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10 Best Sailing Charters for Your Next Visit to San Diego

Going sailing sounds super exciting… Right? Right! Well, as long as you go to the right places and, lucky for you, you do not need to do excessive research because I have done it all for you! Here are the top ten best sailing charters that sail San Diego waters/coastlines! Do keep in mind, after the first three, there is no longer an order of best to less great – and I will no longer apply review references.

  • Sail Stars & Stripes USA-11

The best sailing charter so far, at least to Tripadvisor and yelp reviews, would definitely have to be Sail Stars & Stripes USA-11. This charter has you cruising around San Diego Bay aboard the authentic 1851 America’s Cup racing boat/yacht.

This racing boat/yacht goes twice the speed of an average sailboat so hold on – you’re in for a wild ride! 

There are both public and private charters so choose whichever you please – soft drinks, water, and light snacks will be provided completely free on either charter type. The crew member aboard the boat/ship will also be taking photos and videos to later be posted on Google Web Albums – again, entirely free! So, sit back and enjoy the ride. 

And, to prove that it is a well-loved experience, these are some of the first few reviews left on Tripadvisor about Sail Stars & Stripes USA-11; “Fabulous sailing experience.” “Wow! What a wonderful experience!” “Joy and awe! Amazing day and a crew who loved being on the boat.” 

  •  Classic Sailboat Sunset Sail

This sailing charter is one of the most calm boat/yacht experiences you could possibly find. Not only is there a beautiful sunset that you have the chance to watch, there is also wine, craft beer, and light snacks provided! 

On the two-and-a-half-hour route you will pass landmarks like the USS Midway and the Old Point Loma Lighthouse. You may just see some sea lions, dolphins, and other wildlife around the San Diego Harbor, too! You will have the chance to take some photographs if you want to wish to document your fun experience. 

This is also an all-inclusive, small-group, cruise! So, whether you want to make it a date or a family get-together, it works! 

The first couple reviews left on Tripadvisor were; “Excellent sailing!” and “Amazing! A sailing boat trip was on my bucket list and way exceeded my expectations.” 

However, I did come across one negative review, “Owner did not provide pictures and enough information about the sailboat,” but the company quickly reacted and apologized profusely. Keep in mind, that is the only negative response I came across.

  •  San Diego Whale Watching Cruise

Love seeing wildlife? See a lot with this cruise! 

You will be cruising on the ship America, sailing San Diego waters, spotting migrating whales and see dolphins skipping in the Pacific Ocean. As you are watching the wildlife, your expert guide will share informative and interesting commentary about grey whales, dolphins, and whatever else you may see.

And, a bonus, the boat/yacht that you will be aboard is a replica of the historic, 1851, first America’s Cup sailboat! 

You will be provided light snacks and non-alcoholic drinks, but if you wish, you can bring your favorite bottle of wine to sip onboard. 

I think the first couple Tripadvisor reviews sum up the experience quite well; “The tour was lovely.” “No whales but still lots of fun… We did see a HUGE pod of dolphins.” 

  • Gone Sailing Charters

These charters are actually more towards those wanting to have a party or celebration while onboard. 

They specialize in setting up romantic dates, proposal settings, wedding receptions, graduation parties, birthday parties, anniversaries, and the list goes on. 

Similar to Sail San Diego, they also have private and public charters offered openly. 

  • San Diego Sunset Sail

With this charter you will end up on a very comfortable, cozy, yacht and cruise along, sailing San Diego’s coastline. You will have the ability to take in views of scenic waterfronts, military vessels, and historical landmarks. 

And, if you pay close enough attention to the water, you may just see some marine wildlife! Make sure to take some pictures! 

This tour is specifically for small groups, up to six people, and is usually taken by couples that want to enjoy a glass of champagne (included) on the water.

  •  Sail Away San Diego

For these charters, all are private, no exceptions. Some options would be Proposal Cruise, Sunset Cruise, Dinner Cruise, Day Sail, Wedding Cruise, and the list goes on. 

You will be provided champagne, no matter which cruise you decide on, and non-alcoholic drinks will also be available. 

Sail Away San Diego is a family owned and operated business, so they like to make each of their trips feel as comfortable and easy as possible. 

  •  Cast Off Sailing

This charter gives you private and public charters, again, similar to Stars & Stripes USA-11. Sadly, they do not have boats/yachts large enough for a group quantity over ten. 

When setting sail, you can watch the sunset, go out on the water for an entire day, or do seasonal whale watching! 

Cast Off Sailing encourages their guests to take control and sail the vessel, but you do not have to. If you would like, you may sip on some wine.

  • Imagine Sailing San Diego

Imagine Sailing San Diego gives you options to pass by Bayfront Water’s Edge at San Diego and experience the Downtown Skyline from aboard your sailboat. You can also pass by San Diego Bay and Coastal Waters – this option only allows six people onboard. 

Either way, you will be on a private boat/yacht, sailing San Diego’s coastlines.

Please know that this is not wheelchair accessible, infants must sit on laps, and it is not recommended for travelers with back problems – or any serious health condition, for that matter. 

Snacks and bottled water are included, you can bring your own alcoholic beverages if you wish. 

  •  Lucky Sol Sailing

Lucky Sol Sailing is available for groups up to six people. The most popular tour given by them is the San Diego Bay Tour. 

You will pass all of the landmarks that the Bay has to offer including the USS Midway, Star of India & Maritime Museum, Coronado Bridge, NAS North Island, and so on.

You will see shore birds and if you are lucky, sea lions and maybe even a dolphin or two. You will be provided water and light snacks – feel free to bring your own, too!

  • San Diego Dinner Dance Cruise

This charter offers a three-hour cruise along with a three-course dinner (with choice of entree). You can also purchase cocktails and wine. Beverages included would be water, champagne, or sparkling cider!

Something different about this compared to the others on the list… There is an onboard DJ! So, dance the night away.

Another note, there is sadly a dress code of business casual, so you will have to put your blue jeans away.

Have fun sailing!

Here are two more articles that may interest you regarding the Top Sailing Charters and Top Sailing Tours around San Diego

As well, here are even more resources to help you choose the Best Sailing Charters in San Diego: