Sail San Diego

Jessee, our captain. He was an excellent captain. He was great fun, a great teacher, and very laid-back. We will definitely go back and ask for him!

We had THE MOST fantastic experience on our private sunset sail. We booked for our anniversary and we were met at the check-in desk with an anniversary card signed by the employees at Sail San Diego. Our captain was AWESOME - so friendly and knowledgeable. I HIGHLY recommend booking a sail with this company! You won’t regret it!

I booked a sunset sail with Sail San Diego for an anniversary date night- and we really, really enjoyed it. Captain Greg was knowledgeable and funny. There were lots of snacks. It was such a unique and relaxing experience!

Excellent day out on the water with Captain Frank. Very smooth sailing, relaxing day with a small group of people. 100 % recommend it.

Amazing Captain! The trip was great too. Everything was easy and exactly what was described.

The whole process of booking and checking in was simple with Sail San Diego. I loved riding with a small group of 6 people in total, it made for a really lovely experience. The captain made the sail fun and interactive. The three hour cruise time when by in a flash, and made me want to book again. I would strongly recommend Sail San Diego for its affordability, value, and expertise and friendliness of its staff.

Our private sail was amazing! They volutneered to reschedule our sail due to SD rainy weather so we could best enjoy our time on the water! When we did go, it was beautiful! Our captain was so kind! He made us all feel safe and secure while being laid back and part of the group! We could have easily sailed all day! We have a 3 kiddos with us and they all want to go again! This is the best experience of the money I have ever had! Can't wait to go back to SD and sail again with them!

Great experience. The complimentary snacks and alcohol was a plus! Our captain Madeline was amazing. Friendly, knowledgeable, and was king enough to take pictures of us. Would definitely do it again.

We booked 4 spots on a boat for Labor day. Super easy to book online. We got Capt. Kenley, best captain on the high seas! This was such an amazing and affordable experience! Beautiful boat, great captain, couldn't have asked for anything more. Definitely booking again before summer is over!

Our two hour sail with Captain Greg was the highlight of my wife’s birthday weekend with some our friends from Phoenix. Perfect weather and winds made for some lively jibes and great pictures. We are in San Diego 10x a year but never took the opportunity to sail the harbor like this. Greg passed along a ton of knowledge about the Navy operations we passed and about the area in general. We will be back with our four grandkids. Highly recommend!

Sail San Diego is awesome! We sailed from Shelter Island out past the Coronado bridge and back. It was so much fun and our skipper was great! We saw sea lions, the downtown San Diego sky scrapers, and all the docked Navy ships. Make sure you wear flip flops and shorts or a swimsuit. You’ll feel out of place wearing more than that. You won’t be jumping into the ocean, but you will still have an amazing time. I got to steer the boat at one point which was really cool! There’s also just something about being out on the water, having a few drinks with friends, and listening to great music. I highly recommend Sail San Diego! You will not be disappointed!

What an amazing sunset sail with Chris! He was so knowledgeable about the area, the boat was so beautiful and the scenery amazing. Price was very affordable! We will be back!

We had such a fun time taking our employees on this sunset sail! Captain Greg was talkative, funny, kind and kept things interesting. There was lots to do on the boat and everybody had a good time. Especially with the snacks and drinks provided!

My wife and I celebrated her birthday with a sunset sail through Sail San Diego. It was a wonderful experience. Our captain was awesome, the boat was great, and we had a fantastic time. We will happily go sailing with Sail San Diego again!

We had a great tour with our very experienced sailboat captain, John. We were a bachelorette group for my sisters wedding and he had great music, good stories about his 20 years of sailing, and was overall a fantastic captain and even took a selfie with us all at the end. Absolutely recommend!

Even though it was a cloudy day, we had a great time. Our Captain, Marilyn, was fantastic. She is very skilled and accomplished. She was very informative about the area. We will definitely sail with Sail San Diego again.

We had an excellent charter with Captain John. There were 8 of us out to celebrate a bachelorette party. John was kind, answered all our questions, and seemed to really fit in with our vibe. Thanks so much, John and Sail San Diego!

Cant begin to tell how much we enjoyed the staff and the the actual trip. This is my 3rd time with these guys and i will keep coming back every year.you more then get your $$$$ worth. Thanks Guys and see you soon.