Small-Group San Diego Sunset Sailing

Experience a serene San Diego sunset sail with drinks and snacks. Limited to 6 guests for a semi-private adventure. Book now for an unforgettable evening.

Duration: 3 hours
Cancellation: 24 hours
Highlights
  • Sail San Diego - Whether you’re on vacation, celebrating a special occasion, or simply looking to enjoy a beautiful Southern California day, this small-group sailing trip in San Diego is a fantastic way to spend time on the water with your loved one or a group of friends. Embark on a sunset cruise that takes you out on the Bay and the Pacific to…
What's Included
  • 3-hour evening sailing cruise
  • Alcoholic beverages
  • Complimentary non-alcoholic beverages and light snacks
What's Not Included
  • Hotel pickup and drop-off
  • Gratuities
Additional Information

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, purchase all 6 tickets and grab five friends to have a completely private sail!).
Sit back, relax and enjoy the complimentary…

Location
2720 Shelter Island Dr
Shelter Island Drive
PLEASE NOTE: A physical boarding pass will be required to board your assigned sailboat. Your boarding pass will be provided at our Sail San Diego office. You can find us directly across the road from the Brigantine Restaurant (a few doors down from Paragon Deli, underneath Eye Candy beauty salon).
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(637 Ratings)
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W8446kralisas
Aug 10, 2026
This is a MUST do!!! Ask for Greg. - Highlight of our trip! Met the owners, such a lovely couple. And our Captain, Greg was just the best. I recommend him over & over. It was four moms with their for 12 year old daughters. Greg entertained us, laughed with us and was just amazing with the girls. We hope to do it again next year!! Thanks GREG!!
Review provided by Tripadvisor
Inspire517130
Aug 10, 2026
A Salute to Captain Dave - We took our daughter, son-in-law and two grandsons on their first sunset sail and they LOVED it! Captain Dave is the BEST and having the entire sailboat to ourselves made it even more fun. His experience as a tour guide made him incredibly knowledgable about what we were seeing, especially all of the naval installations. He is also an amazing photographer! Not only did we make special memories, we have pics of those memories to cherish forever (and to use on our annual Christmas card!). Almost everyone had chance to be the ‘captain’ and sail a bit. Can’t forget his yacht rock - best playlist ever! (Might have helped we also ordered a bottle of prosecco to toast the sunset). Highly recommend sailing with Captain Dave. Looking forward to our next trip with him!
Review provided by Tripadvisor
Ranhood
Aug 5, 2026
Capt Dave made it great! - Capt Dave Hobbs was outstanding! He was fun and informative. He made the trip super fun!! Easy and simple process - we had a great time!! Tks!
Review provided by Tripadvisor
851tedk
Aug 4, 2026
6 hours of private sailing - Beautiful day, amazing sailboat, our Captain, Captain Greg was the best.
Review provided by Tripadvisor
Y7740ritedm
Jul 31, 2026
sunset with captain Kinley - Our Captain Kinley was the most kind and personable person imaginable, he was fun to converse with and went out of his way to show us unique features like the submarine base, the sea lions, and he even found Dolphins swimming in the bay. He even gave us information on how he sets sails and indicators in the sails to control the boat. He timed the sunset perfectly so we had the best views ever! The sail boat was the perfect size, large enough to have a bathroom and small enough to have a great sailing experience with no sea sickness. We would highly recommend this company for a great experience and they have many boats that are all top quality with personable captains. Thanks Ted
Review provided by Tripadvisor
Socalmom23
Jul 29, 2026
Couldn't Get Any Better! - Captain Rick took us out for an amazing, private sail on the water (2 adult couples.) He was so friendly, easy going, knowledgeable about the area and all the things happening on the water and in the air. We highly recommend him, the tour company, SAIL San Diego, and the sunset sail experience. We saw seals, dolphins and several species of birds. There was a good selection of complimentary drinks (soda, sparkling water, beer, seltzers) and chips available. We also brought some additional snacks for our charcuterie board. Our out of town guests were so grateful we booked this experience. There is truly not one thing to complain about: from booking to check-in, boarding, the sail itself, and a final send off complete with a great group photo. Very well run operation. Thank you!
Review provided by Tripadvisor
Rebecca_m
Jul 22, 2026
Perfect in every way - Perfect and dreamy. Captain Rick was knowledgeable, kind, and really easy to talk with.. There was nothing confusing or weird at all about the experience. It was just easy and fun and delightful. The check-in was professional and in a nice well kept location, and the on boarding process was smooth. Highly recommend.
Review provided by Viator
Grace_k
Jul 21, 2026
Richard was a great... - Richard was a great captain! Beautiful night, and a great experience. Worth every penny. Would highly recommend.
Review provided by Viator
Travis_j
Jul 15, 2026
Perfect Sunset Cruise! - The sunset cruise was amazing. We did the 3 hour tour and it was well worth it. Henley was an incredible captain. Very knowledgeable and informative. We saw plenty of sea lions and even a couple Navy Seal boats cruising through the harbor. The boat was clean. They even had a fridge to store some of our food. We will definitely sail again on our next visit.
Review provided by Viator
Davidso5922zv
Jul 15, 2026
Captain Dave is the best - Wonderful small group cruise around the harbor. Captain Dave was fantastic. Highly recommend
Review provided by Tripadvisor
From $127
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).