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San Diego Sailing: Semi-Private 3-Hour Bay Cruise
5.0
525 Ratings
San Diego
Join a small-group San Diego sailing excursion. Enjoy complimentary drinks and snacks while soaking in the sun and Bay sights.
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
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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…
- 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 ensure you have an unforgettable time on the water. As you take in the views, enjoy complimentary beer, soft drinks, and snacks. If you feel cold, grab one of the provided blankets, or purchase a jacket or sweater at their store. If the sun is too bright, you can buy sunscreen, sunglasses, and hats at check-in. Use the provided binoculars to admire the coastline or spot wildlife! You can even stream your own music to the boat’s Bluetooth speakers.
Please note: The boat is limited to six (6) passengers. To make it a private adventure, book all six spaces and bring along five friends!
- Point Loma - Sail San Diego’s private marina is located in the Shelter Island area of Point Loma. We will also pass by the actual Point Loma lighthouses during your sailing trip.
- Coronado Bridge - You’ll have the chance to see the Coronado Bridge from the water, aboard a 40-foot luxury sailing yacht.
- Coronado Island - We always sail past the Coronado “North” Island.
- USS Midway Museum - We always aim to sail past the USS Midway so you can experience it from a different perspective.
- Seaport Village - Some of our sailing day trips pass by Seaport Village. Ask your captain.
- San Diego Convention Center - Some of our sails go by the San Diego Convention Center. Ask your captain.
What's Included
- 3-hour sailing cruise
- Complimentary light beers and hard seltzers (21+)
- Complimentary non-alcoholic beverages and light snacks
- 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
- 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….
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. Guest must contact Sail San Diego after purchase for the exact departure time. Please note this activity does require a minimum of 3 guests total in order to sail.
If members in your group are booking their tickets separately, please call Sail San Diego so they can ensure you’re on the same boat. If they don’t know ahead of time, you may be seated on separate boats!
- Please note: Each booking is limited to six (6) passengers. If you have friends or family booking separately, please let the operator know in advance to ensure you’re on the same boat; otherwise, you may be seated on different boats.
- You must contact Sail San Diego after purchase for the exact departure time, as departure times vary throughout the year.
- This is not a guided tour; our captains don’t provide a commentary but are always happy to share what they know! Don’t be shy asking questions.
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
5.0
(525 Ratings)
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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
Y6584qjmichaelr
Sep 5, 2025
Amazing Sail! - My wife and I absolutely loved our three hour sailboat tour with Sail San Diego. We experienced convenient booking. A very friendly staff. An amazing sailboat. A friendly and very informative captain. A great variety of snacks and drink drinks. We sailed out of America’s Cup Harbor out, just passed point Loma and back again. Our favorite seat on the boat was on the beanbag that you will find on the bow of the boat. This being our second tour with Sail San Diego, And having experienced the same passage both times. Our only hope is to Get to go another direction next time, perhaps south in the bay towards downtown and Coronado. Thank you so much, Sail San Diego For a great passage on your 40 foot Catalina sailboat!
Review provided by Tripadvisor
848joer
Sep 2, 2025
Perfect day of sailing on San Diego Bay on a perfect day. - Another delightful day with Sail San Diego. All details of our trip were first class. It was a beautiful day to share this experience with our close friends. Well done, Sail San Diego.
Review provided by Tripadvisor
Kathykh4701ci
Aug 24, 2025
A great time with Sail San Diego - This is our fourth sailboat excursion with Sail San Diego. They never disappoint. Professional, nice boats, great guides. Our captain - Dave Hobbs - was fun and knowledgeable. He provided interesting military and history comments about the sights we saw as we sailed the harbor. Lots of fun.
Review provided by Tripadvisor
Abigaillp4375qc
Aug 11, 2025
The best sail boat trip for our bachelorette trip! - We had the best time with Captain Greg! He created a wonderful time for our bachelorette trip! I highly recommend booking for your bachelorette trip and if you’re lucky you’ll get captain Greg!
Review provided by Tripadvisor
Janetmp1104tu
Aug 10, 2025
Private sailing adventure! - Third time to sail with Sail San Diego! Excellent as always and love Captain Greg! Easy to book and such a great experience!
Review provided by Tripadvisor
P7355zotraceyb
Aug 17, 2025
Not what we expected - Sail San Diego - 3 Hour Cruise Review
Rating: ⭐⭐⭐ (3/5 stars) I wished I could give a 5 star!
My husband and I booked the 3-hour cruise with Sail San Diego and had a mixed experience. As frequent travelers who’ve done many boat tours, we went in with certain expectations based on the price point and description.
The boat itself was ok and the basic sailing experience was enjoyable. San Diego’s coastline is beautiful, and being out on the water was relaxing. The staff were friendly.
For what we paid, we expected a more refined experience. The price point suggested premium touches that weren’t quite there.
The refreshment setup was very basic - snacks and drinks were self-serve from plastic bags in the galley. The promised “pillows and blankets” turned out to be regular boat cushions and one worn gray pillow at the front for everyone to share. Small upgrades here would make a big difference.
The tour felt a bit disorganized with information shared in bits and pieces. No one offered to take photos or asked about playing our music - little touches that other tours have included that make the experience feel more personal.
We were surprised to learn there were two possible routes and had to vote with another group on which way to go. This wasn’t mentioned during booking, and we felt we should have known what we were signing up for.
Sail San Diego has potential and the basics of a good tour, but could really elevate the experience with some attention to detail and service enhancement. The sailing itself was pleasant, but for the price, we expected more polish and personalization.
Would we recommend it? Maybe for a basic sailing experience, but there are likely better value options in San Diego for a premium tour experience.
Review provided by Tripadvisor
Tracey_h
Aug 15, 2025
It’s was OK -
Rating: ⭐⭐⭐ (3/5 stars)
I truly wish I could give them 5 stars.
My husband and I booked the 3-hour cruise with Sail San Diego and had a mixed experience. As frequent travelers who’ve done many boat tours, we went in with certain expectations based on the price point and description.
The boat itself was ok, nothing spectacular. It was a basic sailing experience. San Diego’s coastline is beautiful, and being out on the water was relaxing.
Areas for Improvement
Value for Money: For what we paid, we expected a more refined experience. The price point suggested premium touches that weren’t quite there.
Amenities: The refreshment setup was very basic - snacks and drinks were self-serve from plastic bags in the galley. The promised “pillows and blankets” turned out to be regular boat cushions and one worn gray pillow at the front for everyone to share. Small upgrades here would make a big.
The tour felt a bit disorganized with information shared in bits and pieces. No one offered to take photos or asked about playing our music - little touches that other tours have included that make the experience feel more personal.
Route Transparency: We were surprised to learn there were two possible routes and had to vote with another group on which way to go. This wasn’t mentioned during booking, and we felt we should have known what we were signing up for. Bottom Line:
Sail San Diego has potential and the basics of a good tour, but could really elevate the experience with some attention to detail and service enhancement. The sailing itself was pleasant, but for the price, we expected more polish and personalization.
Review provided by Viator
