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Sail San Diego

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Address: 2051 Shelter Island Dr, Shelter Island Marina, San Diego, CA 92106-3105
Phone Number:
+1 619-297-7426
Website
Recommended length of visit: 2-3 hours
Description:

San Diego's Finest Sailing Experience! With over 26 years of experience and...

San Diego's Finest Sailing Experience! With over 26 years of experience and thousands of happy clients, our crew works diligently to insure each Sail 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 with a few friends,whale watching experience, or a memorable celebration at sea. 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, 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 enough for 12 people.

We Sail (3)Uber clean 40' boats and (1) Brand new 42' boat in our fleet. We can't wait to take you for your next San Diego adventure.

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Book In Advance
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US$ 88.99*
and up
Small-Group San Diego Sunset Sailing Excursion
More Info
US$ 88.99*
and up
Small-Group San Diego Afternoon Sailing Excursion
More Info
US$ 690.00*
and up
Half Day Local Fishing Trips in San Diego

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Whale chasing with Captin Greg

Our little group of 3 (13yo daughter, myself and girlfriend) had a fantastic time on Captain Greg's sailboat. Two pods of beautiful dolphins were quite entertaining, and the good... read more

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Reviewed yesterday
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1,269 Reviews from our TripAdvisor Community

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Showing 1,261: English reviews
A TripAdvisor Member
Reviewed yesterday NEW

Our little group of 3 (13yo daughter, myself and girlfriend) had a fantastic time on Captain Greg's sailboat. Two pods of beautiful dolphins were quite entertaining, and the good tunes from Cap's Ipod and snacks aplenty keep us grooving and chasing "spout/blow sightings" most of the afternoon. The sneaky whales managed to elude our vessel, however, just being on a... More 

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Thank A TripAdvisor Member
1 review
Reviewed 4 days ago NEW

Anthony was awesome - very knowledgeable and fun! I went on a trip with several co-workers and we had a great time. The boat was beautiful, clean, and comfortable. We stopped at a couple bars - what is more fun than bar hopping on a boat?! I highly recommend Anthony and this company for a fun and relaxing trip for... More 

Helpful?
Thank Natalie D
Dallas, Texas, United States
Level Contributor
3 reviews
Reviewed 1 week ago

We went on Sail San Diego's Rum Runner cruise and it was the perfect way to get out of the office, see a new part of San Diego, and bond with some coworkers. The boat itself was beautiful, clean and very well maintained. Thanks Sail San Diego for such a great night on the water!

Helpful?
Thank Julia S
Big Bear Lake, California
Level Contributor
149 reviews
51 attraction reviews
common_n_attraction_reviews_1bd8 74 helpful votes
Reviewed 1 week ago

5 of us women went on this whale watching sail boat and had a fabulous time. We are going to do this next year again. Ask for Captain Greg Tupaj. He really made our trip. His knowledge of whales, ocean and sailing were very entertaining and kept our interest the whole trip. I highly recommend booking this company. You will... More 

Helpful?
Thank Kathy L
Glendale, Arizona
1 review
Reviewed 2 weeks ago

We have sailed with you 3 or 4 times. The joy of sailing in itself is an overwhelming.experience for us. All have been remarkable. However, the prior sail before this one (March 18, 2017), in 2015 with Captain Ron, had a more interactive captain. With regards to this sail, our fellow passengers were; inexperienced, and another had a hangover. That... More 

Review collected in partnership with this attraction

Helpful?
Thank wilmar315
Portland, Oregon
Level Contributor
2 reviews
common_n_attraction_reviews_1bd8 14 helpful votes
Reviewed 2 weeks ago

Simply terrific! Don't miss it! Boat was terrific and so was the captain. The entire experience was top notch.

Review collected in partnership with this attraction

Helpful?
Thank timojhawk
Portland, Oregon
1 review
Reviewed 2 weeks ago

We had a lovely late afternoon harbor sail with Captain Mike. He was adept at sailing and handling the boat. Since he grew up in the area, he had local knowledge of the areas history, fishing and other sea life, and local landmarks. We enjoyed the view of the city across the harbor with a glass of wine in hand.... More 

Review collected in partnership with this attraction

Helpful?
Thank Marge B
Lebanon, TN
2 reviews
Reviewed 2 weeks ago

We had never been sailing before and thoroughly enjoyed Anthony as our captain. He has years of experience and it showed. He kept us entertained with all of his stories and knowledge of boating. By the end of the trip my 16 year old daughter had her life plan figured out. She's going to live on a sail boat and... More 

Helpful?
Thank LiisaRenee
San Francisco, California
1 review
Reviewed 2 weeks ago

I booked the 6-person afternoon sail as a last minute surprise for my boyfriend. It was a random Monday and we ended up having the sail all to ourselves with awesome Captain Greg! He was very informational about sailing and the sight-seeing. I highly recommend this for anyone considering and if you can, request for "Happy Captain Greg" you won't... More 

Helpful?
Thank kjbemis
Level Contributor
26 reviews
common_n_attraction_reviews_1bd8 6 helpful votes
Reviewed 2 weeks ago via mobile

It was my wife Janelle's 50th birthday and she has always wanted to go sailing. This day cruise went above and beyond our expectations. Our Captain Anthony went above and beyond in his hospitality and his knowledge. We were able to see a lot of military activity along the bay in addition to US Navy dolphin training center where we... More 

Helpful?
Thank Hillbilly1234

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  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?