Sail San Diego
Sail San Diego
5
Boat ToursSightseeing ToursPrivate ToursDolphin & Whale WatchingNature & Wildlife Tours
9:00 AM - 6:00 PM
Monday
9:00 AM - 6:00 PM
Tuesday
9:00 AM - 6:00 PM
Wednesday
9:00 AM - 6:00 PM
Thursday
9:00 AM - 6:00 PM
Friday
9:00 AM - 6:00 PM
Saturday
9:00 AM - 6:00 PM
Sunday
9:00 AM - 6:00 PM
About
San Diego's Premier Sailing Tours. With 32+ years of experience and thousands of satisfied clients, our crew strives to make every trip a perfect one. Our team loves what they do and it shows in their service. We offer a variety of options, including intimate sails for two, corporate events, sailing lessons, whale watching, and celebrations at sea with friends. We specialize in private parties, proposals, anniversaries, birthdays, and romantic sunset sails. All of our excursions come with a knowledgeable and friendly captain, complimentary chilled beer, sodas, and snacks. You can take the helm, trim the sails, or simply relax with a cold beer or sparkling water on the bow. Our boats are designed with you in mind, featuring spacious cockpits and spotless interiors. Join us for your next San Diego adventure!
San Diego, California
Meets animal welfare guidelines

Awards
Travelers' Choice
2023

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Tours and Tickets by Sail San Diego
Travelers talk about
(197 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles2,975 reviews
Excellent
2,851
Very good
94
Average
20
Poor
5
Terrible
5

WaOlyMark
1 contribution
5.0 of 5 bubbles
Jan 2020
Had a great three hour cruise with "Happy Captain Greg". He was very informative and provided some great information about San Diego and what we were seeing on the way out of the harbor. Once we got out in the ocean, he did a great job of getting us to where the whales and dolphins were and we saw several of each.
The sailboat was well stocked with snacks, beverages and supplies to keep us warm comfortable (blankets, etc) as it was a cool, overcast morning when we went out.
I would highly recommend Sail San Diego if you want a fun adventure!!
Written January 23, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

volcanogirl
Houston, TX14,927 contributions
5.0 of 5 bubbles
Sep 2021
We did the three-hour afternoon sail with Sail San Diego, and it was wonderful, one of the best excursions we've ever done! We were lucky to have Trevor as our Captain, and he was witty, charming, fun, and knowledgeable; we felt very safe in his hands. There was only one other couple on our tour, so there was plenty of room for everyone, and the boat was really comfortable. There was a restroom on board, and they had a cooler full of beer, bottled water, and soft drinks, as well as prepackaged snacks like chips and peanuts available. We brought our own cocktails from a nearby restaurant, and they had no problems with our doing that. Trevor asked if we wanted music, and we all did, so we were treated to plenty of Jimmy Buffett, Christopher Cross, and other sailing tunes. Saw some neat things along the way - dolphins undergoing naval training, large naval ships, naval planes flying overhead, and plenty of sea lions. Trevor mentioned that the afternoon sail has the best wind of the day, so if you like a lot of wind, that's a good time to go. We had amazing weather - warm with sunny blue skies; we brought jackets just in case, but never needed them. Of all the things we've done in San Diego, this is one of our favorites. Highly recommend for anyone who wants to enjoy a great day out on the water.
Written September 30, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

