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About Sail San Diego
San Diego's Finest Sailing! With over 28 years of experience and thousands of happy clients, our crew works diligently to insure each trip is a perfect one for all! All of our crew love what they do and it shows!! Come out for an intimate sail for 2, corporate event, sailing lessons , fishing trips, whale watching experience, or a memorable celebration at sea with a few friends. We excel at doing private parties, proposals, anniversaries, birthdays or a romantic sunset sail. All or excursions come with a knowledgeable friendly Captain, complementary chilled Wine, Beer, Sodas & yummy snacks. Take the helm, hook A fish, trim the sails,or sit back and enjoy a glass of wine on the bow. Our boats were purchased with YOU in mind.The cockpit is where you will spend much of your time and it's roomy. Our Boats are always clean. 34' power boat, (3) 40' sail and (1) Brand new 42' sail in our fleet. We can't wait to take you for your next San Diego adventure!
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Tours and Tickets by Sail San Diego

Small-Group San Diego Afternoon Sailing Excursion

Soak up the Southern California sunshine and unbeatable views of San Diego Harbor on an intimate sailing cruise. Mingle with a small group onboard, or invite five friends to join you and fill up the boat for a private cruise. Relax while the expert captain and crew handle the sails, and enjoy complimentary beer, wine, soft drinks, and snacks as you cruise.
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3 hours
from $107.67

Small-Group San Diego Sunset Sailing Excursion

Catch the sunset from aboard a sailboat on this intimate small-group cruise in San Diego. Enjoy beer, wine, soft drinks, and snacks (included) during your time on the water. Plus jackets and wind gear are provided in case it’s chilly. Listen to your own music on the boat’s surround-sound speakers.
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3 hours
from $107.67
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MexTravel wrote a review Oct 21
San Diego, California13 contributions1 helpful vote
+1
Very impressed with our first sailing adventure. When arrived, we waited a few minutes to board. Once onboard, we were greeted by Captain Greg and a Happy Anniversary welcome banner. To our surprise, we basically had the sailboat to ourselves. We had a wonderful time site seeing the bay. Capitan Greg was an amazing host, he kept us entertained. We haven’t tried any other sailing companies, however, base on our experience they will be hard to beat. Happy sailing
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Date of experience: October 2020
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Corina M wrote a review Oct 15
1 contribution
Had a wonderful time on the sunset sail. The trip was a lot of fun. Our captain was very knowledgeable and with these challenging time was very relaxing. It was nice to get a chance to have a bit of fun and enjoy the San Diego Bay at sunset.
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Review collected in partnership with this attraction
Date of experience: September 2020
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Pathfinder435606 wrote a review Oct 12
Chandler, Arizona1 contribution
Great sunset sail ! Boat was clean & comfortable...Captain was-amazing ! We met nice people aboard and shared our champagne 🍾 with them to celebrate our anniversary! Great afternoon!
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Date of experience: October 2020
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Susan L wrote a review Oct 9
Yuma, Arizona13 contributions3 helpful votes
Our September 16 sunset sail was our third time sailing with Sail San Diego! They have always been great to work with for booking and communication. Each sail we have had wonderful captains and Captain Frank was no exception! He was just terrific! We just can't recommend this company enough! There were 2 other couples on the sail and we had a great time visiting with them. Thank you so much and we'll see you again!
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Date of experience: September 2020
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AmandaaWood wrote a review Oct 8
Provo, Utah6 contributions
We had a great time on this excursion. I surprised my husband with it for his 30th birthday and it was such a fun way to spend the evening! Happy Captain Greg was the best too! He knew a lot of fun facts which also made the voyage enjoyable!!
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Review collected in partnership with this attraction
Date of experience: September 2020
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