The Best Sailboat Rentals in San Diego

Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

We loved our private sail with captain Matt! The boat was so comfortable and perfectly stocked with drinks and blankets. Matt made sure we saw the sea lions and all the points of interest along the coast. He answered all our questions and couldn't have been nicer. Booking the trip was so easy too! I messed up and booked our initial trip for the wrong date. I panicked and Ryan responded to my inquiry within minutes and saved the day. He was so accommodating and helpful. From the booking to the whole sailing experience I have not one complaint. These guys are truly the best.

Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

This was such an amazing experience! Highlight of our trip, for sure! The catamaran comfortably fit 10 of us and it was so relaxing! The captain was great and communicative! I would 100% book this again! The seating in the front was comfortable, with great views. The boat itself had cushioned seats too that were great. The table was nice for a little picnic and storage space for our stuff. There was definitely enough storage underneath as well as on the beds and in the kitchen. So grateful for this experience!

Enjoy the best of Mission Bay aboard a Captained 85' Wooden Viking Style Ketch

Our experience on the Cloudia was an incredible one! We had originally booked a sailing on the Cloudia several months before our voyage to celebrate our late mother's birthday as a family. Last minute, us kids agreed to spread her ashes of possible. I was so hesitant if this could be accomplished in such a short period of time, but the team was very responsive with support and instructions for us to make it happen. It felt surreal bringing that idea to reality. Certainly an experience that I would recommend to anyone. The boat is breathtaking, and the crew was kind and funny. We look forward to venturing out again in the future. I can't speak highly enough about it.

42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

Best experience I’ve ever had on a boat. Captain Liz did not disappoint. Everything was perfect from the communication to the experience. Nothing like being right under a bunch of fireworks on the 4th of July! If you are looking for an amazing time and an amazing captain definitely book captain Liz!!

60’ Premier Private Sailing Yacht in San Diego

I’ve used many companies in the past and this one BY FAR exceeds all of them. Great and easy communication beforehand, perfect boat layout with a lot of space to sit and hang. Jim and the crew were amazing and very engaging. I would definitely do it again!

60’ Premier Private Sailing Yacht in San Diego

Everything was spectacular! Rented for a combo bachelor bachelorette party and everyone had a great time. Amazing value, boat speakers and the general space was terrific. Great time and would absolutely highly recommend. Jim even knocked us down a price tier out of the kindness of his heart.