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
(585 Ratings)
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1 star
Matt
Nov 11, 2025
100% will do the Sunset Sailboat Cruise again. - One of the absolute best parts of the trip to San Diego. Sailboat was beautiful, well kept, and an easy ride. Our captain, Greg was very friendly and we could tell he had a lot of experience. The boat comes with snacks and some drinks (could have been a bit colder) but we brought our own anyhow. The views were amazing and we got a perfect day weather wise… everyday is perfect is SD. Overall very worth the money as we ended up paying ~$900 for 3 hours for a group of 8ish.
Review provided by Tripadvisor
Leslye_s
Oct 31, 2025
Great time! - The boat is so clean! I crawled on my knees, in my dark navy pants from the bean bag on the bow to the stern and not one speck of white dust was on my knees as I had feared.
Review provided by Viator
554deannaz
Oct 19, 2025
Excellent experience - It was the highlight of our vacation! Our captain was very knowledgeable and went out of his way to make sure everyone was having a good time! The sailing part was extraordinary and I loved watching the captain maneuver the sails! The boat was clean and food and beverages were provided. We will defintely be doing this again with Sail San Diego!
Review provided by Tripadvisor
Karlee_s
Oct 13, 2025
Captain was spectacular... - Captain was spectacular and worked hard to please the group with sights, enjoyment, great stories and beverages He was incredible
Review provided by Viator
G1622jnlisag
Oct 9, 2025
San Diego Sails Rules Supreme! - Happy Captain Greg made the sail just perfect! Only 6 on board- felt like a private sailing experience for decent price!
Review provided by Tripadvisor
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
From $127
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).