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    San Diego Sailing Experiences

    5.0 (74 reviews)
    Open 9:00 am - 7:00 pm

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    Our view.
    Marka E.

    We had an excellent sunset sailing with Captain Stu! Lovely boat, smooth ride and a friendly family that also booked. We would totally do this booking again!

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    Jennifer W.

    Captain Aaron made our 'Elope on a Sailboat (during a pandemic)' THE MOST EXTRAORDINARY special day we could have ever dreamed of on 10-10-2020! What an outstanding captain and big day collaborator from the moment I reached out to him to the moment we left the boat as husband and wife! We cannot thank you enough captain Aaron, what a gorgeous boat, a thoughtful sailor and the chillest energy we could have asked for. We will absolutely sail with your company again!! ***Cast Off Sailing/San Diego Sailing Experiences provides meticulous attention to COVID-19 precautions and operated out of an abundance of caution to keep our very small party safe on the boat while honoring the integrity of our very special day, outstanding work!!

    The view from the bow.
    T S.

    Having taken a sunset tour before, I had high expectations. Captain Kyle and the tour managed to exceed them in every way. Our boat had six guests and we departed at 5:30. Along the way, Kyle explained the history of the area and pointed out sights we would not have seen. We saw seals, a dolphin, and three fast boats with Navy SEALS. The evening was capped off with a glorious sunset with downtown San Diego lighting up. I have been on cruises where you wanted off with an hour to go. I could have relaxed for another two hours on this charter. This was the best cruise we have taken and I would recommend you choose Captain Kyle.

    Troy B.

    Amazing trip. Booked the sunset cruise for 6 of us. It was an awesome experience. Can't recommend it enough. Capt. Rick is a great captain!

    Such an amazing experience! Would recommend to anyone. The wine, chocolate and amazing guide made it a go to when me and my partner come to visit.

    First of all - Cap'n Kyle was fantastic. He's the consummate professional, is extremely knowledgeable and skilled at his craft, and promotes "fun" (with safety) and he did a great job teaching a lot of the unknowns in the Bay (boats, air craft carriers, local spots to eat, and sailing in general). The weather was perfect, sunset was serene, the boat was top notch, but we found ourselves just chatting it up with the two other groups and Kyle the entire time I think we forgot why we booked in the first place; felt like old friends booked the trip and it was a fantastic time. If you want a memorable experience, I highly encourage this excursion. Looking forward to the whale watching venture in the winter and we will be doing this sunset cruise again.

    Corey M.

    My wife and I had an amazing time sailing with Aaron on his 40ft Catalina. Beautiful day on the water, nothing compares to the peace and serenity of open sailing and cruising the bay. Aaron was extremely knowledgeable and friendly. Even though we had other people on the boat it felt like a private tour. Highly recommend this trip, will look no further next time we're in San Diego.

    Captain Aaron with my kids :-)
    Reema S.

    We went out sailing on Aaron's boat last Saturday and it was absolutely perfect. He was very friendly and professional. The booking process was so simple and easy, I was able to book it on my phone. The boat is really beautiful and fully stocked. Aaron had plenty of wine for us and you can bring your snacks. We were quite full since we had just had lunch nearby. He even allowed my son to plug In His phone so we had our own music ...the kids loved that! I know there are choices of boats for sailing at the harbor but try Aaron, you won't regret it ...guaranteed :-)

    Queen Anne's Revenge!

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    1 month ago

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    9 months ago

    We had a wonderful time on the sunset sail! Although chilly, we enjoyed the views, sunset and serenity the water brings.

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    2 years ago

    Rick was a terrific captain on a beautiful night on the bay. Thank you for the wine, water, and chocolate and the views!

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    Aaron B.

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    3 years ago

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    3 years ago

    Great time! Beautiful cruise around the bay. Our captain Rick was informative and fun. We thoroughly enjoyed the whole experience.

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    7 years ago

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    5 years ago

    This is a MUST do if you visit SD. So fun and worth every penny. The captain was really nice and they provided blankets and drinks as well.

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    3 years ago

    Very relaxing and captain made sure we were very comfortable. I recommend this experience after a stressful day of sightseeing.

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    5 years ago

    We loved this!!! Beautiful boat, beautiful sunset, great wine, and Capt Aaron was fantastic! Would absolutely recommend!!!

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    Ask the Community - San Diego Sailing Experiences

    Review Highlights - San Diego Sailing Experiences

    I decided to propose to my girlfriend on a sunset sail and the first person that came to mind was Captain Aaron.

