This was actually a dream! Weather was 75 and perfect. Definitely can bring your own food but our ticket included drinks and chips on board as well which was super nice!! We got to see lots of sea lions, the navy ships, and the water was perfect. Would recommend this sailing in a heartbeat!!!! read more

Sail San Diego - Front of boat - Boating Near Me - San Diego, California

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Did a sunset sail with some friends, Happy Captain Greg was awesome, answered every question he could our friends 2.5 year old came up with. We got to see a lot of awesome military air craft coming and going. read more

Had to go back, luckily got graced with Captain Rhys again! This time we learned he likes mango. He still likes ween so that's good. Very cool day sailing yet again. Snacks , drinks, music and the open ocean. It just can't be beat. Thank you for another day of smooth sailing ! read more

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The local owners have made private sailing so easy! They limited our boat to six and we all enjoyed ourselves. We also had snacks and drinks at the end of the sail. The crew was friendly and helpful all around the bay. I will do it again soon! read more

Sail San Diego - Business photo for contact - Boating Near Me - San Diego, California

This was a delightful sail around Point Loma in San Diego and surrounding area. The boat was beautiful and Captain Greg gladly allowed all passengers that wanted to sail to give it a try under his watchful eye and, "You're doing great," was the resounding theme, lol! This was a perfect activity for my friends visiting from Cleveland that wanted a sailing adventure. Highly recommend! read more

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We booked the Bachelorette Boat experience for 11 guests from 2:30-5:30pm. It was so incredibly worth it and even more fun than I imagined it would be. Our boat was sailed by Captain Kenly who was such a delight. Great smooth sailing, very friendly, and very helpful with getting good pictures and lighting. The boat itself was clean, spacious, and stocked with complementary snacks, drinks, and beers/seltzers. Also included is a speaker you can bluetooth connect your music to for fun energy. The views of the ocean and of San Diego from a distance was stunning. And boating at sunset gave us beautiful horizon and golden hour photos. What made the trip even more amazing was the sea lions, whales, and DOLPHINS we spotted during our ride! Thank you so much for this experience, it was truly my favorite part of our trip!! psa that is your ride is in the afternoon please bring a good jacket especially in the winter months! there are blankets on board but a jacket is a must if you get extra chilly. read more

Sail San Diego - Boating Near Me - San Diego, California

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This was my 2nd time going out with Sail San Diego, and we requested Dave again. He was just as amazing with my large family of parents and kids as he was with my group of girlfriends last summer--he just knows how to adjust to make whatever group you have feel comfortable and welcome. The boat was SO nice! Fully stocked, immaculate, extremely comfortable. He even made a "scavenger hunt" game for the kids, which they were VERY into. It was the best idea, and everyone had the most amazing time. Thank you again, Captain Dave! read more

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Captain Rhyse was cool, accommodating, full of fun facts. Learned a lot and had a great time

Our morning sail was awesome! In two hours we saw seals, dolphins, and submarines. Our 3 kids had such a great time exploring the boat. Captain Kenley was so nice and knowledgeable while giving us the tour. Definitely worth the price. We'll be back! read more

We had the best time sailing today. It was beautiful. Our Captain Richard was the absolute best. He let the kids steer the boat for a while which made their day. I highly recommend Sail San Diego. read more

Sail San Diego - Boating Near Me - San Diego, California

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A fantastic trip, as always. And Captain Rhys was a perfect host. The weather was gorgeous, and we had a spectacular sunset with the dolphins. We'll be back again for sure! read more

We had a wonderful day! Captain Ryhs was great! He took us by the dolphin/seal training facility and out past Point Loma. He was very informative and experienced. Definitely worth the price. I recommend it! read more

Sail San Diego is hands down the perfect sailing experience in Southern California. I've been lucky enough to sail with Sail San Diego a few times now it's become one of my favorite ways to unwind in Southern California. Tucked away on Shelter Island in Point Loma, surrounded by some of the best seafood spots in the city, it's more than just a sailing trip--it's a full experience. From the moment you step aboard, there's this relaxed, welcoming vibe that instantly puts you at ease. The captains have sailed all over the world, but they carry their expertise with this laid-back charm that makes you feel like you're in good hands without any pretension. The boats are sleek, super comfortable, and thoughtfully stocked with drinks and snacks. There's even a dreamy cushioned lounge area up at the bow that's perfect for stretching out and watching the city drift by. One thing I've come to love about Point Loma is how often the weather clears up just in time for sunset. Even on cloudy days, around 4 or 5 PM the skies often open up--and on our last sail, we were treated to one of those golden, glowing San Diego sunsets that makes everything feel right with the world. What really sets Sail San Diego apart is the way they personalize everything. Whether you're celebrating something special or just looking to relax, they go out of their way to make it feel meaningful. On my most recent trip, I brought a dear friend who'd been going through a really tough stretch. As we cruised along the coast, I watched her shoulders drop, her face soften, and a real smile return. That one quiet evening on the water did more for her than weeks of check-ins and phone calls. It was beautiful to witness. If you're ever feeling overwhelmed, celebrating something big, or just need a change of scenery, I can't recommend a sail with them enough. There's something incredibly healing about being out on the water--and this team just gets it. read more

