Captain Keith’s Charters

San Diego, United States

5

13 reviews

Accepts Credit Cards

Contacts

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Telephone:
+1 608-695-8404
Website:
www.captainkeithscharters.com
Address:
5000 N Harbor Dr, San Diego, CA, 92106
at Nimitz Blvd
Point Loma, Fleetridge
Nearby public transportation stops & stations:
1.3 miTerminal 2 West
1.5 miTerminal 2
1.7 miTerminal 1
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Bussiness info

Accepts Credit Cards
Yes
Good for Kids
Yes

Today

Today –
Local time (San Diego) 6:58 AM Saturday, May 31, 2025

Business hours

Monday –
Tuesday –
Wednesday –
Thursday –
Friday –
Saturday –
Sunday –

Description

Specialties

Private sailing lessons and adventures! Non intimidating approach to learning sailing or seeing what it’s all about. Lets get you hooked on sailing first and the lingo will come naturally. If your more interested in sitting back and taking in the salt air, no problem! I’ll sail the boat while you enjoy your company and the great views on the water. My main goal is to deliver a personalized sailing experience, so please call and talk directly with me to answer any questions or set up a time to sail!

History

Established in 2011.

A $ 100 sailboat off the side of the road started it all! I taught myself to sail and my life has never been the same! Progressing through many different boats and sharing my passion with all my friends and family, lead to starting Captain Keith’s Charters. Lake Koshkonong near Edgerton Wisconsin was the beginning waters of my sailing lessons and charters. A four month solo adventure, sailing the Mississippi River from Wisconsin to the Bahamas was when I got a taste of the salt water. Upon returning, I had a great season of sailing in Wisconsin with great people but I needed that salt air again! I moved out to San Diego for the endless sailing season and to be in close vicinity of mountains. The consistency of great weather and wind make it an ideal place to spread my love of sailing to anyone who has a desire to learn or try it out!.

Meet the Business Owner

Keith M.

Business Owner

A true adventurer at heart! I started sailing 10 years ago after buying a $ 100 sailboat on the side of the road in Wisconsin. I’m completely self taught and have progressed through many different boats and sailing adventures. I’d like to share my passion of sailing with anyone who has a desire to learn or try it out. When I’m not sailing, its mountain biking, rock climbing, surfing, and planning for my next adventure!

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13 reviews of Captain Keith’s Charters

No registration required
Place rating: 5
San Diego, CA
Had an amazing 4 hour sailing adventure this past weekend. Captain Keith took us on a smooth sail around point loma. We all enjoyed relaxing on the boast and seeing the incredible views. The boat is very nice and well maintained. Captain Keith was a pleasure, and I will definitely be back on another sailing trip!
Place rating: 5
Oceanside, CA
I’ve sailed with Keith about 5 or 6 times now for various reasons. We took a couple sailing lessons, once we did a sunset sail, and another time we did a surf trip /​party style trip. He’s knowledgable and safe, but knows how to have a good time which is really what you want in a captain.
Place rating: 5
San Diego, CA
I have had the pleasure of going on multiple sailing trips with Captain Keith and I can’t say enough good things about the experience. Keith is very knowledgeable, a great teacher, and a really nice guy! On a few occasions we’ve been fortunate enough to see whales, seals, and dolphins. Even if you don’t see marine life, you can’t beat the views and overall experience.
Place rating: 5
Torrey Pines, San Diego, CA
I can’t say enough fantastic things about Captain Keith! Not only is he a super knowledgeable but he is such a super nice guy. I have sailed with him multiple times and would not consider any other company while in San Diego. He is very accommodating, great with all people and makes you feel like a friend. He also has a great teaching style so it wasn’t intimidating to learn even as a novice. The sailing is always beautiful and relaxing. I would definitely recommend Captain Keith!
Place rating: 5
Bismarck, ND
I planned a bachelorette sunset cruise with Keith. I was planning all from out of town and he got back to me right away and was very helpful – Even recommended a different boating company to me at first thinking they would be closer to where we were staying. I ended up picking Captain Keith’s charters and could not have been more pleased.
The boat ride was fabulous. Keith was a mountain of knowledge from the boat to our surrounding area. He was professional and friendly. Our trip was beautiful and we all loved it.
Place rating: 5
Yucaipa, CA
Went sailing on a 3 hour sunset sail yesterday as a party of 6. It was a great experience. It was very relaxing and everyone had a great time. Captain Keith has a great personality, he is very knowledgeable and his boat very clean. He was a great host showing us the local sites. As a treat we even saw the Greenpeace vessel go by. I would definitely do this again!!! A fantastic day and memorable experience! We loved it.
Place rating: 5
University Village, Chicago, IL
Captain Keith was awesome !! Very knowledgable and accommodating! I would definitely recommend his service!!!
Place rating: 5
San Diego, CA
Captain Keith was such a great captain to take my husband and our friends out sailing for a day. Not only does he have a fair price, but he is wonderful with his communication! He was sure to respond to my emails and phone calls immediately and did not stress me out one bit when trying to surprise my husband with a sunset sail. We appreciate the hospitality and adventure!
Place rating: 5
Corona, CA
Captain Keith delivered our boat from Newport Beach to Chula Vista. He did an amazing job and was great to work with. He gave us a list of items we need to work on and walked us through each one. He is extremely knowledgeable and professional but most importantly friendly and helpful. Definitely check him out for a charter, we already want to book him for a lesson!
Place rating: 5
Clemson, SC
Awesome sunset sail/​cruise! It was such a fun experience. The boat was stocked with jackets and blankets in case we got cold and some snacks as well. There were tons of whale and dolphin sightings during the cruise as well.
I would definitely recommend them if you want an easy sale with a knowledgeable captain.
Place rating: 5
Las Vegas, NV
I had an awesome experience with Captain Keith– as a present, my mom had given me a private sailing lesson. I had been sailing on a dinghy for about a year and wanted to get practical experience on a larger boat. Keith was ready when I arrived and we spent the afternoon on his boat on the ocean.
I was pleasantly surprised at how organized the sailing lesson was– from the start, I was at the helm and Keith was coaching me on everything from safety to managing wind. We spent 4 hours that afternoon, and it felt like we covered every detail. Keith is a friendly guy and really passionate about sailing. It was exactly what I needed– in fact, 2 days later, I rented a 22 ft sailboat from Dana Point Harbor and had a great afternoon with my son.
Bottom line– he is cut from the under promise, over deliver mold. If you want to build your skills, charter a boat, or if you need some help getting started with a boat of your own, definitely contact Keith.
Place rating: 5
Edgerton, WI
We had the pleasure of sailing with Captain Keith while on our honey Moon recently. We had such a wonderful time sailing with him. He made us feel very comfortable on the boat and even let us try our hand at sailing. Professionally, he is very knowledgeable about the area and sailing. Personally, he is very easy to talk to and shared lots of very interesting information about the area. He took us to see sea lions, whales and the most beautiful sunset! The boat is also very clean and comfortable. We could not have been more pleased with our experience and we would highly recommend him to anyone!
Place rating: 5
Alexandria, SD
We had the greatest time ever! Captain Keith was not only professional and polite but very knowledgeable about the area and everything that was going on in the area. The whales came right up to the boat, it was amazing. It was a very private (just my wife and I) yet affordable experience. Keith was recommended to us by some of our local friends and we would recommend him to anyone. He definitely sails because he loves it.