    Mentioned in 26 reviews

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    San Diego Whale Watch - The Privateer

    San Diego Whale Watch

    4.7(1.1k reviews)
    3.8 mi
    15 years in business
    Free parking

    Such a great experience for our first Whale Watching trip, great even with our 3 year old! Worth…read morethe cost, we were out for a bit over 3 hours. Check in process was easy, just follow the email instructions, all very clear. Bring sunscreen, a hat or sunglasses. You can bring your bags and snacks. There is plenty of space under the benches for your belongings. Lots of options for seating all around the boat, both inside and out. Also 2 restrooms available. As well as a Galley with snacks and souvenirs! I didn't realize, but they also sell photo packages of the wildlife from the trip. So you can focus on documenting your group and the good time, They'll capture the animals! :) This crew was Captain Vanessa, Naturalist Ruth, Deck crew Colleen and Sara, and Galley Oscar. They were all so helpful and accommodating. I cannot tell you how warm and inviting they all were. You could definitely tell they loved their jobs. For me...So, despite Dramamine and sea sickness bands I got really nauseous; and I think my 3 year old did too but couldn't verbalize, because she passed out about 1.5 hours into the trip-so I was just kind of sitting towards the back holding my toddler mid trip. Which is about the time when the whales appeared! (Up to that point we saw different birds, pods of dolphins and sea lions.) So these whales on our trip were on the starboard side when they appeared, but I was on the port side, kinda stuck sitting with my sleeping toddler. At one point Colleen came and asked if she could help me move to see the whales, but that was easier said than done, especially not feeling well. I let her know she was sweet but we were okay. Well as the boat tracked the whales, I guess Colleen and Sara both mentioned to the captain that we were kind of stuck in the back on the Port side and the captain ended up turning the boat towards the whales so I could see them. It was the sweetest thing and I felt so seen as a mama. :) I didn't know how a whale watching trip could go above and beyond, but they did! We did a 12:30pm tour on a Monday and there seemed to be a good crowd, but they were not at full capacity, which meant moving around was an option for those that wanted to. We will be back, this was a great choice!

    I'm rounding up a little; if half stars were allowed, this would be a 3.5 from me…read more The good: Nice crew, clean boat, lots of food options available (very pleasant surprise), we saw whales (huge bonus but out of anyone's control on the boat), the captain made sure to spin around to let everyone see them when we did spot some, though - that was cool. One of the crew members took pictures on a DSLR and sold them to us if we couldn't get good enough pics ourselves. You can buy early access to the ship to pick out a good spot, or you can buy a VIP ticket to have access to your own section of the boat right up front. The things I didn't enjoy - which, honestly, I'm not sure how the crew would handle any differently than they did. Some of the people on the boat were super rude. Lots of coughing in close quarters without covering their mouths; one group of people was so hellbent on getting the perfect pictures that they all stood in front of each section of people at least once, running side to side instead of giving everyone turns. The captain did ask that everyone take turns, but the behavior stayed the same all ride. A couple of people actually stood in front of other people who remained seated, completely blocking their views. The bad: You were supposed to get there early to check in and line up, but there is nothing to do in the area, and no seating, so prepare to stand in a line for an hour if you get there right when they say to. The photo package was really expensive for what you got. 3 hours is a long time to be on a boat not learning about things - lots of lulls in programming.

    Photos
    San Diego Whale Watch - Privateer and Whale

    Privateer and Whale

    San Diego Whale Watch
    San Diego Whale Watch - Blue Whales off the coast of San Diego. Sept 2, 2011

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    Blue Whales off the coast of San Diego. Sept 2, 2011

    Tiki Time Bay Tours

    Tiki Time Bay Tours

    4.7(155 reviews)
    2.1 miFleetridge, Point Loma
    Locally owned & operated
    Kid friendly

    I surprised my boyfriend with tickets for Tiki Time Bay Tours for his birthday and had a couple…read morewere friends with tag along as well. Whether you're a local or visiting San Diego this is a really fun activity on the weekend with yummy drinks and good vibes. Originally we were booked for a 10:30am tour that goes out to watch the sea lions out on the bay, unfortunately not enough people booked that one so it was cancelled. Even though our original plan was cancelled Tiki Time Tours went above and beyond to make sure we had a good experience and not only complimentary upgraded our tickets to a more expensive tour, they also gave our party a free round of drinks for the inconvenience! I think this speaks a lot about a company; anyone can be happy with customer service when everything goes according to plan, but the most important times to step up is when plans get cancelled/changed and that's exactly what they did for us! Instead of the sea lion tour we ended up doing the Tiki Live! tour at 3pm. This tour is about 2 hours and while you're out on the water you mingle with everyone else and play games that can win prizes for yourself, your party or the whole boat! The games were fun, interactive and silly. At some points we got close enough to shore and made people on land be a part of our games! Donny was our tiki tour master and he was really funny during the whole tour. In between games he just let the music play so we could enjoy the atmosphere and drinks. My entire group left with nothing but great things to say about the whole experience. My friend even won a free tour for another time so we will definitely be returning for more tiki fun.