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We used this service on a bachelorette trip! We had the best time ! Captain Dave made the trip so much fun. He has a great energy and a lot of knowledge about the city. The boat was immaculate and so comfortable. Highly recommend!! read more

Our captain Reece was great and very personable. Very relaxing nice sail out to the ocean and back with seals and dolphins

The staff was amazing throughout the process! Their customer service is top notch and it really was a wonderful experience. The ladies at the check in/reception were extremely helpful navigating parking and other recommendations. Our captain (Reese) was fantastic overall and was awesome interacting and teaching our boys (ages 7 & 10) how to sail. I would 100% recommend. read more

Captain Rhys took us out on an amazing whale tour. He knew the right spot to go and just as we arrived, the humpback whale breached the water completely in an amazing show! And went on to do so two more times! In total, we saw several species of whales, sea lions, and dolphins played around our boat on the way home. Great sailing advantage and we highly recommend Captain Rhys if you want to see some whales! read more

Happy Captain Greg and the no-judgement zone is tops. We spread my brother's ashes on 7/16. Greg took his time on the way out past Pt Loma, pointing out several items of interest.Giving us a chance to enjoy the trip. He gave us a good heads up when we were getting close to the point where we would scatter ashes. He lowered the swim platform and one by one we took turns spreading ashes. He was considerate and let us take our time. He also marked the Latitude and Longitude of the spot. One thing that may have gone unnoticed but not by me: he took his cap off as a sign of respect. On the way back in he made sure to time the return enjoy as much of the sunset on the bay as possible. From this old sailor, I offer you much thanks Greg. You made an otherwise somber occasion, enjoyable. read more

Sail San Diego - Boating Near Me - San Diego, California

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Unfortunately did not have a good experience because of our captain, Frank. He was on a bit of a power trip in the beginning by taking very long pauses and pointing at any of us who got distracted during his safety talk; which could be easily justified for safety and we all looked over it. But during the boat ride he drove us into a large wake from another boat that he could have easily steered away from. We all got soaked and one of us almost lost her phone and he didn't give us a warning or even apologize. There were other negative instances but at the end of the boat ride he took our group photo and literally flipped us off as he took it. We all felt extremely uncomfortable at that and his behavior in general. We were a Bachelorette party of 9 and had a good time nonetheless in each other's company, but would have obviously preferred a better captain. We took our complaints to the office where we checked in and they dismissed us and did not take them seriously. This was extremely disappointing and thus why I am writing a negative review. Would not want another group to have a similar experience to ours. However, the assistant Chloe was amazing and gets a 5-star rating from all of us!!! (which is why this review is getting 2 stars instead of 1). read more

We absolutely loved our sail experience! Captain Dave showed us a wonderful time as we took to the seas on a search for whales and marine life. The weather could not have been more beautiful and the boat was clean, safe, and comfortable. My kids (10 and 12) loved clambering all over the ship and sitting up front as we went up and down the waves. We weren't able to find any whales but Dave did locate a huge pod of common dolphins that we followed for quite a long way. Seeing the dolphins (including some young babies!) play alongside the boat in the crystal clear water was just incredible. We can't wait to go out again. read more

Sail San Diego - Watching the dolphins play alongside the boat. - Boating Near Me - San Diego, California

We're locals who thoroughly enjoyed our charter. What I most appreciated was being able to pop into the office a few days before to ensure that I had chosen the right boat, time, etc.. What some businesses don't realize is even though it's routine for them, for the guest it's a novel experience and we may need extra information or perhaps a bit of reassurance. Sail San Diego provided that with a caring attitude and I'm very grateful. read more

Sail San Diego - Boating Near Me - San Diego, California

Our Captain was good & the weather not very cooperative. Never sailed out to see the whales. We did a slow sail around the harbor instead. Sailed closely past the USN submarine pens, several very fat sea lions, USS Midway, a couple of mega yachts, & the USCG Eagle. Never got to or below the Coronado bridge. Winds so light we had to motor twice. For the price, I feel we did not get our money's worth. Nevertheless, we did enjoy the company of our Captain and 4 fellow cruisers. I personally would not do this again without first considering the weather. read more

Our group booked a private chartered sailing tour for a bachelorette party and I only have amazing things to say. It was so much fun yet also relaxing and our group absolutely loved our captain's energy. Sail San Diego was also really flexible with us regarding timing, number of guests, and were very communicative regarding weather (there was a chance of rain, but ended up being a beautiful day!) Would totally recommend to anyone looking for a group excursion, where Sail San Diego takes care of so much for you! read more

