The Best San Diego Sailing Experience

Discover, Explore, Experience San Diego. Sailing into Spring 2026 SOON!

We’re still working on deals for 2026, but for now if you are a previous SanDiegoSailingTours.com customer we’ll offer up 25% if you book your crew of 6 before GROUNDHOG day!

Craving a one-of-a-kind ocean adventure? Look no further! Plan your PRIVATE Sail Tour on our spacious and stable American ‘CLASSIC’ monohull sailboat. Plenty of room for everyone to explore.

Our vessel features a traditional ‘BOW SPRIT’ platform, offering a unique stand-over-water experience reminiscent of the ‘Titanic’ movie. Create memories of a lifetime with us!

 
Book Your 'PRIVATE' EXCURSION Now

The Choice is Yours...

If you are looking for an all 'PRIVATE' ocean experience, we offer a refreshing, relaxing, and rejuvenating option, aboard the roomiest of the 'small' San Diego boat tour companies..

Classic sailing yacht on a Day Sail in calm seas, beautiful sunny weather and majestic white clouds.

DAY SAIL

Experience the joy of a nice sail on our classic sailing yacht that gives you a one of kind picturesque view. Great choice to enjoy a beautiful summers day

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An iconic traditional American built sailing yacht on an Off-Shore Adventure, sailing into the horizon as the setting sun peaks through portside belaying pins in anticipation of the approaching sunset over a glassy sea.

OFF-SHORE Adventure

Set forth on an exquisite off-shore journey to refresh, rejuvenate, and re-energize on our iconic Traditional American built sailboat. ADVENTURE awaits...

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The beauty of a Sunset Sailing Cruise with the setting sun on the horizon.

SUNSET Cruise

We have three options to choose from offering different time durations that you can choose from.

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The Happy Hour Evening Sail in San Diego harbor.

Experience the Enchantment of San Diego on the Bay

San Diego is a world class destination, surrounded by scenic beauty and attractive tourist attractions. We make it convenient for you to visit all the beautiful places with our guided tour option.

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Experience the Beauty
of Life at sea.

We will help you experience an ocean life in its truest sense. From seeing the sea-life among the beautiful horizons to experiencing the exhilaration which comes from the rush as the wind and elements forcefully taking control over the vessel, you are sure to walk away with wonderful moments and memories of a lifetime.

A beautiful sunset viewed from the bow of the Happy Hour.

What Our Guests Say...

We take pride in serving our guests with the best experience. Read what they say.

Rated 4.5 out of 5
Sailing for the day!
"Captain Max makes you feel very comfortable we brought our own food and music and it was quite an adventure I would recommend him if you want to have a day to relax."
JANINE D
-TriAdvisor
Rated 5 out of 5
"Captain Max is the best in the business and he makes your trip a one of a kind experience. I highly recommend his service to anyone trying to see the San Diego coast!!"
AUDREY DRAKE
-TripAdvisor
Rated 5 out of 5
"The whole family (2 kids and 2 adults) had a great time sailing in San Diego Bay with Captain Max. While we cruised out to Point Loma he kept pointing out highlights of the area and the different boats we saw, and answered all of the kids many questions. When we turned around and started the darling portion it was wonderful. His boat (the Happy Hour) is nice and spacious with plenty of room to lay around. Since it's a monohull, you really get a sailing experience. Captain Max is awesome and we hope to go out with him on another sailing adventure."
FEDERICO UMANA
-Google Reviews
Rated 4.5 out of 5
An experience of a lifetime!
"Top notch service and experience. We met Captain Max at Shelter Island and sailed off to the open sea. The sail boat was more than we could imagine and we took..."
JAMES H
-TripAdvisor
Rated 5 out of 5
"Chartered a sunset sail to celebrate an anniversary. We had so much fun and the captain was very accommodating. We will definitely do it again the next time we are in San Diego!"
KIM SPENCER
-TripAdvisor
Rated 5 out of 5
"MAX IS THE BOMB! He made our trip truly so special and fun!!! Thank you so so much max!!!"
SOPHIE AMAR
-Google Reviews
Rated 5 out of 5
"Awesome experience and a great captain, Max was just a good cool captain to make your trip unforgettable. Great job Max!"
ABDALLAH AMMAR
-Google Reviews

Plan an Unforgettable Sailing Experience in San Diego Today!

We can help you fit your tour experience within your allotted budget.

Book Your Sailing Adventure Today!

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