    RANDOM SUNDAY -…read moreStunning Views - Drinks + shots - Stunning views - chances to win money and prizes My friends randomly saw this boat and said we should do it for fun. Tickets were around $47 per person for a 2hr water tour around the Bay in a boat decorated in tiki decor. For tourist this tour is great with a ton of fun information about San Diego and stunning views in the water. Minimum 8 people on the boat or there may be cancellation of the tour. PAY ATTENTION TO DETAILS. The guide will have some friendly trivia for a chance to win good cash prices, free drinks, gift cards, etc I think that was pretty fun to include in while getting a tour. If you are sensitive to getting seasick, I would recommend a Dramamine beforehand. Although the boat was spacious, it still felt the wakes from the other boats and you can go rocking. In addition there were slow times of moving and turning. Or you can just chuck down a few drinks and feel numb to it all! They have a Tiki Bar with a drink menu (no food) to purchase from and if you bring snacks to eat - you can't eat it on the boat. Drinks were good but their "house" made shots were pretty good! We had a couple rounds of those while on tour - paid round by a passenger or a free shot in the house by the staff. The awkward but not so awkward would be mingling with other folks on the boat that you don't know. One of my friends kept interjecting with another party and while they seem to not mind I could tell they were being polite but if it were me I'd probs be annoyed if someone kept interjecting while I'm having a good time with my friends. Although we all got along and occasionally shared cheers with shots. Luckily the boat was near empty with just a few of us to have some space to do your thing. Overall, nice little 2hr time in the water. Would highly recommend the later session to catch the sunset. Until the next review....

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    Tiki Time Bay Tours
    Tiki Time Bay Tours
    Tiki Time Bay Tours - Tours hosted by professional comedic improvisors, no scripts.....where anything can happen!

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    Tours hosted by professional comedic improvisors, no scripts.....where anything can happen!

    Eco Boat Rentals

    Eco Boat Rentals

    5.0(355 reviews)
    2.1 miFleetridge, Point Loma
    Kid friendly
    Family-owned & operated

    came all the way from Alaska to find some fun and found it at Eco boats! Cesar at Point Loma was…read moreawesome!

    Had the best time at Eco Boat Rentals! It was so great to find a dog-friendly water activity with…read moresuch friendly staff, such well taken care of boats and of course a fabulous time on the water. It's located in beautiful Point Loma right next to Point Loma Seafoods (definitely recommend going there) on a nice dock with festive decorations and lots of photo ops. Note that parking here is a little difficult especially during summer and weekends but they do make it very clear on their website and provide different areas to park. I really want to note that the staff are so friendly and helpful and love dogs! Directions were very clear and they gave us a Bluetooth speaker free of charge. The boat itself was very clean and comfortable, not to mention easy to operate. My dog loved his first boating experience and wants to return! Maybe we will try the peddle boats next since this time we did the motorized boat. Thank you Eco Boats, you are an admired business in San Diego!

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    Eco Boat Rentals - Pink electric Duffy Boat charter in San Diego Bay! Cruise on your Birthday or Bachelorette party in style!

    Pink electric Duffy Boat charter in San Diego Bay! Cruise on your Birthday or Bachelorette party in style!

    Eco Boat Rentals - Glow Boat ride for couples and families! Uniqie way to see Night lights of Downtown San Diego

    Glow Boat ride for couples and families! Uniqie way to see Night lights of Downtown San Diego

    Eco Boat Rentals - Eco Pedal Boat Rentals in San Diego Bay Area! Kids friendly experience for whole family

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    Eco Pedal Boat Rentals in San Diego Bay Area! Kids friendly experience for whole family

    San Diego Boat Cruise - Interior below deck

    San Diego Boat Cruise

    5.0(75 reviews)
    2.1 miFleetridge, Point Loma

    Captain Paul was fantastic--extremely knowledgeable about the area and wonderfully accommodating,…read moreespecially with five small children in tow. He made the entire experience smooth, fun, and memorable. Couldn't recommend these folks more highly!

    I booked a yacht with San Diego Boat Cruises for my bachelorette party and it was a highlight of…read morethe trip! If you're looking for an amazing private cruise, definitely book with San Diego Boat Cruises!! We were on Miss Jen II (50' yacht) and it comfortably fit 12 women (the max occupancy). We all fit under the covered seating in the back of the boat together as well as on the bow at the same time. Below deck was nice, although we didn't spend much time down there aside from using the two bathrooms or making drinks in the kitchenette. The boat was equipped with a huge JBL speaker, phone chargers, a cooler with ice, soft drinks, water bottles, mixers, cups, and snacks (assorted chips). We brought our own alcohol, sandwiches, and extra snacks since we cruised at lunch time. We were on the water from 12-3:30pm and even though the day was cloudy, it didn't spoil our fun. The time flew by! We started the trip all seated in the covered area as we were cruising by the seals and to Point Loma. We cruised through San Diego Bay and ended up anchoring at Glorietta Bay, partying on the bow. The whole trip was a blast and Captain Paul was wonderful! He even got some great photos and videos for us! I booked the trip with Captain Glenn, who was easy to coordinate with. Overall I highly recommend San Diego Boat Cruise and would book with them again for any special occasion.

    Photos
    San Diego Boat Cruise - Exterior bow

    Exterior bow

    San Diego Boat Cruise - Captain Paul!

    Captain Paul!

    San Diego Boat Cruise - Seals

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    Seals

    San Diego Sailing Experiences - boating - Updated September 2026

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