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
(580 Ratings)
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Lisaohioreview
Sep 27, 2025
Lovely trip - Enjoyed our experience. We had the 2 hour morning trip. Would’ve like to go a little in the open water but overall very enjoyable
Review provided by Tripadvisor
Jillwd6103ws
Sep 20, 2025
Best experience sailing with a captain and meeting wonderful people! - I had one of the most fun experiences sailing with two other couples and Captain Stu! I’m definitely going again and again! and the two owners are very nice and put me with some wonderful people for sailing three hours on Mission Bay . I highly recommend going sailing with a captain like Captain Stu!
Review provided by Tripadvisor
B1216ykdarleneb
Sep 9, 2025
Just what I wanted - I love sailing & this turned out to be a fabulous experience. I chose a great company that was efficient & friendly. The boat was medium-sized with plenty of room for six passengers. There were also rear perch seats & space on the bow which I took. It was a relaxing, beautiful 3 hours. The sail is timed to get to the open sea (we sailed with a large pod of dolphins) then it turns back toward the city (with the sun shining on the harbor) then a final turn home into the sunset itself. Then, on this day, it was nearly a full moon so we had moonlight on the water at the very end. Perfect timely. Our captain was fun & friendly.
Review provided by Tripadvisor
Paul_s
Sep 4, 2025
Sail San Diego / Captain Dave - We had an incredible time! Captain Dave was very knowledgable about the area and engaging! Stunning sunset, fun fellow travelers, and a captain who caught the wind ... couldn't ask for more! Would go sailing with him and Sail San Diego again!
Review provided by Viator
Mojado50
Aug 31, 2025
Highly recommended - Took the sunset sail to celebrate our 43rd anniversary. We had a delightful and relaxed evening. Low key, well organized, and exceeded expectations.
Review provided by Tripadvisor
Wscjr
Aug 29, 2025
Unforgettable Sailing in San Diego – Captain Made It Perfect! - I recently booked a private 44-foot sailboat for my grandson and I with Sail San Diego. It was hands down one of the best experiences we have ever had together. From start to finish, everything was smooth, relaxing, and beyond our expectations. Captain Richard was not only highly skilled and professional but also incredibly friendly and welcoming. You could tell right away that he was passionate about sailing and loved sharing the experience with us. In fact, Captain Richard had my 10-year-old grandson at the helm of the sailboat for well over an hour, undoubtedly an experience he will never forget. The boat was immaculate, well-maintained, and comfortable — perfect for a cruise around the bay and out into the Pacific Ocean. Whether you are a local looking for a unique way to enjoy San Diego, or a visitor wanting to see San Diego from a different perspective, I cannot recommend this experience enough. It was peaceful, scenic, and truly memorable — thanks in large part to Captain Richard’s expertise and wonderful personality. We will definitely be sailing again with Sail San Diego!
Review provided by Tripadvisor
Rolandgalang
Aug 16, 2025
Highly recommend Sail San Diego - Great time and experience. The captain and all their supporting staff were very friendly and responsive. Highly recommend.
Review provided by Tripadvisor
Arlene_f
Aug 15, 2025
Romantic and relaxing! - Be aware, the entire sailing adventure stays in the bay. If you want to go out into the ocean, this is not the trip you want. However, it was very relaxing and romantic!
Review provided by Viator
B2769jowilliamr
Aug 12, 2025
Great sunset sail - We had a great night leaving the harbor. The captain gave us the choice of going further into the bay to see the Coronado Bridge, or to leave the bay, and I’m glad we chose to leave the bay. It was a little overcast, but not too chilly. He also let us try steering the boat too. It was a great time, thank you!
Review provided by Tripadvisor
Ottervic
Aug 4, 2025
Family Sunset Sail - This is a must do when you come to San Diego. We had lunch at the Marina and then boarded our boat for a sunset sail. When checking in, there is a very cute store. As a family of 4, we chose to rent the whole boat which doesn't work out as too much more than if we were to share and we had the freedom to move around the boat as we wished. Up front was our favourite. Our captain was fun and knowledgable and gave the option of where we wanted to go. We chose open water which was fantastic with the sails up. We were then treated to a beautiful sunset. The drinks and snacks are a lovely added touch. I would highly recommend this company.
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).