We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Want the lowest hotel prices? You're in the right place. We check 200+ sites for you.
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Sponsored by:
Get directions
Address: 2051 Shelter Island Dr, Shelter Island Marina, San Diego, CA 92106-3105
Phone Number:
+1 619-297-7426
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.

read more
Book In Advance
More Info
$88.99*
and up
Small-Group San Diego Sunset Sailing Excursion
More Info
$85.00*
and up
San Diego Whale Watching Sailboat Cruise
More Info
$88.99*
and up
Small-Group San Diego Afternoon Sailing Excursion

TripAdvisor Reviewer Highlights

Read all 1,191 reviews
Visitor rating
  • 1130
    Excellent
  • 44
    Very good
  • 6
    Average
  • 2
    Poor
  • 1
    Terrible
Proposal Sunset Sail

The sailing trip was awesome. We got to see whales and a lot of dolphins. The purpose of the trip was to propose to my now fiancee because I wanted to do something romantic and... read more

5 of 5 bubblesReviewed 2 days ago
Erik V
Add Photo Write a Review

1,191 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Language
  • More
Showing 1,183: English reviews
2 reviews
5 of 5 bubbles Reviewed 2 days ago NEW

The sailing trip was awesome. We got to see whales and a lot of dolphins. The purpose of the trip was to propose to my now fiancee because I wanted to do something romantic and something that she wouldn't forget and well the sunset sail was just that. Friendly environment and amazing scenery.

Helpful?
Thank Erik V
Grapevine, Texas
Level Contributor
3 reviews
5 of 5 bubbles Reviewed 1 week ago

We sailed the afternoon of New Year's Day, and the sail and whale watching experience couldn't have been better. It was just my wife, my son, and I with Captain Anthony, who was fantastic in every way--friendly, engaging, a first class Captain, and he knew how to find the spots to give us all the best shot at whale encounters... More 

Helpful?
Thank bmwermuth
Evergreen, Colorado
1 review
5 of 5 bubbles Reviewed 1 week ago

Captain Mike made this sunset cruise unforgettable. He was full of stories and facts about the area. We got to see gray whales--an extra bonus. If you want a relaxing, personalized experience, take a cruise with Captain Mike.

Helpful?
Thank shettel1152
Tijeras, United States
2 reviews
5 of 5 bubbles Reviewed 2 weeks ago

Our captain was very nice. The sailing trip was wonderful. We is will definitely be coming back to this company the next time we're in San Diego!

Review collected in partnership with this attraction

Helpful?
Thank Sean C
1 review
5 of 5 bubbles Reviewed 2 weeks ago

Just got back from a trip to San Diego to celebrate my mom's 60th birthday. My mother has a sailboat of her own and needed a refresher on skills and terminology. Captain Anthony introduced himself and was able to help me feel more comfortable when the boat heels. I can't and will never get used to this. He did a... More 

Helpful?
Thank Stephanie F
Cottonwood, Arizona
2 reviews
5 of 5 bubbles Reviewed 3 weeks ago

Best experience ever! Amazing people. All included sail. I will never forget this trip! Every time I come to San Diego we will sail with you guys! Thank you!

Review collected in partnership with this attraction

Helpful?
Thank Mindy C
Cardiff-by-the-Sea, California
1 review
5 of 5 bubbles Reviewed 3 weeks ago

Our sunset cruise was absolutely awesome. The owner met us at the dock, showed us to the boat, and gave us an orientation. After that, captain Anthony, and crew member Shon, took over. They were both extremely knowledgeable about the local area and treated my large party (7 adults and 4 kids) with the utmost courtesy. They suggested an itinerary... More 

Review collected in partnership with this attraction

Helpful?
Thank cardiffbythec
San Diego, California
1 review
5 of 5 bubbles Reviewed 4 weeks ago

We won this 3 hour sailing tour at auction and were not sure what to expect. After spending the day in San Diego bay with the very pleasant Captain Greg, my husband and I cannot wait to book our next sailing adventure with Sail San Diego. Living in San Diego proves to have a bounty of perks, and this truly... More 

Review collected in partnership with this attraction

Helpful?
Thank mallory_callaway
San Diego, California
2 reviews
5 of 5 bubbles Reviewed 4 weeks ago

My husband and I had a great time. It was a beautiful day with lots of wind once we got out of the bay. We saw a huge pod of dolphins just by chance. They swam along the bow. Our captain was very nice and very knowledgeable about area. We were given munchies to snack on and drinks on the... More 

Review collected in partnership with this attraction

Helpful?
Thank bmishere
Navarre, Ohio
1 review
5 of 5 bubbles Reviewed December 11, 2016

We went out with Captain Art on a Saturday, we had reservations for 3 and ended up having the boat to ourselves. The captain was very knowledgeable about the area and educated us on the area. He was very accommodating and let us choose where we wanted to go. On our way out of the marina we saw other boats... More 

Review collected in partnership with this attraction

Helpful?
Thank DarDar7572

Travelers who viewed Sail San Diego also viewed

 

Been to Sail San Diego? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Sail San Diego and other visitors
7 questions
Ask a question
Catania, Italy
Roxboro, North Carolina
Meredith, New Hampshire
over a year ago
Meredith, New Hampshire
over a year ago
Cupertino, California
over a year ago

See all questions (7)

Questions? Get answers from Sail San Diego staff and past visitors.
Posting guidelines
Typical questions asked:
  • 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?