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
(569 Ratings)
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Neala482
Jul 21, 2025
Happy Captain Greg is awesome! - Happy Captain Greg and the no-judgement zone is tops. We spread my brother's ashes on 7/16. Greg took his time on the way out past Pt Loma, pointing out several items of interest.Giving us a chance to enjoy the trip. He gave us a good heads up when we were getting close to the point where we would scatter ashes. He lowered the swim platform and one by one we took turns spreading ashes. He was considerate and let us take our time. He also marked the Latitude and Longitude of the spot. One thing that may have gone unnoticed but not by me: he took his cap off as a sign of respect. On the way back in he made sure to time the return enjoy as much of the sunset on the bay as possible. From this old sailor, I offer you much thanks Greg. You made an otherwise somber occasion, enjoyable. I would definitely sail with Sail San Diego again!
Review provided by Tripadvisor
Explore475345
Jul 11, 2025
Wonderful experience - The sunset cruise exceeded our expectations. Richard was an excellent sailor and shared many facts about the area. We would definitely do it again and recommend it to others.
Review provided by Tripadvisor
Lori_b
Jul 4, 2025
Best boating excursion and captain! - Wonderful experience all around. Organized logistics from booking to getting on the boat. Our captain (Captain Greg) was fabulous and made our experience the best. We will definitely be back!
Review provided by Viator
Linda_e
Jul 4, 2025
Great way to spend the afternoon seeing San Diego - Very much worth it! Loved our experience. The complimentary drinks and snacks were a great touch. Our guide was amazing and provided great music for our time on the boat. Would book this again with a group of friends!
Review provided by Viator
Tiffanymz6355ug
Jul 1, 2025
The perfect evening! - Such a wonderful experience! Happy Captain Greg was fantastic. The weather was amazing and we even saw dolphins coming back to dock the boat!
Review provided by Tripadvisor
Davidcness
Jun 28, 2025
Best charter in San Diego - An amazing experience, captain Bree made it the best event ever. The 3 hour trip was so relaxing and beautiful. I would thoroughly recommend this to anyone.
Review provided by Tripadvisor
502christid
Jun 22, 2025
Fun for all ages! - What an amazing evening! Easy, relaxed and SO much fun! The trip was easy to book and arriving and getting on the boat was seamless. Absolutely recommend to anyone wanting to spend some time on the water relaxing. Gary was our captain and we were absolutely obsessed with him.
Review provided by Tripadvisor
Rebekah_c
Jun 11, 2025
The staff were really... - The staff were really great! They walked us right to our dock and helped us get aboard. Once onboard Happy Captain Greg was wonderful at explaining everything we needed to know about the boat. We enjoyed some hard seltzers and cuddled up on the front of the boat with a blanket while we sailed around the bay. We saw a lot of wildlife including sea lions. We really enjoyed the experience!!
Review provided by Viator
4boyshere
Jun 8, 2025
You have to meet Happy Captain Greg! - We've done sunset sails in Hawaii and the Carribean and have to say that THIS one with Happy Captain Greg in San Diego was among the very best. All the expected boxes were checked: safety; beautiful water; punctual departure, expert sailing; fine beverages and snacks; and an immacualte and comfortable vessel. The unexpected is what made this our favorite: the wit and humor of Happy Captain Greg entertained the whole family the whole time. He took us to the Wednesday Night Boat Races which was exciting and also shared various interesting facts of the Cornado area, even pointing out a submarine in dry dock and so many other things we never would have spotted on our own. We'd come back and pay to see him again even if the boat never left the dock. We also appreciated Sail San Diego's simple checkin with a friendly host and the great gift shop. We will be back and will tell all our friends!
Review provided by Tripadvisor
Pickybiztraveler
Jun 22, 2025
A unique way to enjoy the sunset - I enjoyed this activity. The setting was a lot more personable than the big boat harbor cruise, and we did do some sailing, which was the part I was looking forward to. The captain was very friendly and happy to answer questions. The sunset view were very pretty. The cockpit was a bit tight for 6 people, but that was not unexpected. The reason I rate it 4 out of 5 is the price - it is quite expensive, and the multiple indications of a suggested $25 tip per person make it even more so, especially when you go with a family.
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).