22TahoeBlue
Denver, CO1 contribution
5.0 of 5 bubbles
May 2022 • Family
My kids grew up on our ski boat on Lake Tahoe (big waves, etc) but had never sailed. In from Denver for daughter's graduation, I booked us on a 3 hr trip so we would leave SD Bay. (We own places on Mission Bay and had seen harbor sights. But Sail SD has a great location to see a bit of carriers and submarine base when leaving SD Bay.) Extended family heard and wanted to join so trip morphed into a large group (9) private charter. There's an extra Coast Guard mandated $150 charge for groups over 6, but oh well. Everyone had a great time. Complimented me even on a great idea!
Wind was up which was just right. 3 hrs was perfect, even with my 70 yo cousin who dislikes boats. No one stayed down below. Capt Greg was cool. Knew how to please: Swung the modern 42ft boat abruptly to to get within 10 ft of dolphins, let my 21yo steer while giving instruction, even let a 12yo have a go. Good safety instructions and reminders about moving around. He'd obviously done it a million times but still made us feel welcome, not a bother.
Written June 4, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Phillip N
1 contribution
5.0 of 5 bubbles
Feb 2021
Had a SD classy old time with Sail San Diego and Captain John! I initially planned a mini surprise small gathering for my fiance and some of her friends she has not seen in a while due to the pandemic. The entire staff from check-in to docking back safely was phenomenal. Capt. John gave us options on where we could sail and safety measures to make us prepped and ready to respond. The sunset view was absolutely breathtaking and priceless as we sailed back in the dock. Best of all we had the entire boat to our selves on a gorgeous beautiful San Diego day. Thank you!
Written March 17, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Scott
Los Angeles, CA1 contribution
5.0 of 5 bubbles
Jul 2020
I chartered a beautiful boat in San Diego this week and we had the most amazing captain, Anthony the "Happy Captain". He is so much more than a positive and welcoming guy, he is one of the most proficient captains I've encountered. Big focus on safety and cleanliness and he really knows San Diego! He shared great stories and he showed us some amazing swim spots, took us dolphin/whale watching and gave us a great tour. His insight really enhanced my cruising experience. At one point he pulled a 74’ boat in sideways In the dark with no bow thrusters and parked it right between two big yachts. With his great skill, professionalism and client care I highly recommend The Happy Captain!
Written July 13, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Sherpa362913
1 contribution
5.0 of 5 bubbles
Jul 2021 • Family
With a 10 am weekend summer sail we easily found free parking prior to our trip. Our captain was great! We enjoyed our time and got the opportunity to see a submarine doing a 'crew change out" while still in the water (not at a dock). We did this to celebrate 4 milestone birthdays in our family (two 50's, 21 and 18) and indicated 4 birthday's accordingly on the "special occasions" - however it didn't seem to mean anything (if you are celebrating something special - likely you may want to call the business in advance if you are expecting any kind of reference to your celebration).
Written July 18, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Mark C
Bethesda, MD85 contributions
5.0 of 5 bubbles
Feb 2022
Had a wonderfully perfect sail with Captain Tom and Sail Dan Diego. Could not have asked for a better 3 hours on the water. There were five of us and Tom made sure we all had a chance to sail, even those that had never been behind the wheel before felt comfortably to try it with great guidance by Tom. The boat was spacious and comfortable, and they had a great selection of drinks and snacks. The sunset on the water was amazing, the city lit up in orange and gold as the sun went down. Great for taking pictures (my friends back home were jealous). When I'm next in San Diego I know who I'll sail with -- "Sail San Diego"!
Written March 2, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

DSSandEWS
Indianapolis, IN1 contribution
5.0 of 5 bubbles
Oct 2021
Our charter consisted of three siblings, their spouses, and our Captain. (Captain Trevor)

Perfect weather, great wind, and calm seas made for a fantastic sail, and Captain Trevor knew how to get the most out of the boat. Our group is not new to sailing and so we spent our time actively pursuing this activity while still enjoying our Captain’s insights and knowledge of the area as we toured the Bay and Point Loma.

Just a fantastic way to spend an afternoon (11:30-2:30) and a fantastic value. Great boat, great location, great staff, and a great time.

Highly, highly recommended, and Captain Trevor is, as far as we are concerned, as good as they get. More than competent, and a super fun personality. You could not ask for a better Captain.
Written October 23, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

charl0tteml0we
Sacramento, CA1 contribution
5.0 of 5 bubbles
Nov 2021
I hosted three friends in San Diego for a few days and we decided to go on a sunset sailing cruise with Sail San Diego. It was by far our favorite part of the trip. The weather was amazing, we were able to go out into the ocean, and got a fantastic tour of the bay as well. Captain Tom was fairly new to town, but was already super knowledgable about the history of the area. He was a great guide and we had the best time. Can't wait to do another sail soon.
Written November 20, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Edward v
1 contribution
5.0 of 5 bubbles
Jul 2021
The ship was comfortable and safe for 8 seniors. We are 4 siblings with spouses celebrating an 80th birthday. The sail was exciting with slight heeling and speed. The captain was knowledgeable, personable and made the landlubber feel safe.
Written July 31, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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