San Diego's #1 Sailing Company
Your Dreams. Our Sails.
Welcome Aboard
Enjoy Spacious Boats
Experience Beautiful Sunsets
Let's Celebrate!
Get in touch with Nature
The Romance of Sailing
Trip Advisor's #1 Boat Tour Business in San Diego

Sailing Tours With Sail San Diego

3-Hour Day Sail

Our famous day sail

Sunset Sail

Learn more

Sunset Sail

Watch for the green flash

Sunset Sail

Learn more

Rum Runner

Rum around the bay!

Rum Runner Sail

Learn more

Corporate Sail

Team building & more

Corporate Sail

Learn more

Whale Watching

Starts soon!

Bavaria Leasing

Learn more

Private Sails

Engagements / Anniversaries

Private Sails

Learn more

Group Sail

Bring the whole gang!

Group Sail

Learn more

Sailing Lessons

Learn to sail

3-Hour Day Sail

Learn more

Quickie Lesson

22' Catalina Sailboat

3Hr Quickie Lesson

Learn more

Gift Cards

The gift of sailing.

Sail San Diego Gift Card

Learn more

Why Choose Sail San Diego?

No Extra Fees

NO EXTRA FEES, NO sales tax, NO Port tax, No handling fees, etc. We do gently suggest a gratuity for the crew but that amount is up to you.

Everything is Included

All beer,wine, non-alcoholic drinks and snacks are complimentary. We don’t give you just one and have you pay for more! Parking is free!

Perfect Tour Length

Our tours are 3 hours, the perfect length – not too short, not too long . We like to raise our sails right away and listen to wind and waves.

You Chart the Course!

The itinerary is up to you, unless you’d prefer the capt. do so. Take the helm as much as you like & learn about the points of interest & wildlife you see.

Flexible Departure

We can be flexible. We have fixed and flexible departure times! Call us for special group sails and times. 619-297-7426.

Yes, we have it!

We provide everything you may need at sea. Hats, jackets, blankets, binoculars, sunscreen, sunglasses, snuggies and more.

What our guests say about Sail San Diego

Don't take our word for it...see what everyone else is saying.

  • Thanks- We loved it! The trip was wonderful.  The Captain was charming A perfect afternoon.

    The Bergman Family, Marblehead, MA
  • We went whale watching new years day and had Captain Art Harrison. he was entertaining and informative. it was very foggy so we came back in but Art took us back out even though our tour time was almost over an he fog lifted. We ended up seeing a mother and a calf Grey Whale, as well as a pod of dolphins. Art was sensational. It was obvious our safety was his first concern but he also really wanted us to have good experience and see whales. They boat had warm clothing and blankets as well as complimentary drinks and snacks. Wonderful experience.
    Yeremenko, Saskatoon
  • Dad & I Out for a Sail My 74 yr old dad and I took an afternoon cruise with Captain Tim a few weeks ago, and I can’t tell you how wonderful it was, and what a lovely time we all had. My dad used to sail (and race) on the Great Lakes back in the 70′s, so he has has had some experience – and *raved* about Capt. Tim’s expert skippering skills and how fabulous the boat is. In my dad’s words “It’s such a pleasure to to be on board a sailboat when the Captain knows what he’s doing!” As for me, I want to come aboard again to whale watch!
    Heather P.
  • This was a great sailing tour. Captain Art Harrison was very entertaining and knowledgeable, and managed to find a pod of 3-4 young whales, even though it was early in the season. This is a strongly recommended tour!

    Colingon, Fairlawn, Ohio
  • Before you die go sailing with Sail San Diego. Saw some whales, dolphins and were overwhelmed by the beauty of the Pacific Ocean. Had a great time with our Captain. It’s worth the extra money……great clean 40 foot sailboat. Wonderful experience!!!

    Mike Green, Madison, Mississippi
  • What an amazing time our party of eight had sailing last Tuesday.  The forty foot Catalina, the steady breeze, a great captain and constant laughter . . . the joy of being one with the water, sun and wind was transcendental. Our friends have emailed from Eureka, CA and said the whole experience was beyond description, “You would have to experience San Diego Sail to understand the embrace of its sacred joy with friends and the earth.”  Sounds mystical but true for all of us Thanks Again
    Alan B., San Marcos, CA
  • Our second trip out on the bay with Captain Mike. This time we brought our friend Kim for her birthday. We enjoyed the company of another couple from Arkansas in town for a conference. Captain Mike gave us history and highlights of the bay area. Steered us safely beyond the point and back. A great afternoon of sunshine and relaxation. They supplied the snacks, sodas, beer and had glasses for our birthday champagne. Captain Mike told us about the whale watching so we’re sailing again in February!
    Karen B., San Diego
  • We travel to San Diego every year, around Christmas, and this is the highlight of our trip. The sailing is terrific and the staff is amazing. Everyone is so friendly and knowledgeable. The various Captains we have sailed with, are so much fun and offer all kinds of information. My son is amazed every time he steps on the boat. This is an awesome company to book with. The Best!
    Varsi M, Las Cruces NM
  • This was by far the best experience we have had. We've never sailed before and this far exceeded expectations. You definitely get more than what you pay for. The accommodations on the boat were exceptional and the captain was an amazing guide! We can't wait to come back and do it again. There are a lot of sailing companies, but I doubt you get treatment like this one. The extras were so great. We did have a hard time finding the location and were running late, and they were still so wonderful. Leave early to make sure you find it-it's definitely worth it!! Can't wait to go back to do it again.
    Kelly W   Columbus, Ohio 
  • We had a first class time on the sail. There was some confusion on the day we were suppose to sail and we offered to sail the next day but they took us the day we thought. We had a great time with the Captain. The boats are first class and the little extras-free drinks, snacks, extra jackets are a real plus. Everyone at SSD gets an A+ for customer service. We would do it again. We have sailed several times in various locations and this was by far the best.
    Ed He,  Brownsburg, Indiana 

Stay Connected with Sail San Diego

“Like” us on Facebook! SailSanDiego

Follow us on Twitter! @sailsandiego

Watch us on YouTube!

Follow us on Instagram!

Have questions? We've got answers!

Give us a call!


Call now