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
(536 Ratings)
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Grandtour12848534307
Mar 3, 2026
Take this sailing trip! It's unbelievable! - Everyone owes it to themselves to take a sailing trip with Sail San Diego! Given the prices of everything in California, this trip is not only completely affordable ($119 for 3 hours) but is also a very memorable experience. We've sailed twice with Sail San Diego...the afternoon and sunset sail. Both are equally rewarding! If you want to go out into the big water the afternoon sail is recommended as evening fog can limit visibility for an ocean sail. Check your weather forcast before you book. This is a great company! Not one complaint! And Captain Dave is the man! Damn can he sail a boat and he's SUPER knowledgeable too. Thank you to everyone at Sail San Diego for the unforgettable experiences!!
Review provided by Tripadvisor
060491
Jan 18, 2026
Great captain! - Awesome captain Dave made this sail extra special. Very knowledgeable and fun! Wonderful weather for a great day.
Review provided by Tripadvisor
Valerie_b
Jan 6, 2026
A wonderful and fun sailing experience! - We had a really wonderful sailing experience with Captain Dave Hobbs. Not only was he a great captain, but we learned an unbelievable amount of history about San Diego itself, the naval base, dolphins, and local attractions. We appreciated his enthusiastic, upbeat, and fun personality!! -Valerie B.
Review provided by Viator
Damira_c
Dec 23, 2025
Happy Captain Greg is awesome! - Had a blast sailing for the first time with my family. The team was super organized, and Captain Greg was awesome 👋!
Review provided by Viator
Chris_h
Nov 29, 2025
Great time on the sail... - Great time on the sail boat. Dave was an awesome captain and shared a lot of knowledge with us along the way. Highly recommend to couples just looking to relax and soak in San Diego’s views.
Review provided by Viator
Judy_b
Nov 11, 2025
Best day ever! - We had an awesome time sailing! Will definitely return to sail again 😊 It’s a fun intimate experience on a sail boat
Review provided by Viator
Goddardcc
Oct 30, 2025
Excellent service. It was a delight dealing with this business. - Excellent service. It was a delight dealing with this business. We will definitely book this the next time we are in San Diego.
Review provided by Tripadvisor
Coastal26188269371
Sep 29, 2025
Great mid day cruise! - We had such a great experience on this tour, we really appreciated the small group size, just six of us plus the captain. We saw amazing activity from the naval station in addition to seals and sea lions.
Review provided by Tripadvisor
Roam607861
Sep 29, 2025
September Harbor Cruise - Our sail with Captain Dave Hobbs was fantastic. His knowledge of the harbor and the environs and the San Diego area is extensive. High recommend this company and Captain Dave.
Review provided by Tripadvisor
Ononru
Sep 6, 2025
Fantastic Sailing Afternoon - What a great sail! We've been on many sailing afternoons like this in Hawaii, but San Diego Sail was so much better. We actually sailed, not just puttered around. Happy Captain Greg was laid back, entertaining, and informative. An afternoon very well spent.
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).