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. read more

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

Memorable, wonderful and spectacular photo opportunities with experience captain providing the best most enjoyable cruise. Captain Nick provided a brief orientation and safety tips, took up out to the harbor and ensured we had a pleasant trip. Very highly recommended. read more

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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! read more

San Diego Sailing Experiences - Our view. - Boating Near Me - San Diego, California

Captain Nick was charming and very knowledgeable! We had no idea how important San Diego was as a national/ international port! The boat was spotless, wine and chocolate was plentiful and the sunset was spectacular. We would highly recommend this adventure. read more

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!! read more

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We had a really wonderful sunset sail (although the clouds didn't cooperate with us, lol). This was a beautiful evening sail with just 6 people. The captain was very friendly and the views were breathtaking! read more

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! read more

San Diego Sailing Experiences - Boating Near Me - San Diego, California

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. read more

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100% would not hesitate to book with them again. Beyond friendly, respectful, knowledgeable, and friendly captain. The ship was amazing, the bean bags were a great touch ! read more

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. read more

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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. read more

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We had an amazing sailing experience this weekend with Captain Rick! The boat was clean and beautiful. Really great tour of San Diego Bay, sea lions, the Midway, and an exciting 2 gun salute from The Californian! We knew we were in good hands and Rick handled the boat like a pro, highly recommend this to anyone who has the chance to go! read more

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

We had the best experience on our sunset cruise. The cruise definitely outperformed our expectations. Captain Nick Sanchez also knew how to treat us and gave an A+ service and sailboat cruise. I would definitely recommend this cruise to everyone! read more

Had a great experience with captain Stu. Have a really relaxing sail out on the bay. Wine was nice and chilled, boat was clean and it was a lot of fun sitting on the bow of the boat on the bean bags they had there. Very kind and good to our kids as well. Would go again for a special family event. read more

I bought the trip as a surprise birthday gift for my boyfriend. The experience was beautiful, fun, peaceful, relaxing and simply perfect! The weather was great, the wind ideal. Aaron was engaging and answered all my silly questions along the way. If you're reading reviews to try to decide, just do it! You won't regret it. The birthday boy (59yrs old) loved it as much as I did too! So as a gift, it was a huge success! We decided we'll be back read more

We had a great sunset sail with Nick aboard his Catalina 400. We received email and text reminders before the cruise, with clear directions to the meeting point. Nick was on time, professional, friendly. He offered us white wine and chocolate on board, and offered to take pictures of our family while sailing. We had a great time. Everything was perfect! read more

Experience was great. Captain had great sense of humor and made sure everyone got front of boat experience. Helped direct everyone as needed through sail in regards to safety (what to hold on to /what side to traverse/etc). Sunset was awesome as well read more

San Diego Sailing Experiences - Boating Near Me - San Diego, California

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

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 :-) read more

San Diego Sailing Experiences - Captain Aaron with my kids :-) - Boating Near Me - San Diego, California

What better way to explore San Diego than by sail boat! Captain Aaron was fantastic and full of San Diego information! His boat is gorgeous and his personality inviting, as if we've all been friends for years! My husband and I, along with our 2 best friends, had the most amazing experience with laughs and relaxation as we watched the sunset shimmer off the San Diego skyline! We're already planning our next adventure with Aaron and Maya! Thank you, Aaron for your wonderful hospitality! read more

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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.

We had an amazing sailing trip with Captain Rick! Despite the fact that it was cold and windy, Rick kept our sail as calm as possible and it never felt rocky. He was definitely working hard to make sure our experience was the best possible...and he succeeded! We had booked the trip for a girls weekend and it was the truly the highlight of our weekend. Can't wait to sail again!!! read more

We had such a great time! Our Captain was super knowledgeable took excellent care of all passengers. The boat is lovely and has refreshments, blankets if you get chilly, and a restroom as well. The views were picturesque and the sunset was dreamy. This was a definite highlight of our trip to San Diego. read more

After a booking error by another company, Aaron was able to accommodate our group on a short 4-day notice on his boat, Queen Anne's Revenge, with DJ as our captain. Aaron was easy to communicate with prior to sail day and Captain DJ was a very cool guy and we had a lot of fun sailing with him! I would recommend DJ and Aaron's company to anyone looking for a fun, relaxing time on the SD waters!! read more