Captain Rhys was excellent! We saw a grey whale up close!!!! We also saw seals, sea lions and dolphins. My family and I thoroughly enjoyed this outing. Our captain was very knowledgeable and easy going! He was great with my teenagers and an excellent sailor! I highly recommend this tour! read more

We had an amazing sail today with Captain Dave, aka Dolphin Dave. The weather was perfect and we saw lots of dolphins and a few whales. Dave was knowledgeable and friendly. All of the Sail San Diego staff are great. We take a tour every year when my parents visit from the east coast and we always choose SSD. read more

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One of the best sailing experiences they we have had this far. Booking was a breeze and we were able to choose the day and time that worked out just fine during our trip without any problems. On the day of the sail, we were running behind a few minutes ( we chose the public sail and were in a group of 6) though the crew were kind enough to have us onboard and not miss on the fun. Quick checkin at the front office ( yes we took a Lyft per their recommendation and not Uber and were dropped right on the spot) and were directed to walk to the boat ( and were handed the passes at the office which were verified before boarding the boat). Rhys was the captain on the boat and started off with a great introduction and as well checked with us on our preferences in terms of we wanted to get a bit in the ocean or if we were to go visit the city spots from the distance and the overwhelming majority was to ride the choppy waves in a bit of the ocean. Off we traversed through the channel in there and saw quite a bit of sea lions , pelicans , seagulls , a lot of naval base, big JP-5 fuel reservoirs , a navy guard boat making its rounds , sea lion and a dolphin training area ( trained by the navy to detect threat) and some amazing views with a fantastic sailing experience. The Sun Gods were on our side along with the Wind Gods and our sails never had a dull moment. The boat was pretty well maintained and the rooms under the boat were kept very clean and pristine as well. The kitchen was stacked with energy bars, snacks (gluten free options as well) along with water (bottles and sparkling). The experience was pretty conversational from start to end and we got to learn a lot about sail boats, things around San Diego and it essentially turned into a fun filled start to the day. Looking forward to more such in the future!!! read more

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We had such a lovely day sailing with Rhys! He was so kind and welcoming to us, and was full of interesting facts about many things we saw on our route. We just loved our time on the water, and he absolutely contributed to our experience!! It wouldn't have been the same without him. Thanks Rhys!!! read more

Excellent company! Excellent customer service and skilled skippers. Very well put together cruises. Highly recommend.

Had a great time for a friend's birthday sailing with happy Greg! Great guy, great boat, great opportunity to practice sailing and the weather was perfect. Would definitely recommend this for a small party since they provide snacks and great views. Much more relaxed than jet skiing and good for those who can't swim but still enjoy being on the water. Thanks for a great experience! read more

We had a wonderful morning sailing with Captain Reece. We highly recommend Sail San Diego. They are very organized and reasonably priced. read more

Sail San Diego - Boating Near Me - San Diego, California

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Always a home run with captain Dave at Sail San Diego! Looking forward to the next reservation. read more

Sail San Diego - The bay from an ideal lens - Boating Near Me - San Diego, California

Reese was great had a good time. Parking before leaving was a nightmare so get there early.

Rhys was a wonderful captain and lovely young man. the weather was fine and so was the company! this was our second time and it was lovely. thanks read more

Our group of 12 had a great time with them! Beautiful and clean boat. Our captain Dave was very nice and skilled. They are kids friendly. We took three, five and six years old kids on board. Kids enjoyed the boat ride and also the variety of snacks. Another plus of Sail San Diego is that they host a large group. Some other charter companies I checked don't host a group of 12. We will for sure be back! read more

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This was a wonderful experience and I highly recommend this to both tourists and locals. My fiancée and I are locals and this was a very fun, intimate experience. Captain Greg was great - he was funny, knowledgable, and did a great job at making everyone feel comfortable and relaxed. read more

Had a great 3 hr. sail w/ Captain Dave! He was very knowledgeable and informative of the San Diego area and maritime attractions. Highly recommend this activity and Captain. read more

Amazing and relaxing trip. Our captain had the perfect balance of offering info and answering questions and letting the silence of nature speak for itself. Very well organized trip and perfectly timed. Highly recommended! read more

Sail San Diego - Boating Near Me - San Diego, California

Reece was very knowledgeable and super friendly. He made sure that everyone on board was happy, comfortable, and having fun- a great sail!

Had the best sailing experience with Captain Greg! We got to see what goes on in the harbor and Captain Greg was so entertaining! He should do stand up! We will definitely book a sail next time we're in town! read more

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I love the sailing experience! Definitely want to come back to do a sunset sail. It was very peaceful and relaxing