San Diego Sailing: Semi-Private 3-Hour Bay Cruise

Join a small-group San Diego sailing excursion. Enjoy complimentary drinks and snacks while soaking in the sun and Bay sights.

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 3-hour daytime adventure in San Diego Harbor.
    Your captain will…
What's Included
  • 3-hour sailing cruise
  • Complimentary light beers and hard seltzers (21+)
  • Complimentary non-alcoholic beverages and light snacks
What's Not Included
  • Hotel pickup and drop-off
  • Gratuities
Additional Information

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the complimentary beer, soft drinks and snacks as you soak in the warm sun and Bay sights.
Departure times vary throughout the year….

Location
2720 Shelter Island Dr
Shelter Island Drive
PLASE 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
5.0
(520 Ratings)
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Jfksck
Jul 15, 2025
Smooth sail on the Bay - Great experience. The captain was knowledgeable about what we were seeing. Very personable. The whole family enjoyed the afternoon.
Review provided by Tripadvisor
Lovetravel679492
Jul 5, 2025
Beautiful trip on the Bay - Fantastic trip. Captain Greg was terrific. Sailboat was spotlessly clean and very well maintained. My wife and I love sailing and "Sail San Diego" will definitely be our go to for future trips.
Review provided by Tripadvisor
Elizabeth_g
Jul 4, 2025
Fun in the sun!! - My family and I had such a great time on our sailing adventure. We just wanted to relax with some fun in the sun, and this trip delivered. Captain Greg was fantastic and offered us great recommendations for restaurants and things to do in the area.
Review provided by Viator
R3941zvlarryw
Jun 22, 2025
Love it - I would definitely do this again. It was so nice to be on the water sailing the bay. I went in and out of San Diego many times when I was in the Navy but really had no time to enjoy it. This was really relaxing.
Review provided by Tripadvisor
Trek007034
Jun 19, 2025
Great trip with Captain Reese - We booked a three hour tour with sail San Diego and it was amazing. We went to the edge of the bay and to downtown. The views were amazing and captain Reese made the whole trip very enjoyable. We will definitely sail again with this crew!
Review provided by Tripadvisor
Suzanne_d
Jun 17, 2025
Captain Breezy is awesome! - Captain Breezy was wonderful! Not only was she a great captain, she also was very knowledgeable in answering our questions about sailing and the areas we sailed past.
Review provided by Viator
A9482erconniew
Jun 13, 2025
Now that’s Sailing! - We had a lovely sail through the bay out towards Point Loma with Captain Stu. Not too much sun which was appreciated. Blankets available when the wind got sharp. Snacks are not plentiful, but drinks and chips were nice to have. Small group of six was perfect. We felt safe and enjoyed the afternoon ride. A true SAILING experience.
Review provided by Tripadvisor
Hannahvhawker
Jun 9, 2025
I will only sail with Sail San Diego! - I used Sail San Diego previously for a birthday and it was a great experience so I had to return. This time was certainly no different! Kate was incredible from every step of planning down to day-of details. We had the pleasure of going on the Maile, rhe Gulfstar 50 and WOW, she is stunning!! The owner Cal is super friendly and captain Frank and Kayla were absolutely phenomenal! I will only sail with Sail San Diego. Thank you all for making my birthday so special!
Review provided by Tripadvisor
Q4444veangelal
Jul 18, 2025
Great time - Very relaxing time on the water. So relaxing I was able to take a short nap. Enjoyed by all. Nice weather. Kids enjoyed snacks and kicking back on our last full day of vacation.
Review provided by Tripadvisor
Myraj3742
Jul 15, 2025
Don't waste your money. - Your crowded into a boat and you sit in one position for the full 3 hours. They offer snacks but you have to go the cabin which is very tight and uncomfortable. There's no tour you can only ask questions if you think of one. They don't tell you anything about the ride. The boat operator explains he is not a tour guide. The footwell is too small The cushions are very flat and your feet can barely have any room. There's no room to walk around.
Review provided by Tripadvisor
From $116
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).