San Diego Sailing Experiences - Boating Near Me - San Diego, California

Had a spectacular evening sail with Captain Aaron. The boat was ready with bean bags, beverages, snacks and blankets. This will become a tradition for every visit to SD. Coolest Captain ever! Surprise fly-by from the Navy's finest added to the thrill! read more

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This was such an awesome and fun experience! Aaron is a great host, very personable and a great captain. My boyfriend and I enjoyed this sailing trip and a beautiful sunset. If you are in San Diego, go join Aaron! read more

San Diego Sailing Experiences - San Diego from the water - Boating Near Me - San Diego, California

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Nothing more relaxing than a day of sailing in San Diego Bay. Aaron was so accommodating and friendly and my family and I couldn't have asked for a better time! The boat was spacious and Aaron supplied cushions and blankets to make our sail more comfortable. Aaron was very educated on the area and the scenic spots to take us. We were able to see some dolphins and it was a perfect day. The prices are the most reasonable out of the companies we looked at and I'm so glad we went with Aaron and he will definitely be our go to anytime we want to get back out on the water! read more

This was a wonderful evening. Aaron was a great captain. We had some champagne when we boarded and also enjoyed some wine and snacks that we brought. The views where amazing and the boat was nice. We definitely will do this again very soon!! Thanks Aaron for a splendid evening! read more

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We just finished our sunset sail with Aaron. Although the wind was dismal, we still had a fantastic time. The sunset from near the Coronado bridge was amazing. The downtown city lights were spectacular! Cold champagne, great conversation. We'll definitely do this again! read more

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We had such a fantastic time with Capt DJ! He was very knowledgeable about San Diego and sailing. Funny jokes and great music. Perfect day on the water, sunny with a nice breeze! We got to sit at the front of the boat on bean bags.. best view of the waters.. it's Veterans day so we even saw some air shows and saw lots of seals sleeping and barking on the docks. Lots of entertainment and the drinks were a refreshing bonus! Thanks for a memorable experience! read more

We did a combo birthday sunset cruise last Friday night and we had an awesome time. Capt. Aaron was so kind and considerate. We brought some small sandwiches, fruit tray and cheese and crackers. We also had some beers and sodas for birthday boys. It was a short 2 hour cruise which was just perfect. I highly recommend viewing the city like this. Very special and people were great. Can't wait to do again so!! read more

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Aaron was an absolute delight to work with! I called first thing in the morning with the hopes of setting something up day of for a sunset cruise proposal (I know, I know, lack of planning...). Aaron picked up the phone immediately and talked me through some ideas and plans for the day. He was actually away on the road but still managed to set up something on his ship with another captain he knew. My fiancé actually gets sea sick when on the ocean and Aaron helped to assure the conditions of the day would allow us "smooth sailing" (pun intended). When we arrived at the doc not only were immediately comforted by the level of professionalism shown by the captain he charted and the condition of the boat. While on the boat we got to enjoy the many treats he provides such as fruit, champagne, chocolates, and to top it off we got to sit in the front of the boat (the bow) in bean bags and watch the sunset in a place not many will ever get the luxury of seeing it from. From beginning to end Aaron and Cast Off Sailing far exceeded our expectations and made a lasting impression on us. We have already made plans to go back again the next time we are in San Diego with our girls and have another adventure with them. read more

San Diego Sailing Experiences - View from the bean bags on the bow - Boating Near Me - San Diego, California

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

Captain Aaron is a great Captain and this was a great experience that I will never forget I would definitely recommend this. Worth it hands down best experience you can have read more

We had such a great time on Aaron's boat this past weekend!! The boat is cozy and accommodating and the tour was very beautiful. Aaron was very knowledgable and was a great host. I highly recommend this tour to tourists or locals like me. We boroughs our own snacks aboard but Aaron did provide champagne, soda and water! Awesome day! Thanks Aaron!! read more

San Diego Sailing Experiences - Boating Near Me - San Diego, California

Great trip with Aaron! So glad we booked the trip. My family was in from out of town and he made it an incredible trip! read more

San Diego Sailing Experiences - Awesome times & beautiful views on a PRIVATE boat - Boating Near Me - San Diego, California

Had a great time sailing over Labor Day! Had an amazing experience! Will definitely be back! read more

Could not say better things about the company. We messed up the booking (our fault) and missed our sail time and the host was beyond accommodating to welcome us back to the boat for another day with no hesitations. Highly recommend this experience for an awesome time with great people!!! read more