255-4705 lynn.hanna@sailusa11.com

Our Annual Guide to Private Sailing Charters in San Diego

If you are visiting San Diego, for the first time or the one hundredth time, you’ve probably thought about sailing the San Diego open water. If you haven’t then you should. It is one of the most recommended activities for the city of San Diego. Sailing San Diego is an experience you will never forget and will want to do again. If you are a first-time sailor or a first-time visitor to the area, you may need some guidance on how to go about booking your San Diego sail. 

There are many ways to embark on your sailing adventure. There are multiple tours available. You can book a tour and enjoy the open water sailing experience with along with other patrons. This type of tour provides you with the opportunity to fellowship with new people who may have common interests. During your sail, you may be provided the opportunity to learn a few sailing skills from the onboard crew. If you aren’t new to sailing, you may even be able to share some of your knowledge with others as they enjoy their first sail. 

In addition to the numerous public tour options available to you, there are is also the option of chartering a private sail across the San Diego Bay. With Sail Stars and Stripes you can choose anything between an adventurous private sail event to a romantic private sail for two. No matter the occasion, you are sure to be more than pleased with your experience. One of the many benefits of choosing to sail with Sail Stars and Stripes, is the tangible memories you get to take home with you after your journey is complete. There is a photographer on board to capture your excitement and experience so that you can live in the moment. Photos and videos are made available to you at no additional cost. 

So, let’s talk private sail options!

Romantic Getaway

Do you have a wedding anniversary coming up? Maybe you are planning a romantic proposal or just a special activity for the special someone in your life. A private sail across San Diego Bay is perfect for a romantic outing no matter the occasion. As mentioned previously, there are opportunities for learning the art of sailing. Learning a new skill together is a great way to bring you and your significant other even closer. Sailing San Diego on the open water, learning the basics of sailing and taking in the tranquility, will surely rank high on your list of romantic date ideas. 

“It is a marvelous outing for a group of friends, a corporate outing or a romantic date!”– SDSavvy from San Diego, CA

Perfect Proposal

Knowing that you want to spend the rest of your life with someone is no small feat. It comes easier to some than it does to others. But whether you knew from the moment your eyes first locked or it took you years to be sure, when you know you know. And when it’s time to ask that life-altering question, you want it to be special. You want it to be perfect. A romantic sail for two may just be the missing piece to your perfect proposal plan. You can start your journey by expanding on your sailing skills and taking in the sights. And when you muster up the courage to ask the question that is sure to change your life for the better, there will be a camera ready to capture the moment. Since photographers are on each public and private tour, your soon to be fiancé will not be suspicious. And as a bonus to your romantic journey and perfect proposal, you will leave with tangible evidence of the joyous moments you shared during your sail at no extra cost! 

Private Party

Private sail tours are a great way to throw a party. Whether you are celebrating a birthday, anniversary, promotion, corporate event, etc. you and your guests are sure to have an unforgettable time with the welcoming crew from Sail Stars and Stripes. You may even consider a private sail tour for your friend’s bachelor or bachelorette party.  What better send-off than a San Diego sail with the bridal party? No matter the occasion, plan to give your family, friends, employees, or co-workers an experience they will be talking about for years to come. 

“Each person that was on our private charter still talks about it (5 years later) – what a perfect and fun day it was.” – Lynn T

“I was with a group that did a private charter, and the entire trip was enjoyable, relaxing, memorable and fun.” – 15Glaser from Albuquerque, NM

Fun with Friends

We’ve talked about many awesome occasions for which you may book a private sail. However, you don’t need an excuse to throw a party. Perhaps you just want to set sail with a few of your friends for no special reason. Why do you need a reason to sail with your close friends? Exactly. You don’t. If you have a few friends that are interested in setting sale without the added anxiety of other people, a private tour is perfect for you. With your closest friends there to enjoy it with you, you are sure to have the time of your life. And again, you don’t have to worry about taking a camera, because there will always be a crew member there to capture memories for you. 

Team Building

The art of sailing has the potential to be a fantastic team building exercise. When sailing San Diego Bay with Sail Stars and Stripes, you get the crew experience as well. This gives your team the opportunity to learn a new skill together and work together to secure a successful journey. With team building in mind, your group members will have the chance to rotate through all crew positions. This is an exciting way to raise morale and induce bonding. Your team is sure to thank you for planning something so memorable. 

Sailing San Diego Bay is a wonderful experience, no matter how you choose to embark. You can’t go wrong with any of the Stars and Stripes sail tour options, public or private. But, depending on your occasion, privacy may just be the added bonus to your sailing journey. There are several ways to maximize your sail experience by going private. Take the plunge and trust your instincts. If you choose a private tour, no matter the reason, you won’t be left disappointed!

To book or to check availability of our private sailing charters please click here. We also have a quick contact form and we will get back to you within a few hours. We look forward to hosting a private sailing charter for you and your guests…


  1. https://sailusa11.com/
  2. https://www.tripadvisor.com/Attraction_Review-g60750-d1049968-Reviews-Sail_Stars_Stripes_USA_11-San_Diego_California.html
  3. Sail San Diego Bay in style | America’s Cup Sailing Charter

Sailing News

  1. https://www.luxurytravelmagazine.com/news-articles/motorboat-vs-sailboat-charter-what-is-the-best-for-you
  2. https://www.latimes.com/california/story/2019-09-04/california-conception-dive-boat-fire-victims
  3. https://www.csfkids.org/


Contact Lynn Hanna Direct: (619) 255-4705

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