Imagine Sailing San Diego — Local services in San Diego

We did a sail with Peter over the weekend. I booked this very close to the day because I had an important conversation to have with a family member and was hoping for a little privacy for one part of the sail. It was a short conversation so we didn't need to book the whole boat. We were able to get a ride with only one other person and snagged the front of the boat. The start of the boat ride really supported our purposes and we were able to create a much needed healing and memorable moment that I'm grateful for. Thankfully we were all done with our conversation when Peter came up and quickly told us "You can stay up here if you want but you'll have to lay down as we are about to start using the sail." We turned back confused to ask a question and he had already gone back down. We were confused until the first sail change but we were able to navigate the changes. It would have been a better experience overall if he had taken a little more time to explain to us what was happening, why it was necessary or wait for clarifying questions. As I'd been on another larger sailboat here in San Diego with another tour company about 6 months ago for a birthday celebration were we also sat upfront and did not have this experience, I wasn't sure if it was necessary or if he just made a decision that wasn't in consideration of our experience. Also had we known we'd be up and down about 6-7 times we may have just come down with him for that part of the ride. With more clear communication we would have been empowered to choose our best experience. We got off the boat a little confused by that part of our sail. We would have loved to give him the 5 star tip we brought with us but we landed around a 3 star experience because of the gap in consideration and communication. Overall, you can't beat being on the water in San Diego and I'm happy I booked a sailing experience for my purposes. If I book again with Imagine Sailing I'll aim to try a different...

I was visiting San Diego from Los Angeles. Having previously lived in San Diego for years, I had sailing friends at the bay but none of them were available that day. Then I came across Imagine Sailing and Captain Mike. I had never met Mike and there were not many reviews to go by. However, I was liking everything on the website, so I took a chance.

Hands down, Mike is the best captain you will find in San Diego. Right after I booked, I texted Mike and he responded straight away. We were texting about the best sailing times while he was checking on the optimal weather conditions. Mike asked about special accommodations and what he could to make it the perfect sailing experience.

When I came on the boat, I was pleasantly surprised. The boat is just beautiful, both inside and outside. Mike is very personable, down to earth and he makes for great conversation. He even gave us a couple of sailing lessons. On top of it all, he gave us a full extra hour so we got to experience the entire sunset and the mesmerizing colors of dawn...while drinking champagne.

I have nothing bad to say at all. I could not imagine a better option out there. If you need to make your day picture perfect, look no...

We booked a 2-hr. sailing trip from 2-4 pm at the end of March for a joint landmark birthday celebration for my son and I. We went with a party of 5 and rented out a private excursion. Captain Mike was very responsive to my questions before and during our trip, in order to make it a very special celebration for our family. We were able to reschedule due to inclement weather, and it ended up to be a fabulous day that we ended up setting sail. I was glad we went on a weekday when the Bay was relatively quiet. Captain Mike was personable and filled with knowledge, historical facts, and intriguing tidbits about the sights we were seeing. We were interested in learning and so he generously taught us about the basics of sailing as well. We all enjoyed the trip immensely. If you’re thinking of doing this, I highly recommend...